
Vacation rentals with a pool in San Gimignano
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Top-rated rentals with a pool in San Gimignano
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is an ancient and authentic farmhouse dating back to the 17th century located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional local style of old Tuscany: ancient wooden beams, terracotta floors, and unique furniture. In the large outdoor courtyard, you'll find a large swimming pool on a panoramic terrace at your disposal, overlooking the valley with breathtaking views of vineyards and olive groves, where you can enjoy spectacular 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.

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.

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.

Wonderful Loft in Villa with Pool in Chianti
Located on the second and top floor of the "Suites le Valline" complex, the Piazzale Michelangelo loft offers a unique style in an ideal location for exploring Tuscany, a 15-minute drive from Florence and San Casciano! Treat yourself to a moment of relaxation on the beautiful panoramic terrace overlooking Florence, or cool off in the bio pool among the olive trees... and remember that all the vegetables from the Valline vegetable garden are at your disposal!

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.

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.

Tenuta Chiudendone in Tuscany
Great place in the middle of Tuscan Hills, you will be sorrounded by nature but close to all the beautiful cities of Tuscany! We rent two apartments, one on the upper floor called Balla and one on the ground floor called Modigliani. Tell us which one you prefer. PLEASE NOTE YOU WILL NEED A CAR DURING YOUR STAY.

Countryside Dream farm in Tuscany
Great place in the middle of Tuscan Hills, you will be surrounded by nature but close to all the beautiful cities of Tuscany! We rent two apartments, one on the upper floor called Balla and one on the ground floor called Modigliani. Tell us which one you prefer. PLEASE NOTE YOU WILL NEED A CAR DURING YOUR STAY.

Nada Home
My house is immersed in the Tuscan countryside among olive trees and vineyards in the heart of Chianti, wonderful views, relaxation, I offer cooking schools and exclusive dinners, my garden can be the perfect setting for a wonderful candlelit dinner prepared exclusively for my guests 🤗

Podere Guidi
Apartment in a panoramic villa between Florence and Siena in the heart of the Chianti region in a charming village. The pool is open from May 1 to September 30, from 9 am to 1 pm, with exclusive use for guests during these hours. For different needs, ask the host.
Popular amenities for San Gimignano rentals with a pool
House rentals with a pool

dependance in villa Toscana

Ancient Barn in Chianti with Pool

Casa Bada - Barn

Private villa/swimming pool in Tuscany

Explore Chianti from a Charming Stone House

Casetta Melograno – Cozy farmhouse in Chianti

Antico Borgo Ripostena – n. 8 Old House

Casa di Lyndall - Entire house with exclusive pool
Condo rentals with a pool

Chianti La Pruneta, Michelangelo apartment.

Loggiato 3 apartment in Tuscany near Siena

Lornano Winery Farm - ''Trebbiano'' villa

House between Firenze, Arezzo, chianti e Siena

Vintage Apartment with Pool in Chianti

Manuela apartment with pool in farmhouse

Garden & SPA -FlorArt Boutique Apartment

Tenuta di Pomine Certaldo (Fi) Edera Apartment
Home rentals with a private pool

Il Giglio Farmhouse by Interhome

Sole by Interhome

Ambrogetta by Interhome.

Villa Alba by Interhome

The Leccio by Interhome

Podere San Lorenzo by Interhome

Santa Margherita by Interhome

Casa 360 by Interhome
When is the best time to visit San Gimignano?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $230 CAD | $238 CAD | $224 CAD | $230 CAD | $240 CAD | $265 CAD | $288 CAD | $294 CAD | $277 CAD | $211 CAD | $201 CAD | $231 CAD |
| 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 |
Quick stats about vacation rentals with a pool in San Gimignano

Total vacation rentals
Explore 550 vacation rentals in San Gimignano

Nightly prices starting at
San Gimignano vacation rentals start at $14 CAD per night before taxes and fees

Verified guest reviews
Over 13,990 verified reviews to help you choose

Family-friendly vacation rentals
340 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 240 rentals that welcome pets

Rentals with dedicated workspaces
130 properties have a dedicated workspace

Wifi availability
540 of San Gimignano vacation rentals include wifi 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
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- Santa Maria Novella
- Mercato Centrale
- Piazzale Michelangelo
- Duomo di Firenze
- Basilica of Santa Maria Novella
- Ponte Vecchio
- Spiagge bianche
- Cala Violina
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Uffizi Gallery
- Piazza del Duomo (Pisa)
- Fortezza da Basso
- Gulf of Baratti
- Piazza della Repubblica
- Pitti Palace
- Parco delle Cascine
- The Boboli Gardens
- Spiaggia Libera
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Avignonesi Winery Fattoria Le Capezzine
- Medici Chapels
- Palazzo Vecchio
- Stadio Artemio Franchi
- Spiaggia Marina di Cecina
- Things to do San Gimignano
- Nature and outdoors San Gimignano
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- Things to do Siena
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- Things to do Tuscany
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