
Vacation rentals with a pool in San Gimignano
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Quick stats about vacation rentals with a pool in San Gimignano

Total vacation rentals
Explore 490 vacation rentals in San Gimignano

Nightly prices starting at
San Gimignano vacation rentals start at G$10,455 GYD per night before taxes and fees

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Over 12,170 verified reviews to help you choose

Family-friendly vacation rentals
300 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 230 rentals that welcome pets

Rentals with dedicated workspaces
150 properties have a dedicated workspace

Wi-Fi availability
480 of San Gimignano vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across San Gimignano rentals

4.7 Average rating
San Gimignano stays receive an average rating of 4.7 out of 5 from guests
Top-rated rentals with a pool in San Gimignano
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Relaxation and charm in the Chianti hills
Beautiful stone farmhouse, detached, surrounded by olive trees and the Chianti hills, with private garden and panoramic swimming pool. Ground floor with large living rooms, antique fireplace and wood-burning oven, bright living room and fully equipped kitchen. On the first floor, three suites consisting of a bedroom, study and private bathroom. Access via gate and white road on private property just 500 meters from the village of Strada in Chianti. Ideal for peace and relaxation. Convenient location for visiting Tuscany.

Podere Vergianoni immerso nelChianti con piscina
Podere Vergianoni is an ancient family-run property from the 1600s located in the beautiful hills of Chianti in Tuscany, with the possibility of arranging a private shuttle and local experiences directly with our family. The apartment is available for 2 adults with the possibility of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard you'll find a saltwater pool with a relaxation area on a panoramic terrace overlooking the castle and vineyards with incomparable sunsets.

Palazzo Monaci - Pool in the Crete Senesi
Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Podere La Castellina - No. 1 COTTAGE
Independent stone and brick cottage inside the "Podere la Castellina" (former 13th century convent), in the magnificent natural park of Montagnola Senese. The cottage can comfortably accommodate 5 people and includes: - large living room with TV and fireplace - kitchen with oven - master bedroom - bedroom with three single beds - bathroom with shower Guests have access to a panoramic swimming pool, solarium and terrace with breathtaking views, equipped with a wood-burning oven and barbecue.

Stone House with Exclusive Pool Codilungo in Chianti
Welcome to your Tuscan dream between Florence & Siena. Perfect for families or romantic getaways. • 360° views of iconic Chianti hills. •Huge Exclusive Infinity Pool (17x9m), lit at night (open from May 1st to October 15th) • Total privacy, yet restaurants/shops are 10-15 mins away. • Comfort for 6: 3 bedrooms (2 double, 1 twin) & 3 full baths. • Modern amenities: Fully equipped kitchen area, Smart TV. • Outdoor bliss: Large dining loggia, professional BBQ, poolside porch & bath.

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.

Private Chianti Cottage, Garden & Vineyard Views
Set in a picturesque hamlet, overlooking the Chianti hills, this charming country house is just 10 minutes from Siena and Castellina in Chianti. Recently renovated, it blends authentic Tuscan charm with modern comforts. The house features two bedrooms, two bathrooms, a cozy living area and a fully equipped kitchen with a dishwasher, two fridges, and a washing machine. Outside, enjoy a beautiful garden and relax in the outdoor marble hot tub, soaking in the breathtaking views.

SuiteLouise.pool, Hot Tub,homeGym & private Garden
SuiteLouise, in the chianti region is the perfect retreat for those seeking design,comfort and authentic tuscan vibes.Relax in the outdoor lounge,enjoy a bbq in the rose garden, or unwind in the private hot tub or home gym. Feel at home embraced by the rolling tuscan hills, whille i help you create tailor-made stays with 10+experiences. Contact me to craft your tuscan escape and create unforgettable memories in this strategic and amazing area between Florence and Siena.

The Castle of Ferrano - Castle in Tuscany
Try the experience of staying in a real Castle! Il Castello di Ferrano offers to its hosts the chance of living an unforgettable experience: you will be the only guests in the castle, and everything will be for you (private pool from June to September, gardens etc..). Historical building, surrounded by nature, finely decorated, frescoes/moulding on the ceiling, ample terrace w/ stone and terracotta floor, private outdoor pool.. Good position. Preferably come by car.

Infinity pool in Chianti area
On the Chianti hills, portion of an old stone farmhouse from the 1800s, located in S. Filippo, a small hamlet of Barberino Tavarnelle, halfway between Florence and Siena, a 30-minute drive from Florence airport, 1 hour from Pisa airport. Three bedrooms, two bathrooms, large living room with fireplace, eat-in kitchen and dining room. Magnificent view of the hills from every window! Beautiful infinity pool with whirlpool area, unheated and open from April to October.

Old hayloft on the Chianti hills
Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

Cercis - La Palmierina
E' un appartamento facente parte di una tenuta completamente recintata di 60 ettari di natura incontaminata: più di 1000 ulivi, innumerevoli cipressi e foreste profumate creano un ambiente idilliaco per coloro che ricercano tranquillità e silenzi. La tenuta Palmierina è in prossimità di Castelfalfi (un vero gioiello di architettura medievale) e nelle vicinanze di Firenze (50 Km), Siena (50 Km), Pisa (50 Km). Nelle vicinanze ci sono due campi da golf.
Popular amenities for San Gimignano rentals with a pool
House rentals with a pool

Ancient Barn in Chianti with Pool

Tuscany stoned house with private pool

Explore Chianti from a Charming Stone House

Villa of the Hydrangeas

Leonardo - Chianti/Siena, Florence, San Gimignano.

Borgo Ripostena – No. 8 Casa Vecchia

Collina Power

Country House w/ heated Pool near the City Centre
Condo rentals with a pool

Loggiato 3 apartment in Tuscany near Siena

Adalberto Apartment inside the Manor of Fulignano

Scenic Stilish Country

House between Firenze, Arezzo, chianti e Siena

Vintage Residence with Pool in Chianti

Poggiolieto Suite - on hills 10' from city center

Manuela apartment with pool in farmhouse

Farmhouse near Florence - Fienile
Home rentals with a private pool

Villa il Palagio in the Tuscan countryside

Casa Luigi Suite with exclusive pool

Farmhouse , pool, 13 px. Lucca 10km

Luxe Estate nr Florence. Vineyard, Pool, Privacy

TREEhouse / casaBARTHEL
Historic villa x8 with exclusive pool

Villa Fonteintanata Ground floor
When is the best time to visit San Gimignano?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$44,120 GYD | G$46,420 GYD | G$37,638 GYD | G$34,710 GYD | G$36,174 GYD | G$39,938 GYD | G$43,492 GYD | G$44,329 GYD | G$41,820 GYD | G$38,474 GYD | G$35,547 GYD | G$44,329 GYD |
| Avg. temp | 7°C | 8°C | 11°C | 14°C | 18°C | 23°C | 25°C | 25°C | 21°C | 16°C | 11°C | 7°C |
Destinations to explore
- Rentals with outdoor seating San Gimignano
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- Rentals with pools Siena
- Rentals with pools Tuscany
- Rentals with pools Italy
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Piazza del Duomo (Pisa)
- Cala Violina
- Stazione Santa Maria Novella
- Uffizi Gallery
- Pisa Centrale Railway Station
- Spiagge Bianche
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Fortezza da Basso
- Piazza della Repubblica
- Gulf of Baratti
- Parco delle Cascine
- Piazzale Michelangelo
- Del Chianti
- Pitti Palace
- Boboli's Garden
- Palazzo Vecchio
- Piazza della Signoria
- Medici Chapel
- Stadio Artemio Franchi
- Things to do San Gimignano
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- Nature and outdoors San Gimignano
- Food and drink San Gimignano
- Art and culture San Gimignano
- Things to do Siena
- Sports activities Siena
- Sightseeing Siena
- Art and culture Siena
- Entertainment Siena
- Nature and outdoors Siena
- Food and drink Siena
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- Things to do Tuscany
- Nature and outdoors Tuscany
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- Things to do Italy
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