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Vacation home rentals in San Gimignano

Find and book unique vacation home rentals on Airbnb

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Popular amenities for San Gimignano vacation home rentals

Family-friendly vacation home rentals

Superhost
Vacation home in Crespina
4.9 out of 5 average rating, 10 reviews

Poggio al Casone - Barrique basic apartment

MosheRating, 5 stars22 months ago
The property and surrounding area is beautiful, We loved the estate and especially the pool area. Had a great experience there and would highly recommend if you’re looking for a quiet getaway. Exploring the area was fun, especially Pisa and Lucca. Our only issue was finding good food, I guess we had high expectations after visiting Florence. Overall it was a nice stay and the staff was very nice and accommodating.
Superhost
Vacation home in Empoli
5 out of 5 average rating, 3 reviews

La Masseria Holiday Home - Private Pool and View

ElenaRating, 5 stars11 months ago
Beautiful, clean and equipped with every comfort! Three apartments with independent entrances in a spectacular place with breathtaking views nestled in a very nice garden. Everything is taken care of in the smallest details. Newly remade pool, not very large but very nice and collected to share with the people you go on vacation with. Especially suitable for large groups of friends/family to enjoy a dreamy relaxation.
Top guest favorite
Vacation home in Montespertoli
4.95 out of 5 average rating, 136 reviews

Tuscan Orchard

MaryseRating, 5 stars1 month ago
Our host was really warm. and attentive. We had a chance to try their products. She gave us some good recommendations. She was very responsive to our late arrival due to our delayed flight. We would highly recommend this beautiful home and will definitely come back. Thanks for your hospitality. ❤️
Superhost
Vacation home in Laterina Pergine Valdarno
4.67 out of 5 average rating, 3 reviews

Apartment in Residence with swimming pool and restaurant

NinaRating, 5 stars5 months ago
when we arrived the apartment was already warm. the host was always responsive. it was great for one night. the kitchen is very simple, I would miss it if I stayed longer. oven
Superhost
Vacation home in Rignano sull'Arno
4.88 out of 5 average rating, 120 reviews

Panoramic apartment with pool, terrace, wifi

NathanRating, 5 stars9 months ago
Very nice house in a secluded part of Tuscany. Beautiful views, pool and a bbq that we used a couple of times during our stay. Bernardo was very responsive and friendly and he was always available for any questions that we had.
Guest favorite
Vacation home in Puntone
4.95 out of 5 average rating, 42 reviews

Beautiful apartment near the sea

GillesRating, 5 stars4 months ago
I stayed in January and it was a perfect location for me as it is close to the marinas. And close to the freeway to sightseeing. Easy to park. So clean and it’s a big plus as my GF and I are allergic. Many times, first thing we do is clean the place!!! There is a washer. Dishwasher too. WIFI is strong. Nice patio but it was freezing. Would be great to entertain the family during warmer weather. There was a bottle of Prosciutto to welcome me and chips. I am often worried about sheets cleanliness as sometimes there are in color so no bleaching possible. But Erika has all the white sheets and towels straight from the professional laundry still packed and professionally ironed. This is a big plus that should be copied by so many other Airbnb. I will stay again with no doubts.
Superhost
Vacation home in Sovicille
5 out of 5 average rating, 6 reviews

SienaEntire TuscanProperty PoolHottub OutdrKitchen

MadelineRating, 5 stars19 months ago
My family came from the UK, Germany, and the US to Liesbeth's place for a grand reunion. We had three young children and they absolutely loved the property, the pony, Polly, the swings, the pond, and the trampoline. Even though it was too cold to swim, we loved hanging around and wandering through the olive groves. I think if it was warmer, we would have had a tough decision whether to stay and enjoy all the outdoor cooking and swimming opportunities or venture out to Siene and other areas. The three apartments were great though it was tough to pick a central kitchen and living room to congregate. The beds were comfy and there were tons of bathrooms and showers. We explored Siene three times because it was only a 30 minute drive. The Etruscan necropoli close by was a cool hike as well as walking along the river near Colle D'Elsa. It was the perfect home base for all the area offers as well as a great spot to stay home and spend time together; a long stay is highly recommend.
Guest favorite
Vacation home in Campiglia Marittima
4.8 out of 5 average rating, 10 reviews

Vacation flats in Tuscany2 two rooms apartment

AndrewRating, 5 stars9 months ago
We had an amazing stay! The highlight was definitely the pool – it was clean, well-maintained, and perfect for the whole family to enjoy. The kids had an absolute blast swimming and playing for hours, and we loved relaxing by the poolside. The host was very accommodating, and the apartment itself was comfortable, spacious, and fully equipped with everything we needed. We can't wait to come back and make more memories here. Highly recommend this place for families looking for a fun and relaxing getaway!

Vacation home rentals with a patio

Guest favorite
Vacation home in Greve in Chianti
4.94 out of 5 average rating, 18 reviews

Cuculo - Rifugium

SusanRating, 5 stars8 months ago
Daniele was always helpful and lived close by therefore very responsive. Such a beautiful place to stay with the most beautiful view. As it is high up, I would definitely recommend hiring a small car - Narrow and spiralling roads. Lots of wine tasting! Close by for venturing out to Florence and Sienna.
Top guest favorite
Vacation home in Altopascio
5 out of 5 average rating, 36 reviews

Tina's house

GiordanRating, 5 stars1 week ago
Tina welcomes her guests in person and makes sure guests are comfortable. Highly recommended. New, spacious and clean accommodation with everything you need for a comfortable stay
Superhost
Vacation home in Torrenieri
5 out of 5 average rating, 4 reviews

Orchid apartment with terrace

GiuseppeRating, 5 stars7 months ago
I had the pleasure of staying in a really great apartment. From the entrance, the atmosphere is welcoming and attention to detail. The modern decor blends perfectly with stylish design touches, creating a comfortable and relaxing environment. The cleanliness is impeccable, and the kitchen is fully equipped with high quality appliances, perfect for those who love to cook even on vacation. The rooms are spacious, with comfortable beds that guarantee a refreshing sleep. The bathroom is also modern and equipped with all the necessary amenities, with a spacious shower and soft towels. One of the highlights is the location: the apartment is located in a quiet area but at the same time close to the main points of interest, with supermarkets, restaurants and public transport easily accessible on foot. The owner was extremely helpful, ready to respond to our every request and to provide useful tips about the area.
Top guest favorite
Vacation home in Monticiano
5 out of 5 average rating, 39 reviews

Casa Dani with private pool

HelenRating, 5 stars1 week ago
A beautiful apartment. Gorgeous pool. Fantastic host. 100%
Guest favorite
Vacation home in Scarlino
4.95 out of 5 average rating, 21 reviews

Glamping Green Sensations "Suite Dream"

UweRating, 5 stars1 week ago
Dear Hosts, we were very satisfied with the accommodation, location and service. We were well taken care of and informed by Lella, the hostess. The furnishings leave nothing to be desired. The tranquility and privacy as well as the location are awesome. The place is absolutely clean, cozy and well equipped. For couples looking for peace and quiet without sacrificing luxury, this address is just right. We will be happy to come back.
Top guest favorite
Vacation home in Petrignano del Lago
4.97 out of 5 average rating, 75 reviews

Fontarcella, H&R- mediterranean home with jacuzzi

SsRating, 5 stars4 days ago
It is a great place to stay. You can feel the love for life and the house in many details. The check in instructions are clear and you can always expect a timely response. It was a pity that it was a short stay and wish I could get have time to stay longer.
Superhost
Vacation home in Montaione
4.83 out of 5 average rating, 29 reviews

Podere Sant'Anna | Fiordaliso House

PatrickRating, 5 stars2 weeks ago
We stayed 8 nights in the accommodation and were very satisfied. The location is great! The view is beautiful and you have many beautiful places in an easily accessible environment (Pisa, Siena, Florence, Montepluciano, Lucca, etc.). The pool in the property is also great for relaxing. The apartment offers everything you need. Romanella is a warm person and communication went absolutely smoothly. Absolute recommendation!
Guest favorite
Vacation home in Figline Valdarno
4.86 out of 5 average rating, 91 reviews

Vacation home Il piccolo rifugio

CeliaRating, 5 stars1 month ago
Totally recommended. The apartment had everything you need to spend a few days. Annalisa was very nice and left us for breakfast. Communication with her was very easy and gave us total flexibility to get to the apartment. The only upgradeable is that in the small bed two people fit very fair. Everything else was excellent!

Vacation home rentals with a washer and dryer

Superhost
Vacation home in Capannori
5 out of 5 average rating, 6 reviews

Beautiful rustic shabby, swimming pool on request

ElisaRating, 5 stars31 months ago
Carla's house is beautiful,finished. The owner was very kind and accommodated our requests. He welcomed us with a great aperitif. We were all pleasantly amazed and satisfied. We couldn't have expected better. We will definitely be back! Thank you Carla!
Top guest favorite
Vacation home in Lucca
5 out of 5 average rating, 24 reviews

Casa Lucca Pace

CarmenRating, 5 stars2 months ago
For anyone who wants to experience the peace of the Tuscan countryside while being just a few minutes from Lucca center, book Anna Lisa’s place! Her home is the best of Airbnb, a gorgeous, warm, peaceful opportunity to experience the true dolce vita! She is an exceptional host and her home is truly beautiful. She is a very kind, responsive, and thoughtful host. We stayed with our young toddler son who thoroughly enjoyed running around in her garden. We highly recommend booking here and look forward to when we are able to return!
Guest favorite
Vacation home in Centro Storico
4.91 out of 5 average rating, 274 reviews

Melarancio Residence

PeggyRating, 5 stars1 week ago
We stayed here for 4 nights. 3 of us had enough space and the place was exactly as described. The location could not be better than this. Lots of great restaurants around it and all the main tourist sites are walking distance. Also walking distance from the train station (we came to Florence via train from another location and we walked to this place. It was short distance so we were able to walk with very large luggage). We were so relieved that the building has an elevator. Check in process was easy and flexible. I highly recommend this place.
Superhost
Vacation home in Petriccio
4.57 out of 5 average rating, 7 reviews

Pietra Giglia in Tuscany

TomRating, 5 stars5 months ago
Casita isolated in the middle of Tuscany, 40 minutes from Florence and Siena. 1h from Pisa. In the middle of the Chianti valley. Ideal for visiting both cities and small towns in Tuscany.
Top guest favorite
Vacation home in Pistoia
4.98 out of 5 average rating, 132 reviews

Podere Docciolino Vacation Home

VanessaRating, 5 stars2 weeks ago
beautiful rustic but modern renovated, furnished with care as if it were an inhabited house. Spotless cleanliness of the rooms and linens, generous and perfectly organized spaces. I wanted to live there all year round! Very kind host and always available. Really great stay. Thank you
Superhost
Vacation home in Colle di Val d'Elsa
4.75 out of 5 average rating, 36 reviews

Tower House of the 1000

JeanRating, 5 stars3 weeks ago
Marta’s place is chock full of books, interesting art, antique furniture, a piano and a huge array of cooking equipment. That’s on the inside. Then there are the fabulous views. For us, it is one of the most unique and wonderful B&B’s ever!!!
Guest favorite
Vacation home in Bagni di Lucca
4.88 out of 5 average rating, 193 reviews

Hausbe Room, Vacation Home

AndreaRating, 5 stars4 weeks ago
Wonderful location, immersed in the green of Lucca bathrooms. Under the house there is a stream that gives you an extra relaxing experience, apartment with a good view. Clean and tidy house, Gaetano made us find everything ready... and in addition he left us a little thought to take home. Recommended
Guest favorite
Vacation home in Centro Storico
4.85 out of 5 average rating, 179 reviews

TOSCANELLA STUDIO TOPAZIO

DannyRating, 5 stars2 weeks ago
Andrea and Italy were great hosts and communicated very well throughout our stay. The place is in an amazing location and was close to many landmarks and restaurants. I highly recommend this place if you want a central place to stay. Pros: - Great Location - Great hosts that communicate well - Great price Cons: - Not as spacious as we’re used to - Electric powered water heater (hot water lasts ~8 minutes and needs 20/30 minutes to recharge) - Not a lot of bathroom space

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