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Condo vacation rentals in Province of Siena

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Popular amenities for Province of Siena condo rentals

Weekly condo rentals

Superhost
Condo in Pergine Valdarno
4.81 out of 5 average rating, 16 reviews

Relaxing holiday, 5 apts +pool among the vineyards

FelixRating, 5 stars10 months ago
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.
Top guest favourite
Condo in Poggibonsi
4.94 out of 5 average rating, 83 reviews

Gallery Apartment near Chianti

MeghanRating, 5 stars2 weeks ago
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!
Guest favourite
Condo in Piazze
4.95 out of 5 average rating, 20 reviews

Canonica, Camporsevoli.

NikolajRating, 5 stars9 months ago
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!❤️
Superhost
Condo in San Gimignano
5 out of 5 average rating, 4 reviews

Apartment Melissa

StéphanieRating, 5 stars83 months ago
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.
Top guest favourite
Condo in Siena
4.86 out of 5 average rating, 343 reviews

Apartment in the heart of Siena

GiedreRating, 5 stars6 months ago
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.
Guest favourite
Condo in Castellina in Chianti
4.79 out of 5 average rating, 325 reviews

relaxation among the vineyards of Chianti1-IlVillinoFarmhouse

AudreyRating, 5 stars4 weeks ago
Loved our stay. Perfect location for vineyard tour
Guest favourite
Condo in Colle di Val d'Elsa
4.86 out of 5 average rating, 106 reviews

Casa Agrestino

ElenaRating, 5 stars4 days ago
The house was very clean, comfortable, equipped with everything and matched the description. Laura was patient and hospitable. We really appreciated the quiet location and the ease in reaching the beautiful places nearby.
Guest favourite
Condo in Castiglione della Pescaia
4.8 out of 5 average rating, 44 reviews

Verdoliva farmhouse, “Leccino” apartment

MelanieRating, 5 stars4 months ago
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

Superhost
Condo in Siena
4.84 out of 5 average rating, 51 reviews

Il Nido

ShawnRating, 5 stars5 months ago
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.
Guest favourite
Condo in Arezzo
4.95 out of 5 average rating, 42 reviews

'Mediterraneo' Cozy two-room apartment with garden

RobertoRating, 5 stars4 months ago
Nice apartment, comfortable and very well equipped. Ideal for those with a small dog. Downtown is within walking distance. Friendly and helpful host.
Guest favourite
Condo in Arezzo
4.86 out of 5 average rating, 93 reviews

Il Piccolo Ristoro

IliasRating, 5 stars1 week ago
Great experience in Arezzo! Great host and impeccable apartment!
Superhost
Condo in Arezzo
4.77 out of 5 average rating, 30 reviews

Cozy house in the vineyard -Fogliadalloro-

DavideRating, 5 stars1 week ago
Beautiful accommodation in the magnificent Tuscan countryside, between vineyards and olive trees. At the same time you are just a few minutes' drive from the beautiful center of Arezzo. Bianca was a very kind, caring and discreet host. Highly recommended!
Top guest favourite
Condo in Siena
4.96 out of 5 average rating, 169 reviews

Elegant vintage decorated home in the old Siena

LaurieRating, 5 stars2 weeks ago
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 !
Superhost
Condo in Laterina
5 out of 5 average rating, 4 reviews

Le Fornaci Holiday Home - Dondo Apartment

AndreaRating, 5 stars2 weeks ago
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
Guest favourite
Condo in San Gimignano
4.83 out of 5 average rating, 228 reviews

Historic centre - cozy apartment

AnneRating, 5 stars1 day ago
We really enjoyed our stay here in San Gimignano. The Airbnb was lovely and was located inside the walls, allowing us to walk anywhere in town in a short period of time. The town itself is very lively and very compact with lots of beautiful sites, restaurants and shops. We liked the character of the town as well as the airbnb. The bed was very comfortable, the shower and washing machine was great and there is a clothesline for your use.
Superhost
Condo in Siena
4.81 out of 5 average rating, 282 reviews

Liberty Siena Flat 2

AgnesRating, 5 stars1 month ago
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

Superhost
Condo in Gambassi Terme
5 out of 5 average rating, 3 reviews

Tuscan Escape with Pool, Close to San Gimignano

AnnaRating, 5 stars8 months ago
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! :)
Guest favourite
Condo in Radda in Chianti
4.84 out of 5 average rating, 88 reviews

💜 "Gaia" at Podere Le Fontanelle

Urte AruneRating, 5 stars1 week ago
Very peaceful and beautiful stay!!
Top guest favourite
Condo in Pieve Vecchia
4.93 out of 5 average rating, 46 reviews

Ebe Rooms - La Cruna Apartment

ElenaRating, 5 stars8 months ago
Gorgeous tranquil place, divine swimming pool and lovely hosts. Would love to stay again!
Guest favourite
Condo in Certaldo
4.81 out of 5 average rating, 85 reviews

Tenuta di Pomine Certaldo (Fi) Edera Apartment

ÉricRating, 5 stars7 months ago
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.
Guest favourite
Condo in Montefollonico
4.88 out of 5 average rating, 59 reviews

Il Chicchino, Swimming Pool, Tennis, Wi-Fi, Park

TravisRating, 5 stars5 days ago
Amazing place to stay if you want peace and quiet! We booked here to break up our highly adventurous, active trip where there was a lot of night life. There are a few fantastic restaurants and bars in the area to go to and the views are very nice. It’s very clean and the bathroom tub and shower are super. The pool was not open because we came little too early in the season but the view and peacefulness was stunning there as well. Highly recommend for anyone who wants peace and quiet!
Superhost
Condo in San Gimignanello
5 out of 5 average rating, 5 reviews

Il Loggiato, 2 bedrooms with a view

LaurenRating, 5 stars7 months ago
Stunning place. Loved the vineyard, olive trees and pool. Exactly what I was looking for in a Tuscan experience!!
Guest favourite
Condo in Castelnuovo Berardenga
4.91 out of 5 average rating, 35 reviews

Beautiful countryside annex with swimming pool!

YoavRating, 5 stars8 months ago
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
Top guest favourite
Condo in Barberino Tavarnelle
5 out of 5 average rating, 27 reviews

Entire house for couple with exclusive pool

RussellRating, 5 stars7 months ago
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.

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