Skip to main content

Featured vacation rental destinations

Destination inspiration for your trip – find a vacation rental

Siena

384 vacation rentals

San Gimignano

247 vacation rentals

Montepulciano

195 vacation rentals

Gaiole in Chianti

128 vacation rentals

Montalcino

96 vacation rentals

Pienza

81 vacation rentals

Castellina in Chianti

68 vacation rentals

Rapolano Terme

61 vacation rentals

Poggibonsi

61 vacation rentals

Castelnuovo Berardenga

59 vacation rentals

Radda in Chianti

58 vacation rentals

Castiglione dʼOrcia

48 vacation rentals

San Quirico dʼOrcia

47 vacation rentals

Monteriggioni

44 vacation rentals

Asciano

43 vacation rentals

Sarteano

39 vacation rentals

The best vacation rentals in Siena Area

Check out our selection of great vacation rentals in Siena Area

Filter by:

Star Rating
Review score

b&b BORGO CAPITANO COLLECTION Albergo diffuso, Village Experience - Centro Storico

San Quirico dʼOrcia

B&b BORGO CAPITANO COLLECTION Albergo diffuso, Village Experience - Centro Storico features air-conditioned rooms in San Quirico dʼOrcia.

D
Diego
From
Mexico
Andrea was amazing and very kind and helpful.
Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 1,092 reviews
Price from
$226.64
1 night, 2 adults

Il giardino di Pantaneto Residenza D'Epoca

Siena City Centre, Siena

In the heart of Siena, Il giardino di Pantaneto Residenza D'Epoca offers rooms with free Wifi.

C
Carmen
From
Puerto Rico
Location, security, customer service
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 1,849 reviews
Price from
$122.76
1 night, 2 adults

Rooms and Wine al Castello

Monteriggioni

Featuring city views, Rooms and Wine al Castello in Monteriggioni offers accommodations and a shared lounge.

A
Alessandro
From
Italy
Monteriggioni is a location that still maintains its magic from the old times. Rooms and wine at castello offers the best location right over the main square. They bring you fresh breakfast to your room every morning. Highly recommended. They also offer a bar with wine tasting and their own cocktails.
Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 1,042 reviews
Price from
$145.85
1 night, 2 adults

B&B Il Corso

Siena City Centre, Siena

Just 131 feet from Siena’s Piazza del Campo, B&B Il Corso is located on the first floor of a 16th-century building. It offers free Wi-Fi and elegant rooms.

E
Eliud
From
Puerto Rico
The location was excellent with a short walking distance to everything. The room was super clean and beautifully decorated. The staff was super friendly and helpful, gave us helpful tips on where to eat and what to do.
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 1,228 reviews
Price from
$254.19
1 night, 2 adults

Casa Di Campagna In Toscana

Sovicille

Set 5.6 mi from Siena, this 19th-century country house features a restaurant and outdoor pool. It offers traditional Tuscan rooms with wood-beamed ceilings, surrounded by sunflower fields.

M
Monika
From
Switzerland
Fantastic staff, wonderful restaurant, free bikes, quiet location, very clean
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 1,130 reviews
Price from
$111.01
1 night, 2 adults

Villa Nottola

Montepulciano

Villa Nottola is a former noble residence in the countryside of Montepulciano, besides the namesake winery. It offers a sun terrace with swimming pool.

T
Tereza
From
Denmark
Very nice area. Very helpful staff and a nice restaurant! Very nice place for a weekend getaway!
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 2,070 reviews
Price from
$181.82
1 night, 2 adults

B&B San Francesco

Siena City Centre, Siena

Set in a 15th-century building in the historic center of Siena, B&B San Francesco is just opposite the Bruco Fountain, a 5-minute walk from Piazza del Campo. All rooms offer city views and free WiFi.

M
Maria Lucia
From
Costa Rica
Roberto was so kind and helpful, the bed was very comfortable and the breakfast was great.
Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 1,620 reviews
Price from
$74.96
1 night, 2 adults

Borgo Grondaie

Siena

Borgo Grondaie is a large property built out of an old Tuscan farm, just 1.2 mi from the historical center of Siena.

B
Balazs kcs
From
Poland
Very unique stay with a fantastic pool overlooking the old town.
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 1,921 reviews
Price from
$90.30
1 night, 2 adults

Agriturismo San Sano

Gaiole in Chianti

Agriturismo San Sano offers a solarium and air-conditioned accommodations in Gaiole in Chianti, 15 miles from Piazza del Campo. This property offers a pool with a view and free private parking.

J
Justin W
From
Belgium
We absolutely loved this place! My family stayed in two rooms: one superior room with a terrace overlooking the vineyard, and one in the tower. It was incredible. The tower rooms actually let you see into the bird nests of the old dovecote. Breakfast was amazing, huge, and so delicious! Everything is local or from Italy. Just so good. Their wine is also exceptional. They even do a spritz with their vin santo!
Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 1,131 reviews
Price from
$137.35
1 night, 2 adults

Casa nel centro storico

San Gimignano City Centre, San Gimignano

Casa nel centro storico is a recently renovated apartment in the center of San Gimignano, 24 miles from Piazza Matteotti and 27 miles from Piazza del Campo.

A
Amanda
From
United States
The property was super clean and stocked with everything anybody could need. Our host had great communication and I felt right at home. Check-in was also really easy.
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 129 reviews
Price from
$253.92
1 night, 2 adults
All vacation rentals in Siena Area

Most booked vacation rentals in Siena Area this month

See all

Popular with guests booking vacation rentals in Siena Area

Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 2,895 reviews

Popular with guests booking vacation rentals in Siena Area

Scored out of 10, guest rating 8.3
Very Good - What previous guests thought, 1,453 reviews

Popular with guests booking vacation rentals in Siena Area

Scored out of 10, guest rating 5.8
Fair - What previous guests thought, 1,536 reviews

Popular with guests booking vacation rentals in Siena Area

Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 114 reviews

Popular with guests booking vacation rentals in Siena Area

Scored out of 10, guest rating 8.2
Very Good - What previous guests thought, 1,341 reviews

Popular with guests booking vacation rentals in Siena Area

Scored out of 10, guest rating 9.9
Exceptional - What previous guests thought, 406 reviews

Popular with guests booking vacation rentals in Siena Area

Scored out of 10, guest rating 8.9
Excellent - What previous guests thought, 1,645 reviews

Popular with guests booking vacation rentals in Siena Area

Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 2,090 reviews

Popular with guests booking vacation rentals in Siena Area

Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 171 reviews

Popular with guests booking vacation rentals in Siena Area

Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 1,831 reviews

FAQs about vacation rentals in Siena Area

Vacation Rentals That Guests Love in Siena Area

See all
Avg. price/night: $169.67
Scored out of 10, guest rating 8.7
Excellent - What previous guests thought, 414 reviews
Beautiful views, very quiet location and comfortable stay. The pool was clean and the small playground on site, as well as the friendly cats kept our 4 year old very entertained. The restaurant at the sister villa was also good. We did self-catering so cannot speak for the breakfasts but the olive oil we bought on site was great!
Guest review bySeemat
Family with young children
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 177 reviews
The beautiful views of vineyards and hills, we felt very welcome and on vacation. The appartment on two storeys was well decorated and the swimming pool very refreshing with a stunning view. Wow Tuscany at its best. The owners and their friendly dog were also nice. The village is closeby to get the grocery and that's where you do the check-in before arrival.
Guest review byCaroline
Young couple
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 528 reviews
The location of the villa was perfect. The hosts were really kind and helpful.
Guest review byMónika
Young couple
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 273 reviews
Great host, very friendly and excellent service. Beautiful villa, amazing view from breakfast area (breakfast was great as well). Perfect location (close to Montepulciano, Pienza and other cities). Room was spacious, large bathroom/bedroom. highly recommended ! I would definitely return.
Guest review byWim
Young couple
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 101 reviews
Several (small) holiday appartments/houses, offering a lot of privacy though, with nice and authentic decoration, and with airconditioning (a bless with temperatures reaching between 34 and 38°C). Wonderful place to stay, in a huge wild garden on a hill, with a swimming pool, near to the small village of Le Piazze. Very friendly, enthousiastic and helpful hosts, who also provide fresh bread for breakfast.
Guest review byDieter
Young couple
Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 38 reviews
Big and clean swimming pool, well-equipped house, great spot if you want to visit local towns and villages in Toscania. Each family has their own patio and even grill. Great contact with the owned who will respond to all your questions. My tip is to follow Elisa's directions instead of GPS (beacuse of Google Maps, i ended up on impassable, rocky road)
Guest review byJarosław
Family with young children
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 131 reviews
I like from the village to all the detail of the place. The host was so nice and kind that took care of us all the time. Even the restaurant near the place was fantastic!😆
Guest review byHyunkyung
Travelers with friends
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 53 reviews
I loved everything about the villa. It was wonderful. And the hosts - Silvia and her gorgeous mother - were absolutely delightful. I couldn’t fault the beautiful apartment. It’s the best value accommodation I’ve ever booked in all my years of travel. My wife and my daughter feel exactly the same. Can’t wait to come back.
Guest review byScott
Family with young children
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 157 reviews
Great place on the ground floor. Large bedrooms, nice bathroom. A quiet place during the whole day . Excellent base point for exploring nearby towns and villages. Easy communication with Alessandro who gave us complete and detailed instructions regarding our stay (parking, keys...) We hope that in some future we will be back to this place.
Guest review byDusan
Family with young children
Avg. price/night: $193.91
Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 1,042 reviews
Wonderfull room and bathroom. Exceptionally clean. Very comfortable beds. Great A/C. Quiet. Excellent location. Provided a good boxed breakfast. Steffano was welcoming and provided a good restuarant recommendation - even made the reservation for us. The room was very well designed - they kept the old charm and had modern equipment/facilities. It was wonderful to stay inside a walled village. Would highly recommend.
Guest review byAkil
Family with young children