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Vacation rentals with a pool in San Gimignano

Find and book unique homes with a pool on Airbnb

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Popular amenities for San Gimignano rentals with a pool

House rentals with a pool

Guest favorite
Home in Florence
5 out of 5 average rating, 5 reviews

New Florence "Afrodite" suite with pool

SarahRating, 5 stars2 weeks ago
Simone was great during our stay. Super responsive and helpful. The space was beautiful and comfortable for 2 people. Also, central to bus stops that get you into the city within 10 or so minutes. Would definitely recommend!
Superhost
Home in Montopoli
4.93 out of 5 average rating, 42 reviews

Villa Due Pini Marti with private pool

FreyaRating, 5 stars8 months ago
We had a wonderful week here. It was baking hot but the pool, the shady garden and the air conditioning made it the perfect peaceful place to relax between Rome and Florence.
Guest favorite
Home in Florence
5 out of 5 average rating, 9 reviews

The Limonaia della Torretta

OksanaRating, 5 stars1 week ago
I had the most amazing experience staying at this beautiful villa in Florence. The location was perfect—peaceful, private, and surrounded by stunning views that took my breath away, especially from the parking area. The villa itself was incredibly cozy and charming—so well maintained and full of character. Honestly, I didn’t want to leave. I’d live there if I could! The pool was a dream—relaxing, and the perfect spot to unwind with the Tuscan countryside all around you. Our host, Leonardo, was absolutely fantastic—so friendly, welcoming, and helpful throughout our stay. You can tell he really cares about making guests feel at home. This place was everything I hoped for and more. I would 100% come back again. Highly recommend!
Top guest favorite
Home in Pistoia
5 out of 5 average rating, 8 reviews

Country Cottage with Pool "Il Melograno"

FedericaRating, 5 stars8 months ago
Charming villa in total relaxation. Lots of green space and a beautiful pool... all just for us. Giovanni was super welcoming and kind. An experience to repeat, highly recommended! Greetings from Fede and Kevin
Guest favorite
Home in Fornaci di Barga
4.87 out of 5 average rating, 75 reviews

Nature and relax with swimming pool

GiuliaRating, 5 stars5 days ago
We only stayed 3 days and unfortunately we met bad weather, but this did not stop us from taking advantage of the immense garden that with two small children was the salvation🙂 The house offers many spaces (we were two families) leaving way to have the right tranquility and privacy as needed. Alessandro was very helpful and kind and his mother, whom we met before leaving, is a very nice and friendly lady.
Guest favorite
Home in Cortona
4.96 out of 5 average rating, 57 reviews

"Casa Elisa", house with swimming pool at the foot of Cortona

AlessandroRating, 5 stars4 months ago
I had an unforgettable stay at Casa Elisa, located at the foot of the beautiful Cortona. The atmosphere is magical: a perfect fusion of Tuscan tradition and modern comfort. The rooms are elegant and quite spacious, tastefully furnished and equipped with all the necessary comforts. The garden with pool is an oasis of tranquility, ideal to relax with a good book or to enjoy an aperitif at sunset. But it's the warmth and hospitality of Elisa's family that makes the stay really special. Their availability in providing information about places to visit and recommended restaurants makes all the difference. I highly recommend Casa Elisa to anyone who wants to discover the beauty of Tuscany, living an authentic and unforgettable experience.
Superhost
Home in Casanova
4.89 out of 5 average rating, 37 reviews

Casa Liliana

LaurienRating, 5 stars1 week ago
We really loved our stay, the beautiful surroundings and the place was even better than the pictures. Alfredo was very responsive and friendly. Would really recommend if you’d like a peaceful stay with close proximity to local Tuscan villages to explore.
Guest favorite
Home in Lucca
4.91 out of 5 average rating, 22 reviews

Casa Orfeo in estate with pool and beautiful view

EmmaRating, 5 stars8 months ago
The perfect place to stay in Tuscany, beautiful home and gardens. We loved the views and the amazing swimming pool. The house had loads of character and was very homely and comfortable. Loved the location, not too far from Lucca and only 30 mins from Pisa airport. Andrea was a very friendly and helpful host too. Wonderful stay - thank you!

Condo rentals with a pool

Superhost
Condo in Loro Ciuffenna
5 out of 5 average rating, 9 reviews

""Beautiful Villa with PRIVATE pool in Tuscany""

BahrinRating, 5 stars16 months ago
Nice scenary, quiet romantic Town, Nice small cafe beside the river. But what impress Me marco property I felt like Home right away. Secured electeric gate leaving Me no worries. Kids love it and kitchen are well equip!! Thanks marco for your beautiful place and hosting us!!! I recommend this place for quiet country side place.
Superhost
Condo in Pergine Valdarno
4.67 out of 5 average rating, 6 reviews

Relax in farmhouse among the Chianti vineyards

MeganRating, 5 stars7 months ago
Tuscan retreat = THIS. Set in a lovely, quiet area with gorgeous views of the landscape. Easy to get to Arezzo and only 1 hour from Florence. So many amazing local restaurants and Vineyards. The property itself has a traditional vibe to it. The kitchen is not well equipped, so just bare that in mind! minimal pots, pans etc. But otherwise looks exactly like the photos.
Superhost
Condo in Rosignano Solvay-Castiglioncello
4.74 out of 5 average rating, 23 reviews

100mt from the sea - apt w/pool, wifi & tv

ShaneRating, 5 stars7 months ago
Brilliant host. Lovely apartment and nice area. Never bored.
Top guest favorite
Condo in Bibbiena, AR
5 out of 5 average rating, 16 reviews

ideal for two + porch, swimming pool on the farm

ChloéRating, 5 stars9 months ago
We had a great time at this beautiful place. The farm has several apartments, each with their own privacy. The pool was very clean and warm, there was shade available and a shower and toilet right next door. The apartment was as shown in the pictures, there was no air conditioning but it was very cool inside during the day. A few days before our arrival, Isabella sent us all the necessary information and it was her brother Piero who welcomed us very warmly upon arrival. The place was very clean, the kitchen well-equipped and towels were provided. There are many things to do and see in the area, we even had recommendations available. Overall we are really happy and would definitely recommend this place!
Guest favorite
Condo in Uzzano
4.81 out of 5 average rating, 21 reviews

Tuscan country apartment in a lovely olive grove

VeraRating, 5 stars8 months ago
The place is really a dream! We had a lovely, relaxing time with Deborah. The pool and location are great and Deborah gives great recommendations, is totally warm and you feel right at home. And we liked it so much that we want to come back!
Superhost
Condo in Gavinana
5 out of 5 average rating, 25 reviews

Luxury Views aircon Shared Pool parking cooking

JeevanRating, 5 stars20 months ago
We had a lovely stay here - there were 8 of us in total across 4 spacious bedrooms and 3 bathrooms. It is a beautiful old villa with a big garden and a cute pool and barbecue area. It is possible to walk into the city of Florence (30 - 40 minute stroll) but we found a car was necessary to ensure that we could get around and eg buy groceries. There is a cash deposit required for check in, so it’s useful to withdraw that before you arrive. Our host was very responsive and helpful throughout our stay. Overall, we had a lovely time!
Guest favorite
Condo in San Casciano In Val di Pesa
4.83 out of 5 average rating, 215 reviews

lovely farm- apartment (Fox)

DavidRating, 5 stars6 months ago
My fiance and I loved our stay here. beautiful views and prestige grounds. there were also a few friendly cats which made my fiancé's day. You need a car when staying here. you can find good restaurants and a grocery store a few minutes away in San casciano. It's centrally located in tuscany. 30 minutes to florence, 45 mins to siena. With lots of historic towns and wineries close by. The apartment was well accommodated, clean, and we'll equipped for cooking. We did pick up a few extra necessities from the grocery store and found the shower a little small, but otherwise found the stay comfortable and relaxing. Would totally recommend to friends and come back.
Superhost
Condo in Fiesole
4.88 out of 5 average rating, 183 reviews

Poggiolieto Studio - on hills 10' from city center

CerisRating, 5 stars6 days ago
Chiara and Giovanni’s place is absolutely stunning. The accommodation is rustic and comfy; however the real gem are the grounds. Their land is beautiful and the pool is really special. They were kind and helpful hosts, we would definitely recommend this property to anyone staying in the area. Thank you both

Home rentals with a private pool

Home in Camaiore
4.9 out of 5 average rating, 10 reviews

Versilia Holiday by Interhome

GatisRating, 5 stars7 months ago
This is an amazing villa with stunning views of the surrounding countryside and mountains. The villa really has everything you need for a comfortable stay. The closest shops are only a 10-15 minute drive away from the villa. I would definitely return.
Guest favorite
Cottage in Barberino Tavarnelle
4.98 out of 5 average rating, 188 reviews

Stone House with Exclusive Pool Codilungo in Chianti

ElizabethRating, 5 stars1 week ago
Incredible location and hosts! The house was immaculate and exactly as described. We really had the best time and made use of all of the recommended restaurants and towns to visit nearby. We had an incredible trip and could not be more thankful to such kind hosts that made sure we had everything we needed and more.
Top guest favorite
Farm stay in Arezzo
4.97 out of 5 average rating, 224 reviews

Explore nature in the center of Vigneti Chianti

CameronRating, 5 stars1 week ago
We had a wonderful stay and Rita is a fantastic host. Beautiful and accommodating! Would recommend - only 10 min outside city center.
Top guest favorite
Villa in San Miniato
4.88 out of 5 average rating, 40 reviews

Historic home with exclusive pool

AylaRating, 5 stars9 months ago
We (7 girlfriends) enjoyed the stay in the villa very much! The house, especially the front yard and pool, are wonderful. Maria is great! She has sent us a lot of tips about the area (also the necessary things, such as shopping). In addition, we were surprised with a very fine cake and if you needed anything, there was a very quick response. The villa is well equipped and the surroundings beautiful. Parking has enough. Only the potholes and the access to the villa are a bit challenging - but doable!
Guest favorite
Home in Pescia
4.84 out of 5 average rating, 19 reviews

Aurora by Interhome

Dr. KristinaRating, 5 stars6 months ago
A paradise! Difficult access that is rewarded. A fantastic villa with spectacular views of the Tuscan hills. Greatly restored with modern and classic parts, plus an absolute calm, all around beautiful nature. A highlight: The spacious indoor Jacuzzi, we had a wonderful week, thank you!!
Top guest favorite
Home in San Casciano In Val di Pesa
5 out of 5 average rating, 42 reviews

Charming villa in the Chianti hills

Kihun (KI)Rating, 5 stars1 week ago
The place I stayed at this time was really artistic and beautiful. Thanks to the carefully placed objects and the unique interior, I felt like I was staying in a small gallery. From the natural light coming in through the window, to the colors that go well with it, to the quiet and cozy atmosphere — I was satisfied with everything. In particular, the details filled with the sensibility of the accommodation were impressive, so every moment felt special throughout my stay. This is a place I'd like to recommend to those who want to escape from everyday life and heal in an artistic atmosphere.
Guest favorite
Villa in Pian di SCO
5 out of 5 average rating, 26 reviews

Villa il Palagio in the Tuscan countryside

LizRating, 5 stars7 months ago
Stunning home in the middle of a lovely vineyard (Probably one of the best homes on AirBnB). It's even more beautiful in person - full of art, thoughtful design/luxury finishes, and Tuscan charm. Highly reccomend!!
Home in Castagneto Carducci
4.67 out of 5 average rating, 3 reviews

Il Pezzo Farm by Interhome

KristianRating, 5 stars1 week ago
Great house - fantastic view over olive trees and vines to the sea - perfect for relaxing !

Quick stats about vacation rentals with a pool in San Gimignano

  • Total rentals

    530 properties

  • Nightly prices starting at

    ﺩ.ﺇ37 before taxes and fees

  • Total number of reviews

    12K reviews

  • Family-friendly rentals

    320 properties are a good fit for families

  • Pet-friendly rentals

    240 properties allow pets

  • Rentals with dedicated workspaces

    130 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Siena
  5. San Gimignano
  6. Rentals with pools