
Villa holiday rentals in San Gimignano
Find and book unique villas on Airbnb
Top-rated villa rentals in San Gimignano
Guests agree: These villas are highly rated for location, cleanliness and more.

The Farmhouse Cottage
Entire upper floor of the newly renovated Manor House in traditional Tuscan style. High ceilings with exposed beams make the place cozy and perfect for families or groups of friends. In the house, there are two large functional fireplaces (in the living room and kitchen). Private, non-shared accommodation. The house has a large covered terrace, garden with sofas, BBQ, fire pit, private parking. The swimming pool among the olive trees and vineyards is ideal for relaxation and has private access to the shared area

Villa in Chianti near Florence with stunning view
The apartment is part of a 14th-century Tuscan Villa, with a stunning view over Chianti hills and organic vineyards from our family. With its 100 square meters and two gardens can comfortably accommodate 2 people. The villa, while historic and beautiful, is equipped with all the modern amenities you will need. The location is relaxing, yet very close to Florence, Pisa, Siena, and many other Tuscan tourist spots. Read the reviews to understand what you can expect from your stay in our house!

Tuscany Country House Villa Claudia
La Nostra Country House è incastonata in un bellissimo Casale antico, finemente ristrutturato, panoramicissimo, costruito a margine dell'antico Borgo di Canneto, insediamento rurale nel territorio di San Miniato, risalente al 785 d.c. Il Casale, immerso nella Natura ma dotato di ogni comfort moderno, vi regalerà momenti indimenticabili, potendo scegliere tra vacanze in assoluto Relax, attività culturali (vicinissime le città d'Arte della Toscana), gustosi tour enogastronomici e tanto altro!

Virgi House
Virgi House is a 160 sqm villa, located 3 km far from Siena’s hystorical center. The villa is distributed over three floors. On the first one there is a double bedroom with bathroom and terrace, a large open space living room, a modern kitchen and a bathroom. Downstairs a double bedroom (or 2 single beds), a large bathroom, a study and a bright living room with a loggia from which you can access the private car park and the garden. The property also provides free wifi, air conditioning.

Villa Gourmet Food, Pizza, Chef, Pool and Nature
Villa Gourmet Typical farmhouse in the heart of Tuscany with 6 bedrooms that can comfortably accommodate up to 14 guests. - Exclusive saltwater infinity pool - Gourmet cuisine - Large garden with private parking - Two Free Charging Station (3,75 KW) - Veranda with table and Weber barbecue by the pool - Children's play area and table tennis - Football pitch - Home Restaurant service available - Cooking class and pizza workshop using a wood-fired oven - Shuttle Services

Belforti Tower
Torre dei Belforti is the perfect place for people who love beauty, nature and art. Sleeping at the Tower is like traveling trough the time, between knights and princesses. The wonder of this place is enriched by a big garden, with its swimming pool, the cypresses alleys and the olive trees. The village is also a magic place well preserved and still alive. We are Emilia and Luca, we live here and our mission is to give the best to our guests, to fully enjoy this marvelous place.

San Giovanni in Poggio, villa Meriggio 95mq
Detached house, two double bedrooms, two bathrooms with shower, living room with fully equipped kitchen (dishwasher, washing machine, oven, microwave), double sofa bed, private garden with equipped pergola. Satellite TV and free Wi-Fi. Additional services at the property, upon reservation, include Focus brand Jarifa2 6.7 pedal-assisted bicycles and a wellness area with a Forest outdoor Finnish sauna and a heated mini-pool with hydromassage and chromotherapy with panoramic views.

Tuscan Dream Villa @ Rustic Elegance Near Florence
🌿Welcome to Villa La Conigliera🌿, an ideal retreat for a romantic getaway or a relaxing stay, just a few kilometers from Florence. 🌟Set in the peaceful Tuscan countryside, overlooking an ancient courtyard, it blends rustic charm with modern comfort. Perfect for couples or families with a newborn, with a crib available upon request 👶. Two adjacent villas for 4 and 6 guests complete the hamlet. 🚗 A car/motorbike is recommended for exploring the beautiful surroundings.

Luxury Villa in the very heart of Chianti
The views, the views, oh my word the VIEWS! Originating in the early 12th century this spectacular home once served as the bakery for the entire village. Now fully renovated, the entrance and ground level have been opened with glass arches allowing natural light to illuminate the exposed walls, 4 large bedrooms, 3 with ensuite baths ( including a jacuzzi ). Only Minutes away from the famous Wineries of Chianti, this is THE Spot for a glass amongst friends.

The Tower
Ancient Tuscan villa, beautiful, with exclusive private garden, completely renovated, surrounded by the beautiful and gentle Tuscan hills. The villa has a breathtaking view, is very sunny, well furnished and equipped with all amenities, quiet and not isolated. The house is located in Bagnolo, a small hamlet of Impruneta at the gates of Chianti, an area of olive groves, vineyards and peace. The house is about 10 km by car from the center of Florence.

Farmhouse in Chianti
Beautiful portion of a farmhouse immersed in Chianti with a beautiful swimming pool, surrounded by vineyards and olive trees, perfectly furnished with a large garden and parking spaces. It is located 20 minutes from Florence, 40 from Siena and 50 from Pisa, in a few minutes you can reach Certaldo (birthplace of Boccaccio) and Vinci (birthplace of Leonardo Da Vinci). The house is halfway between Montespertoli and San Casciano (7km).

Villa Isabella
Villa Isabella is a comfortable Tuscan style villa located in the splendid Chianti hills in Tuscany with a large garden and a spectacular breathtaking panoramic swimming pool for exclusive use where you can experience the Tuscan tradition in full local style with the possibility of organizing private shuttles service for reach the property traditional experiences, services and tours only and exclusively for our guests.
Popular amenities for San Gimignano villa rentals
Private villa rentals

Villa with pool in Chianti Area

Luxury Villa on Chianti Wine Estate

Valluccia 51

Luxury Tuscany Villa on the hill with private pool

Lilium,delux farmhouse in the chianti hills

The Lazy Oak

Villetta dei Fagiani - pools, Jacuzzi in Florence

Beautiful Country House, near Siena with jacuzzi
Luxury villa rentals

Romantic Villa with private pool and fabulous view

Il Timignano

Villa Oliva w/pool+ ensuite - Pillo Holiday Villas

Tenuta del Podestà villa di charme in Firenze

Country house with view over San Gimignano hills

Private Villa with semi-Olympic pool and Tennis

A Charming Country House in the Tuscan Chianti

Farmhouse , pool, 13 px. Lucca 10km
Villa rentals with a pool

Villa La Gemma

Dream in Tuscany, Villa with pool

Casanova of Bricciano

Villa Le Panteraie - located between Florence and Pisa

[Le rondini in Tuscany] Exclusive View Pool Villa

Beautiful tuscan country house

Villa sii felice

Pompana Rustic Charm Casale
Quick stats about villa rentals in San Gimignano
Total rentals
70 properties
Nightly prices starting at
$107 AUD before taxes and fees
Total number of reviews
1.4K reviews
Family-friendly rentals
70 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
60 properties have a pool
Destinations to explore
- Farmstay rentals San Gimignano
- House rentals San Gimignano
- Rentals with a hot tub San Gimignano
- Rentals with pools San Gimignano
- Luxury rentals San Gimignano
- Rentals with a patio San Gimignano
- Rentals with an EV charger San Gimignano
- Rentals with breakfast San Gimignano
- Rentals with a fire pit San Gimignano
- Smoking-friendly rentals San Gimignano
- Fitness-friendly rentals San Gimignano
- Pet-friendly rentals San Gimignano
- Rentals with outdoor seating San Gimignano
- Rentals with a fireplace San Gimignano
- Cottage rentals San Gimignano
- Condo rentals San Gimignano
- Hotel rentals San Gimignano
- Apartment rentals San Gimignano
- Rentals with a washing machine and dryer San Gimignano
- Holiday home rentals San Gimignano
- Bed and breakfasts San Gimignano
- Family-friendly rentals San Gimignano
- Villa rentals Siena
- Villa rentals Tuscany
- Villa rentals Italy
- Santa Maria Novella
- Duomo di Firenze
- Piazza del Duomo (Pisa)
- Basilica of Santa Maria Novella
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Ponte Vecchio
- Cala Violina
- Gulf of Baratti
- Uffizi Gallery
- Mugello Circuit
- Mercato Centrale
- Piazzale Michelangelo
- Fortezza da Basso
- Parco delle Cascine
- Spiagge bianche
- Pitti Palace
- Piazza della Repubblica
- Careggi University Hospital
- Spiaggia Libera
- The Boboli Gardens
- Avignonesi Winery Fattoria Le Capezzine
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Spiaggia Marina di Cecina
- Stadio Artemio Franchi
- Things to do San Gimignano
- Food and drink San Gimignano
- Nature and outdoors San Gimignano
- Things to do Siena
- Food and drink Siena
- Art and culture Siena
- Sightseeing Siena
- Nature and outdoors Siena
- Tours Siena
- Things to do Tuscany
- Wellness Tuscany
- Sightseeing Tuscany
- Nature and outdoors Tuscany
- Art and culture Tuscany
- Tours Tuscany
- Entertainment Tuscany
- Food and drink Tuscany
- Sports activities Tuscany
- Things to do Italy
- Art and culture Italy
- Sports activities Italy
- Sightseeing Italy
- Wellness Italy
- Food and drink Italy
- Entertainment Italy
- Tours Italy
- Nature and outdoors Italy