
Condo holiday rentals in Province of Siena
Find and book unique condos on Airbnb
Top-rated condo rentals in Province of Siena
Guests agree: These condos are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Province of Siena condo rentals
Weekly condo rentals

Relaxing holiday, 5 apts +pool among the vineyards
Beautifully located domain near the tiny Pieve a Presciano with a beautiful view of the village and the surrounding cypresses. The pool is the great asset of this accommodation, cleanly maintained and very large. Furthermore, basic equipped and typical Tuscan, but everything you need is present.

Gallery Apartment near Chianti
We booked our stay at Giuseppe’s place last minute and he was very accommodating. The kitchen was very well equipped for us to prepare our meals and the beds were comfortable. The apartment was squeaky clean!! A short trip to San Gimignano but away from all of the busyness! Highly recommend!

Canonica, Camporsevoli.
No other than Amazing! A hidden gem in the heart of Tuscany. Never have we felt so truly welcome and almost part of the family from day 1. Stunning views from the apartment windows, beautiful and authentic furnitures and cool rooms in the tuscan heat. Many, many, many recommendations from the whole family!❤️

Apartment Melissa
We stayed in the Melissa apartment and it was great, very spacious and bigger than expected. The apartment is self-catering and has all that you need to cook and have a great time. There is no terrace for this apartment, but they are many areas around the property that allow for some outdoor time. The location was beautiful, amazing views, great swimming pool and an overall very relaxed place. The property is 15 mins away from San Gimignano and very close to the bigger towns/villages to visit. Having a car is a must. The staff, the welcome and overall communication was lovely and easy, I would definitely recommend staying here.

Apartment in the heart of Siena
The suite matched the description and photos. Very convenient location - both sights and train station within easy walking distance, right outside the bus stop. Clear check in instructions, hosts send a lot of helpful tips and recommendations of places to visit. The suite maybe a little dark, the windows go out to the backyard, but you can't hear the street noises behind you. We had a good time and we loved it.

relaxation among the vineyards of Chianti1-IlVillinoFarmhouse
Loved our stay. Perfect location for vineyard tour

Casa Agrestino
We had a lovely stay at Laura's. Laura is very considerate and provides everything we may need. The accommodation is well located for visiting San gimigniano or Siena.

Verdoliva farmhouse, “Leccino” apartment
We really enjoyed our stay with Norma. The family is very kind, helpful and warm. We felt very comfortable. Ideal for a stay with a dog. Easy access for shopping by car, to reach the city and close to very beautiful beaches. We were there in winter and it was very cozy. We'd be happy to go back any time.
Pet-friendly condo rentals

Il Nido
There are no better views in Siena as this is possibly the highest flat in the city. Windows on three sides with fantastic scenery out of each. The flat has everything needed for a longer stay. The walk up to the door and the stairs inside could be difficult for some. Good water pressure and fine heat. Come for the views, stay for the life in medieval Tuscany.

'Mediterraneo' Cozy two-room apartment with garden
Nice apartment, comfortable and very well equipped. Ideal for those with a small dog. Downtown is within walking distance. Friendly and helpful host.

Il Piccolo Ristoro
Great experience in Arezzo! Great host and impeccable apartment!

Cozy house in the vineyard -Fogliadalloro-
quiet place both for us and for our dog who immediately made friends with the host's 2 dogs (Bretta and Charly)❤️❤️❤️, we will return as soon as possible!!!

Elegant vintage decorated home in the old Siena
Grazia was a wonderful host ! Very communicative and shared wonderful recommendations! Her home is beautiful and just as the pictures show . Would definitely recommend her home !

Le Fornaci Holiday Home - Dondo Apartment
Very nice location , essential but functional. Great convenience to be able to use the restaurant (with prior reservation). Improvement points, more equipment in the kitchen(cutlery , bottle opener, nothing not recoverable after reporting), the bed pillows are quite uncomfortable. We will gladly return

Historic centre - cozy apartment
We loved our place in San Gimignano. Federico was extremely helpful. We tried not to ask too much of him, but, when we needed something, he was very quick to respond and always quite helpful. The place is lovely ... very clean and comfortable. The washing machine was great, and we enjoyed hanging our laundry out the window, above the road. The location was excellent ... right inside the wall of the old town, at Porta San Matteo. There are many excellent restaurants and gelaterie, and the gelato is amazing. There is a Coop supermarket, not terribly close, but still within walking distance. We highly recommend this apartment, and we would certainly stay there again.

Liberty Siena Flat 2
Perfect apartment in the middle of Siena, a stones throw away from everything you would like to see as a tourist. Great, helpful and communicative host who went out of her way to make sure we had a great stay and took the time to give personal tips. ❤️ A few things in the apartment description did not quite match – the apartment is not on the ground floor but on the first floor (it matters to us traveling with a stroller and had to fold up and carry it up the stairs), and the free parking refers to the free parking spaces that can be found around town. Those are small things in the context - overall we were super happy with both accommodation and host!
Condo rentals with a pool

Tuscan Escape with Pool, Close to San Gimignano
Small and cozy apartment with an amazing pool. The apartment was clean and had everything we needed for the vacation. Francesca gave us some tips for restaurants near the apartment and in San Gimignano which was very nice. We had a very pleasant stay, thank you Francesca and Mauro! :)

💜 "Gaia" at Podere Le Fontanelle
Very peaceful and beautiful stay!!

Ebe Rooms - La Cruna Apartment
Gorgeous tranquil place, divine swimming pool and lovely hosts. Would love to stay again!

Tenuta di Pomine Certaldo (Fi) Edera Apartment
My family and I really enjoyed our stay in Tuscany at Bettina's. The place was very cozy and quiet. This apartment has two terraces, a larger one accessible from the kitchen and one from the bedroom with the double bed. This terrace certainly has the best view of the three apartments offered for rent. Bettina was very nice and easily reachable on the AirBNB app. You have to be careful to take the route indicated by Bettina to get to the accommodation without going through a private road that is more difficult to access. On the right path, the view along the way is stunning. The accommodation is near Certaldo with everything you need. The accommodation must be very nice for a longer stay in summer with the pool.

Il Chicchino, Swimming Pool, Tennis, Wi-Fi, Park
We thoroughly enjoyed our stay at Daphne's place. It is set amongst beautiful manicured gardens, a large pool (which was covered due to seasons end), a tennis court and the views across the Tuscan landscape are incredible. The apartment itself was immaculate and looked better than the photos. It is well appointed, spotlessly clean and modern. We found Montefollonico to be quieter than other tourist destinations and it's a short walk/drive from the residence. It too is beautiful and charming. There's only one Grocery store specializing in Tuscan products and more, It catered for pretty much all we needed. There's also a pharmacy, a quaint bar and a restaurant that was surprisingly good, and the owner is quite the character, in a good way :). Montepulciano is a short 15 or so minute drive away. Having a car is a must unless you just want to spend quality time away from everything and relax in a most beautiful, tranquil and private setting. Thank you Daphne, we loved our stay.

Il Loggiato, 2 bedrooms with a view
Stunning place. Loved the vineyard, olive trees and pool. Exactly what I was looking for in a Tuscan experience!!

Beautiful countryside annex with swimming pool!
Our stay at Fiamma's agritourism farmhouse near Siena was absolutely incredible. The location is like something out of a dream—surrounded by stunning landscapes that make you feel like you're in a postcard. The house itself is beautiful, with cozy, well-appointed rooms that made us feel right at home. Our kids had a blast, especially with the swimming pool overlooking vineyards, which was perfect for relaxing after a day of exploring the Tuscan countryside. Fiamma and her husband were fantastic hoss, always making sure we had everything we needed. We couldn't have asked for a better experience, and we can't wait to return

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.
Destinations to explore
- Farmstay rentals Province of Siena
- Loft rentals Province of Siena
- Luxury rentals Province of Siena
- Rentals with a balcony Province of Siena
- Hotel rentals Province of Siena
- Barn rentals Province of Siena
- Nature eco lodge rentals Province of Siena
- Pet-friendly rentals Province of Siena
- Waterfront rentals Province of Siena
- Villa rentals Province of Siena
- Rentals with a fire pit Province of Siena
- Rentals with a washing machine and dryer Province of Siena
- Rentals with lake access Province of Siena
- Fitness-friendly rentals Province of Siena
- Holiday home rentals Province of Siena
- Private suite rentals Province of Siena
- Tiny house rentals Province of Siena
- Apartment rentals Province of Siena
- Rentals with a kayak Province of Siena
- Smoking-friendly rentals Province of Siena
- Guesthouse rentals Province of Siena
- Bed and breakfasts Province of Siena
- House rentals Province of Siena
- Rentals with breakfast Province of Siena
- Rentals with a sauna Province of Siena
- Kid-friendly rentals Province of Siena
- Boutique hotel rentals Province of Siena
- Rentals with an accessible height bed Province of Siena
- Rentals with an EV charger Province of Siena
- Castle rentals Province of Siena
- Serviced apartment rentals Province of Siena
- Rentals with a fireplace Province of Siena
- Rentals with outdoor seating Province of Siena
- Family-friendly rentals Province of Siena
- Rentals with a hot tub Province of Siena
- Townhouse rentals Province of Siena
- Cottage rentals Province of Siena
- Rentals with pools Province of Siena
- Rentals with a patio Province of Siena
- Condo rentals Tuscany
- Condo rentals Italy
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Santa Maria Novella
- Duomo di Firenze
- Ponte Vecchio
- Lake Trasimeno
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mugello Circuit
- Basilica of Santa Maria Novella
- Fortezza da Basso
- Uffizi Gallery
- CavallinoMatto
- Piazzale Michelangelo
- Parco delle Cascine
- Marina di Grosseto beach
- Piazza della Repubblica
- Stadio Artemio Franchi
- Pitti Palace
- Kite Beach Fiumara
- Mercato Centrale
- The Boboli Gardens
- Cavallino Matto
- Teatro Tuscanyhall
- Teatro Verdi
- Palazzo Vecchio
- Basilica di Santa Croce
- Things to do Province of Siena
- Food and drink Province of Siena
- Sports activities Province of Siena
- Nature and outdoors Province of Siena
- Sightseeing Province of Siena
- Art and culture Province of Siena
- Tours Province of Siena
- Things to do Tuscany
- Food and drink Tuscany
- Nature and outdoors Tuscany
- Art and culture Tuscany
- Sports activities Tuscany
- Sightseeing Tuscany
- Tours Tuscany
- Entertainment Tuscany
- Wellness Tuscany
- Things to do Italy
- Art and culture Italy
- Nature and outdoors Italy
- Wellness Italy
- Tours Italy
- Sightseeing Italy
- Food and drink Italy
- Entertainment Italy
- Sports activities Italy