Compare Vacation Homes with Pools in San Gimignano

31 available villa offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
San Gimignano villas
Choose vacation accommodation with a pool
Price per night
Accommodation type
Rating

Choose from Top-Rated Vacation Homes with Swimming Pools in San Gimignano

Podere La Quercia - San Gimignano
9.7 537 reviews
San Gimignano
07/17 – 07/21
$434/nighttotal: $1736 (4 )

Podere La Quercia

2 5
farm, San Gimignano
Podere La Quercia farm is located in San Gimignano, 23 miles from Piazza Matteotti and 28 miles from Piazza del Campo.
This family-friendly farm offers air-conditioned units with a swimming pool, jacuzzi, garden, and bicycle rentals, located 34 miles from Florence Airport.
Agriturismo Macinatico - San Gimignano
9.4 102 reviews
San Gimignano
09/16 – 09/25
$215/nighttotal: $1935 (9 )

Agriturismo Macinatico

2 4
farm, San Gimignano
Surrounded by Tuscan vineyards producing its own wine, Agriturismo Macinatico is located a 10-minute drive from San Gimignano's iconic towers and 3.7 miles from Certaldo Train Station.
This farm stay offers a genuine agriturismo experience with a swimming pool, a garden with BBQ facilities and a children's playground, plus complimentary bike rentals.
Agriturismo Casa Alle Vacche - San Gimignano
9.1 58 reviews
San Gimignano
10/16 – 10/24
$130/nighttotal: $1040 (8 )

Agriturismo Casa Alle Vacche

1 2
house, San Gimignano
Agriturismo Casa Alle Vacche is located in San Gimignano, approximately 28 miles from Piazzale Michelangelo and Pitti Palace, with Florence Airport 33 miles away.
This house offers a swimming pool with a scenic view, an on-site restaurant serving authentic Italian cuisine, and complimentary Wi-Fi, perfect for a getaway with a pool.
Torraccia Di Chiusi Agriturismo Relais - San Gimignano
9.7 445 reviews
San Gimignano
06/27 – 06/30
$215/nighttotal: $645 (3 )

Torraccia Di Chiusi Agriturismo Relais

1 2
farm, San Gimignano
Torraccia di Chiusi Agriturismo Relais is a historic country manor located just outside San Gimignano, offering picturesque Tuscan countryside views.
This farm provides an excellent escape with a swimming pool, air conditioning, on-site restaurant, and complimentary Wi-Fi, perfect for a family-friendly stay.
Il Casale Del Cotone - San Gimignano
9.3 1251 reviews
San Gimignano
08/17 – 08/28
$332/nighttotal: $3652 (11 )

Il Casale Del Cotone

1 2
house, San Gimignano
This 17th-century farmhouse, Il Casale del Cotone, is located in the Tuscan countryside, 1.6 miles from San Gimignano and 25 miles from Florence, offering a peaceful setting surrounded by vineyards and olive groves.
Enjoy a relaxing stay with a swimming pool at this family-friendly house, featuring a kitchen with a fridge and microwave, air conditioning, and a terrace, with room service and a bar available.
Margherita Double Room With Pool In San Gimignano - San Gimignano
9.7 290 reviews
San Gimignano
10/12 – 10/14
$91/nighttotal: $182 (2 )

Margherita Double Room With Pool In San Gimignano

1 2
gîte, San Gimignano
Located in Montegonfoli, this gîte is just a 5-minute drive from the historic towers of San Gimignano, offering serene Tuscan countryside views.
This family-friendly gîte features a swimming pool, private terrace, and on-site WiFi, making it an excellent base for exploring Tuscany.
Holiday Home Podere Conte Francesco-la Palma By Interhome - San Gimignano
8.5 18 reviews
San Gimignano
07/11 – 07/18
$218/nighttotal: $1526 (7 )

Holiday Home Podere Conte Francesco-la Palma By Interhome

3 4
house, Certaldo
This house in Certaldo offers a serene retreat, located 23 miles from Piazza Matteotti and 27 miles from Piazzale Michelangelo, Pitti Palace, and Strozzi Palace.
Enjoy this 910 square foot house with a refreshing swimming pool, private patio, garden, and complimentary Wi-Fi, perfect for a getaway with a pool.
120 M² House ∙ 4 Bedrooms ∙ 8 Guests - San Gimignano
8.2 6 reviews
San Gimignano
06/24 – 06/27
$284/nighttotal: $852 (3 )

120 M² House ∙ 4 Bedrooms ∙ 8 Guests

4 8
house, Certaldo
Enjoy a Tuscan countryside retreat at this rustic 6-room house, located in a rural district just 1290 square feet from Certaldo's attractions, offering convenient on-site parking and peaceful views.
This family-friendly house with a pool accommodates up to 8 guests, featuring two living spaces with fireplaces, multiple terraces including a 24 m² area perfect for outdoor dining with a barbecue, and a washing machine for your convenience.
Il Rosolaccio - San Gimignano
9.4 838 reviews
San Gimignano
06/16 – 06/19
$343/nighttotal: $1029 (3 )

Il Rosolaccio

1 2
house, San Gimignano
This Tuscan farmhouse offers stunning views of the countryside, vineyards, and olive trees, located just a 10-minute drive from San Gimignano, nestled between Siena and Florence.
Enjoy characteristic Tuscan dinners on the terrace, take a dip in the outdoor swimming pool with sun loungers, and utilize amenities like free Wi-Fi, a mini-bar, and TV, with staff available to assist with excursions and walking routes.
Upper Country Relais Tuscany - San Gimignano
8.8 4 reviews
San Gimignano
08/10 – 08/12
$545/nighttotal: $1090 (2 )

Upper Country Relais Tuscany

3 2
house, San Gimignano
Enjoy a Tuscan countryside escape just outside San Gimignano, approximately 22 miles from Piazza Matteotti and 23 miles from Piazza del Campo.
This spacious 3-bedroom, 3-bathroom house with a pool offers air conditioning, a well-equipped kitchen, a garden, and a hot tub for 11 guests, providing a perfect getaway with a pool.
Podere San Luigi - San Gimignano
9.8 246 reviews
San Gimignano
10/16 – 10/24
$131/nighttotal: $1048 (8 )

Podere San Luigi

1 2
house, San Gimignano
Enjoy a relaxing stay at this house with a pool, located a 15-minute drive from San Gimignano, a UNESCO World Heritage site, and near Colle Val d'Elsa and Siena.
This family-friendly house offers air conditioning (available upon request for a daily fee), a full kitchenette, and a garden, perfect for exploring Tuscany.
53 M² Farmhouse ∙ 2 Bedrooms ∙ 6 Guests - San Gimignano
9.4 61 reviews
San Gimignano
07/11 – 07/18
$175/nighttotal: $1225 (7 )

53 M² Farmhouse ∙ 2 Bedrooms ∙ 6 Guests

2 4
farm, Gambassi Terme
Farm rental for up to 6 people with an excellent rating of 94% based on 61 reviews. You will be in Gambassi Terme.
Services and facilities: a washing machine, a swimming pool and a restaurant. Take advantage of the Free Parking with this accommodation.

Find a Luxury Vacation Home with a Private Pool in San Gimignano

100 M² Farmhouse ∙ 2 Bedrooms ∙ 4 Guests - San Gimignano
San Gimignano
07/25 – 07/29
$241/nighttotal: $964 (4 )

100 M² Farmhouse ∙ 2 Bedrooms ∙ 4 Guests

2 4
farm, San Gimignano
Enjoy a Tuscan escape at this farm with a pool, located just 3 miles from San Gimignano and 3 miles from Certaldo, with Volterra 15 miles, Siena 19 miles, and Florence 25 miles away.
This 1080 square foot farm accommodates up to 4 guests with 2 bedrooms and 3 bathrooms, featuring a private outdoor area with a seasonal whirlpool, garden, barbecue, and modern amenities including Wi-Fi and a dishwasher.

Best Family-Friendly Vacation Homes with Pools in San Gimignano

Among the 31 accommodations in San Gimignano, here are the 8 best family friendly villas and beach houses

Il Pascolo - San Gimignano
San Gimignano
08/23 – 08/28
$703/nighttotal: $3515 (5 )

Il Pascolo

4 2
house, San Gimignano
Located in San Gimignano, this house is 24 miles from Piazza Matteotti and 27 miles from Piazza del Campo, offering a spacious retreat with a swimming pool for your getaway.
This 2580 square foot house accommodates up to 11 guests with 4 bedrooms and 3 bathrooms, featuring a full kitchen, air conditioning, a terrace, garden, and complimentary on-site parking.
400 M² Villa ∙ 4 Bedrooms ∙ 8 Guests - San Gimignano
San Gimignano
09/14 – 09/28
$748/nighttotal: $10472 (14 )

400 M² Villa ∙ 4 Bedrooms ∙ 8 Guests

4 2
house, San Gimignano
This restored Tuscan farmhouse sits on a hilltop near San Gimignano, offering breathtaking panoramic views of the Val d'Elsa and is conveniently located for exploring Siena, Volterra, the Chianti region, and Florence, all within easy day trip distance.
Enjoy a spacious 4310 sq ft house with 4 bedrooms and 4 bathrooms, perfect for up to 8 guests, featuring a heated swimming pool with a Roman staircase, air conditioning, a garden, and a terrace ideal for soaking in the Tuscan atmosphere.
Montegonfoli 6 San Gimignano Countryside Apt. With Amazing Views And Pool - San Gimignano
San Gimignano
09/14 – 09/17
$202/nighttotal: $606 (3 )

Montegonfoli 6 San Gimignano Countryside Apt. With Amazing Views And Pool

2 2
farm, San Gimignano
Perched high on a panoramic hill in San Gimignano, Montegonfoli Six offers unparalleled 360-degree views of Tuscan vineyards and golden fields, situated just 2 miles by road from the historic center.
This 17th-18th century restored farmhouse features apartments with a swimming pool, a fitness center, and private outdoor dining, perfect for a family of four exploring the Tuscan countryside.
Villa With Swimming Pool In San Gimignano - San Gimignano
10 4 reviews
San Gimignano
08/17 – 08/22
$952/nighttotal: $4760 (5 )

Villa With Swimming Pool In San Gimignano

4 2
house, San Gimignano
Enjoy a secluded villa with a private swimming pool, located 23 miles from Piazza Matteotti in San Gimignano and 28 miles from Piazza del Campo.
This family-friendly villa offers 3010 square feet of space with 4 bedrooms, 4 bathrooms, air conditioning, a full kitchen, and a fitness center, perfect for accommodating up to 15 guests seeking a relaxing getaway.
18 M² Farmhouse ∙ 1 Bedroom ∙ 2 Guests - San Gimignano
9.8 72 reviews
San Gimignano
08/10 – 08/12
$175/nighttotal: $350 (2 )

18 M² Farmhouse ∙ 1 Bedroom ∙ 2 Guests

1 2
farm, San Gimignano
Farm listing for up to 2 people with an excellent rating of 98% based on 72 reviews. You will be in San Gimignano.
Services and facilities: air conditioning, a washing machine and a fridge. Pets are welcome in this accommodation.
Villa ∙ 8 Bedrooms ∙ 20 Guests - San Gimignano
San Gimignano
07/25 – 07/28
$1896/nighttotal: $5688 (3 )

Villa ∙ 8 Bedrooms ∙ 20 Guests

8 4
house, San Gimignano
Breathtaking views of the Tuscan hills and San Gimignano's medieval towers surround this spacious 4,300 sq. ft. country house, located just 1.5 miles from the historic town.
This family-friendly house accommodates up to 20 guests in 8 bedrooms, offering a private swimming pool, air conditioning, Wi-Fi, and a furnished annex for al fresco dining.
Casa Vacanza Le Case - San Gimignano
9.1 995 reviews
San Gimignano
06/27 – 06/30
$152/nighttotal: $456 (3 )

Casa Vacanza Le Case

1 2
house, San Gimignano
Located in San Gimignano, Casa Vacanza Le Case is 26 miles from Piazza Matteotti and 29 miles from Piazza del Campo, offering a serene escape with garden and inner courtyard views.
This house provides an excellent option for travelers seeking a getaway with a pool, featuring a year-round outdoor pool, complimentary WiFi, and barbecue facilities for outdoor dining.
Mormoraia - San Gimignano
9.4 1916 reviews
San Gimignano
10/12 – 10/14
$431/nighttotal: $862 (2 )

Mormoraia

1 2
farm, San Gimignano
Enjoy an idyllic Tuscan countryside retreat with a pool, located just 2.5 miles from the iconic medieval towers of San Gimignano.
This farm offers an authentic Tuscan experience with homemade breakfast, on-site dining, wine tasting, and panoramic views, perfect for a relaxing getaway with its swimming pool and spa facilities.

Popular destinations

Explore Our Top Pet-Friendly Vacation Homes with a Pool in San Gimignano

Among the 31 accommodations in San Gimignano, here are the 8 best pet friendly villas and beach houses

Agriturismo Torre Prima Holidays - San Gimignano
9.7 40 reviews
San Gimignano
07/25 – 07/29
$197/nighttotal: $788 (4 )

Agriturismo Torre Prima Holidays

2 4
gîte, San Gimignano
Located in the San Gimignano countryside, this gîte is within 3 miles of Piazza delle Erbe and Torre Grossa, offering an authentic farm stay experience.
Enjoy a Tuscan getaway with an on-site winery and a seasonal outdoor swimming pool, perfect for relaxation and family-friendly stays with complimentary WiFi and parking.
Villa Renina By Posarellivillas - San Gimignano
10 49 reviews
San Gimignano
07/17 – 07/21
$1107/nighttotal: $4428 (4 )

Villa Renina By Posarellivillas

3 5
house, Gambassi Terme
Villa Renina offers a private swimming pool for exclusive guest use in Gambassi Terme, located approximately 29 miles from Piazzale Michelangelo and Pitti Palace, and 30 miles from Piazza Matteotti.
This 2580 square foot house features 3 bedrooms, 2 bathrooms, air conditioning, free Wi-Fi, and a fully equipped kitchen, perfect for families or groups seeking a getaway with a pool.
Santa Maria A Poneta - San Gimignano
9.7 98 reviews
San Gimignano
06/16 – 06/19
$209/nighttotal: $627 (3 )

Santa Maria A Poneta

1 2
farm, Barberino Tavarnelle
Santa Maria a Poneta is a historic working farm located in the Chianti hills, just a 5-minute drive from Barberino di Val d’Elsa and 15 miles from San Gimignano.
This elegant manor house farm, offering apartments with private terraces, features a seasonal swimming pool (May-September) and is perfect for travelers seeking a getaway with a pool.
Il Pascolo, San Gimignano, Siena And Chianti - San Gimignano
San Gimignano
08/23 – 08/28
$716/nighttotal: $3580 (5 )

Il Pascolo, San Gimignano, Siena And Chianti

4 2
house, San Gimignano
Offering breathtaking views of San Gimignano's medieval towers, this secluded villa provides a private rural escape just a 15-minute drive from the historic town.
This 2580 square foot house, perfect for up to 6 guests, features three self-contained apartments, a garden, and a stunning private swimming pool with a poolgetaway.com experience.
Apartment Giuggiolo - Giuggiolo 5 By Interhome - San Gimignano
8.7 113 reviews
San Gimignano
07/11 – 07/18
$132/nighttotal: $924 (7 )

Apartment Giuggiolo - Giuggiolo 5 By Interhome

2 4
apartment, Poggibonsi
Apartment Giuggiolo - Giuggiolo 5 is located in Bibbiano, 19 miles from Piazza Matteotti and 22 miles from Piazza del Campo.
This spacious 3-bedroom, 3-bathroom apartment offers a fully equipped kitchen, a terrace, and a garden, perfect for relaxation and convenience for families, with a swimming pool making it an ideal getaway.
Azienda Agricola Fornacelle - San Gimignano
9.5 143 reviews
San Gimignano
09/24 – 09/29
$222/nighttotal: $1110 (5 )

Azienda Agricola Fornacelle

2 4
farm, San Gimignano
Azienda Agricola Fornacelle is located 23 miles from Piazza Matteotti in San Gimignano, offering convenient access to local landmarks and transportation hubs like Florence Airport, 33 miles away.
This farm stay provides a refreshing swimming pool with solarium and pool views, alongside a private balcony and terrace offering mountain views, making it an ideal choice for travelers seeking a getaway with a pool.
Fattoria Di Mugnano - San Gimignano
8.9 420 reviews
San Gimignano
08/10 – 08/12
$142/nighttotal: $284 (2 )

Fattoria Di Mugnano

1 2
farm, Colle di Val d'Elsa
Fattoria di Mugnano is located in Colle di Val d'Elsa, 21 miles from Piazza del Campo and 28 miles from Piazza Matteotti.
This farm offers air-conditioned units with Wi-Fi and private parking, perfect for a relaxing getaway with a pool.
Papavero Rosso - San Gimignano
9.7 14 reviews
San Gimignano
09/16 – 09/25
$240/nighttotal: $2160 (9 )

Papavero Rosso

3 4
house, San Gimignano
PAPAVERO ROSSO is a house located in San Gimignano, 20 miles from Piazza Matteotti and 23 miles from Piazza del Campo.
This accommodation offers a private swimming pool, a garden, and a fully equipped kitchenette, perfect for travelers seeking a getaway with a pool.
©2026 poolgetaway.com