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Cottage holiday rentals in San Gimignano

Find and book unique cottages on Airbnb

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Popular amenities for cottage rentals in San Gimignano

Cottage rentals with a hot tub

Top guest favourite
Cottage in San Gimignano
4.97 out of 5 average rating, 70 reviews

Romantic House in Tuscany with jacuzzi

JosephRating, 5 stars2 weeks ago
Davide and Annalisa's cottage was absolutely gorgeous, exactly as the pictures showed. It was the perfect place for us to relax and enjoy our last week in Italy. Breakfast out on the patio with the birds chirping and surrounded by nature was a great way to start the day. Davide lit the heater for the hot tub for us and we were able to enjoy a wonderful evening relaxing. Davide and Annalisa were full of good recommendations for restaurants and local places to visit. The cottage is within driving distance of so much - Pisa, Florence, Siena and of course San Gimignano just to name a few. All the amenities we needed were included, the WIFI was great and the cottage was very comfortable. I would highly recommended staying here and if we are ever in the vicinity we would certainly stay here again.
Guest favourite
Cottage in Sovicille
4.93 out of 5 average rating, 223 reviews

From Simone, podere santi Lucia and Pietro

LesleyRating, 5 stars8 months ago
Lovely, peaceful, spacious place with a kind and generous host in Simone. He met us as we arrived and used his wagon to help move our luggage into the cottage. Big rooms, lots of space, many handy supplies in the kitchen. Good shower, comfortable bed. Enough bench space in the bathroom to put your things. Simone was really helpful with local recommendations for restaurants and where to park the car. One day he made a delicious tart and bought us in half. Would recommend staying at his place.
Cottage in San Quirico
3.67 out of 5 average rating, 3 reviews

Belvilla by OYO Olivi Verde (Green)

MarkusRating, 5 stars1 month ago
Exceptionally beautiful house in Tuscany. In a wonderful mountainous location with incredible views. Lucca, Pisa, Florence and many other destinations can be easily reached by car 😁 Mr. Biondo, who is actually the host, is an extremely courteous and friendly man. Helpful and always available. I'd be happy to come back 😁
Superhost
Cottage in Trequanda
4.75 out of 5 average rating, 142 reviews

"Rosso Poggiolo" farmhouse with swimming pool.

EliotRating, 5 stars7 months ago
Very good, it was perfect The host were so friendly Thank you very much
Cottage in Lorenzana
4.34 out of 5 average rating, 38 reviews

Indipendent country house

EstelleRating, 5 stars10 months ago
The house is very spacious and the garden is really very pleasant. The kitchen and the master bathroom (huge) are renovated. We really appreciated that the rooms were air conditioned especially since we were there in the hottest period. However, we were surprised to have to buy garbage bags, as there was only one for each trash can, except for the compost that had several. Same for toilet paper, there was just 1 per bathroom. The pool was very hot and the garden was very well-equipped. We had a crib for an additional charge of €10/day which was a little expensive. There were children's toys, but no high chair (good to know). You should know that the access is a little bumpy and that you have to open your eyes to see the bend for the path that leads to the house. It has the advantage of being very quiet and private.
Cottage in San Quirico - Pescia
4.42 out of 5 average rating, 19 reviews

Cottage in San Quirico with pool

NicoleRating, 5 stars15 months ago
Beautiful views, 20 min by car from the nearest town, not accessible without a car. The communication went great, the house was easy to find with navigation & the area is very nice
Cottage in Pescia
4.74 out of 5 average rating, 27 reviews

Private house with private pool | pet friendly

SabineRating, 5 stars9 months ago
We really enjoyed our holiday at cas nel bosco, the house is very quiet and close to nature. We liked that very much. The pool and the garden offer total relaxation. We already miss everything very much. In the valley it was often 32 degrees in the first week and upstairs in the house it was very pleasant. The pool was super refreshing. The house has everything you need and the small village of Medicina is very charming. The access road is narrow and very winding, but we also saw some wildlife. Communication with Francesca and Paola was straightforward and enquiries were answered immediately. Thank you very much, we had a great holiday.
Guest favourite
Cottage in Reggello
5 out of 5 average rating, 10 reviews

Independent cottage with private spa

MarcRating, 5 stars10 months ago
Dreamy and beautiful place! You can't ask for better. A breathtaking view, nothing is missing inside, comfortable bed, etc. Not to mention Elena's warm welcome and the good wine 🍷 she left us as well as a large bottle of water.

Pet-friendly cottage rentals

Superhost
Cottage in Bagno A Ripoli
5 out of 5 average rating, 31 reviews

Borgo Spedaletto 3 – Dolcevita Holiday

ErinRating, 5 stars2 days ago
BOOK THIS PLACE. I cannot express this enough. This beautiful place offers a true sense of peace, spectacular beauty, a fairytale like garden to walk about in the mornings with your coffee (that they provide in your kitchen), a gorgeous heated pool, a massive tennis court, extremely kind hosts, an adorable little outdoor covered area to do your laundry, and so SO SO much more. This place will transport you. You will actually feel like you’re living in a fairytale. A Tuscany fairytale. I choked and teared up on our last day because I was already missing it. It is everything you’re hoping for. I promise.
Top guest favourite
Cottage in Pergine Valdarno
4.78 out of 5 average rating, 58 reviews

Tuscan Countryside Holiday Home with Pool

Aneta & StefanRating, 5 stars9 months ago
We had a lovely time at Vito's. Great location, great garden and pool. We were able to enjoy our peace and the place was equipped with everything you need. We'd love to come back.
Superhost
Cottage in Montespertoli
4.91 out of 5 average rating, 54 reviews

Cottage with panoramic view

JamesRating, 5 stars3 weeks ago
Our stay was wonderful. The location is stunning, set in the hills away from it all with an amazing view. The property is simple and authentic.
Superhost
Cottage in Montaione
4.78 out of 5 average rating, 27 reviews

la villetta

DanielRating, 5 stars2 weeks ago
We booked this Airbnb as a big family vacation and wanted to spend a few nice quiet days in the middle of Tuscany. The house is super nice and the view from the pergola is really breathtaking. The pool was just the thing for the hot days. The house had a great Tuscan flair and we enjoyed our stay very much. The landlord was always easily accessible and very friendly. We will be very happy to come back and can only recommend the house.
Superhost
Cottage in Castellina in Chianti
4.85 out of 5 average rating, 27 reviews

Casa degli ulivi, live Chianti with swimming pool

KatieRating, 5 stars1 month ago
This villa was so beautiful in a such a classic way. There were 5 of us, 2 couples in the upstairs room and one single in the pull out couch, near the kitchen. Both bathrooms are upstairs. One in the master and the other outside both rooms. We were only there two nights but wished we stayed in this region longer. The property was stunning, the pool was heaven, and the closest restaurant (4 min drive) Uscio e Bottega was the best meal I had my two weeks in Italy. (That’s obviously saying a lot). The local olive oil farm you can walk to surrounded by the sweetest Great Pyrenees’ was such a treat to find. We ended the visit with a tasting at Nittardi which is a 10 min drive from the property. It was an absolute hidden gem of a place rich with history, beautiful grounds, and amazing wine. We how to come back and stay here again’.
Guest favourite
Cottage in Castelfranco Piandiscò
4.9 out of 5 average rating, 71 reviews

Villetta Belvedere

AndrewRating, 5 stars2 weeks ago
Fantastic stay, incredible views and perfect location. Couldn’t recommend this place highly enough. Thank you Simone :)
Guest favourite
Cottage in Pienza
4.95 out of 5 average rating, 37 reviews

Cottage San Lorenzo

Brandon and TiffanyRating, 5 stars3 weeks ago
We stayed here with our two young adult daughters. The home and the views are just magical! The home was well stocked and provided everything we needed. It very peaceful and quiet. The grounds are stunning and well kept! Only a 15 minute drive to the town of Pienza which had some of the best local restaurants. The pool was very nice to enjoy on a hot summer day with a glass of Rose in hand. We we would stay here again in a heartbeat! You will not be disappointed!
Superhost
Cottage in Bagno A Ripoli
4.89 out of 5 average rating, 45 reviews

The Cottage

SuzanneRating, 5 stars1 month ago
We spend 4 nights in Paradise...the best place we stayed in Italy Thank you so much to open your door to this gem

Private cottage rentals

Guest favourite
Cottage in Capannori
5 out of 5 average rating, 21 reviews

Entire accommodation in the Lucca countryside

NicolasRating, 5 stars1 month ago
Very nice house tastefully renovated. Large garden ideal for children and evening aperitivo, watching the sunset over the mountains in the distance. Very clean and very functional with everything you need for a great stay. The host family is very friendly and gave us good advice on sightseeing and restaurants where to go. Great
Superhost
Cottage in Villa Parigini
4.75 out of 5 average rating, 4 reviews

Restored Barn in Chianti property, pool, terrace

VeronicaRating, 5 stars34 months ago
We spent a beautiful and relaxing week of vacation in the restored barn of Villa Parigini . The house is very quiet, cozy and comfortable and is well organized. It has a nice garden and pool to cool off and relax. Great location to visit Siena and the Chianti area. Giada and her mom are very kind and helpful Hosts. We look forward to coming back.
Top guest favourite
Cottage in San Martino in Grania
5 out of 5 average rating, 43 reviews

Crete Senesi - Asciano Cavoni Hut

IreneRating, 5 stars5 days ago
There are so many great things to say about Laura’s villa in Tuscany, it’s hard to know where to begin. The house is so beautifully designed and decorated. The area is spectacular, remote and peaceful but just 30 minutes from the heart of Siena. It was the perfect space for our family of 4. We enjoyed meals on the private patio as well as lounging by the shared pool. The air conditioning worked really well although we didn’t always need it with the cool Tuscan evening breeze. We took day trips to a nearby vineyard and an olive grove, and always looked forward to coming back to the house to enjoy both the lovely interior and incredible vistas and sunsets. I would recommend Laura’s place to anyone looking for an idyllic and comfortable Tuscan retreat!
Top guest favourite
Cottage in Centro Storico
5 out of 5 average rating, 10 reviews

Loft & patio under the vineyard

PedroRating, 5 stars3 days ago
Cozy, comfortable, very well renovated, pleasant and quiet loft. It is 10 minutes from any area of the center. It has a lot of charm, and Daniela was attentive at all times of arrival, needs or questions during the stay or departure. 100% recommended!
Top guest favourite
Cottage in Impruneta
4.93 out of 5 average rating, 27 reviews

Cottage with private swimming pool

JoeRating, 5 stars9 months ago
My wife and I stayed here as part of our honeymoon and we absolutely fell in love with this place! The scenery is gorgeous, the view from the cottage did not get old! Very private setting in a peaceful neighborhood. Andrea was a fantastic host, along with the help of his lovely parents. He communicated with me at every step of the way making sure all of our needs were taken care of. Could not be happier with our stay and it made our honeymoon very special.
Superhost
Cottage in Buonconvento
4.83 out of 5 average rating, 60 reviews

QuarterApartment for 6P Agriturismo Quarantallina

LisaRating, 5 stars2 weeks ago
The property was beautiful amd loved the scenery and friendly animals such as the donkeys and horse which greeted us each night. Serena and Mario were exellent hosts and made us feel at home at welcomed. We enjoyed a home cooked dinner with a view and breakfast. Very comfortable rustic farmhouse accomodations. Highly recommend and would love to go back as it is close to all in Tuscany.
Top guest favourite
Cottage in Casale Marittimo
5 out of 5 average rating, 9 reviews

L'Ondiana, centenary olive trees and seaview

FabianRating, 5 stars9 months ago
An excellent accommodation in the middle of the beautiful hills of Tuscany. Everything was perfect. Thank you Giada & Simone ❤️
Guest favourite
Cottage in Florence
4.94 out of 5 average rating, 53 reviews

Meriggio Luxury - Overview Florence

KateRating, 5 stars4 weeks ago
Yet another wonderful stay in Meriggio in Settignano. The location and views are so beautiful, and the house is so comfortable and perfect for two people. As it is our third visit, we know what to expect and yet again, it met all our expectations easily. A perfect place to relax and unwind, yet with easy access to Firenze when you want a change of scene.

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Siena
  5. San Gimignano
  6. Cottage rentals