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Villa holiday rentals in San Gimignano

Find and book unique villas on Airbnb

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Popular amenities for San Gimignano villa rentals

Private villa rentals

Superhost
Villa in Poppi
4.8 out of 5 average rating, 5 reviews

Villa for 22 people w/private pool

Marie-ClaireRating, 5 stars7 months ago
This little hamlet was ideal for a group of several families wanting a Tuscan holiday. Christina was a very responsive host, always available for help and suggestions. One down side was the distance from many of the Tuscan attractions such as Florence and Sienna. The hamlet is reasonably remote so is ideal for those who want a secluded holiday rather than those who want to see the sights of Tuscany.
Superhost
Villa in Fornaci
5 out of 5 average rating, 15 reviews

Villa with pool,tennis court,village walk distance

EmelineRating, 5 stars8 months ago
Superb spacious and well-located villa with a great view! Awesome pool and tennis class Big tables for eating out There are enough sunbeds for everyone We had a lovely time at this beautiful villa It is just missing a large oven (there is a mini oven that troubleshoot well) and be careful the washing machine is in a residence next door and for a fee (€4 laundry detergent)
Superhost
Villa in Florence
4.88 out of 5 average rating, 16 reviews

Villa La Cingallegra

MiltonRating, 5 stars6 months ago
Fantastic all around experience. Thank you Elio and team 🙏🙏
Superhost
Villa in Marlia
4.87 out of 5 average rating, 23 reviews

Charming Villa -private swimming pool -16 people.

LauraRating, 5 stars8 months ago
Beautiful house in a stunning location. Pool was great. Perfect for a large family. Owners were very helpful and available when needed. Rooms were hot overnight but this is expected in peak summer in Italy.
Guest favourite
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!!
Superhost
Villa in Provincia di Arezzo
4.91 out of 5 average rating, 43 reviews

Villa near Florence: Pool, AC, Vast natural garden

JackRating, 5 stars8 months ago
Stunning villa in a beautiful setting. Francesco gave excellent directions & the peace & tranquility out in the Tuscan countryside was wonderful. Francesco was exceptionally responsive & gave great local advice. We loved the little towns nearby and can’t wait to return soon. Highly recommended. Jack.
Superhost
Villa in Florence
4.8 out of 5 average rating, 41 reviews

Villa with great view over Florence, pool, Wi-Fi

JeffRating, 5 stars4 days ago
Great place, responsive host. Will be back.
Guest favourite
Villa in Gaiole in Chianti
5 out of 5 average rating, 9 reviews

Casa Faraona, villa with private pool

VaughanRating, 5 stars6 months ago
A beautiful property in a stunning location with great views. The property was easy to find using Waze. Once inside everything was clean and all rooms were luxurious and clean.

Luxury villa rentals

Guest favourite
Villa in Palaia
5 out of 5 average rating, 9 reviews

Villa La Gemma

DeryaRating, 5 stars7 months ago
The stay was wonderful! The villa was amazing, the views, the furniture, the rooms and the pool. We were so happy to be there. The rooms were new and clean. Every detail was taken care of. Christina was incredibly helpful and always available. Without her, we'd be lost. Unfortunately, we often had private problems and every time she helped us and brought us solutions. For me and my friends, this stay was unforgettable!
Top Guest favourite
Villa in Montecucco
4.9 out of 5 average rating, 39 reviews

Villa Angiolina

ErinRating, 5 stars6 months ago
Villa Angiolina is truly beautiful!!! The view is incredible and everything was spotless and beautifully decorated. Our host was lovely and gracious and responded very quickly to all communications. She even arranged for an amazing pizza party with a private chef that was just one or the memorable moments from our time at the Villa. If this Villa is available…just book it!!! You will be glad that you did!!!!
Guest favourite
Villa in Casale
4.96 out of 5 average rating, 23 reviews

Villa with pool in chianti Rufina area 13 sleeps

NilsRating, 5 stars7 months ago
Great stay in a lovely remote area. The pizza oven was a major highlight
Top Guest favourite
Villa in Rignano sull'Arno
5 out of 5 average rating, 9 reviews

villa "La Fonticina"

Maria ElenaRating, 5 stars5 days ago
This house is a jewel and I feel so lucky Cesare shared it with us. Highly recommend to anyone looking for a comfortable and beautiful place!
Top Guest favourite
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 friends) enjoyed staying at the villa very much! The house, especially the front yard and pool, are wonderful. Maria is great! She sent us a lot of tips about the area (including the necessary things, such as shopping). In addition, we were surprised with a very fine cake and if you needed something, an answer came very quickly. The villa is well equipped and the surroundings are beautiful. There is plenty of parking space. Only the potholes and the access to the villa are a bit challenging - but doable!
Guest favourite
Villa in Fiesole
4.86 out of 5 average rating, 22 reviews

Villa Lualdi

SallyRating, 5 stars7 months ago
Had a lovely week at the villa. Amazing place and beautiful views! Florence a short drive away, but we also enjoyed walking about 35 minutes to Fiesole for restaurants and views.
Guest favourite
Villa in Colle di Val d'Elsa
4.95 out of 5 average rating, 21 reviews

Villa L 'elsa

MarcelaRating, 5 stars3 days ago
The house is amazing and the exterior is beautiful
Top Guest favourite
Villa in San Ginese di Compito
4.99 out of 5 average rating, 128 reviews

Farmhouse , pool, 13 px. Lucca 10km

EduardoRating, 5 stars1 month ago
We had an amazing stay at Juri's beautiful villa in Tuscany! The place is super spacious, easily accommodating our group of 11, and it was spotless and very well maintained. Juri and his mom were incredible hosts—always responsive and ready to help whenever we needed anything. The location is also perfect for day trips to Florence, Pisa, and Lucca. If you're looking for a charming, well-kept and very clean villa with top-notch hospitality, this is the place. Highly recommend! Let me know if you'd like any tweaks!

Villa rentals with a pool

Guest favourite
Villa in Baco
4.86 out of 5 average rating, 83 reviews

Tuscan Villa

DeeRating, 5 stars7 months ago
Five friends made to feel very welcome to this beautiful spacious villa with a lovely pool set amongst olive groves. The scenery that surrounded us was beautiful. Invited to Mark's villa who shared his knowledge and history of the olive groves which was very interesting and the hospitality received was first class (vino and yummy bruschetta's). This was the perfect place to stay and would highly recommend.
Guest favourite
Villa in Montepulciano
4.91 out of 5 average rating, 121 reviews

Villa in Montepulciano with a Pool

LindaRating, 5 stars1 week ago
We had a wonderful time in Tuscany! We were able to make use of the pool on the first day with our two boys, 7 and 4. We visited Pienza, Montepulciano and Montelccino. We also purchased two of the wines from the estate. Alex made everything very easy and was a great host!
Superhost
Villa in Petrognano
4.86 out of 5 average rating, 7 reviews

Villa Iris with Swimming Pool

KateRating, 5 stars7 months ago
I have so much positive to say about this place! Despite what some reviews mention about the drive, it's absolutely worth it. There's a small restaurant just 2-3 minutes away, easy access to the city, and you're only about an hour from Pisa and some beaches. The house was perfect—everything well thought out and worth every penny. The pool was amazing, and the host was very responsive. If you're visiting in autumn or spring, bring warm clothes for the chilly evenings. We were sad to leave, and I can't wait to come back to this dreamy property!
Superhost
Villa in San Casciano In Val di Pesa
4.83 out of 5 average rating, 30 reviews

Poggio degli Ulivi, charming Chianti with pool

MicaelaRating, 5 stars8 months ago
The stay was beautiful. The view is fantastic, the pool very clean, surrounded by a beautiful, huge garden. Breakfast on the terrace is fantastic as the kitchen goes right to the terrace. The house is beautifully decorated and very clean. the air conditioning works perfectly, the nearest supermarket can be reached by car in less than 15 minutes, as well as there are various restaurants that can be reached in less than 20 minutes by car. Like that of The Sor Paolo or the Barrachina.
Superhost
Villa in Capannori
4.96 out of 5 average rating, 23 reviews

Luxury Tuscany Villa on the hill with private pool

JanetRating, 5 stars1 week ago
This villa was something out of a dream. Stefania was so lovely and wonderful with recommendations and booking us a rez at a fantastic local gem of a restaurant. The views were incredible and the atmosphere was so relaxing. The villa itself was cozy and inviting. The outside seating area was well used by us for nightcaps, dinner and conversations about falling in love with Tuscany and all it's amazing nooks and crannies. We wanted a picturesque and home-like central base for our 10 day adventure in Italy and we're delighted with the accommodations that really was like something out of a movie. Lucca was only a short drive away and offered the best grocery store-Esselunga! Thank you Stefania for your warm generosity, kindness and suggestions. This was a birthday trip that we will never forget and cemented our longing to return soon!
Superhost
Villa in San Gimignano
4.79 out of 5 average rating, 24 reviews

Elisa Villa

DominiqueRating, 5 stars5 months ago
Beautiful house in the vines surrounded by sumptuous hillsides in an incredible postcard setting. Perfect for gatherings for families or with friends. The location is ideal to radiate between Siena, Florence and Chianti or resting while enjoying the pool. Elisa, always attentive, is very responsive and will respond almost without delay.
Guest favourite
Villa in Volterra
4.98 out of 5 average rating, 51 reviews

Villa Casa al Povero

AnthonyRating, 5 stars1 week ago
I don’t even know where to begin describing this place. It was the most amazing place I have ever stayed. If you are looking for a peaceful and private villa with incredible views, then stop looking. This is it !! All of the reviews we read before we arrived talked about how amazing the views are and that you must take up the offer if Paola and Alessandro offer to cook a meal for you. Both recommendations are spot on. The sliced beef was one of the best meals I have ever had, and I often found myself wandering around outside the villa looking at the 360 degree views in all directions. We all felt so sad to leave this magic place. Paola and Alessandro were perfect hosts. Always friendly and with a smile on their faces. It’s a long way from Australia but I really hope we get an opportunity one day to return to this majestic place.
Top Guest favourite
Villa in Montaione
4.95 out of 5 average rating, 22 reviews

Private Villa with semi-Olympic pool and Tennis

SuzanneRating, 5 stars6 months ago
Francesca’s home was beautiful and in a breathtaking, peaceful location. There is a short, beautiful walk with Mountain View’s and olive groves to an incredible pool and pool house. She was incredibly helpful in helping us not only access the home, but also in providing us local recommendations. The meal that Ettore prepared for us was one of the highlights of our trip.

Quick stats about villa rentals in San Gimignano

  • Total rentals

    70 properties

  • Nightly prices starting at

    $141 AUD before taxes and fees

  • Total number of reviews

    1.1K reviews

  • Family-friendly rentals

    70 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with a pool

    60 properties have a pool

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Siena
  5. San Gimignano
  6. Villa rentals