
Condo holiday rentals in Siena
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Top-rated condo rentals in Siena
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Popular amenities for Siena condo rentals
Weekly condo rentals

Chianti Apartment in 12th Century Tuscan farmhouse
I highly recommend Bryan's place it is extremely beautiful and well maintained with an amazing back drop. Bryan and his family are very welcoming. If you want a taste of Tuscany you need to stay here.

The highest wonderful view in Siena
Perfectly located apartment with everything you need and amazing views from every window. The host provided plenty of helpful instructions and advice. Great place to stay in a beautiful 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!!

[9 minutes from Montalcino] Elegant House Mafalda
Marco’s place is away from the hustle and bustle of Siena very quietly comfortable and super clean. The view from the balcony alone is worth the night rate. Close to all the lovely sights in Val D’Orcia. In a very quaint town with locals who actually live here. Marco is very responsive and clearly explained everything to us. Must try the pizza at Pizza I’ll Vecchio…a hidden gem in Tuscany

The View of Sangiorgio
A perfect stay in Florence. Mattia’s house is not only perfectly located with an amazing terrace but so welcoming with lovely relaxing spaces with incredible views , extremely comfortable beds, and attention to all those small details that make a stay special. We throughly enjoyed our stay and can highly recommend to others.

The Nest in Chianti
Brilliant Airbnb in Greve.. location superb overlooking the square. The apartment is spacious and felt like home. Wonderful restaurants to walk to and a great bakery opposite for morning coffee and pastries. Easy to park the car just a few minutes walk away. Lovely villages to explore nearby and picture perfect everywhere you look. If you come to Greve book here, relax and soak up the Italian atmosphere. Cora is a fantastic host who regularly communicates to make sure you have everything you need. 10/10 ❤️

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❤

Residence In cerca d'Autore
We absolutely loved our week stay here and couldn't have been happier. It was spacious, beautifully furnished and steps away from nearby restaurants and shops. Best of all was the huge terrace –it had insanely gorgeous views of the Tuscany landscape which never got old. Looked forward to our morning coffee and early evening aperitivo with the views of the Tuscan landscape. The views were fabulous (including a nice sunrise if you're an early riser)! We didn't have reservations for dinner one night and wandered just across the street to Rosso Rubino Trattoria. The owners could not have been nicer, and the food was delicious. Berardino graciously held us a spot in the coveted "Parcheggio 7" and drove our luggage up the hill upon arrival. He gave us a tour of the apartment and several great recommendations. It was a very welcoming start to our stay. It was the perfect base for exploring Tuscany and hope to return soon.
Pet-friendly condo rentals

Cozy apartment in stunning National Park forest
Sweet, easy amd nice place

The Bell
great location on a quiet street. the flat was superb in every respect - one of the nicest we've ever stayed in. Gabrielle was super helpful arranging a taxi for us due to the transport strike. we had a really great time - can't praise it enough

" Il teatro " apartment - Prato Centro Storico
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

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!

Adalberto Apartment inside the Manor of Fulignano
A beautiful apartment with stunning views. Easy access to many beautiful places to visit such as San Gimignano, Florence and Sienna. The apartment was clean and comfortable with amenities as listed. The views from the communal terrace were stunning and there was plenty of space to sit without being on top of other guests. We would highly recommend.

Central apartment overlooking Santa Maria Novella
We enjoyed the stay at Claudio’s place , the apartment is conveniently located . Claudio was waiting for us at the apartment to greet us and to shows the functionality of all amenities , we found the apartment nicely decorated and squeakily clean . We highly recommend this place for a family of 3 or 4 traveling to Florence . We will be back .

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.

Liberty Siena Flat 2
What a fantastic stay! The location is right in the heart of Siena, it's down a sweet side street which means you get both privacy as well as being only a few footsteps away from all the beautiful sights of Siena. Luciano was quick to respond, friendly and generous with his recommendations. The perfect host! We adored Siena and this Airbnb added to the charm and the romance of our trip with its wooden beams and a large window that we could open up and watch the passing by of the people below us. It's opposite a delicious bakery and a tasty bar/restaurant as well as a coffee shop - what more could you want? We travelled from Florence and the journey was so straight forward, one bus, the 131 R, and then a 5-10 minute walk to the apartment. We learnt that we were staying in the Goose quarter and this made us laugh! (Siena is famous for having different "areas", I'd highly recommend a walking tour!) Such a perfect place and such a perfect taste of Tuscany. Thank you!
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.

La Foresteria | Granary House
This place is even more beautiful than the photos show! We are travelling round Italy for our honeymoon and this has been our highlight. From the amazing grounds to the incredible food at the little restaurant it’s all been perfect. Thank you Marian for excellent communication and being so accommodating. What a fantastic place - Grazie!!

San Rocco – Bellavista – Castello di Bossi
The property is wonderful, surrounded by greenery and with a pool with an incredible view. The room was super clean and with all possible comforts. We interacted a lot with a very kind lady at the reception, very friendly and helpful. The wine we tasted was also exceptional , it's worth staying there for just one night! Extremely recommended

Spinosa Apartment in Podere Capraia
We had a wonderful time at Alberto‘s and Laura‘s - it turned out that we didn’t do as many trips into the surroundings as planned because we just wanted to enjoy the beauty of the garden and the amazing views. It was the perfect ending of a fantastic vacation in Italy - I hope we will be back next year :) We received a fantastic welcome, home made bread, jam and pasta - and immediately felt like home. Grazie! One thing to mention is that the apartment is kind of thin-walled towards the second apartment - that didn’t bother us at all, but might be of interest for fellow travellers who are sensitive to noises. All in all, certainly one of the best accommodations we have stayed in!

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
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.

Ginestra: Private Pool Overlooking Florence
Rafaella's place was nothing short of amazing! We had such a great time her place had everything you could need and more. She and her husband were super responsive. My only wish is that I wish it was warmer so that we could have enjoyed their beautiful outdoor space more. They even gave our girls sweet easter eggs. Thanks for letting us stay in your lovely home.
Quick stats about condo rentals in Siena
Total rentals
240 properties
Nightly prices starting at
$46 AUD before taxes and fees
Total number of reviews
14K reviews
Family-friendly rentals
110 properties are a good fit for families
Pet-friendly rentals
70 properties allow pets
Rentals with dedicated workspaces
150 properties have a dedicated workspace
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- Santa Maria Novella
- Duomo di Firenze
- Ponte Vecchio
- Lake Trasimeno
- 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
- Marina di Grosseto beach
- Kite Beach Fiumara
- Mercato Centrale
- Pitti Palace
- Stadio Artemio Franchi
- Giardino Bardini
- Avignonesi Winery Fattoria Le Capezzine
- Medici Chapels
- Cavallino Matto
- Teatro Verdi
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