
Condo vacation rentals in San Gimignano
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Bilocale Artimino campagna Toscana
Appartamento grazioso in un borgo piccolo lontano dalla frenesia e dal caos. Ti vien voglia di prendere una sedia e di mettersi vicino a dei anziani del borgo a sentire commenti sul raccolto, sul caldo che sta arrivando e su come ha parcheggiato male il nipote. Host super disponibile e casa attrezzata il giusto. Super consigliato!

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!

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!!

Florentine Experience - Chiara e Simone
We had a lovely stay. The apartment is beautiful and had everything we needed. Chiara has put a lot of effort into providing information on anything one needs to know about the surrounding neighborhood. Food, transportation, emergency needs and entertainment that made us feel comfortable in our new surroundings right away. There were several great places to eat just a few steps away. Loved getting cappuccinos & pastries every morning at Cosi on the corner. Not open on Mondays but just a few blocks another bar is. Also wonderful. Bus stop is also very close and easy. Loved the convenience. We were able to get everywhere and back very quickly by bus. Upon checking out our taxi didn’t come. Traffic in Florence is busy. Another reason the bus is the best option. Within 25 minutes Chiara son & neighbor picked us up and got us to the train station. We felt lucky to have found such a beautiful apartment, neighborhood and great host for our stay. Impossible not love. The best❤

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.

Residenza 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!!

Amazing apartment in Palazzo Pfanner
This historic apartment inside Palazzo Pfanner is a unique stay with a splendid view into the magnificent palazzo gardens! I highly recommend staying for a once in a lifetime experience. Dario and his family own and manage the property and are very welcoming hosts. Depending on whether you intend to cook, we found the kitchen small and not very well equipped. Also, the bathroom is functional but rather dated. Overall a great stay for a unique experience!
Pet-friendly condo rentals

Appartamento" Il teatro "- Prato centro storico
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.

"Mercanti" cozy attic in a tower house
Die Wohnung war sehr stilvoll eingerichtet und gut gelegen, um die Stadt zu Fuß zu erkunden. Die Küche war sehr gut ausgestattet und es hat Spaß gemacht dort zu kochen. Die Kommunikation mit Elisa war perfekt und wir durften sogar früher ein- und später auschecken. Das Bad war klein, aber funktional. Leider war uns nachts trotz Klimaanlage zu warm, da das Bett direkt unter das Dach gebaut ist. Die Wasserpumpe war zudem recht laut (auch wenn kein Wasser lief). Insgesamt können wir die Wohnung auf jeden Fall empfehlen, wenn man kein Problem mit steilen Treppen hat :)

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.

Suite "La Rocca Romantica" 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!

Amazing view of Val d'Orcia Pienza
Wir hatten einen tollen Aufenthalt in dieser Unterkunft. Ruhig gelegen mit allem Komfort für eine entspannte Urlaubswoche in Val D’Orcia. Der Ausblick vom Garten des Grundstücks ist einfach nur wunderschön!
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.

Appartamento Loggiato 3 in toscana vicino 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 con piccola piscina privata
Das Ferienhaus und der Garten mit Pool ist wunderschön. Das Haus ist liebevoll im eingerichtet im Toskana Stil. Alles war sehr sauber und es hat an nichts gefehlt. Wir haben uns wie zu Hause gefühlt und haben in den Betten sehr gut geschlafen. Benedetta und ihr Vater sind sehr liebe und hilfsbereite Gastgeber, die uns jederzeit unsere Fragen beantwortet haben und sehr gute Empfehlungen für Besichtigungen und Restaurants gegeben haben. Als unser Auto repariert werden musste ist der Vater mit uns in die Werkstatt gefahren und war bei der Übersetzung behilflich. Danke nochmals für die selbstlose Hilfe. Wir werden diesen schönen Urlaub immer als das kleine Paradies in Erinnerung behalten, das von sehr lieben Menschen geführt wird. Wir können es nur empfehlen.

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!

Castello di Orgiale Charme Residenz
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
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 vista piscina e natura toscana
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! ❤️
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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