
Holiday rentals with a pool in San Gimignano
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in San Gimignano
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Oleandro double room with pool in San Gimignano
Double room in the peaceful countryside of San Gimignano, just 5 min from town by car. Located in Montegonfoli Farm, an ancient estate like a hidden hamlet, surrounded by olive trees, vineyards, and a private forest with a stream. Guests can enjoy the pool during the warm season. The room has a 160x190cm queen bed, large bathroom, fridge, microwave, and a terrace with dining table (no kitchen/fires). A perfect place for couples or solo travelers seeking tranquility, charm, and a touch of Tuscany

Palazzo Monaci - Piscina nelle crete Senesi
Benvenuti a Palazzo Monaci ! Un' oasi di natura e bellezza unica, nel cuore delle Crete Senesi, in Toscana. Un residence con piscina e vista mozzafiato sulle crete senesi. Perfetta per coppie o famiglie in cerca di una vacanza rilassante. La posizione è perfetta per esplorare le zone limitrofe. Potrete fare escursioni nella campagna toscana, visitare i borghi medievali caratteristici, assaggiare i vini locali prelibati e immergervi nella cultura e nella storia di questa affascinante regione.

Podere Vergianoni immerso nelChianti con piscina
Podere Vergianoni è un antica e autentica casa colonica risalente al 1600 situata nelle splendide colline del Chianti in Toscana . L'appartamento è arredato in perfetto stile tradizionale locale dell'antica Toscana : antiche travi in legno, pavimenti in cotto e arredamenti unici. Nel grande cortile esterno troverete a vostra disposizione una grande piscina con terrazza panoramica che si affaccia su una valle con vista mozzafiato su vigneti e oliveti dove godersi tramonti spettacolari.

Infinity pool in Chianti
Sulle colline del Chianti, porzione di antica casa colonica in pietra del 1800, situata a S. Filippo una piccola frazione di Barberino Tavarnelle, a metà strada tra Firenze e Siena, a 30 minuti di macchina dall'aeroporto di Firenze, a 1 ora da quello di Pisa. Tre camere da letto, due bagni, ampia sala con camino, cucina abitabile e sala da pranzo. Vista magnifica sulle colline da ogni finestra! Splendida piscina a sfioro con zona idromassaggio, non riscaldata e aperta da Aprile a Ottobre.

La Casa di Nada Suite
From every window of the house, beautiful views open onto the rolling Tuscan hills, a constant delight throughout the stay. The home is bright and welcoming, with comfortable bedrooms each featuring a private bathroom, a living room with a fireplace, and a fully equipped kitchen, the true heart of the home. For those who wish, it is possible—upon request—to enjoy a simple and authentic moment of cooking together, just like in a family home. A peaceful retreat in the heart of Chianti.

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.

holidays with swimming pool in Tuscany
Piccolo e confortevole appartamento per 2 persone arredato in stile toscano e con travi a vista,immerso tra le dolci colline della campagna toscana. A disposizione degli ospiti spazio esterno con tavolo,piscina condivisa,forno a legna e barbecue,piccola lavanderia,wi-fi. L'appartamento è stato ricavato da una graziosa casa colonica in pietra del 1800 recentemente ristrutturata secondo la tradizione toscana e suddivisa in tre comodi appartamenti.

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.

Podere Villetta La Colombaia
The apartment has its own entrance , large living room with well equipped kitchen , 3 bedrooms and 2 bathrooms. It has a private garden with BBQ and gazebo , which offers a beautiful view of Vico d' Elsa , San Gimignano and the sunset. Swimming pool from 23/04 to 31/10.

Charming Farmhouse Suite
Tenuta Barosi, Isabella Suite - Experience the charm of Tenuta Barosi, a newly renovated agriturismo in 2024. Perched on a hilltop amidst olive groves, this serene retreat in Malmantile, a medieval village near Florence, offers stunning views and modern comforts.

Adalberto Apartment inside the Manor of Fulignano
Nella campagna di San Gimignano, in antica fortificazione risalente all'anno 1000 ora dimora di campagna, situata su di un colle con veduta panoramica, affittasi bellissimo appartamento di ca. 60mq con vista su San Gimignano e sui vigneti circostanti
Popular amenities for San Gimignano rentals with a pool
House rentals with a pool

Mini country house Podere Scorno with pool

StageROOM03 - Idyllic Chianti cottage near Siena

Cercis - La Palmierina

Ancient Barn in Chianti with Pool

Casa Bada - Barn

Private villa/swimming pool in Tuscany

“il colle” nice house surrounded by vineyard

Explore Chianti from a Charming Stone House
Apartment rentals with a pool

Appartamento Loggiato 3 in toscana vicino Siena

Stone House in Chianti with pool and parking

Fattoria Lornano Winery- villa ''Trebbiano''

💜 "Gaia" Podere Le Fontanelle

House between Firenze, Arezzo, chianti e Siena

Poggiolieto Suite - on hills 10' from city center

Tenuta di Pomine Certaldo (Fi) Appartamento Edera

La Casetta
Home rentals with a private pool

Stone House with Exclusive Pool Codilungo in Chianti

Historic home with exclusive pool

Villa Alba by Interhome

Aurora by Interhome

Podere San Lorenzo by Interhome

Villa di charme sulle colline del Chianti

Villa il Palagio nelle campagne toscane

Farmhouse , pool, 13 px. Lucca 10km
When is the best time to visit San Gimignano?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $212 SGD | $219 SGD | $207 SGD | $212 SGD | $221 SGD | $243 SGD | $265 SGD | $270 SGD | $255 SGD | $235 SGD | $217 SGD | $270 SGD |
| 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 holiday rentals with a pool in San Gimignano

Total holiday rentals
Explore 510 holiday rentals in San Gimignano

Nightly prices starting at
San Gimignano holiday rentals start at $51 SGD per night before taxes and fees

Verified guest reviews
Over 13,420 verified reviews to help you choose

Family-friendly holiday rentals
310 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 250 rentals that welcome pets

Rentals with dedicated workspaces
140 properties have a dedicated workspace

Wifi availability
500 of San Gimignano holiday 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
Destinations to explore
- Rentals with an EV charger San Gimignano
- Family-friendly rentals San Gimignano
- House rentals San Gimignano
- Rentals with a fireplace San Gimignano
- Smoking-friendly rentals San Gimignano
- Rentals with a hot tub San Gimignano
- Rentals with a patio San Gimignano
- Fitness-friendly rentals San Gimignano
- Bed and breakfasts San Gimignano
- Farm stay rentals San Gimignano
- Flat rentals San Gimignano
- Rentals with a washing machine and dryer San Gimignano
- Luxury rentals San Gimignano
- Apartment rentals San Gimignano
- Hotel rooms San Gimignano
- Pet-friendly rentals San Gimignano
- Villa rentals San Gimignano
- Rentals with breakfast San Gimignano
- Rentals with a firepit San Gimignano
- Cottage rentals San Gimignano
- Rentals with outdoor seating San Gimignano
- Holiday home rentals San Gimignano
- Rentals with pools Siena
- Rentals with pools Tuscany
- Rentals with pools Italy
- Santa Maria Novella
- Cathedral of Santa Maria del Fiore
- Strozzi Palace
- Mercato Centrale
- Santa Maria Novella
- Ponte Vecchio
- Great Synagogue of Florence
- Basilica Di San Miniato A Monte
- Marina di Cecina
- Del Chianti
- Basilica of Santa Maria Novella
- Pisa Centrale Railway Station
- Cala Violina
- Eremo Di Camaldoli
- Spiagge Bianche
- Porta Elisa
- Piazza del Duomo (Pisa)
- Fortezza da Basso
- Uffizi Gallery
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Piazza della Repubblica
- Piazzale Michelangelo
- Pitti Palace
- Parco delle Cascine
- Things to do San Gimignano
- Food and drink San Gimignano
- Nature and outdoors San Gimignano
- Things to do Siena
- Food and drink Siena
- Sports activities Siena
- Sightseeing Siena
- Art and culture Siena
- Nature and outdoors Siena
- Tours Siena
- Things to do Tuscany
- Nature and outdoors Tuscany
- Sports activities Tuscany
- Art and culture Tuscany
- Food and drink Tuscany
- Tours Tuscany
- Sightseeing Tuscany
- Entertainment Tuscany
- Things to do Italy
- Art and culture Italy
- Wellness Italy
- Food and drink Italy
- Nature and outdoors Italy
- Sightseeing Italy
- Entertainment Italy
- Tours Italy
- Sports activities Italy






