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

A View Over Tuscany's Countryside
Incredible experience! Filippo’s place was as described! All the amenities present and spot clean. We really enjoyed our stay and recommend to everyone!

Apartamento Chiusdino - Old Town
Excellent accommodation, house as shown in the photos and description, located in a very nice little village. Clean and tidy property, Host always available for any information and kind.

"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.

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!!

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.

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.
Pet-friendly condo rentals

Apartment "Il Teatro" - Prato historic center
Sandra was the perfect hostess, what a lovely person and a lovely place, it felt like home, very quirky which I loved. Will definitely go again if I'm in Prato. Only criticism which was a very minor one was finding the place, but Sandra came and met us which was nice of her. Extremely happy with our stay, highly recommend

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!

"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!!

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.

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.

Lovely Suite in the Heart of historical Lucca
This place is a dream. Luciano is a fabulous host. Friendly and very helpful. Fully remodeled for being inside ancient think wall structure. Location is a historian’s dream. Shutters over all windows really close out the sound at night. New modern kitchen fully stocked. Great location with bedroom French door style windows opening to overlook the Anfiteatro. We spent most evenings sitting there with a glass of wine. Great restaurants there too. Had great meals at Old Charlie’s restaurant a number of times. Supermarket 5 min walk. Great local shopping, many piazzas with outdoor cafes. Train station about 15 minutes walk. 1.5 hour ride on train to Firenze, 30 minutes to Pisa, 2 hours by bus to Siena. Lucca is cooler than Firenze with a nice breeze in the afternoon. I am a painter so this is a great location. If the flight from California was not so long, I would come back every year. We Love it here and love Luciano.

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!

Amazing view of Val d'Orcia Pienza
Very comfortable accommodations and gorgeous property and views
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.

Il Giaggiolo – Chianti with a view
We stayed in Monica’s home for five nights and four days, and it was incredible. The second we checked in Monica sent me an extensive list of instructions and places to visit during our stay. My favorite list was restaurants and local food shops in the area she recommends as a local. The house had all the amenities you could need/want, comfortable beds, and a really nice patio area. We are a few meals outside and enjoyed the stunning view. We saw some of the most beautiful sunsets as well. The pool was really well kept. There were many wineries the were nearby. The location was also great for taking day trips to Florence and Siena. The nearest town was so cute and had a lot of nice shops and restaurants. We are so appreciative of Monica’s food recommendations and suggestions of things to do. Overall we had an amazing time, and we highly recommend staying here!!

La Foresteria | Granary House
Such a beautiful, peaceful place to spend a few days! It was central to many tours and activities, great for exploring! Luca was a wonderful host and ensured we were happy and had everything we needed. The restaurant was great! I can’t think of anything that would have made our stay better! Completely exceeded our expectations!

Agriturismo Casavecchia, l'Olivo
We absolutely loved our stay and it exceeded our expectations. The staff were friendly and very helpful, the food was delicious and the apartment was a great size with all the amenities we needed. It was family friendly and our children loved the pool. It’s a beautiful location and very relaxing. We would love to come again. Thank you for making our holiday so lovely.

Apartment with terrace and stunning view
Staying at Raisa's was incredibly nice. The accommodation and especially the view is much nicer than shown in the pictures. Raisa went to great lengths to make everything as pleasant as possible for us. The dogs (Saila and Yango) are mega cuddly, the pool is great and the whole property is really picturesque. By car, beautiful city trips, etc. are easily doable and we would be happy to come back again sometime.

Orgiale Charme Residenz Castle
Property is amazing, host so friendly and helpful… Honestly we spent very little time on the property as we were exploring so much of Tuscany during our stay with the lovely location as our home base. But it was so beautiful to wake to every day and come “home” to late every evening :) During our 6 days, we explored Florence, hung out in Siena, hiked Chianti trails, visiting all over from Monteriggioni to San Gimignano to Volterra… and throughout Val d’Orcia from Montepulciano to Pienza , Pitigliano to Serano… and north to Lucca & Pisa. Just wonderful location :) Thank you so much!

Entire house for couple with exclusive pool
Great stay! Beautiful views and great location only about five minutes from the main highway to go north to Florence or south to Siena.

Charming Tuscan home with pool, garden & Air-Con
The accommodation was perfect, clean, well arranged and as described. And especially ideal for 2 couples thanks to the 2 bedrooms and 2 bathrooms. Its location in the countryside makes it a quiet and relaxing place. And its location close to San Giminiano is impeccable. It is an ideal base for visiting Tuscany because it is ideally located for visiting Pisa, Florence and Siena, the Chianti region and otherwise going to the seaside. In addition, our Hostess, Eleonora is charming, responsive and full of good advice for visiting and enjoying the area. This place is definitely worth a visit. Thank you.
Quick stats about condo rentals in San Gimignano
Total rentals
60 properties
Nightly prices starting at
ﺩ.ﺇ184 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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