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Featured Villas in San Gimignano

San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
10.0 out of 10, Exceptional, (79)
"This was our second villa rental in the San Gimignano area, our first at Alessandro's villa and it was amazing! Alessandro was very responsive and helpful from the moment we booked the year prior, until the day we checked out. We were a group of 6 adults and had plenty of room. The villa has every amenity you might need during your stay. At check in Alessandro provided us with helpful information about the surrounding area. The villa is in a beautiful setting surrounded by vineyards and olive...
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
10.0 out of 10, Exceptional, (92)
"Lovely large 4 bedroom house with spectacular views of San Gimignano. Really enjoyed our stay and highly recommend this rental. Everything was perfect including the pool. Alessandro "
Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
- Top Location - Villa in San Gimignano, Top View, 4 DBL En-Suite, Pool, A. C, WiFi
10.0 out of 10, Exceptional, (96)
"The spacious accommodation on the first floor offered captivating views over the Tuscan countryside to San Gimignano on the horizon.The garden with its spacious swimming pool and outdoor eating area was greatly enjoyed by everyone. San Gimignano itself was a lovely town to explore with great restaurants and cafes. And the meal prepared for us by Barbara was very special."
- Top Location - Villa in San Gimignano, Top View, 4 DBL En-Suite, Pool, A. C, WiFi
VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN SUITE ROOMS, SWIMMING POOL, SPA, SAUNA.
10.0 out of 10, Exceptional, (111)
"My husband and I spent 2 weeks at Villa Iris with our adult children and their spouses. The villa location is ideal and the views are even better in person, just breathtaking. The outdoor space is where we most of our living, and the pool is exceptional. Centrally located to Florence, Siena, Lucca and such easy access to San Gimignano for dinner, we all agreed it was ideal location. The chef services made us feel like royalty! If we can be back, we will! "
VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN SUITE ROOMS, SWIMMING POOL, SPA, SAUNA.
Villa Sarah Luxury Villa a San Gimignano 5 room en suite swimming pool spa
10.0 out of 10, Exceptional, (38)
"Villa Sarah was lovely and the setting was spectacular. The outdoor spaces and pool were great for cooking and relaxing. The view was postcard perfection! The staff gave us great recommendations and helped to organize transportation. We had a welcome dinner at the Villa which was a highlight."
Villa Sarah Luxury Villa a San Gimignano 5 room en suite swimming pool spa
San Gimignano - Panoramic garden and beautiful pool!
9.8 out of 10, Exceptional, (36)
"This magnificent villa and the hosts, Cristina and Simone, surpassed our expectations and made a blissful stay in beautiful San Gimignano. The 300+ year old home was clean, charming and authentic and the grounds were well maintained and serene. The views of the countryside were breathtaking! At our request, the hosts arranged for a chef, Patrizia, to come to prepare dinner on 3 evenings. She was delightful and used fresh produce and ingredients from her own farm in the multi-course meals she...
San Gimignano - Panoramic garden and beautiful pool!
VILLA CAROL LUXURY five minutes from San Gimignano, Private Pool A/C WI-FI
9.8 out of 10, Exceptional, (78)
"We stayed at Villa Carol for a week and had a fantastic time. The owners were extremely helpful and made a wine tasting reservation that was phenomenal with breath-taking views! The villa is well stocked and has a beautiful pool and views. We spent a lot of time on the terrace! We will return! Thank you for a memorable vacation. "
VILLA CAROL LUXURY five minutes from San Gimignano, Private Pool A/C WI-FI
Macinella Friendly and Artistic apartment "Sunflower 1"
9.0 out of 10, Wonderful, (20)
"I rated as a 4 instead of 5 for two reasons. 1) the beds were fine but could have been better. (2) the drive on gravel roads were a bit iffy when it rained. Stelio and the rest of the group were very friendly and responsive and the views were amazing . If you walk across the road you can see San Gimignano which was very cool. Also convenient to many of the towns."
Macinella Friendly and Artistic apartment "Sunflower 1"
Entire Tuscan farmhouse with private pool between Siena and Florence
10.0 out of 10, Exceptional, (3)
"We had a wonderful visit to the area and loved the home and property. The check-in and departure was very easy. We had many questions before our arrival and every time we received a prompt reply"
Entire Tuscan farmhouse with private pool between Siena and Florence
Villa Sabrina - Luxury Villa Rental with private swimming pool in San Gimignano, Tuscany
10.0 out of 10, Exceptional, (72)
"The villa was exactly as advertised, and just as lovely as the pictures demonstrated. It was much better than we expected. Sabrina was a wonderful host and surprised us with goodies throughout our stay. We all hated to leave but I hope to return."
Villa Sabrina - Luxury Villa Rental with private swimming pool in San Gimignano, Tuscany
Villa Panizzi – Vacation Rental with swimming pool in San Gimignano, Chianti
9.2 out of 10, Wonderful, (11)
"Villa was beautiful. However, listing should specificaaly say need a car. All the taxi's were booked so we needed to rely on tours we booked and a lovely restaurant that actually picked us up. If you need consistent wifi this is not the place for you."
Villa Panizzi – Vacation Rental with swimming pool in San Gimignano, Chianti
Lilium, splendid villa with outdoor space, on the hills of San Giminiano
9.6 out of 10, Exceptional, (5)
"The property was beautifully situated in the hills of Tuscany. It was in a lovely area of Tuscany offering beautiful views all around! The house was nicely furnished, well equiped and very comfortable. From the villa we drove to San Gimignano, Siena, Colle Val d'Este, all very close by. Our hostess, Concetta, was incredibly responsive and obviously cared about making sure our vacation was special."
Lilium, splendid villa with outdoor space, on the hills of San Giminiano
Villa with private pool overlooking San Gimignano. Exclusive use of the property
10.0 out of 10, Exceptional, (20)
"The villa is beautiful and homey and well stocked — and Simon, Pham and Aliah were the most helpful and generous managers. I want to come back for longer!!"
Villa with private pool overlooking San Gimignano. Exclusive use of the property
Villa San Gimignano View by MMega
Villa San Gimignano View by MMega
Intera Casa Vacanze con Giardino e Piscina ad uso Esclusivo a 2km da S.gimignano
10.0 out of 10, Exceptional, (1)
"Wir hatten die Gelegenheit in dem charmanten Haus von Paola und Daniele 14 wundervolle Tage zu verbringen. Es liegt wunderschön zwischen den Weinbergen im San Gimignano und ist herrlich für Ruhe suchende. Der Pool wird täglich von Daniele gereinigt und ist komplett privat mit Blick in die Toskana. Einfach wundervoll. Vielen Dank an Paola und Daniele für die Herzlichkeit und entspannten Tage. Wir kommen sehr gern wieder."
Intera Casa Vacanze con Giardino e Piscina ad uso Esclusivo a 2km da S.gimignano
Villa Il Caggio - Villa with pool near san Gimignano in Tuscany
9.8 out of 10, Exceptional, (8)
Villa Il Caggio - Villa with pool near san Gimignano in Tuscany
Villa Benedetto By MMega
10.0 out of 10, Exceptional, (3)
"We enjoyed our stay very much. The hosts were very friendly and helpful. Beds very comfortable. Very quiet area with beautiful views. Pool nice. Well-equipped kitchen. 10 minute drive to San Gimignano."
Villa Benedetto By MMega
Villa Bandellina
Villa Bandellina
Exclusive Farmhouse Pool & View of San Gimignano
10.0 out of 10, Exceptional, (1)
Exclusive Farmhouse Pool & View of San Gimignano
Truly tuscan villa with pool, ideal for groups, 6Km to San Gimignano
9.6 out of 10, Exceptional, (4)
"Giulia made our stay a truly 5-star experience. She assisted us in planning every detail of our vacation over a six month period, responding quickly to every question we had. She allowed us to drop off our luggage before the official check-in time and made lunch reservations for us the first day at an amazing restaurant in San Gimignano. There was an incredible welcome basket waiting for us in the kitchen with bottled water, breads, pastries, fresh pasta, sauce, juice, coffee, fruit and more!...
Truly tuscan villa with pool, ideal for groups, 6Km to San Gimignano
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in San Gimignano

Camping Boschetto Di Piemma
3.0 star property
9.0 out of 10, Wonderful, (68)
"Nice quiet spot in the woods but very close to San Gimignano. Very clean. Comfortable beds. They don’t provide towels or soaps, but that is clear up front. You can rent towels if you want and they sell soap/ shampoo in the office. "
The price is NZ$98
includes taxes & fees
24 Sept - 25 Sept
Camping Boschetto Di Piemma
Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
10.0 out of 10, Exceptional, (92)
"Lovely large 4 bedroom house with spectacular views of San Gimignano. Really enjoyed our stay and highly recommend this rental. Everything was perfect including the pool. Alessandro "
Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
10.0 out of 10, Exceptional, (79)
"This was our second villa rental in the San Gimignano area, our first at Alessandro's villa and it was amazing! Alessandro was very responsive and helpful from the moment we booked the year prior, until the day we checked out. We were a group of 6 adults and had plenty of room. The villa has every amenity you might need during your stay. At check in Alessandro provided us with helpful information about the surrounding area. The villa is in a beautiful setting surrounded by vineyards and olive...
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much do villas in San Gimignano cost?
Villas in San Gimignano range between and per night. These escapes give you the privacy of your own space at a price that won’t stretch the budget. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many villas are there in San Gimignano?
You can choose from 64 villas in San Gimignano. No matter if you’re travelling with the family or organising a weekend break with friends, Expedia can help you find the right space for your entire crew.
What is there to do near my villa in San Gimignano?
San Gimignano has enough sights and activities to keep you going for weeks (or months!), beginning with Tenuta Torciano Winery. Sovestro in Poggio Winery, Museo Civico and Museum San Gimignano 1300 are other impressive attractions. If you have time to spare, Podesta’s Palace and Piazza Duomo will put the finishing touches on your itinerary.