Holiday Rentals in San Gimignano

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in San Gimignano

Beautiful apartment in San Gimignano - RoccaiaCasa'70
Outdoor pool, an infinity pool

Beautiful apartment in San Gimignano - RoccaiaCasa'70

9.8 out of 10, Exceptional, (34)
"This place is a treasure! Beautiful views and a lovely clean home with everything we needed. The pool was immaculate and the backyard was the perfect shady spot to relax. Homemade bread, a bottle of vino, and chocolate! Rita made our stay perfetto!!!"
Beautiful apartment in San Gimignano - RoccaiaCasa'70
Camping Boschetto Di Piemma
Superior Mobile Home | Private kitchenette

Camping Boschetto Di Piemma

3.0 star property
8.8 out of 10, Excellent, (71)
"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. "
Camping Boschetto Di Piemma
BRUNELLO - Cozy cottage located in a peaceful & panoramic position in Tuscany
Outdoor pool

BRUNELLO - Cozy cottage located in a peaceful & panoramic position in Tuscany

10.0 out of 10, Exceptional, (62)
"The setting for this property was magical. The house, located on a hill overlooking valleys with small family farms, met all our needs during our 8 night stay. We enjoyed breakfasts in the dining area and used the property as a base as we explored Tuscany, Pisa, Lucca and Florence. This was the perfect place for us. The views from the master bedroom and the pool area, including sunsets, were like nothing I have seen in my life. We could not believe we were staying in such a wonderful...
BRUNELLO - Cozy cottage located in a peaceful & panoramic position in Tuscany
san gimignano apartment in historical center, courtyard and fast free wifi
Outdoor dining

san gimignano apartment in historical center, courtyard and fast free wifi

9.6 out of 10, Exceptional, (28)
"Amazing place with great location "
The price is €115
includes taxes & fees
5 Jan - 6 Jan 2025
san gimignano apartment in historical center, courtyard and fast free wifi
Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
Outdoor pool

Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano

10.0 out of 10, Exceptional, (95)
"Our host was responsive to our questions and needs. He also arranged a women to come to the property and prepare dinner for us on two separate nights.To our host, thank you."
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
Outdoor pool

San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view

10.0 out of 10, Exceptional, (84)
"Alessandro was a fantastic host! He always made us feel right at home. Addressing all of our questions regarding the local area. The property was exactly what we expected. The surrounding area was magnificent. "
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
San Gimignano - Panoramic garden and beautiful pool!
Pool

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!
"Sunflower 4" Romantic for two
Pool

"Sunflower 4" Romantic for two

9.4 out of 10, Exceptional, (28)
"The property is very beautiful and rustic-it is off a gravel road so a car is needed, but it is not far from a supermarket and restaurants. The pool was delightful after a long hot day exploring the region, and the property was very large and perfect for multiple evening strolls. Stelio and Rossella were extremely friendly, accommodating, and helpful hosts. We were even greeted by one of the chickens and their dog! Stelio arranged a wine tasting with one of his friends, which was delightful. The...
"Sunflower 4" Romantic for two
Vittoriana 1 - Country house with swimming pool in San Gimignano, Tuscany
Pool

Vittoriana 1 - Country house with swimming pool in San Gimignano, Tuscany

9.8 out of 10, Exceptional, (17)
"The photos don't capture the incredible 360 degree views. The complimentary tour with wine and olive tasting was exceptional. The apartment is rustic, as pictured, but could use a deep cleaning.The 500 cypress tree lined road winding up to the property only adds to the adventure. There was a very bad storm that took out the electricity. Sabrina and Fabrizio did all they could to make sure all the guests were comfortable."
Vittoriana 1 - Country house with swimming pool in San Gimignano, Tuscany
SIMONA STUDIO WITH PRIVATE GARDEN AND STUNNING VIEW
Exterior

SIMONA STUDIO WITH PRIVATE GARDEN AND STUNNING VIEW

10.0 out of 10, Exceptional, (5)
"We absolutely loved our time here, and found the room and space perfect for a week. There were good facilities to cook for ourselves if we wanted to, and the pool area and private garden were great for relaxing. Everyone in the village was really friendly, even playing the England World Cup matches for us, and made us feel at home. Studio Simona is in a good location for exploring Tuscany, and you can even walk to a local vineyard for some wine tasting. We’d definitely recommend staying here,...
SIMONA STUDIO WITH PRIVATE GARDEN AND STUNNING VIEW
Relax Apartment with Sauna -- Historic Center on the Via Francigena
View from property

Relax Apartment with Sauna -- Historic Center on the Via Francigena

The price is €140
includes taxes & fees
2 Jan - 3 Jan 2025
Relax Apartment with Sauna -- Historic Center on the Via Francigena
Macinella Friendly and Artistic apartment "Sunflower 1"
Pool

Macinella Friendly and Artistic apartment "Sunflower 1"

9.0 out of 10, Wonderful, (21)
"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
Outdoor pool

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
Pool

Villa Sabrina - Luxury Villa Rental with private swimming pool in San Gimignano, Tuscany

10.0 out of 10, Exceptional, (73)
"Great place. Great host Driveway….needs work "
Villa Sabrina - Luxury Villa Rental with private swimming pool in San Gimignano, Tuscany
Holiday Home 'La Loggia di Giulia' with Private Terrace, Whirlpool and Garden
Terrace/patio

Holiday Home 'La Loggia di Giulia' with Private Terrace, Whirlpool and Garden

9.2 out of 10, Wonderful, (13)
"This is the best vrbo we have stayed at in our lives. Host was communicative and easy check in process with a great welcome gift. Absolutely stunning views. Kitchen and bathrooms are updated and clean. Television and WiFi worked great as well as A/C. The only issue was the hot tub that really never warmed up so it was unusable for us. Otherwise It was the best stay of our trip which included Rome, Cinque terre, Venice and Paris. Will be back soon!"
Holiday Home 'La Loggia di Giulia' with Private Terrace, Whirlpool and Garden
- Top Location - Villa in San Gimignano, Top View, 4 DBL En-Suite, Pool, A. C, WiFi
Outdoor pool

- Top Location - Villa in San Gimignano, Top View, 4 DBL En-Suite, Pool, A. C, WiFi

10.0 out of 10, Exceptional, (98)
"The entire experience (pre-booking, booking, and our stay) was positive. Barbara quickly responded to my inquiries before and after booking and greeted us upon arrival. Plus, she prepared two delicious meals for our group that we enjoyed at the outside dining area—from which we had gorgeous views of the San Gimignano skyline. There are uninterrupted views of San Gimignano from inside, too: from the kitchen, the living room, and one of the bedrooms. We savored those views our entire stay. The...
- Top Location - Villa in San Gimignano, Top View, 4 DBL En-Suite, Pool, A. C, WiFi
The house is located in the heart of Tuscany, in the historic center of San Gimignano.
Dining

The house is located in the heart of Tuscany, in the historic center of San Gimignano.

10.0 out of 10, Exceptional, (19)
"I stayed here two nights while on a girls trip to Italy. This place was perfectly located and offered everything we needed for our stay. The directions to the apartment were very clear and we found a place to be neat and clean. The apartment was just off of the town center, perfect walking distance to everything. Parking was safe and only about a 10 minute walk through town. Would highly recommend this place and would definitely return."
The house is located in the heart of Tuscany, in the historic center of San Gimignano.
Beautiful apartment with historical charm in Piazza delle Erbe in San Gimignano
Fridge, stovetop, coffee/tea maker, cookware/dishes/utensils

Beautiful apartment with historical charm in Piazza delle Erbe in San Gimignano

8.0 out of 10, Very good, (2)
"Pros- Great location in the heart of the village, 16th century townhome. Cons - bizarre setup, two floors, the first consisting of one large room with a old kitchen and a bathroom, the second accessed either from a very small winding wooden staircase inside or a outside larger normal staircase. The second floor had two bedrooms, a very small not really usable bathroom and a eat in kitchen., - appliances were hard to use. - This apartment could not be used by anyone with mobility issues"
Beautiful apartment with historical charm in Piazza delle Erbe in San Gimignano
Villa Panizzi – Vacation Rental with swimming pool in San Gimignano, Chianti
Pool

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
Beautiful apartment for 2 guests with A/C, WIFI, pool, TV, panoramic view and parking
Terrace/patio

Beautiful apartment for 2 guests with A/C, WIFI, pool, TV, panoramic view and parking

10.0 out of 10, Exceptional, (9)
"We had a great stay and we were in the perfect area to visit many places around Tuscany. "
Beautiful apartment for 2 guests with A/C, WIFI, pool, TV, panoramic view and parking
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.
Don't see what you're looking for?
See all available properties in San Gimignano
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other types of properties in San Gimignano you may be interested in

L'Antico Pozzo
Restaurant

L'Antico Pozzo

3.0 star property
9.2 out of 10, Wonderful, (239)
"Nice place"
The price is €126
includes taxes & fees
27 Dec - 28 Dec
L'Antico Pozzo
Cappuccina Country Resort
Seasonal outdoor pool, pool umbrellas

Cappuccina Country Resort

4.0 star property
8.6 out of 10, Excellent, (59)
"Very friendly staff, great breakfast, magnificent panoramic view of the Tuscan hills. Delicious dinner and great wine. "
The price is €94
includes taxes & fees
7 Jan - 8 Jan 2025
Cappuccina Country Resort
Poderi Arcangelo
3 outdoor pools, open 9:00 AM to 7:00 PM, pool umbrellas, pool loungers

Poderi Arcangelo

8.8 out of 10, Excellent, (281)
"This place was perfect. Spectacular views of the tuscan hills and gorgeous sunsets. Breakfast and dinner was also delicious. Perfect location for day trips to Florence, Sienna and Pisa."
The price is €112
includes taxes & fees
23 Dec - 24 Dec
Poderi Arcangelo
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

Are there holiday rentals in San Gimignano?

Yes, there are holiday rentals close to the most popular sights in San Gimignano, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to San Gimignano speak positively about the beautiful countryside and wineries in this destination. Make sure you have time to check out the museums and cafés during your trip.

What are some of the best holiday rentals that San Gimignano has to offer?

Independent house in the hills of the Sienese countryside: This holiday home rental outside of San Gimignano is located in a rural location, and has a fireplace, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in San Gimignano?

With 65 Expedia holiday rentals, you're guaranteed to find just the right place for your San Gimignano stay.

What’s there to see and do in San Gimignano?

Cultural attractions include Collegiate Church of Santa Maria Assunta and San Gimignano Communal Palace, whereas Rocca of Montestaffoli and Castelvecchio Natural Reserve are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Piazza della Cisterna and Torre Grossa.

What’s a holiday rental in San Gimignano like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in San Gimignano. Holiday rentals offer extras such as kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of privacy away from shared hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for a small group gathering.