Some info has been automatically translated. Show original language

Cottage vacation rentals in San Gimignano

Find and book unique cottages on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for San Gimignano cottage rentals

Cottage rentals with a hot tub

Top guest favorite
A stone cottage is surrounded by lush greenery, featuring a rustic facade with wooden accents. Potted plants are placed near the entrance, and the roof is topped with a small chimney. A pathway of stones leads to the door, inviting guests to explore.
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 favorite
A spacious area of well-kept grass is seen in the foreground, with a rustic Tuscan farmhouse in the background. The building features a tiled roof and multiple windows. Bare trees and some greenery surround the property, under a clear blue sky with scattered clouds.
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.
A warm sleeping area features a spacious bed with green bedding against a backdrop of exposed stone walls. A modern chair and small table are positioned near the window, with light filtering through sheer curtains. An artwork of yellow fruits enhances the room's character.
Cottage in Molina di Quosa
4.75 out of 5 average rating, 4 reviews

Tuscan apartment in the hills Pisa and Lucca

EmerRating, 5 stars34 months ago
We had a fantastic stay in the cottage for nine nights. Villa Alta is in a beautiful location and the grounds around the house are so well maintained. We enjoyed both the shared pool and our own private terrace with hot tub. The cottage itself was spotlessly clean and perfect for our needs. It was a perfect base for us to explore the area. Raffaella was so friendly and accommodating and we enjoyed both dinner and breakfast at the villa on a couple of occasions. We would highly recommend a stay here.
Superhost
A glass-enclosed veranda offers a view of the private garden and pool area. A round dining table with decorative tiles is surrounded by iron chairs. Light filters through the glass, enhancing the rustic charm of the exposed stone walls.
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
The two-story red farmhouse features green shutters and a terra cotta roof. A covered patio extends along one side, furnished with tables and chairs. Surrounding the house, the well-maintained garden includes potted plants and a vast lawn dotted with trees.
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.
The two-story villa features a rustic exterior with a tiled roof and brick accents. A private pool is visible in the foreground, surrounded by well-maintained grass. A staircase leads to the upper level, and large windows allow for natural light. Lush greenery frames the property.
Cottage in Montepulciano
4.62 out of 5 average rating, 13 reviews

Tuscany Villa Girasole

DavidRating, 5 stars1 week ago
What a great place to stay. Everything we needed during our stay was available, from a cot for our baby to an iron and a full kitchen etc. The location was great for Tuscany, with Siena, Montelpulciano and others an easy drive away. The pool was just what we needed in the afternoons to cool down and relax after spending our mornings out and about. We hosted a dinner with family in the large dining table overlooking the pool, a lovely end to our stay at a superb family spot.
A private pool is surrounded by a wooden railing, offering scenic views of the surrounding nature. The clear blue water reflects the sky and nearby greenery, contributing to a serene ambiance, while the area is bathed in soft natural light.
Cottage in Pescia
4.73 out of 5 average rating, 26 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.
A charming rustic villa is surrounded by lush greenery, featuring a terracotta roof and white walls. A patio area with a shaded pergola and a BBQ grill is visible, alongside a gravel pathway leading to the entrance. The inviting outdoor space is complemented by potted plants.
Cottage in Campiglia Marittima
4.59 out of 5 average rating, 39 reviews

Farmhouse in the Tuscan countryside "Stars" apartment

JulienRating, 5 stars9 months ago
Complete accommodation and very well-equipped. Its private terrace offers very good tranquility. Daniela and Alberto are very welcoming and friendly. 20 minutes to the most beautiful beaches in Tuscany! Grazie Daniela and Alberto!🙂

Pet-friendly cottage rentals

Superhost
A charming exterior of a rustic cottage is surrounded by lush greenery and neatly trimmed hedges. A table is set for outdoor dining under the shade of trees, while a fresh pomegranate hangs nearby, adding a touch of nature to the inviting scene.
Cottage in Bagno A Ripoli
5 out of 5 average rating, 30 reviews

Borgo Spedaletto 3 – Dolcevita Holiday

MathewRating, 5 stars1 month ago
Charming little cottage perfect for a small family in the hills near Florence. Had everything we needed. About 25 minutes drive through the country to central Florence so perfect for day trips in. Lovely walks in the olive groves around the cottage.
Top guest favorite
An outdoor terrace features a rustic wooden ceiling supported by brick columns. Comfortable seating is provided by a light-colored couch and benches, alongside a dining table with chairs. The surrounding greenery and pathways lead to additional buildings, creating a serene and inviting space.
Cottage in Pergine Valdarno
4.77 out of 5 average rating, 57 reviews

Holiday Casa Vacanze Tuscan countryside with swimming pool

Poussin Bertrand Rating, 5 stars9 months ago
We had a pleasant stay at Vito's. The house is very well arranged and offers many amenities. The place is idyllic surrounded by olive groves and high up allowing exceptional views of Tuscany. The pool is simply fantastic, spacious and extremely well maintained thanks to Vito's right-hand man who takes great care of the entire property. This is a property to remember that we highly recommend.
Superhost
A rustic stone cottage is framed by lush greenery and a sprawling lawn. The structure features green wooden shutters and a chimney, blending harmoniously with the natural surroundings. The landscape is dotted with trees and shrubs, creating a serene atmosphere.
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 favorite
A bright interior is featured, with soft pink walls and two large arched windows offering expansive views of the hills. A potted plant adds a touch of greenery beside two white armchairs. A low wooden table displays decorative items, completing the inviting atmosphere.
Cottage in Montepulciano
4.95 out of 5 average rating, 20 reviews

ELENA COTTAGE

TobyRating, 5 stars1 week ago
This casa is an absolutely spectacular place to stay when in Tuscany - I was amazed by the photos, but in real life the place is somehow even more beautiful and scenic! The hosting is absolutely faultless - we were made to feel right at home immediately with homemade treats, and every arrangement we needed was made super smoothly. Utterly perfect - this was our first introduction to Tuscany and we will remember it forever!
Guest favorite
The exterior features a spacious garden surrounded by greenery, showcasing a variety of plants. A shaded area provides seating with lounge chairs and a large tree offers additional shade. The house structure is visible in the background, with large windows reflecting the landscape.
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 :)
Superhost
A rustic two-story building constructed from warm brick is surrounded by lush greenery. Large windows invite natural light, while wooden shutters add charm. The exterior features a gravel path leading to lounge chairs, creating a serene outdoor space for relaxation.
Cottage in Buonconvento
4.83 out of 5 average rating, 60 reviews

QuarterApartment for 6P Agriturismo Quarantallina

LisaRating, 5 stars1 week 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.
Guest favorite
A bright living area features large glass doors, inviting natural light and showcasing views of the garden. Wooden furniture, including a dining table with chairs and a cozy sofa, is accentuated by soft, light-colored curtains that gently frame the windows.
Cottage in Pienza
4.95 out of 5 average rating, 37 reviews

Cottage San Lorenzo

Brandon and TiffanyRating, 5 stars2 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!
Guest favorite
A cozy bedroom is featured with a spacious bed dressed in a floral quilt. Natural light enters through an open door, revealing views of the countryside. The room includes decorative lamps and a small table beside the bed, alongside textured walls and a wooden ceiling.
Cottage in Florence
4.94 out of 5 average rating, 53 reviews

Meriggio Luxury - Overview Florence

KateRating, 5 stars3 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.

Private cottage rentals

Guest favorite
A tranquil salt-water pool, measuring 10x5 meters, is surrounded by lush greenery and olive trees. Two shaded sun loungers offer a relaxing space to unwind, while an umbrella provides additional shade. Golden stones form the pool deck, reflecting the sunlight.
Cottage in Cavriglia
4.85 out of 5 average rating, 71 reviews

Il Fienile, characteristic stone cottage for 2

JanRating, 5 stars1 month ago
Beautiful location, remote and quiet. Nice base for city visit (Arezzo, Siena, Florence) Beautiful hike in the Balze made!! Friendly Host!
Guest favorite
Cottage in Capannori
5 out of 5 average rating, 20 reviews

Entire accommodation in the Lucca countryside

NicolasRating, 5 stars1 month ago
Very nice house, tastefully renovated. Large garden ideal for children and evening aperitif, 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 to visit. Super
Top guest favorite
Cottage in San Martino in Grania
5 out of 5 average rating, 42 reviews

Crete Senesi - Asciano Cavoni Hut

InezRating, 5 stars2 weeks ago
Laura is the perfect host and the house is really amazing: very large and stylish, with a nice private garden and pool area. The best rental place ever!
Top guest favorite
A narrow stone pathway is framed by an archway, leading to quaint buildings with rustic stone facades. The sunlight filters through, casting soft shadows. Greenery is seen along the edges, creating a connection with the surrounding nature.
Cottage in Pistoia
5 out of 5 average rating, 53 reviews

Relax among the olive trees

KarinRating, 5 stars1 week ago
Very occasionally, you arrive at a place and meet people who make you feel so incredibly at home, and that's what Sandra and Cristiano and their B&B do for you. Everything is right, the view, the hospitality, the house, the tasty things in the fridge. In short, a small paradise on earth with 2 very special warm sweet people who we already have in our hearts. The cottage on top of the mountain is in our top 5 most beautiful and best places and Sandra and Cristiano at number 1❤️. Hope to see you again soon and you are always welcome with us in the Netherlands. Tanti Baci, Koos, Karin and Jax
Top guest favorite
A cozy courtyard is framed by lush grapevines, showcasing large glass doors that open to the living space. A dining table with chairs is visible, accompanied by a comfortable sofa. Natural light brightens the area, enhancing the serene atmosphere.
Cottage in Centro Storico
5 out of 5 average rating, 9 reviews

Loft & patio under the vineyard

AlesRating, 5 stars1 week ago
Just a short walk to the city center and main attractions. The apartment is nicely furnished and very cozy. Daniela gave us great tips on restaurants and activities. The only downside was that the stay was too short. Excellent.
Superhost
Cottage in Volterra
4.89 out of 5 average rating, 9 reviews

Indipendent barn over the Hills around Volterra

MarinaRating, 5 stars11 months ago
We spent two and a half wonderful weeks in this holiday home. Both Andrea from Be Home Services and in particular the owners Nara and Nino welcomed us warmly and were always available for questions and very helpful. We liked the secluded location of the house very much - you have a stunning panoramic view and it is largely very quiet despite the neighbors. It should be known that the nearby Villa Ulignano is used as a wedding location. On two weekends, there was live music until the early hours of the morning, which was clearly audible, but did not bother us excessively. It is worth mentioning that the lower floor shown on the exterior shots of the house cannot be used, but serves as a storage room for the owners. The drive to the house is - as already described here - quite adventurous and leads a few kilometers over unpaved, partly steep paths. If you drive slowly, this is easy to cope with.
Top guest favorite
A stone pathway leads through lush greenery, surrounded by olive trees and colorful flowering shrubs. The vibrant pink flowers contrast with the refreshing greenery, creating a serene outdoor space. Sunlight filters through the leaves, enhancing the tranquil ambiance of this natural setting.
Cottage in Casale Marittimo
5 out of 5 average rating, 9 reviews

L'Ondiana, centenary olive trees and seaview

FabianRating, 5 stars8 months ago
An excellent accommodation in the middle of the beautiful hills of Tuscany. Everything was perfect. Thank you Giada & Simone ❤️
Guest favorite
The image captures a lush garden filled with blooming rose bushes, set against a backdrop of rolling hills and a clear blue sky. A variety of greenery, including trees, adds depth to the scene while a distant view of towns and valleys is visible in the background.
Cottage in Carmignano
4.95 out of 5 average rating, 61 reviews

Tuscan cottage swimming pool near Florence Pisa.

lorenaRating, 5 stars9 months ago
Alberto and his son are super nice and very attentive. We loved the place (it's even better than the pictures). The pool is magnificent. We spent a week with our 15-month-old son and everything was very well suited to a baby. We recommend this listing and will definitely be back

Destinations to explore

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