
Condo vacation rentals in Siena
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Top-rated condo rentals in Siena
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Chianti Apartment in 12th Century Tuscan farmhouse
It’s hard to describe just how incredible this place is. The garden is immaculate and pictures cannot do it justice, once you’re immersed in it and you hear the birds and look at the Tuscan scenery, it’s like you’re in a fairy tale. The owners have clearly worked incredibly hard to make this everything that it is, and my wife and I would easily plan our next trip around this place with more time here. The owners are also incredibly friendly and responsive, they welcomed us in and walked us around the property, gave us great recommendations for the surrounding area, loaned us an umbrella, and let us play with their dog. Magical experience and I cannot recommend it enough. We even saw fireflies!

Amaryllis House
very nice and cozy house, well equipped and very clean. Lisa was very nice and helpful, always timely in responding to messages. Very different experience from the cold and "industrial" BnBs that are increasingly frequently found... it's a real home!

Apartment in Florence, Italy
Very cozy and safe home. We took the tram from the airport and Eugenia gave us directions on the easiest way to get to the apartment from the recommended stop. She explained and show how the multiple doors locks to the apartment and made sure we were able to open everything. She also provided a book with instructions on how to use the washer and food recommendations in the area. The bus stop is really close (5 min walk) and the train station is also a 15 minute walk away. At night it was pretty quiet and the bed was really comfy.

The View of Sangiorgio
This is the second time I have stayed at this Airbnb. Mattia is a consummate host. He responds quickly and is always pleasant. The apartment and especially the terrace are phenomenal. I hate to give it such high marks because everybody is gonna wanna steal it from me! But it is a well-deserved high recommendation.I really love this place and it feels like my second home.

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 ❤️

DorminColle - Tuscan-style apartment
This place is great, I strongly recommend it. The hosts are also amazing. We stayed while doing a bike trip around Tuscany and the hosts allowed us to store our bikes in their garage.

"Dimora Valinda" Montepulciano Piazza Grande +A/C
We had the best time!! The cutest little apartment with a nice little balcony. Loved the exposed beams and the kitchen. It was very walkable to great restaurants and scenic views, also far enough away were you are not worried about noise at night. Host was super responsive and had excellent recommendations on where to eat and what to do!

Il Vecchio Noce
A super nice place to stay. The way there is a bit adventurous and not recommended for low-riding vehicles, but otherwise doable if you drive slowly. But it's also totally quiet there. The cottage is nicely furnished. Everything important was available and Alessandro even greeted us with a bottle of wine. The bed and pillows are extremely comfortable. Somewhat disturbing is the squeaky gas heater and the fact that the water temperature in the shower fluctuated quite a bit. Maybe it can still be repaired. But that's whining at a high level. All in all, a great place to stay with a very nice and accommodating host.
Pet-friendly condo rentals

Apartment "Il Teatro" - Prato historic center
Sandra was the best. She was a great host, always responsive and has such a lovely place. I have stayed in 4 other places in Prato and this is the best! Thank you Sandra!

A View Over Tuscany's Countryside
We spent 8 days in Filippo's apartment and explored Tuscany. Our destinations were relatively centrally accessible. That's why we chose this place. Beautiful Tuscan-style apartment that leaves nothing to be desired. There is everything you need. We were also able to use the small cozy terrace in front of the entrance more often! The car is safe in the locked courtyard and there are also shopping facilities nearby. Upon our arrival, Filippo was personally present and gave us tips and explanations! Our conclusion: Very nice and reliable host and a great place to stay!

Francesco's house
The apartment was great and met all my expectations! It was very clean and comfortable. The location is perfect — close to the city center and just a short walk from charming streets ideal for walking and exploring. The host provided all the information we needed, which made our stay smooth and easy. I would definitely recommend this place and would love to stay here again.

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.

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.

Suite with 3 terraces at Ponte Vecchio
Josephine was extremely proactive with her communication. She provided easy to follow check-in/check-out instructions and was quick to respond to any questions. Check-in was a breeze and we received a quick tour of the place. The AirBnB was exactly like the pictures with a spectacular rooftop view of Florence. The place was spacious and spotless with an extremely comfortable bed and all the needed amenities. This place was hard to leave and has moved to the top of our list for our next trip to Florence.

Historic centre - cozy apartment
We loved staying at Helga and Federico’s apartment! The place was very clean and nearby one of the main gates, with many restaurants, parking options, and things to do. Federico gave us recommendations for places to go, and it is clear he loves this town!

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!
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
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!

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

Casa Rebecca with a small private pool
Amazing place !! It really worth !

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.

Apartment with terrace and stunning view
The apartment was lovely. We stayed there for 6 days from end of May into start of June. The view is incredible and the fact there is a nice balcony and a swimming pool that look over it are a bonus. Raisa was very helpful with suggestions for the area, and they let us do our own thing on the land peacefully. The dogs are very adorable and friendly too! For anyone looking for a peaceful getaway with the occasional trip into Castelina in Chianti (would recommend there are many lovely spots to eat), this is a perfect getaway.

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!

La Casetta
Both Barbara and Andrea were very welcoming and forthcoming when we encountered a hitch in our travel plans. They are unusually friendly, and accommodating hosts. The house is a great base for exploring the surrounding area and is tastefully decorated. Highly recommended!
Quick stats about condo rentals in Siena
Total rentals
240 properties
Nightly prices starting at
G$6,274 GYD 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
- Fortezza da Basso
- Cala Violina
- Parco delle Cascine
- Uffizi Gallery
- Piazzale Michelangelo
- Piazza della Repubblica
- Kite Beach Fiumara
- Marina di Grosseto beach
- Mercato Centrale
- Pitti Palace
- Giardino Bardini
- Stadio Artemio Franchi
- Avignonesi Winery Fattoria Le Capezzine
- Medici Chapels
- Teatro Verdi
- The Boboli Gardens
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