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Villa holiday rentals in San Gimignano

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Popular amenities for villa rentals in San Gimignano

Private villa rentals

Guest favourite
Villa in Palaia
4.92 out of 5 average rating, 12 reviews

Villa La Gemma

JoshRating, 5 stars1 week ago
I was genuinely impressed by this place. So beautiful! The pool is incredible, they had prosecco and limoncello for us and provided several supplies for a successful stay. I would 100000% come back here!
Top guest favourite
Villa in Rignano sull'Arno
5 out of 5 average rating, 15 reviews

villa "La Fonticina"

KathyRating, 5 stars2 weeks ago
Incredible host and property. We feel fortunate to have had the opportunity to stay here. Cesare was beyond helpful with recommendations and flexible with our check in. Secluded, peaceful and a great place for making memories during our travels around Italy.
Top guest favourite
Villa in San Gimignano
4.97 out of 5 average rating, 68 reviews

Truly Tuscan villa with pool 6km to San Gimignano

SarahRating, 5 starstoday
The villa was simply stunning and we had a wonderful time. The indoor and outside spaces were very spacious and looked exactly as described, if not better! The villa was very clean and Giulia organised everything for us, including pool towels and towel sets. She welcomed us and gave us a tour of the villa when we arrived. I highly recommend Villa Francigena if you want to spend time immersed in the Tuscan beautiful landscape and in a peaceful and spacious typical villa, not far from wine tasting spots and the beautiful town of San Gimignano! Thank you Giulia for a wonderful stay from all of us.
Superhost
Villa in Capannori
4.96 out of 5 average rating, 26 reviews

Luxury Tuscany Villa on the hill with private pool

SandraRating, 5 stars1 day ago
We were very satisfied with our vacation home from Stefania. Great, spacious, secluded garden with many olive trees. Pergola with seating area invites you to linger. The cleanliness of the place was also extremely good. The beds or mattresses were very comfortable and the bedrooms nicely furnished. Stefania provided us with many tips and recommendations. She also booked a table for us twice at the nearby Osteria di Valgiano. Great food at a reasonable price with a great view of Lucca. Stefania responded quickly and kindly to questions. We would have liked to stay longer and will definitely come back!
Top guest favourite
Villa in Monsummano Terme
4.98 out of 5 average rating, 127 reviews

Le Maggioline Your Tuscany country house

LisaRating, 5 stars1 week ago
Olga's villa is absolutely stunning. Our family of 9 had the most wonderful visit. We enjoyed cooking in the beautiful and well appointed kitchen, eating outside on the terrace, swimming in the pool, and relaxing outside on the terrace, enjoying the peaceful beauty and breathtaking views of Tuscany. Olga's place is truly special. Olga was very communicative, helpful and kind. We highly recommend her villa to others.
Top guest favourite
Villa in Gaiole in Chianti
5 out of 5 average rating, 24 reviews

Montemarcoli

TorbjørnRating, 5 stars3 weeks ago
We had an amazing stay at the villa. A modern house in a quiet environment with beautiful views. Brigitta was very helpful and responded quickly to our inquiries both before and during the stay.
Guest favourite
Villa in Buonconvento
5 out of 5 average rating, 12 reviews

Beautiful tuscan country house

AlexRating, 5 stars2 days ago
An incredible, beautiful house where you’ll feel right at home. The villa is spacious and welcoming, perfect for cooking and relaxing with friends. My only suggestions would be the need for fans in the bedrooms as without AC it gets quite warm during those hot evenings.
Superhost
Villa in Volterra
4.95 out of 5 average rating, 22 reviews

Podere La Casetta - 2 People - Private Pool

ShemaiahRating, 5 stars10 months ago
My husband and I stayed here to celebrate our anniversary. This was our first experience in Tuscany and it did not disappoint. The house is very private, there is only 1 house behind it however from most viewpoints you cannot see it and we never saw anyone. Volterra is a beautiful medieval place that will make you feel like you are in a movie. An hour from Pisa, drivable to many many wineries in the surrounding regions, this air bnb is a perfect place to stay and we hope to return again.

Luxury villa rentals

Top guest favourite
Villa in Panzano
4.93 out of 5 average rating, 75 reviews

Luxury Villa on Chianti Wine Estate

StevenRating, 5 stars1 month ago
Wonderful stay at the Villa among the vineyards in Panzano. Vicky, the host, is the owner of Le Fonti winery with the villa surrounded by their vineyards and olive groves. The view from the villa is absolutely stunning. The town of Panzano is very cute. We bought groceries at the Coop and made breakfast each morning, gathering in the cozy well equipped kitchen. There is a courtyard immediately outside the doors of the villa with a large table, and again amazing views. Our time in the villa was so relaxing! Though we went to several wineries, a highlight was a very personal tour of the winery, wine making process and wines by Vicky at Le Fonti. She spent time discussing/pouring the different wines, even bringing over the same wine from different years to show us the difference the weather/grape stress influences the final taste. Overall exactly what we wanted from a Tuscan experience and really enriched by an extremely friendly and knowledgeable host.
Guest favourite
Villa in Peccioli
4.92 out of 5 average rating, 12 reviews

Luxury villa with Pool, games room & Bocce court

KathleenRating, 5 stars8 months ago
My family and I -- six adults and a 9 month old -- spent two delightful weeks at Il Granaio. Before our arrival, Greg (the host) put me in touch with Ally, the property manager, who provided much useful information in advance and ensured we could find our way to the hidden gem that is Il Granaio. Once we arrived, Ally was available as needed, responsive to my queries as we settled in. We enjoyed the Villa and property immensely, using it as a base camp as we did day trips all around Tuscany and a longer visit to the Ligurian coast. The house was comfortable, attractive, and well-outfitted, with fantastic views from the second floor; the surrounding countryside was peaceful and beautiful; the pool was a perfect place to cool off and relax after being out and about; and the billiard table provided enjoyment for all! And having our own washer and dryer was incredibly convenient, especially when traveling with a baby. Wonderful memories were made for our family at Il Granaio!
Guest favourite
Villa in Montepulciano
4.91 out of 5 average rating, 126 reviews

Villa in Montepulciano with a Pool

SantiagoRating, 5 stars1 week ago
We just checked out of this wonderful villa today, and it has truly been one of the most special places we’ve ever stayed. We arrived with my husband’s parents, my husband, and our toddler, and from the moment we got there, everything exceeded our expectations. Alex greeted us warmly, gave us a tour of the villa and the property, and provided detailed printed information about nearby restaurants, supermarkets, cafés, bakeries, and wine tours. The property also produces its own wine, which was available for purchase and could be conveniently delivered to our villa during our stay. Alex shared his contact number and made himself available in case we needed anything—which we really appreciated. One of the highlights of the property was the stunning infinity pool overlooking the vineyard and offering breathtaking views. It was the perfect setting to disconnect and truly live in the moment. The air conditioning and hot water worked perfectly. Thank you Alex!
Top guest favourite
Villa in Loro Ciuffenna
4.98 out of 5 average rating, 51 reviews

The Lazy Oak

JordanRating, 5 stars2 weeks ago
The Lazy Oak Villa is everything we dreamed of and more for our honeymoon. The house is beautiful, well furnished and feels so homely and comfortable. The surroundings are simply stunning; the view from the house and pool never get old! Mario and Alessandro were super helpful, offering to help us book restaurants and vineyards if needed. Mario keeps to himself so still feels very private but is happy to help with anything and it was nice to see him around (with his cute little dog!) and know he was about if we needed anything. Couldn’t recommend the Lazy Oak Villa more, and we’re already talking about when we could come back!! Thank you Mario and Alessandro!
Guest favourite
Villa in Buti
4.96 out of 5 average rating, 46 reviews

Villa sii felice

KristinRating, 5 stars1 week ago
We had an unforgettable stay at this villa for our bachelorette getaway! The host was incredibly responsive and made everything smooth from start to finish. The views were absolutely breathtaking — even better than in the pictures! The villa had everything we needed to set the perfect atmosphere: fully stocked kitchen with plates and glasses, plenty of towels, and thoughtful details throughout. We loved picking fresh lemons from the garden and finding peaceful spots around the property to read and relax. It’s incredibly private and serene — the perfect escape. While the drive-up can be a bit tricky at first, it quickly becomes second nature and is well worth it.This place exceeded all of our expectations. Highly, highly recommend — we'd come back in a heartbeat!
Top guest favourite
Villa in Monticchiello
4.98 out of 5 average rating, 154 reviews

Villa unesco heritage, Jacuzzi & garden. BB Daria

MelindaRating, 5 stars1 month ago
This was true Tuscany! We enjoyed the quaintness of the village with amazing restaurants and views! Tony transported us to and from the villa! Seamless planning. Deborah arranged transportation for us to visit other villages where we enjoyed the day, people and food! Wished we had more time!!
Guest favourite
Villa in Castiglione d'Orcia
4.95 out of 5 average rating, 102 reviews

Wp Relais Villa Vignalunga

MatthewRating, 5 stars1 week ago
Family of 5 here, 3 small kids. A wonderful stay! We toured surrounding villages in the morning and came back to the pool to beat the heat in the afternoon. The private cooking class with Valentina was the absolute highlight of the trip!
Top guest favourite
Villa in San Ginese di Compito
4.99 out of 5 average rating, 129 reviews

Farmhouse , pool, 13 px. Lucca 10km

EduardoRating, 5 stars3 months 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 Buonconvento
4.95 out of 5 average rating, 57 reviews

Bellagatta, an Enchanting spot in Val d'Orcia

MartinRating, 5 stars8 months ago
We had an amazing four weeks staying at Bellagatta, using it as a base to explore Tuscany & surrounds, and it met all our expectations and more. Bellagatta is a positioned on a hilltop with stunning 360 degree panoramic views, more beautiful than the photos. The annexe that we stayed in was exceptionally clean and comfortable and well fitted out. Air con was useful on the first few days of our stay which were very hot. The property is well situated, 10 minute drive into Buonconvento (not quite an easy return walk up the hill!) which was convenient for restaurants & shopping. Gaetano was a most delightful host, very welcoming, & always taking interest in which towns we were travelling to and providing useful tips for our visits. His property manager, Susil, was also readily available and looked after us with anything we needed , even providing fresh eggs, vegetables & olive oil from the property. Highly recommended!
Top guest favourite
Villa in Barberino Tavarnelle
5 out of 5 average rating, 36 reviews

Valluccia 51

FlorisRating, 5 stars1 month ago
We had an amazing time in the villa from Tommaso. It has all the amenities that you expect from a villa in this price class. The view looking over the valley is beautiful. The communication with the host was very pleasant and swift. As an example; The existing tv got broken in the evening and the next morning Tomasso installed a new one with all the modern features like Apple Airplay. Since the weather was not great the first days you can imagine that this was very nice to have a good working tv. Anyone who is considering renting a villa in the surrounding of San Donato, I highly recommend this villa from Tommaso.
Superhost
Villa in Colle di Val d'Elsa
5 out of 5 average rating, 9 reviews

Il Timignano

PhilippRating, 5 stars8 months ago
Beautiful House and perfect for bigger groups! We had a great time there:)
Superhost
Villa in San Gimignano
4.81 out of 5 average rating, 27 reviews

Elisa Villa

PaulRating, 5 stars3 weeks ago
We had a wonderful stay at Elisa's place with an extended family group. The setting is beautiful among the vines and olives with a view of San Gimignano on the horizon. The house is spacious and cool.
Top guest favourite
Villa in Toscana
4.88 out of 5 average rating, 60 reviews

Chianti Villa at Mulino del Cerchiaio

MathildeRating, 5 stars8 months ago
Thank you!! We enjoyed our vacation with 9 friends! A little humid because of the weather, but the place is ideal in summer and comforting by the fire when the good weather is not present!
Top guest favourite
Villa in Sinalunga
5 out of 5 average rating, 45 reviews

The twigs

JeffreyRating, 5 stars2 weeks ago
Pictures don’t do it justice, prettier in person. Very relaxing get away after spending a few days in Florence.
Top guest favourite
Villa in Montaione
4.96 out of 5 average rating, 25 reviews

Private Villa with semi-Olympic pool and Tennis

JosephineRating, 5 stars1 month ago
absolutely amazing!! Francesca made us feel right at home. the place was amazing and we definitely want to come back. the property is beautiful and great if you want to play tennis , ping pong, or swim… super fun. Francesca was so sweet, gave us great recommendations, and helped us with all our questions. She even graciously helped our grandma get a doctor to see her when she sick. 10/10 amazing !
Guest favourite
Villa in Volterra
5 out of 5 average rating, 31 reviews

Detached villa with private pool

KatjaRating, 5 stars3 weeks ago
Curio greeted us very kindly and gave us a tour of the house. He was always available for questions. The place was great, very nice location. Each bedroom has its own bathroom with toilet and shower. The view from the terrace is fantastic. The large pool is for your exclusive use and can be separated by a gate. The property is bordered on both sides by hedges, so you have a lot of privacy. My personal highlight was the fireflies that we could watch there in the evening.

Quick stats about villa rentals in San Gimignano

  • Total rentals

    70 properties

  • Nightly prices starting at

    ₹7,789 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