
Holiday rentals with a pool in San Gimignano
Find and book unique homes with a pool on Airbnb
Quick stats about holiday rentals with a pool in San Gimignano

Total holiday rentals
Explore 490 holiday rentals in San Gimignano

Nightly prices starting at
San Gimignano holiday rentals start at €44 per night before taxes and fees

Verified guest reviews
Over 12,170 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 230 rentals that welcome pets

Rentals with dedicated workspaces
150 properties have a dedicated workspace

Wifi availability
480 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
Top-rated rentals with a pool in San Gimignano
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Infinity pool in Chianti 1
Our house is a part of a stone farmhouse completely independent from the rest of the adjacent property. Arranged on three floors, on the ground floor there is a large entrance hall, a large living room with fireplace, a bedroom with 1 double bed and a bathroom with window. On the first floor there are two bedrooms (2 +2 beds) with a bathroom with window. In the basement, at garden level, there is the kitchen and the dining room. From the kitchen you access the outside where you will find an area for outdoor dining with a large dining table under a pergola. You then go down towards the garden with barbecue area.
5.0 out of 5 average rating, 143 reviews
Montegonfoli 5 apartment in farmhouse, 4+2 guests
Comfortable apartment for 4 adults and 2 babies under 12yo, in San Gimignano countryside, in a resort/farmhouse. Here in Montegonfoli you can spend a vacation in absolute relax, in an enchanted natural context, far from the noise but at the same time very close to the most beautiful attractions of the world. First floor with amazing views on San Gimignano and Chianti Hills. No aircon, but every bedroom has a large fan for the few hot nights we are getting in July/August. We usually have 15°C!
4.84 out of 5 average rating, 266 reviews
Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is a family-run, historic 17th-century property located in the beautiful Chianti hills of Tuscany, with the option of arranging a private shuttle and local experiences directly with our family. The apartment is available for 2 adults with the option 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 unique sunsets.
5.0 out of 5 average rating, 352 reviews
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.
4.98 out of 5 average rating, 218 reviews
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
4.98 out of 5 average rating, 127 reviews
Villa L'Olivo w/Private pool (Close San Gimignano)
Villa L'Olivo is located in the Tuscan countryside, about 10 kilometers from San Gimignano and a few minutes from the supermarkets and various services in Poggibonsi. Our Villa is a great starting point to discover all the beauty of Tuscany, but it is also an ideal place for those who love to take a break from the hectic life of the city. At Villa L'Olivo, you can book a dinner with a private chef, directly in the villa, to enjoy a Tuscan dinner in peace. Write to us for info!
4.99 out of 5 average rating, 101 reviews
Podere Tignano, 4-bedroom villa in the Chianti!
Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.
4.98 out of 5 average rating, 107 reviews
Farmhouse in Chianti with Swimming Pool
Agriturismo Il Colle is located on one of the Chianti hills. The structure has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence just 35 minutes by car The apartment is located on the ground floor of the main farmhouse, with independent access and private space. The care taken in the restoration and furnishing make the house particularly welcoming, respecting the rural style.
4.99 out of 5 average rating, 516 reviews
Poggio Massiccioli
A cosy apartment for 4 people, furnished in Tuscan style with exposed beams, nestled among the rolling hills of the Tuscan countryside. Guests have access to a garden with facilities, free Wi-Fi, a shared swimming pool with facilities, a wood-fired oven and barbecue, and a washing machine. The apartment was created from a charming 19th-century stone farmhouse that was recently renovated in the Tuscan tradition and divided into three comfortable apartments
4.92 out of 5 average rating, 389 reviews
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).
4.95 out of 5 average rating, 221 reviews
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.
4.96 out of 5 average rating, 209 reviews
Cercis - La Palmierina
The apartment is part of a completely fenced estate of 60 hectares of unspoiled nature: more than 1000 olive trees, countless cypresses and fragrant forests create an idyllic environment for those seeking tranquility and silence. The Palmierina estate is near Castelfalfi (a true jewel of medieval architecture) and close to Florence (50 Km), Siena (50 Km), and Pisa (50 Km). There are two golf courses nearby.
4.96 out of 5 average rating, 146 reviewsPopular amenities for San Gimignano rentals with a pool
House rentals with a pool

Borgo Ripostena – No. 8 Casa Vecchia
4.95 out of 5 average rating, 201 reviews
Relaxation and charm in the Chianti hills
4.99 out of 5 average rating, 114 reviews
Ancient Barn in Chianti with Pool
4.89 out of 5 average rating, 125 reviews
SuiteLouise.pool, Hot Tub,homeGym & private Garden
4.91 out of 5 average rating, 128 reviews
Collina Power
4.93 out of 5 average rating, 203 reviews
Country Rentals - La Canonica
4.86 out of 5 average rating, 101 reviews
I Limoni Apartment in Tuscany
4.85 out of 5 average rating, 151 reviews
Explore Chianti from a Charming Stone House
4.98 out of 5 average rating, 123 reviewsApartment rentals with a pool

La Casetta
4.93 out of 5 average rating, 197 reviews
Adalberto Apartment inside the Manor of Fulignano
4.95 out of 5 average rating, 152 reviews
Scenic Stilish Country
4.88 out of 5 average rating, 136 reviews
Charming Tuscan home with pool, garden & Air-Con
4.88 out of 5 average rating, 100 reviews
Tenuta di Pomine Certaldo (Fi) Edera Apartment
4.85 out of 5 average rating, 110 reviews
Apt. Panzanello-Panzano in Chianti
4.96 out of 5 average rating, 282 reviews
Casa Luna-Splendida overlooking the pool and Tuscan nature
4.97 out of 5 average rating, 151 reviews
The House in Chianti - IlVillinoFarmhouse
4.78 out of 5 average rating, 246 reviewsHome rentals with a private pool

Farmhouse , pool, 13 px. Lucca 10km
4.99 out of 5 average rating, 148 reviews
TREEhouse / casaBARTHEL
4.88 out of 5 average rating, 821 reviews
Casa Luigi Suite with exclusive pool
4.95 out of 5 average rating, 122 reviews
Luxe Estate nr Florence. Vineyard, Pool, Privacy
4.97 out of 5 average rating, 73 reviewsHistoric villa x8 with exclusive pool
4.87 out of 5 average rating, 46 reviews
Villa Fonteintanata Ground floor
4.8 out of 5 average rating, 76 reviewsWhen is the best time to visit San Gimignano?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €184 | €193 | €157 | €168 | €193 | €199 | €181 | €185 | €174 | €160 | €148 | €185 |
| 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 |
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- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Piazza del Duomo (Pisa)
- Stazione Santa Maria Novella
- Cala Violina
- Mugello Circuit
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mercato Centrale
- Spiagge Bianche
- Pisa Centrale Railway Station
- Fortezza da Basso
- Gulf of Baratti
- Uffizi Gallery
- Piazza della Repubblica
- Parco delle Cascine
- Piazzale Michelangelo
- Palazzo Vecchio
- Del Chianti
- Piazza della Signoria
- Pitti Palace
- Boboli's Garden
- Things to do San Gimignano
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- Things to do Tuscany
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- Things to do Italy
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