Luxury Villas in Santa Maria a Grignano, Italy
Results 41 - 60 of 79
- 10
- 5
- 5
Description
Up to 10 guests, 5 beds / 5 baths: this old tuscan farmhouse is located in the heart of the Arno Valley, between Firenze/Florence, Arezzo, Chianti and Siena.
Very centrally located to explore the region, what make this area unique is its authenticity and opportunity to discover Tuscany off the beaten path, thank to our connections: ASK for our concierge service or service list!
Remote but yet very close to nearby towns (about 6 km away from shops, supermarket, train station and highway). You will get to the property by a short private dirt road, driving through vineyards and beautiful mountain and hills views.
Fully immersed in nature and countryside, this is THE getaway to rejoice with nature, silence and breathe Tuscany in every way. The villa is very big, with very spacious rooms and surrounded by greenery and birds singing.
The indoor is typical tuscan, with every comfort such as wifi, wood oven, television with streaming mode and a private Home Cinema!
Wide property with fields and woods for you to take lovely walks around the property, do your yoga sessions or to simply sit under the shade of the pergola. The villa is open also for private events, small weddings, ceremonies or any project we could help realize!
The private pool is 12*5 mt, open from May 1st until Sept 30, with decks, chairs and lots of reading corners!
PETS LIVE ON PROPERTY, housekeeper lives nearby. Villa Marina
Book your vacation for the period from 30 March 2026 to 20 December 2026 and save 15% (minimum 7 nights).
Book your vacation for the period from 30 March 2026 to 30 June 2026 and save 10% (minimum 3 nights).
Book 5 days or less before the arrival date and receive a 10 % discount off the published rental rates.
This Offer is valid only for stays of 2 nights minimum and can not be combined with any other special offers.
Villa Fabbri
Amazing private vacation rental with private pool, WIFI, A/C, TV, patio and panoramic view
- 22
- 9
- 9
Description
Villa Fabbri is located 4 km (3 mi) from Montebenichi, Italy and only 33 km (20 mi) from Siena in the tourist area "Siena And Surroundings". Holiday rental Villa Fabbri is a lovely stone building (565 sq m) that includes private pool, WiFi internet and air conditioning. The property can sleep up to 22 people comfortably in nine bedrooms with nine bathrooms.
What to Expect
After arriving at Villa Fabbri you’ll find a beautiful clean well-maintained property with views of the hills perfect for a splendid holiday in Tuscany. Regardless of how you spend your days - visiting museums, shopping, sightseeing or just driving in the countryside, when you arrive home you can relax with your family and friends at the pool for a perfect ending to another day in Tuscany. For your pleasure, on the grounds there is a barbecue grill and patio. Sharing a meal with friends and family is a big part of the Tuscan culture. Take advantage of the well-equipped kitchen to prepare meals using local produce while on your vacation. The kitchen includes coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to 22 people. Dine 'al fresco' like a real Tuscan, the fully furnished veranda is the ideal setting to enjoy food, family and the nice Tuscan weather.
Places Nearby
Most people enjoy visiting close-by cities and towns while on vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Siena 33 km (20 mi), Arezzo 37 km (23 mi), Montepulciano 48 km (30 mi), Cortona 58 km (36 mi) and Greve In Chianti 59 km (37 mi).
Some other major tourist destinations you should consider visiting are: Florence 83 km (52 mi), Viareggio 170 km (106 mi), Forte Dei Marmi 177 km (110 mi), Rome 224 km (139 mi), Milan 371 km (230 mi) and Naples 415 km (258 mi).
Additional Information
Check-In Time: 16:00 - 19:00
Check-Out Time: 09:30 - 10:00
Pool Open: 15 May - 15 October (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 89 km (55 mi), Pisa (psa) 151 km (94 mi), Bologna (blq) 175 km (109 mi), Roma Ciampino (cia) 233 km (145 mi) and Roma Fiumicino (fco) 246 km (153 mi).
More Services
Cooking Lessons - If you're interested in discovering more about Tuscan cooking, inquire about the cooking lessons that can be scheduled at the property. It's a fun way to spend time with friends and family while discovering the techniques required to master Tuscan cuisine. For more details and the extra cost, please contact us.
Professional Chef - Are you looking for a real treat during your vacation? Why not book a professional chef to prepare and serve you a delicious meal using local produce? The chef will arrange the meal based on your preferences and dietary requirements. The chef will offer suggestions for the various courses and the wine. Ask for more details and the supplemental costs.
Tours - Custom tours can be scheduled by the owner for your group. For more details about the tours available, speak to the owner when you arrive or inquire prior to booking. The cost will vary depending in the exact tour and number of people.
Maid Service - Upgrade your holiday with maid service. This service can be arranged by the owner. Ask for more details about the supplemental cost.
Pre-Stocked Fridge - Take advantage of the pre-stocking service to save time and start your vacation hassle-free after a long trip. Inquire for more details, including the supplemental cost and how to arrange this service.
Baby Sitting - If you're traveling with children and would like an evening alone, a babysitter can be scheduled. Speak to the owner directly about this service when you arrive.
Villa Fabbri
- 24
- 11
- 11
Description
Holiday rental Villa Felciai is a nice stone building (545 sq m) that includes WiFi internet, private pool and air conditioning. The property can sleep up to 24 guests comfortably in 11 bedrooms with 11 bathrooms. Conveniently located 4 km (3 mi) from Montebenichi, Italy in the tourist area "Siena And Surroundings" and only 32 km (20 mi) from Siena.
Your Experience
After arriving you will be greeted by the owner or manager where you’ll find a beautiful clean well-maintained property with views of the hills ideal for a splendid holiday in Tuscany. For your enjoyment you will find a private pool where you can relax while enjoying a nice cold beverage after a busy day of sightseeing. Outdoors you will also find a patio and barbecue grill. Dining with friends and family is a huge part of the Tuscan culture. Take advantage of the well-equipped kitchen to prepare meals using local produce while on your vacation. The kitchen includes microwave, toaster and refrigerator, as well as, plenty of tableware and cutlery for up to 24 people. Dine 'al fresco' like a real Tuscan, the fully furnished veranda is the ideal setting to enjoy food, family and the beautiful Tuscan weather.
Places Nearby
Most people enjoy visiting close-by cities and towns while on vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Siena 32 km (20 mi), Arezzo 38 km (23 mi), Montepulciano 48 km (30 mi), Greve In Chianti 59 km (37 mi) and Montalcino 60 km (37 mi).
Some other major tourist destinations you should consider visiting are: Florence 83 km (52 mi), Viareggio 170 km (106 mi), Forte Dei Marmi 177 km (110 mi), Rome 225 km (139 mi), Venice 327 km (203 mi) and Milan 370 km (230 mi).
Additional Information
Check-In Time: 16:00 - 19:00
Check-Out Time: 09:30 - 10:00
Pool Open: 1 May - 3 November (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 91 km (56 mi), Pisa (psa) 151 km (94 mi), Bologna (blq) 175 km (109 mi), Roma Ciampino (cia) 234 km (145 mi) and Roma Fiumicino (fco) 246 km (153 mi).
More Services
Cooking Lessons - Discover from a local chef the techniques needed to master Tuscan cuisine. The owner can schedule to have a chef come to the property for a cooking lesson for any number of people in your group. It's a enjoyable way to spend time with friends and family while discovering the secrets vital to prepare delicious Tuscan meals when you return home. For more details and the extra cost, please contact us.
Professional Chef - Are you looking for a real treat during your holiday? Why not book a professional chef to prepare and serve you a delicious meal using local produce? The chef will schedule the meal based on your preferences and dietary needs. The chef will offer suggestions for the various courses and the wine. Inquire for more details and the extra costs.
Maid Service - If you'd like maid service during your visit that can be scheduled by the owner. Inquire for more details about the extra cost.
Pre-Stocked Fridge - If you'd like to have the fridge and pantry stocked before you arrive that is possible at Villa Felciai. Ask for more details, including the supplemental cost and how to schedule this service.
Baby Sitting - If you're traveling with children and would like an evening alone, a babysitter can be scheduled. Speak to the owner directly about this service after arriving.
Villa Felciai
- 16
- 7
- 7
Description
Property Villa Rossa is a nice property (340 sq m) that includes WiFi internet and private pool. The property can accommodate up to 16 people comfortably in seven bedrooms with seven bathrooms. Conveniently located 4 km (2 mi) from Rota, Italy in the tourist area "Florence And Surroundings" and only 31 km (19 mi) from Greve In Chianti.
What to Expect
Upon arrival at Villa Rossa you’ll find a nice clean well-maintained property perfect for a peaceful holiday in Tuscany. Regardless of how you spend your days - sightseeing, visiting museums, shopping or just driving in the countryside, when you arrive home you can relax with your family and friends at the pool for a perfect ending to another day in Tuscany. Dining with friends and family is a huge part of the Tuscan culture. Take advantage of the well-equipped kitchen to prepare meals using local produce while on your holiday. The kitchen includes coffee machine, microwave, toaster and refrigerator, as well as, plenty of tableware and cutlery for up to 16 people.
Places Nearby
Most people enjoy visiting nearby cities and towns while on vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Greve In Chianti 31 km (19 mi), Florence 48 km (30 mi), Arezzo 57 km (36 mi), San Gimignano 78 km (48 mi) and Montepulciano 88 km (55 mi).
Some other major tourist destinations you should consider visiting are: Florence 48 km (30 mi), Viareggio 132 km (82 mi), Forte Dei Marmi 142 km (88 mi), Rome 261 km (162 mi), Venice 291 km (181 mi) and Milan 335 km (208 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on holiday that is not a problem at Villa Rossa. If you have a large dog or multiple pets, please inquire for permission prior to booking.
Pool Open: 1 May - 30 September (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 55 km (34 mi), Pisa (psa) 116 km (72 mi), Bologna (blq) 140 km (87 mi), Roma Ciampino (cia) 270 km (168 mi) and Genova (goa) 273 km (170 mi).
Villa Casa Rossa
Ricavoli
Stunning private house with WIFI, private pool, TV, terrace and panoramic view, close to Florence
- 12
- 6
- 5
Description
Conveniently located 660 m (2112 ft) from Torre A Cona, Italy in the tourist area "Florence And Surroundings" and only 20 km (13 mi) from Florence. Property Ricavoli is a nice stone building (450 sq m) that includes WiFi internet and private pool. The property can accommodate up to 12 guests comfortably in six bedrooms with five bathrooms. If playing a round of golf is important while on holiday, you are in luck because there is a course nearby.
The Experience
When you arrive you will be greeted by the owner or manager where you’ll find a nice clean well-maintained property with views of the hills ideal for a peaceful vacation in Tuscany. Regardless of how you spend your days - visiting museums, sightseeing, shopping or just driving in the countryside, when you arrive home you can unwind with your family and friends at the pool for a perfect ending to another day in Tuscany. Sharing a meal with friends and family is a huge part of the Tuscan culture. Take advantage of the well-equipped kitchen to prepare meals using local produce while on your holiday. The kitchen includes coffee machine, microwave, toaster and refrigerator, as well as, plenty of tableware and cutlery for up to 12 people. Dine 'al fresco' like a real Tuscan, the fully furnished veranda is the ideal setting to enjoy food, family and the lovely Tuscan weather.
The swimming-pool is located in the higher part of the garden, where is also a changing-room and a shower-room.
What's Nearby?
Most people enjoy visiting close-by cities and towns while on vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Florence 20 km (13 mi), Greve In Chianti 30 km (19 mi), Arezzo 63 km (39 mi), San Gimignano 67 km (42 mi) and Siena 82 km (51 mi).
Some other major tourist destinations you should consider visiting are: Florence 20 km (13 mi), Viareggio 123 km (76 mi), Forte Dei Marmi 130 km (81 mi), Rome 267 km (166 mi), Venice 279 km (173 mi) and Milan 322 km (200 mi).
Additional Information
There is a table tennis in the house.
Pool Open: 15 May - 30 September (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 43 km (27 mi), Pisa (psa) 104 km (64 mi), Bologna (blq) 129 km (80 mi), Genova (goa) 263 km (164 mi) and Roma Ciampino (cia) 276 km (171 mi).
Special Services
Maid Service - If you'd like maid service during your stay that can be arranged by the owner. Inquire for more details about the supplemental cost.
Cleaning service is included 3 hours a day, 5 days a week. Ricavoli
Medieval Castle Living: Vineyards, Swimming Pool &
Fantastic holiday home with private pool, WIFI, A/C, balcony and panoramic view, close to Siena
- 12
- 6
- 6
Description
Vacation rental Medieval Castle Living: Vineyards, Swimming Pool & is a beautiful stone building (800 sq m) that includes air conditioning, private pool and WiFi internet. The property can accommodate up to 12 guests comfortably in six bedrooms with six bathrooms. Conveniently located 4 km (2 mi) from Sovicille, Italy in the tourist area "Siena And Surroundings" and only 14 km (8 mi) from Siena.
Nestled in the lush greenery of the Montagnola Senese, this magnificent property is a masterfully preserved 13th-century castle located just a 15-minute drive from the historic heart of Siena. The estate has been meticulously restored by its owners, who reside in the main tower in a secluded area that remains entirely private and separate from guest accommodations.
The estate is thoughtfully designed to offer both community and privacy. The first floor of the main castle features two charming apartments. Adjacent to the castle is a separate cottage housing two additional apartments, providing an ideal retreat for couples or guests seeking extra seclusion. With fully equipped kitchens in every unit and expansive common areas, the property perfectly balances independent living with shared moments.
Surrounded by rolling vineyards producing a refined selection of "Super Tuscan" wines, the estate invites you to embrace the slow pace of Italy. The grounds are a masterpiece of landscape design, featuring manicured lawns, traditional terracotta planters, and vibrant blooms. At the heart of the garden lies a generous swimming pool, fully outfitted with elegant sun loungers and umbrellas.
This elegant and spacious holiday home is perfectly suited for a luxurious escape with family or friends. The property comfortably accommodates up to twelve guests (with capacity for an additional two guests upon request).
The Experience
After arriving you’ll find a lovely clean well-maintained property with views of the hills perfect for a peaceful holiday in Tuscany. For your pleasure you will find a private pool where you can relax while enjoying a nice cold beverage after a hectic day of sightseeing. For your pleasure, on the grounds there is a barbecue grill and playground. Dining with friends and family is a big part of the Tuscan culture. Take advantage of the well-equipped kitchen to prepare meals using local produce while on your holiday. The kitchen includes coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to 12 people. Dine 'al fresco' like a real Tuscan, the fully furnished balcony is the perfect setting to enjoy food, family and the lovely Tuscan weather.
Places Nearby
Most people enjoy visiting close-by cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Siena 14 km (8 mi), San Gimignano 46 km (28 mi), Montalcino 49 km (31 mi), Greve In Chianti 53 km (33 mi) and Montepulciano 72 km (45 mi).
Some other major tourist destinations you should consider visiting are: Florence 76 km (47 mi), Viareggio 170 km (105 mi), Forte Dei Marmi 177 km (110 mi), Rome 248 km (154 mi), Venice 322 km (200 mi) and Milan 372 km (231 mi).
Additional Information
Pool Open: 15 May - 30 September (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 88 km (55 mi), Pisa (psa) 124 km (77 mi), Bologna (blq) 175 km (109 mi), Roma Ciampino (cia) 257 km (160 mi) and Roma Fiumicino (fco) 270 km (168 mi).
Additional Services
Cooking Lessons - If you're interested in discovering more about Tuscan cooking, inquire about the cooking lessons that can be arranged at the property. It's a pleasant way to spend time with friends and family while discovering the techniques required to master Tuscan cuisine. For more details and the additional cost, please contact us.
Professional Chef - Are you looking for a real treat during your holiday? Why not book a professional chef to prepare and serve you a mouth-watering meal using local produce? The chef will organize the meal based on your preferences and dietary requirements. The chef will offer suggestions for the various courses and the wine. Ask for more details and the additional costs.
Meals - If you'd like to have meals provided during your visit, either half-board or full-board is available. If you prefer only breakfast be provided, that can be scheduled as well. Inquire about the additional costs.
Tours - The owner can arrange custom tours for your group. To learn about the tours offered, speak to the owner upon arrival or ask prior to booking. The cost will vary depending in the individual tour and number of people.
Owner Assistance - Since the owner lives nearby, he is always available to offer advice and suggestions during your visit. In case you need assistance, it's nice to have someone available to help. In any case, the owner will always respect your privacy.
Exclusive Estate Inclusions : elevate your stay, we offer these bespoke services upon reservation:
When you choose the Castle Experience, your stay includes a curated selection of authentic local luxuries:
- Gourmet Farm-to-Table Breakfast: Start your morning in the castle’s elegant common wing with a signature breakfast prepared by the Castellana (the Lady of the Castle). Every ingredient is organic and locally sourced ("Km 0"), with each dish prepared à la minute to your preference upon your arrival at the table.
- Estate Wine Tasting: Enjoy an exclusive guided tour of the castle with a private tasting in the castle’s historic cellar. This experience can be scheduled at your convenience with a simple advance reservation.
Bespoke Guest Experiences (Optional)
To further enhance your Tuscan retreat, we are pleased to arrange the following premium services:
- Dining with the Castellana: Enjoy an elegant, candlelit dinner hosted in the castle's private courtyard—an intimate glimpse into authentic noble life.
- Culinary Arts: Participate in private cooking classes or enjoy professionally catered buffet dinners.
- Outdoor Adventures: Explore the region with curated wine tours, guided bike excursions, or scenic hiking trips through the Montagnola Senese.
- Tuscan Traditions: Experience the thrill of a professional truffle hunting.
Medieval Castle Living: Vineyards, Swimming Pool &
Book now and save 10%. Offer valid until 10 May 2026 and for a minimum stay of 2 nights.
Villa Dorothea
Beautiful independent vacation home with WIFI, A/C, private pool, TV, patio and panoramic view
- 12
- 5
- 5
Description
Villa Dorothea is a lovely stone building (500 sq m) with private pool, WiFi internet and air conditioning. The property can accommodate up to 12 guests comfortably in five bedrooms with five bathrooms. Villa Dorothea is located , Italy and only 33 km (21 mi) from Arezzo in the tourist area "Arno Valley".
What to Expect
When you arrive you will be welcomed by the owner or manager where you’ll find a nice clean well-maintained property with views of the hills ideal for a splendid vacation in Tuscany. For your enjoyment you will find a private pool where you can unwind while enjoying a nice cold beverage after a hectic day of shopping. For your pleasure, on the grounds there is a patio and barbecue grill. Sharing a meal with friends and family is a huge part of the Tuscan culture. Take advantage of the well-equipped kitchen to prepare meals using local produce while on your holiday. The kitchen includes coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to 12 people. Dine 'al fresco' like a real Tuscan, the fully furnished veranda is the perfect setting to enjoy food, family and the nice Tuscan weather.
Visit the Area
Most people enjoy visiting close-by cities and towns while on vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Arezzo 33 km (21 mi), Siena 38 km (24 mi), Greve In Chianti 47 km (29 mi), Montepulciano 55 km (34 mi) and Cortona 66 km (41 mi).
Some other major tourist destinations you should consider visiting are: Florence 75 km (47 mi), Viareggio 162 km (100 mi), Forte Dei Marmi 169 km (105 mi), Rome 232 km (144 mi), Venice 318 km (198 mi) and Milan 360 km (224 mi).
Additional Information
Check-In Time: 15:30 - 19:00
Check-Out Time: 06:00 - 10:00
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 81 km (50 mi), Pisa (psa) 143 km (89 mi), Bologna (blq) 167 km (104 mi), Roma Ciampino (cia) 241 km (150 mi) and Roma Fiumicino (fco) 253 km (157 mi).
Additional Services
Cooking Lessons - If you're interested in discovering more about Tuscan cooking, ask about the cooking lessons that can be organized at the property. It's a enjoyable way to spend time with friends and family while discovering the techniques vital to master Tuscan cuisine. For more details and the extra cost, please contact us.
Tours - The owner can arrange custom tours for your group. To learn about the tours available, speak to the owner when you arrive or ask prior to booking. The cost will vary depending in the specific tour and number of people.
Owner Assistance - Since the owner lives nearby, he is always available to offer advice and suggestions during your visit. In case you need assistance, it's nice to have someone available to help. In any case, the owner will always respect your privacy.
The Italian caretaker lives on site and will accommodate you with travel information to historic towns, organising private Tuscan cooking classes and wine tastings. Villa Dorothea
- 14
- 7
- 6
Description
Villa Vigliano is a lovely stone building (700 sq m) with WiFi internet and private pool. The property can sleep up to 14 guests comfortably in seven bedrooms with six bathrooms. Conveniently located in Rignano Sull'arno, Italy in the tourist area "Florence And Surroundings" and only 31 km (19 mi) from Greve In Chianti.
The Experience
After arriving you’ll find a beautiful clean well-maintained property perfect for a splendid holiday in Tuscany. Regardless of how you spend your days - sightseeing, shopping, visiting museums or just driving in the countryside, when you arrive home you can relax with your family and friends at the pool for a perfect ending to another day in Tuscany. There is a kitchen including coffee machine, toaster and refrigerator, as well as, plenty of tableware and cutlery for up to 14 people. If you prefer to dine 'al fresco', there is a fully furnished garden where you can enjoy the weather while dining outdoors.
Places Nearby
Most people enjoy visiting nearby cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Greve In Chianti 31 km (19 mi), Florence 50 km (31 mi), Arezzo 59 km (36 mi), San Gimignano 81 km (50 mi) and Montepulciano 90 km (56 mi).
Some other major tourist destinations you should consider visiting are: Florence 50 km (31 mi), Viareggio 136 km (85 mi), Forte Dei Marmi 143 km (89 mi), Rome 262 km (163 mi), Venice 293 km (182 mi) and Milan 334 km (208 mi).
Additional Information
Check-In Time: 17:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 May - 30 October (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 55 km (34 mi), Pisa (psa) 117 km (73 mi), Bologna (blq) 141 km (88 mi), Roma Ciampino (cia) 271 km (169 mi) and Genova (goa) 276 km (172 mi).
Villa Poggio Cherici
- 6
- 12
- 6
- 6
Someone else is looking at this property right now!
| Accommodation | ||||
|---|---|---|---|---|
| La Castellana | 2 | 1 | 1 | |
| Canto al Sole | 2 | 1 | 1 | |
| Bellina | 2 | 1 | 1 | |
| All 3 Accommodations | 6 | 3 | 3 |
Description
Hospitality, Osteria "Gentile" with veg garden, Cooking School and a stunning infinity pool overlooking the valley: il Canto del Maggio, owned by Simona and her family, isn’t just a place to sleep — it’s a place where you meet a family deeply rooted in this land and in its rhythms.
Here guests are welcomed into six charming units that reflect a rare and authentic form of hospitality: the Albergo diffuso—literally, a ‘scattered hotel’. Developed in Italy, this model revitalizes once-abandoned villages by blending comfort with local tradition in a truly immersive experience- in fact the "borgo" is a shared community between locals that live here permanently, and travelers that was born in the late 1980's.
Our collaboration with this placa was born to promote a network of local chefs, farmers, winemakers, guides, and hospitality professionals — all working together to create meaningful moments that we hope will make your stay one to remember.
My team (I am Tuscany) and I will take care of the accommodation side of your experience — from the moment you book to the day you arrive. Before your stay, we’ll coordinate with you to plan any extra services or personalized experiences, so everything is ready and tailored to your needs before you arrive.
Simona, the soul of this place, will welcome you into her world: her home, her kitchen, around her table, or walking through the vegetable garden — the orto. On the plate, a cuisine that arises spontaneously: the garden decides the menu, and we simply follow its lead.
Together, we can plan special dinners in the garden or by the pool, enjoy breakfast on the terrace or your private patio, and explore much more — from local farmers’ markets and tastings to our favorite go-to places in the area.
Available experiences include:
-Harvesting ingredients directly from the garden and discovering the joy of simple, farm-to-table cooking
-Themed culinary workshops (vegetarian, pastry-making, regional cuisine)
-Activities that immerse you in the natural beauty, culture, and traditions of the area
-Private meals (including breakfast) served anywhere on the property
-Pop-up events hosted by the restaurant or the outdoor kitchen
-Private events and retreats tailored to your needs Il Canto Del Maggio
Special Offer for La Castellana
Book your vacation for the period from 30 March 2026 to 20 December 2026 and save 15% (minimum 7 nights).
Book your vacation for the period from 30 March 2026 to 30 June 2026 and save 10% (minimum 3 nights).
Apartment:
Canto al Sole
Bellina
Last-Minute Offer for La Castellana
Book 5 days or less before the arrival date and receive a 10 % discount off the published rental rates.
This Offer is valid only for stays of 2 nights minimum and can not be combined with any other special offers.
Other apartments with last-minute offers:
Canto al Sole
Bellina
- 8
- 4
- 4
In high demand!
Description
Property Summary
Poggio all'Aia is a large and comfortable vacation rental located in the charming hamlet of Lucciana, just 3 kilometers from the center of Casole d'Elsa, Italy. This renovated two-story house offers a tranquil and secluded retreat for up to 8 adults. It features a terraced garden, a 5,000 square meter fenced area with a wildlife garden, trees, and a natural garden. Enjoy the seasonal availability of an above ground swimming pool (12 x 5 meters, depth 140 cm), an outdoor shower, a terrace, garden furniture, a barbecue, and parking for up to 4 cars on the premises. The property also includes Internet Wifi and a yard.
Outdoors
Perched on a sunny slope with an elevated position, Poggio all'Aia boasts breathtaking views of the countryside. The property offers a terraced garden and a 5,000 square meter fenced area with a wildlife garden, trees, and a natural garden. Guests can enjoy the seasonal availability of an above ground swimming pool (12 x 5 meters, depth 140 cm) and an outdoor shower. The garden is also equipped with a terrace, garden furniture, a barbecue, and parking for up to 4 cars on the premises.
Other Information
Poggio all'Aia is suitable for groups of up to 8 adults or groups of teenagers upon request only. Baby equipment is included in the rental for families with young children.
Distances and Attractions
Although Poggio all'Aia offers a peaceful retreat, it is conveniently located near many amenities and attractions. A grocery store, bakery, bar, and restaurant are just 3 kilometers away in Casole d'Elsa. A supermarket is 11 kilometers away, and the Colle Val d'Elsa railway station is also 11 kilometers away. Nearby attractions include an outdoor swimming pool and an indoor swimming pool (11 kilometers), a sandy beach (62 kilometers), Volterra (23 kilometers), Siena (38 kilometers), and Florence (64 kilometers). Poggio All'Aia
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- 2
- 2
Description
Property Summary
At "Il Fienile," a recently renovated two-story vacation rental near Casole D'elsa, Italy, you can find comfort and delight amidst the surrounding meadows and vineyards. The property offers a private, fenced area of 3,000 square meters with trees, a meadow, and amenities like a seasonal above-ground swimming pool (8x4 meters), an outdoor shower, garden furniture, and a barbecue. It also features Internet WiFi, parking, and a yard, ensuring a convenient and enjoyable stay.
Outdoors
The property boasts a beautiful outdoor space with a private and fenced area of 3,000 square meters, complete with trees and a meadow. Guests can enjoy a refreshing swim in the above-ground swimming pool, measuring 8 meters by 4 meters, which is available seasonally from May 1st to October 15th. The pool maintenance is taken care of by the owner/gardener. Additionally, the outdoor area features an outdoor shower, garden furniture, and a barbecue, allowing you to make the most of the pleasant Tuscan weather.
Other Information
This vacation rental is suitable for families and comes equipped with baby equipment included, accommodating up to 4 adults and 2 children comfortably. The property is ideal for those seeking a peaceful retreat away from the hustle and bustle of city life, providing a tranquil and rejuvenating experience.
Distances and Attractions
The property is conveniently located just 3 kilometers from the charming village of Casole d'Elsa, where you can find various amenities such as grocery stores, restaurants, bars, and bakeries. The Colle di Val d'Elsa railway station is also within a short 11-kilometer distance. For those interested in exploring the surrounding area, popular attractions like San Gimignano, Volterra, Siena, and Florence are accessible by car, offering ample opportunities for sightseeing and cultural immersion. Il Fienile
Villa Melinda
Independent House with private pool, WIFI, A/C, TV, terrace, pets allowed, close to San Gimignano
- 6
- 3
- 3
Description
Beautiful villa located in the countryside between Siena and Florence, renovated in 2015 maintaining and enhancing the rustic style and at the same time equipping it with all comforts to ensure a relaxing and welcoming environment. The house is arranged over three floors and has an attractive design with a taste of modern combined with some antique furniture. The property also has a small fenced garden of 1,000 sq m. equipped with pool for exclusive use of the guests (11m. x 5m. prof. 150cm.), there is also a nice loggia equipped for outdoor dining with barbecue.
Possibility to arrange chef service and cooking classes (upon request and to be paid on the spot); possibility of massages by professionals (to be arranged directly on the spot).
Free Wi-Fi internet. Air conditioning throughout. Parking near the property (30 meters). Access to the house with 150m. of unpaved road. The property is located at 8km. from the center of "Certaldo", at 19km. from "San Gimignano", at 20km. from the golf course, at 55km. from Siena and 59km. from Florence. Villa Della Meletta
Book 42 days or less before the arrival date and receive a 10 % discount off the published rental rates.
This Offer is valid only for stays of 7 nights minimum and can not be combined with any other special offers.
Casa Meletta
Private Villa with private pool, WIFI, A/C, hot tub, TV, patio, panoramic view, near San Gimignano
- 6
- 3
- 3
Description
Casa Meletta is located 2 km (1 mi) from Gambassi Terme, Italy and only 19 km (12 mi) from San Gimignano. Casa Meletta is a lovely stone building (140 sq m) with hot tub, private pool and air conditioning. The property can sleep up to six guests comfortably in three bedrooms with three bathrooms.
The Experience
Upon arrival you’ll find a nice clean well-maintained property with views of the hills and the city perfect for a splendid holiday in Tuscany. For your pleasure you will find a private pool where you can unwind while enjoying a nice cold beverage after a hectic day of sightseeing. Outdoors you will also find a patio, barbecue grill and hot tub. Sharing a meal with friends and family is a big part of the Tuscan culture. Take advantage of the well-equipped kitchen to prepare meals using local produce while on your holiday. The kitchen includes coffee machine, microwave, stove and refrigerator, as well as, plenty of tableware and cutlery for up to six people. Dine 'al fresco' like a real Tuscan, the fully furnished patio is the ideal setting to enjoy food, family and the lovely Tuscan weather.
What's Nearby?
Most people enjoy visiting close-by cities and towns while on vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: San Gimignano 19 km (12 mi), Greve In Chianti 50 km (31 mi), Siena 55 km (34 mi), Florence 57 km (35 mi) and Pisa 73 km (45 mi).
Some other major tourist destinations you should consider visiting are: Florence 57 km (35 mi), Viareggio 102 km (63 mi), Forte Dei Marmi 114 km (71 mi), Rome 290 km (180 mi), Venice 301 km (187 mi) and Milan 347 km (216 mi).
Additional Information
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 April - 1 October (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 58 km (36 mi), Pisa (psa) 75 km (46 mi), Bologna (blq) 162 km (100 mi), Genova (goa) 247 km (154 mi) and Roma Ciampino (cia) 299 km (186 mi).
L'antica Meletta
Book now and save 10%. Offer valid until 30 June 2026 and for a minimum stay of 14 nights.
- 20
- 9
- 9
Description
Borgo Gerlino is a nice stone building (650 sq m) with WiFi internet and private pool. The property can sleep up to 20 guests comfortably in nine bedrooms with nine bathrooms. Borgo Gerlino is located 3 km (2 mi) from Rapale, Italy and only 30 km (18 mi) from Siena in the tourist area "Siena And Surroundings".
What to Expect
Upon arrival you will be welcomed by the owner or manager where you’ll find a nice clean well-maintained property with views of the hills ideal for a splendid holiday in Tuscany. For your enjoyment you will find a private pool where you can unwind while enjoying a nice cold beverage after a busy day of visiting museums. Dining with friends and family is a huge part of the Tuscan culture. Take advantage of the well-equipped kitchen to prepare meals using local produce while on your holiday. The kitchen includes microwave and refrigerator, as well as, plenty of tableware and cutlery for up to 20 people. Dine 'al fresco' like a real Tuscan, the fully furnished garden is the ideal setting to enjoy food, family and the lovely Tuscan weather.
Places Nearby
Most people enjoy visiting close-by cities and towns while on vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Siena 30 km (18 mi), Arezzo 40 km (25 mi), Montepulciano 46 km (29 mi), Greve In Chianti 57 km (36 mi) and Montalcino 59 km (36 mi).
Some other major tourist destinations you should consider visiting are: Florence 86 km (53 mi), Viareggio 172 km (107 mi), Forte Dei Marmi 180 km (111 mi), Rome 223 km (138 mi), Venice 329 km (204 mi) and Milan 372 km (231 mi).
Additional Information
Pool Open: 15 April - 15 October (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 93 km (58 mi), Pisa (psa) 153 km (95 mi), Bologna (blq) 178 km (110 mi), Roma Ciampino (cia) 232 km (144 mi) and Roma Fiumicino (fco) 244 km (152 mi).
More Services
Professional Chef - Are you looking for a real treat during your vacation? Why not book a professional chef to prepare and serve you a mouth-watering meal using local produce? The chef will organize the meal based on your preferences and dietary needs. The chef will offer advice for the various courses and the wine. Inquire for more details and the additional costs.
Maid Service - Upgrade your holiday with maid service. This service can be organized by the owner. Ask for more details about the additional cost.
VILLA + ANNEX (650 sqm)
The structure is equipped with underfloor heating/cooling, both in the main body and in the annex.
Maid service is included in the price for 4 hours per week.
Borgo Gerlino
Fonte di Pillo
Unique private holiday villa with private pool, A/C, WIFI, TV, terrace and panoramic view
- 14
- 6
- 6
Description
Property Summary
Villa Fonte di Pillo is a stunning vacation rental located just 4 kilometers from Gambassi Terme and Castelfiorentino, and 20 kilometers from San Gimignano. This villa offers a peaceful retreat with excellent amenities such as a swimming pool, yard, internet WiFi, parking, and an EV charging station.
Outdoors
The property boasts an impressive 60,000 square meters of land with a well-maintained garden featuring a lawn and various trees. The highlight of the outdoor area is the 12 x 6 meter swimming pool with a depth of 150 centimeters, available seasonally from April 22nd to October 14th. The pool is equipped with an outdoor shower, and the owner/gardener ensures it is always in pristine condition.
Other Information
Inside the villa, guests can enjoy air conditioning and a burglar alarm system for added comfort and security. Access to the property is via a 200-meter-long unmade road, and covered parking is available for up to 2 cars.
Distances and Attractions
Nearby attractions include the cities of Volterra, Firenze, Pisa, and Livorno. Additionally, there is an 18-hole golf course located just 15 kilometers away, making Villa Fonte di Pillo an ideal vacation rental for those seeking relaxation and luxury in a convenient location. Fonte di Pillo
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- 2
- 2
Description
Duomo Suite is a nice property (80 sq m) with WiFi internet. The property can accommodate up to four guests comfortably in two bedrooms with two bathrooms. Duomo Suite is located in the centre of Florence, Italy and only 32 km (20 mi) from Greve In Chianti in the tourist area "Florence And Surroundings".
The Experience
After arriving you will be welcomed by the owner or manager where you’ll find a beautiful clean well-maintained property with views of the city ideal for a relaxing vacation in Tuscany. Regardless of how you spend your days - visiting museums, shopping, sightseeing or just driving in the countryside, when you arrive home you can relax with your family and friends for a perfect ending to another day in Tuscany. Dining with friends and family is a huge part of the Tuscan culture. Take advantage of the well-equipped kitchen to prepare meals using local produce while on your holiday. The kitchen includes coffee machine, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to four people.
What's Nearby?
Most people enjoy visiting nearby cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Greve In Chianti 32 km (20 mi), San Gimignano 55 km (34 mi), Siena 75 km (47 mi), Arezzo 81 km (50 mi) and Pisa 81 km (51 mi).
Some other major tourist destinations you should consider visiting are: Viareggio 103 km (64 mi), Forte Dei Marmi 110 km (68 mi), Rome 284 km (177 mi), Venice 256 km (159 mi), Milan 301 km (187 mi) and Naples 475 km (295 mi).
Additional Information
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 8 km (5 mi), Pisa (psa) 83 km (52 mi), Bologna (blq) 108 km (67 mi), Genova (goa) 241 km (150 mi) and Venezia (vce) 262 km (163 mi).
More Services
Tours - Custom tours can be organized by the owner for your group. For more details about the tours offered, speak to the owner when you arrive or ask prior to booking. The cost will vary depending in the exact tour and number of people.
Duomo Suite
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- 2
- 3
Someone just enquired about this property!
Description
Elegant Suite: Florence Apartment with View on Med is a beautiful property (300 sq m) with air conditioning and WiFi internet. The property can accommodate up to four guests comfortably in two bedrooms with three bathrooms. Elegant Suite: Florence Apartment with View on Med is located in the centre of Florence, Italy and only 32 km (20 mi) from Greve In Chianti in the tourist area "Florence And Surroundings".
The Experience
When you arrive you will be welcomed by the owner or manager where you’ll find a nice clean well-maintained property with views of the city perfect for a relaxing holiday in Tuscany. A real benefit of renting a home, instead of multiple hotel rooms, is the ability to relax after a busy day of sightseeing with family and friends. Enjoy a meal together along with some local wine to finish the day. If you enjoy cooking for family and friends there is a well-equipped kitchen including coffee machine, microwave, toaster and refrigerator, as well as, plenty of tableware and cutlery for up to four people.
Visit the Area
Most people enjoy visiting close-by cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Greve In Chianti 32 km (20 mi), San Gimignano 56 km (35 mi), Siena 75 km (47 mi), Lucca 78 km (49 mi) and Arezzo 81 km (50 mi).
Some other major tourist destinations you should consider visiting are: Viareggio 99 km (62 mi), Forte Dei Marmi 106 km (66 mi), Rome 284 km (177 mi), Venice 260 km (161 mi), Milan 303 km (188 mi) and Naples 475 km (295 mi).
Additional Information
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 8 km (5 mi), Pisa (psa) 83 km (52 mi), Bologna (blq) 108 km (67 mi), Genova (goa) 237 km (147 mi) and Venezia (vce) 262 km (163 mi).
More Services
Pre-Stocked Fridge - If you'd like to have the fridge and pantry stocked before you arrive that is possible at Elegant Suite: Florence Apartment with View on Med. Inquire for more details, including the supplemental cost and how to arrange this service.
Elegant Suite: Florence Apartment with View on Med
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| Accommodation | |||
|---|---|---|---|
| Lion Nero | 6 | 3 | 2 |
Description
Conveniently located in the centre of Florence, Italy in the tourist area "Florence And Surroundings" and only 27 km (17 mi) from Greve In Chianti. Appartamenti Troise is a nice property with air conditioning and WiFi internet. Appartamenti Troise is a apartment / condo that has a total of four independent apartments. The property can sleep up to 14 guests comfortably in seven bedrooms with six bathrooms.
Your Experience
Upon arrival you’ll find a beautiful clean well-maintained property perfect for a splendid vacation in Tuscany. After a hectic day of sightseeing, spend some time with friends and family enjoying a glass of wine - a perfect way to relax at the end the day. Each apartment has its own private living area with a kitchen with plenty of utensils, tableware and cutlery, a bedroom and bathroom. Many people traveling with friends prefer a multi-unit holiday home where they can spend time together in the common areas but still have their own private living quarters.
What's Nearby?
Most people enjoy visiting nearby cities and towns while on vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Greve In Chianti 27 km (17 mi), San Gimignano 60 km (37 mi), Arezzo 77 km (48 mi), Siena 79 km (49 mi) and Pisa 86 km (53 mi).
Some other major tourist destinations you should consider visiting are: Viareggio 114 km (71 mi), Forte Dei Marmi 124 km (77 mi), Rome 281 km (175 mi), Venice 273 km (169 mi), Milan 316 km (196 mi) and Naples 472 km (293 mi).
Additional Information
Check-In Time: 14:00 - 00:00
Check-Out Time: 07:00 - 10:30
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 12 km (7 mi), Pisa (psa) 87 km (54 mi), Bologna (blq) 122 km (76 mi), Genova (goa) 254 km (158 mi) and Venezia (vce) 275 km (171 mi).
La Croce D’oro Suite Apartments
Villa Badia
Superb private holiday home with private pool, WIFI, A/C, TV and pets allowed, close to Arezzo
- 12
- 6
- 4
In high demand!
Description
Villa Badia is a beautiful property (300 sq m) with private pool, air conditioning and WiFi internet. The property can accommodate up to 12 guests comfortably in six bedrooms with four bathrooms. Villa Badia is located 4 km (3 mi) from Badia Agnano, Italy and only 21 km (13 mi) from Arezzo in the tourist area "Arno Valley".
The Experience
Upon arrival you will be welcomed by the owner or manager where you’ll find a nice clean well-maintained property with views of the hills perfect for a peaceful holiday in Tuscany. After a busy day of shopping, spend some time with friends and family poolside enjoying a glass of wine - a perfect way to relax at the end the day.
Places Nearby
Most people enjoy visiting close-by cities and towns while on vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Arezzo 21 km (13 mi), Cortona 40 km (25 mi), Siena 46 km (28 mi), Montepulciano 51 km (31 mi) and Greve In Chianti 53 km (33 mi).
Some other major tourist destinations you should consider visiting are: Florence 80 km (50 mi), Viareggio 167 km (104 mi), Forte Dei Marmi 174 km (108 mi), Rome 223 km (139 mi), Venice 323 km (201 mi) and Milan 365 km (227 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on holiday that is not a problem at Villa Badia. If you have a large dog or multiple pets, please ask for permission prior to booking.
Pool Open: 1 May - 30 September (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 86 km (53 mi), Pisa (psa) 148 km (92 mi), Bologna (blq) 172 km (107 mi), Roma Ciampino (cia) 232 km (144 mi) and Roma Fiumicino (fco) 245 km (152 mi).
Villa Caccianello
Cafaggio di Sopra
Stunning independent villa rental with private pool, WIFI, TV and balcony, near Florence
- 11
- 6
- 3
Description
Property Summary
Nestled in the heart of Tuscany, Italy, the farm estate "Cafaggio di Sopra" is a remarkable holiday rental set in a quiet and elevated position atop a hill, just 8 km from Sieci and 19 km from Florence, in the municipality of Pontassieve. Originally built as a watchtower during the Middle Ages, the main building has been fully renovated and thoughtfully furnished with a harmonious blend of antique and rustic pieces, preserving the authentic character of its historic origins. The property comprises a main house and an annex building, together offering a total of 9 rooms across an impressive 455 m2 of living space. Situated at an altitude of 400 m above sea level, the estate commands breathtaking panoramic views of the rolling Tuscan countryside surrounding Florence, with olive groves, woods, and meadows stretching across the landscape in every direction. Guests have access to a private 6 x 12 m swimming pool, a generous yard that invites relaxation and outdoor enjoyment, and on-site parking reached via a 1 km unmade road. Internet Wi-Fi access is also available, ensuring connectivity throughout your stay.
Outdoors
The outdoor spaces of "Cafaggio di Sopra" are as captivating as the property itself, offering a wealth of areas designed for leisure, dining, and exploration. A charming pergola provides a shaded setting ideal for alfresco meals, complemented by a traditional pizza oven that adds a distinctly Italian touch to outdoor entertaining. The estate is equipped with garden furniture and a barbecue, making it perfectly suited for long, convivial evenings under the Tuscan sky. A children's playground ensures that younger guests are well catered for, while a table tennis table offers additional recreational options for all ages. The surrounding landscape is laced with forest paths leading to a lake, inviting guests to explore the natural beauty of the estate at their own pace. The private swimming pool, measuring 6 x 12 m, serves as the centrepiece of the outdoor area and is set against the stunning backdrop of the hilly Florentine countryside.
Other Information
The main house and annex building of "Cafaggio di Sopra" together form part of a distinguished farm estate, offering a total of 9 rooms across 455 m2. Central heating is available at the property, though it is provided exclusively during the period from 01.11 to 07.04. For guests requiring additional housekeeping services, midweek cleaning can be arranged upon request for an extra fee. For larger groups wishing to make full use of the estate, it is possible to book the entire villa for up to 9 people under the reference IT5270.899.3, in an arrangement that does not include the use of the Suite.
Distances and Attractions
"Cafaggio di Sopra" enjoys an enviable location that places guests within easy reach of some of Tuscany's most celebrated destinations and practical amenities. The property is situated just 8 km from Sieci and 19 km from Florence, with a train connection to Florence available nearby, offering a convenient and scenic route into the city. Pisa airport is also well connected to the estate, providing straightforward access for international travellers arriving from abroad. Among the nearby attractions, guests will find the charming hilltop town of Fiesole, the prestigious Luxury Outlet The Mall, the picturesque village of Monteloro, and the tranquil forest sanctuary of Vallombrosa. Wine enthusiasts will appreciate the proximity to Greve in Chianti, a quintessential destination in the heart of the Chianti wine region, while San Casciano in Val di Pesa offers further opportunities to discover the authentic flavours and traditions of rural Tuscany. Cafaggio di Sopra
