
Condo vacation rentals in San Gimignano
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Top-rated condo rentals in San Gimignano
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Weekly condo rentals

Two-room apartment Artimino Tuscan countryside
Lovely apartment in a small village away from the hustle and bustle. You feel like grabbing a chair and sitting next to the village elders to hear comments about the harvest, the heat that's coming, and how the grandson parked badly. Super helpful host and well-equipped house. Highly recommended!

Studio Duomo Michelangelo a Place to fall in love
I cannot recommend this listing enough! Perfect location close to major ‘tourist’ attractions such as the Duomo, Baptistery, Uffizi Gallery, and Ponte Vecchio. Also walkable to other major Piazza’s, museums, the Boboli gardens and Firenze SMN train station. Surrounded by some of the best trattorias, gelaterias and sandwich shops. Monica is very attentive to her guests and makes check-in and check-out smooth and easy! The space is exactly as listed and incredibly clean and well kept and contains all the essentials. If we are ever back in Florence we hope to stay with Monica again!

"Mercanti" cozy attic in a tower house
The apartment was lovely and well located. Elisa was very helpful and and an excellent communicator. A thoroughly enjoyable experience all round.

TWIN TOWER unica al mondo unique in the world
Absolutely stunning views of Tuscany, a must book for the first time in the city. I loved every second of it, it is the best location and you are in the heart of the city

Elegant Apartment With Frescoes 209
What a beautiful room! Once owned by princess of Poland, it is fit for a princess indeed. Loved sleeping amidst the frescoes. It’s spacious, clean, and comfortable. AC keeps the room very cool, and the view of the dome from the roof simply can’t be beat! The location is fantastic, right in the heart of the city and close to everything. Very helpful with lots of recommendations too. Grazie!!

[Historic Center - 5 Stars] Chalet with Suite
This apartment was clean, charming, and is one of a kind. The host was very friendly and easy to communicate with. The view of Tuscany from the apartment is spectacular. There are many excellent restaurants, all over and it was such fun to not only explore the town but the surrounding area as well. Highly recommend!

Dimora”La Porta Verde”
We stayed at Patrizia’s home in SG for a month & it was perfect! The walk into the town was right up the street. We went at least once a day for meals & just to explore. You can turn down any block & find something new. We never tired of it. The location was also convenient for side trips. We went to Florence, Lucca & Modena on weekends which we loved, but were always glad to come back ‘home’ to SG. When not exploring, my husband helped out a The Montese Cooking Experience where he became friends with the Chef on our last visit to Tuscany. If you have the time on your trip, I would highly recommend taking the class. It’s knowledgeable as well as entertaining, and of course great food!! This is what brought us to SG for the month & we will definitely be back for more time at Montese & the town. We would also stay at Patrizia’s home again. It was spotless, well equipped with lots of special ‘extras’ plus had enough space for us to unpack and settle in comfortably.

Residence In cerca d'Autore
I can’t say grazie enough to Gessica and Bernardino! Such nice people. The apartment is one of the best Airbnb’s I’ve stayed in. Pictures don’t do it justice. It has everything you could ever need. The view from the balcony made it hard to leave. Hopefully we will be back! Grazie Mille!!
Pet-friendly condo rentals

Apartment "Il Teatro" - Prato historic center
Beautiful one of a kind Airbnb in the heart of Prato. I highly recommend you rent this place, you can easily get to Florence in 25 mins by train, and discover the hidden gem that Prato is.

Elegant vintage decorated home in the old Siena
Perfectly located vintage decorated home within walking distance of historic center of Siena. We spent a month here and used her place as a center base to discover Tuscany. Close to shopping and restaurants. WiFi is excellent as my husband worked remotely for a few days a week. Kitchenette and washing machine were a big help as we cooked a few nights staying in. Mattress is very comfy and the apartment is very quiet. Church bells rang daily and drummers in the contrade practice for parades and Palio. Experience Medieval Siena here. We were very comfortable in Grazia’s place. Nice to have a 1/2 bath on main level, as bedroom and bathroom with shower is on the upper level. Grazia provides everything you could possibly want and has excellent suggestions for places to eat and sights to visit. She was indispensable helping us always responding within minutes if we had a question or needed help. Perfect place for the Tuscan vacation! Grazia is a wonderful and caring host!

Stylish Terrace on Boboli Gardens
We loved this space and when we come to Florence again we will most definitely book here. It was a cool, quiet oasis on the beautiful relaxing side of the Arno. The location was perfect with an easy walk to all the sites but also so quiet and peaceful. We loved the kitchen and cooked multiple days and sat on the sweet patio and enjoyed the local wine. The space was clean and cool and the layout was perfect for 2 people. There’s also a couch bed if another person or one or two children were there. Our hosts were so accommodating and friendly! We have so much love for this special spot in Florence.

"La Rocca Romantica" Suite in San Gimignano
I loved this place. Duccio (the host) told me that this used to be a convent around the 1500. The bed is really confortable and the water pressure and temperature is great. Also, you are at just around 100 meters from the main squares. Highly recommended!!

Designer Apartment with Breathtaking Views
I enjoyed my stay at Dan's apartment. It was large (even more so when you factor in the adjacent terrace), beautifully furnished and well stocked. Appreciated the dishwasher and clothes washer. Having a second bathroom was an extra perk. Only slight downside was the walk into the center of town (25 min to the Ufizzi) as it rained nearly every day during my weeklong stay -- I imagine on dry/temperate days it's a pleasant walk along the river. Overall I would gladly stay again.

Florentine Hills "LE SCALETTE"
Lovely stay in Tuscany! Patrizia had started a warming fire going for us in the fireplace upon arrival, as the weather was chilly and rainy. The house was very cozy, artistically decorated, and well appointed -- it made us feel very much at home away from home. Gorgeous views of Tuscany from the bedroom windows, and a well cared for garden which had lemons, rosemary, basil and many flowering plants. Patrizia was the absolute best hostess and provided for all our needs during our stay. There was plenty of room for everybody in the house, and there was even a lovely little kitchen which was fully stocked (salt, pepper, spices, coffee, milk, and more!). Note there is not an oven, but we were able to cook breakfast every day, and even a few dinner meals for our small group in the mini kitchen (there is a mini fridge which fit a lot of perishable food for its size!, and a small induction stove top). Thank you for the perfect stay!

Asso's Place, Luxury Apartment with stunning view
Asso's Place was the perfect home for our family in Florence! The most luxurious Air BnB we've found to date - with original paintings, a generous supply of records, DVDs, and books galore. The Duomo felt so close that we could reach out the window and touch it. The location was walking distance from all the major attractions and excellent restaurants. Piero and Raffaela were perfect hosts, reaching out to us with information about restaurants, shopping, and sites to visit, and answering every question quickly. Raffaella greeted us in person and pointed out important features of the apartment. All of our needs were met to perfection.

Palazzo del Taja - in the center with whirlpool
We had a wonderful stay at Riccardo’s apartment in Siena. You cannot beat the location - it’s perfectly situated in the center of everything and made a great home base to explore Siena and the surrounding area. The apartment is beautifully designed and very clean. Riccardo was beyond helpful with local recommendations and helped us secure dinner reservations. Highly recommended when staying centrally in Siena.
Condo rentals with a pool

Chianti La Pruneta, Michelangelo apartment.
Lovely stay in this rural location. Comfortable, scenic, friendly hosts! Nice pool!! Clean and everything we needed! Massimo made us feel as comfortable as possible down to the details!! We loved Iris the dog too (and we think she loved us!) Recommend the meal which helped make my wife’s birthday very special.

Loggiato 3 apartment in Tuscany near Siena
We had a great stay in Francesca's agriturismo. beautiful place with breath taking views. the place was very clean and tidy and it had all we needed and much more. it was a good base for traveling the area. take a ride on the SP146 - you won't regret it! all in all this place is highly recommended! wish i would visit here again. Toscany is soo beautiful.

Casa Rebecca with a small private pool
Benedetta is an amazing and gracious host, the property was easy to locate and the room was beautiful, absolutely amazing Tuscan style with beautiful views and a private pool. She also recommended us a restaurant for dinner and that was one of the beat meals we had in Italy! 100% recommend

VILLA LE PERGOLE - Florence
Anna was a fantastic host, who treated us with the upmost respect and kindness. While her place is a bit difficult to find at first, once you're there, you're in one of the most beautiful scenes we've seen during our time in Italy. Also, it was close enough that we were still early able to travel into Florence each day we were there. Anna was so nice in providing us with breakfast each morning, which included apricot jam from her fruit trees and homemade bread. We would recommend this spot for anyone looking for a quiet place to stay outside of the busy city.

Agriturismo Casavecchia, l'Olivo
This place is such a gem! The hosts work hard to make sure your stay is very comfortable. Someone is at reception most of the time to answer questions or help with recommendations! The room we stayed in (Olivo) was perfect. It had a small kitchen with beautiful views and the nature of the building is "Tuscany Picture Perfect" You definitely need a vehicle to Get around unless you plan on taking a taxi and staying at the location (which is very doable since they have a restaurant and serve you breakfast every morning) The pool is beautiful with picture perfect hills of Tuscany while you swim! They have a small playground and a large yard with tables where you can sip wine or have a picnic! The bed was very comfortable and our stay here was very relaxing! The restaurant had such an amazing food as well! 10/10 would recommend!

Entire house for couple with exclusive pool
The highlight of our tour around Italy, simply stunning. The outside area is the obvious highlight; the lovely pool overlooking iconic Tuscan scenery, but the inside is also perfect (didn’t think we’d fully use the two bathrooms but we did!!!). Matteo was a great host and couldn’t do enough for us - he even led the way in his car to help us find the restaurant he’d recommended when we arrived (one of our best meals of our holiday). A truly magical stay.

Casa Luna-Splendida overlooking the pool and Tuscan nature
A little paradise in Tuscany with the most breathtaking view. We spend alot of the days at the house, swimming in the pool, cooking and generally feeling at home! They surprised us with fresh cherries 🍒 a few times and were happy to explain the beautiful routes you can walk around. We will def be back! ❤️

Poggiolieto Studio - on hills 10' from city center
We had a lovely a time at the property. It was exactly as described and had amazing views. The host was very welcoming and was exceptionally helpful. It is fairly easily to get to the city centre from the property. There are two fairly regular buses and we were able to use a maps app pretty successfully to predict travel times.
Quick stats about condo rentals in San Gimignano
Total rentals
60 properties
Nightly prices starting at
G$10,461 GYD before taxes and fees
Total number of reviews
2.9K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
20 properties have a pool
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- Santa Maria Novella
- Duomo di Firenze
- Ponte Vecchio
- Piazza del Duomo (Pisa)
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Gulf of Baratti
- Basilica of Santa Maria Novella
- Mugello Circuit
- Cala Violina
- Fortezza da Basso
- Uffizi Gallery
- Parco delle Cascine
- Piazza della Repubblica
- Piazzale Michelangelo
- Mercato Centrale
- Pitti Palace
- Stadio Artemio Franchi
- Giardino Bardini
- Avignonesi Winery Fattoria Le Capezzine
- Medici Chapels
- Cavallino Matto
- Spiaggia Libera
- Teatro Verdi
- Palazzo Vecchio
- Things to do San Gimignano
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- Things to do Province of Siena
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