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Holiday Homes in San Gimignano

Find and book unique holiday homes on Airbnb

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Popular amenities for San Gimignano holiday homes

Family-Friendly holiday homes

Top Guest favourite
Holiday home in Montecatini Val di Cecina
4.88 out of 5 average rating, 8 reviews

I Castagnini - Orange

MaryRating, 5 stars8 months ago
My partner and I spent four days in Marco's apartment, they were four days of relaxation, we felt welcomed as family. Antonietta and Francesco, Marco's father and mother (two people like there aren't many, kind, generous, two people with whom it is pleasant to get lost in their stories) who live upstairs from the apartment, pampered us and made us feel at home. We'll definitely be back next time, the three of us.
Guest favourite
Holiday home in Casole d'Elsa (SI)
4.9 out of 5 average rating, 223 reviews

Studio in Tuscan farmhouse with pool & views

MarleneRating, 5 stars6 days ago
Beautiful accommodation in Tuscany with fantastic views. Simply great, we are thrilled and definitely want to come back. Fabio is super nice and the place offers everything you need. Highly recommended !
Top Guest favourite
Holiday home in Sovicille
4.97 out of 5 average rating, 143 reviews

Podere La Castellina - No. 1 COTTAGE

GudrunRating, 5 stars4 days ago
Very nice and quite retreat, Simona was an excellent host, very friendly and and always reachable and responsive!
Top Guest favourite
Holiday home in Montespertoli
4.95 out of 5 average rating, 135 reviews

Tuscan Orchard

FabiolaRating, 5 stars1 month ago
I loved the house! It was so beautiful, cozy and clean. I will definitely book it next time I am in Montespertoli. Fiammetta and Leonardo were very sweet!
Guest favourite
Holiday home in Castelnuovo Berardenga
4.89 out of 5 average rating, 70 reviews

PIERFANTINI private Chianti house ♿️ 🏊‍♂️ 🐶

RichardRating, 5 stars2 weeks ago
Our family of six had a great stay at Pierfantini. Arnaldo and her family were very welcoming and helpful, even when we accidentally set off the alarm and locked ourselves out of one of the apartments. The spacious grounds were perfect for our two dogs, and the layout of three separate apartments meant that each person/couple had their own private space. We also enjoyed grilling steaks outdoors and using the fire pit when weather permitted. We visited in the off season, so the pool was closed, but the setting looked lovely. We found the kitchen to have everything we needed and more. As for the area, it felt a little remote, and some of the businesses were closed for the season. We enjoyed day trips to Siena, Cortona and Florence, along with wine tasting at some of the local estates. The drives to Siena and Cortona were easy, but if we had to do it over again, I would be tempted to take the train to Florence from Montevarchi as traffic and parking in Florence were a bit stressful.
Superhost
Holiday home in Arezzo
4.71 out of 5 average rating, 49 reviews

Ancient stone farmhouse with park and pool

JessicaRating, 5 stars2 months ago
We had a wonderful stay at Stella’s farmhouse. The grounds and surroundings were excellent for walking and exploring in the mornings and late afternoons. The accommodations very comfortable for our multigenerational family. Stella was an excellent host! Very kind, helpful with all our questions, and provided us some nice recommendations for the region. We would love to return!
Top Guest favourite
Holiday home in Cecina
4.97 out of 5 average rating, 39 reviews

Podere il Pozzo_relax in Tuscany_Marina di Cecina

UlrichRating, 5 stars6 months ago
We had a pleasant week at Alessandro and Giulia's. The accommodation is as described and was impeccably clean. The location is perfect: slightly set back to be quiet but close enough to the city or the beach for example (bike path a few meters away). Alessandro and Giulia were responsive hosts. They were able to guide us on things to do and see in the area, places to eat, beaches... The on-site electric terminal was a real plus to make travel easier and optimize our time! Thank you for this stay, we'll be happy to go back!
Guest favourite
Holiday home in Lucca
4.76 out of 5 average rating, 148 reviews

Apartment in Lucca Walls

AnnaRating, 5 stars1 week ago
We had a wonderful stay at Ilaria’s place for just over 2 weeks with our 10 month old baby. The location is fantastic and we quickly got used to the stairs, which weren’t a problem. We loved the high ceilings and big windows but found we couldn’t really open them because of mosquitos, which attacked our baby on the first few nights after leaving the window open for a short time on the first afternoon, oh dear! The place closely resembles the photos, particularly the light, although there are quite a few more personal items and decorations since the family uses the apartment for vacations too. The kitchen and bathroom were clean but not super clean and this was the only place in our 7 week stay in Italy that didn’t provide things like body wash, shampoo, sugar etc, so that might be a bit annoying to have to buy these for a short stay. Overall we loved the apartment and had such a wonderful stay with loads of great memories. Thank you!

Holiday home rentals with a patio

Guest favourite
Holiday home in Monticiano
5 out of 5 average rating, 37 reviews

Casa Dani with private pool

LorenzoRating, 5 stars3 days ago
Great location to visit the Abbey of San Galgano and the hermitage, even on foot in just halfanhour through a beautiful forest, and also convenient to Siena (30/40 min by car). Fantastic private pool and outdoor courtyard!
Top Guest favourite
Holiday home in Lucca
5 out of 5 average rating, 40 reviews

Penthouse with terrace and panoramic views of the city

DaveRating, 5 stars2 months ago
A great small rooftop apartment in the walls of Lucca. Great location, nice locals style cafe next door and walkable to all the other restaurants and cafes and shops in Lucca. Great view from the rooftop and areas to sit and enjoy the weather, great thing about being on the tip floor is the view and it makes the many stairs to the top worth it. Limited paid Street parking in the street next to the apartment 3 euros per hour. (we had no problem finding a space but it was off season) or larger parking areas outside the walls with day rates of around 10 euros per day or parking lots around 10 mins walk. Apartment is very well equipped in the kitchen but is compact. Perfect for 2 people or 3 if you don't mind being cosy. Would highly recommend if you are looking for a place to enjoy all Lucca has to offer
Top Guest favourite
Holiday home in Chianni
5 out of 5 average rating, 41 reviews

5*Casa Serena,Fab 1 bed with aircon,parking garden

TammyRating, 5 stars6 months ago
We loved Chianni - the people, the setting, the overall coziness of the town. Tim and Joy are so welcoming!
Superhost
Holiday home in Montaione
4.81 out of 5 average rating, 26 reviews

Podere Sant'Anna | Fiordaliso House

RobertoRating, 5 stars2 weeks ago
Staying in the house was very good and Romanella is the perfect host. She is very attentive and extremely friendly. The house is secluded, which is perfect if you are looking for peace and quiet. The house offers great views and a very nice outdoor area, lots of nature all around. It is perfectly located. From here you can reach all the important places of the provinces of Pisa and Firenze as well as the Chianti area within 60 minutes.
Guest favourite
Holiday home in Figline Valdarno
4.86 out of 5 average rating, 91 reviews

Vacation home Il piccolo rifugio

CeliaRating, 5 stars4 days 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!
Guest favourite
Holiday home in Bagno A Ripoli
5 out of 5 average rating, 8 reviews

Villa dei Pavoni-Swimming pool,Jacuzzi in Florence

KasonRating, 5 stars2 weeks ago
Emiliano was an amazing host. From start to finish he was helpful, friendly and professional. The house was filled with entertainment for all of us. Whenever we needed help or had questions, he and his team were there for us and made us feel like family. We will miss you all. 100% recommendation worthy!!!
Top Guest favourite
Holiday home in Pienza
4.95 out of 5 average rating, 77 reviews

Pienzalettings

MeganRating, 5 stars1 week ago
This place is as lovely and beautiful as it gets. We had a fantastic stay. Perfect location, and absolutely spotless.
Top Guest favourite
Holiday home in Terranuova Bracciolini
5 out of 5 average rating, 25 reviews

"Podere Carpognane" Tuscany Holiday House

JudithRating, 5 stars7 months ago
The best Airbnb experience I’ve ever had. Sara & Alessio were extremely welcoming, friendly, & helpful. I felt like I was visiting family. We were welcomed with a basket of pasta, olive oil, sauce & a bottle of Prosecco ( I was celebrating my birthday)! We were also given veggies from the garden, a delicious plum tart & homemade eggplant Parmesan (made by mama) that was amazing! Both Sara & Alessio were very helpful for suggestions for transportation & local places to visit. We enjoy cooking & we found the kitchen to be well stocked with all the tools necessary. The grounds were well manicured & the views were great and very relaxing. It made it very conducive for outdoor yoga. I recommend this house& the hosts It’s not only & Airbnb it’s truly a great experience.

Holiday home rentals with a washing machine and dryer

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

Beautiful rustic shabby, swimming pool on request

ElisaRating, 5 stars30 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! Thanks Carla!
Top Guest favourite
Holiday home in Monteroni d'Arbia
4.9 out of 5 average rating, 69 reviews

White lily with a view of Siena

RonRating, 5 stars5 days ago
The white lily was the perfect location for us to explore Tuscany’s towns and wineries and to return in the evenings to a lovely villa with breathtaking views. The sunrises were spectacular and the apartment was very clean and well equipped with everything we needed. Close to a small village for grabbing a few groceries if needed and the patio was a great place to sit and relax with some morning coffee or an evening wine while fully appreciating the Tuscan countryside. Thank you Marta for such a wonderful holiday we enjoyed our stay immensely. Ron
Superhost
Holiday home in Scandicci
4.79 out of 5 average rating, 33 reviews

"VERDE" apartment 2/5 people, swimming pool, garden

MassimoRating, 5 stars4 months ago
My partner and our two dogs only stayed two days from December 31 to January 2 in the "Green Apartment"; The apartment was very clean and well-stocked from every point of view ( kitchen, bathroom and bedroom) the spaces are quietly there for a long vacation. We are from the Florence area, and finding ourselves in the middle of all that greenery very close to the center and all the services did not seem true. The entire farm is very well cared for and you can enjoy the stay in relaxation, being very quiet. Unfortunately, staying in winter we could not enjoy the very large outdoor pool, but you can see that it is well maintained. We'll definitely be back to get away from the routine towards the hottest season. Highly recommended for those who want to visit Florence and its surroundings and spend a long vacation.
Guest favourite
Holiday home in Centro Storico
4.91 out of 5 average rating, 268 reviews

Melarancio Residence

HeidiRating, 5 stars2 weeks ago
The apartment is in the best location! You can easily walk to the Firenze Santa Maria Novella train station and the Cathedral of Santa Maria del Fiore. There is a small grocery store next door and so many restaurants and cafes nearby. The apartment itself is very clean and check-in was very smooth. The apartment was comfortable for our group of 6 people. Be advised one of the bedrooms has a loft which requires climbing up a ladder which was fine for us adults. We really enjoyed our 3 night stay and would definitely rent this AirBnb again if we ever return to Florence.
Guest favourite
Holiday home in Siena
4.9 out of 5 average rating, 40 reviews

Apartment in historic Villa in Siena_"IL MANGIA"

YuRating, 5 stars1 month ago
This was such a wonderful experience, enjoyed the beautiful courtyard for 4 days, clean rooms, quaint and textured furnishings and set up, it does have a warm home feel.Many times I want to be lazy in the room, enjoy the sunshine of the courtyard, and enjoy all the amenities provided in the room.I highly recommend this homestay, take a bus at the door for a few minutes to the ancient city of Siena, we go up each time to the ancient city on foot, you can enjoy the pastoral scenery of Tuscany all the way, thank you Cristina and her brother for their warm and thoughtful service, and the opportunity to come back here later.
Superhost
Holiday home in Colle di Val d'Elsa
4.76 out of 5 average rating, 33 reviews

Tower House of the 1000

KatherineRating, 5 stars4 days ago
We really enjoyed staying at Marta’s apartment! It was so beautiful and spacious, and it had such a great view of the city. Marta was very responsive and helpful!
Guest favourite
Holiday home in Centro Storico
4.84 out of 5 average rating, 340 reviews

The Cricket's Cage <Anna Maria> (A-04)

CarlingRating, 5 stars3 weeks ago
We thoroughly enjoyed our stay. This was such a perfect location. It was very central, but so quiet and extremely peaceful! The space was beautiful and everything was as described. The staff was very helpful, friendly and accommodating! We would love to stay again when we visit Florence!
Guest favourite
Holiday home in Bagni di Lucca
4.87 out of 5 average rating, 189 reviews

Hausbe Room, Vacation Home

CinziaRating, 5 stars2 weeks ago
Gaetano was very kind and always available to give directions. We booked the studio with a garden to do the Easter egg search, a Nordic tradition, and of course we also used the garden for an afternoon aperitif. The sound of the river is constant. The street is just below, but the house is high enough for you to ignore. Nearby you can walk to Bagni di Lucca, which is like a forgotten village, surrounded by water and paths - the bridges of that entire area are very interesting. I found the price very convenient: the studio had full equipment. Thanks to Gaetano and see you soon!

Destinations to explore