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Compare 109 Vacation Homes in Siena with updated reviews, rates, and availability.

Porcilaia tiny countryside property, shared pool, ideal base to discover Tuscany

10.0 out of 10, Exceptional, (22)
"Lovely place, lovely people, lovely environment "
Porcilaia tiny countryside property, shared pool, ideal base to discover Tuscany

Charming apartment in the Historic Center of Siena

10.0 out of 10, Exceptional, (16)
"Excellent!"
Charming apartment in the Historic Center of Siena

GIULIA -1 Bedroom Country House in Monteriggioni - Siena

10.0 out of 10, Exceptional, (2)
"Ha sido una estancia maravillosa. El lugar estupendo. =)"
GIULIA -1 Bedroom Country House in Monteriggioni - Siena

Beautiful stone house with garden and private pool.

9.6 out of 10, Exceptional, (59)
"Cottage is larger than described and outfitted nicely for a couple. We used the kitchen everyday for meals and while the bed was firm, it wasn’t bad. Directions to there were confusing. Basically, head to To"
Beautiful stone house with garden and private pool.

detached villa with private pool and garden

8.8 out of 10, Excellent, (20)
"We had a wonderful time in the nice little house on the quiet edge of a lively village, with spectacular Tuscany scenery, a super clean pool and friendly and helpful owners. Both Florence and Siena are fully worth a trip, or you just stay at the house for perfect relaxing."
detached villa with private pool and garden

Beautiful house on garden with shared pool just a few minutes Siena Tuscany

10.0 out of 10, Exceptional, (32)
"This is a fantastic place, with lots of space, a wonderful kitchen and amazing views. Wine tasting with Lorenzo was great and the wines are top notch. "
Beautiful house on garden with shared pool just a few minutes Siena Tuscany

Capanna, Typical Tuscan Farmhouse With Fruit Garden

10.0 out of 10, Exceptional, (67)
"Loved our stay the host was fantastic and the property is beyond beautiful. This is a type of place that has spectacular views and a magical atmosphere."
Capanna, Typical Tuscan Farmhouse With Fruit Garden

Federico farmhouse with swimming pool and jacuzzi, panoramic position in Chianti

9.6 out of 10, Exceptional, (65)
"The place is great, large appartement, great surroundings."
Federico farmhouse with swimming pool and jacuzzi, panoramic position in Chianti

Belvilla by OYO Oliveta

8.0 out of 10, Very Good, (2)
"Fantastisch huis, alles wat je nodig hebt, mooi uitzicht, dichtbij de stad"
Belvilla by OYO Oliveta

Domus Nannini SPA - Belvedere Loggia - Palazzo Nannini

10.0 out of 10, Exceptional, (7)
"Great spot to stay when visiting Sienna. Grocery stores near by and lots of recommended restaurants. Our host was easy to get a hold of and his directions for entering were easy to follow as we ended up getting to the place late in the evening."
Domus Nannini SPA - Belvedere Loggia - Palazzo Nannini

Legnaia countryside luxury property, shared pool, ideal base to discover Tuscany

10.0 out of 10, Exceptional, (11)
"Had a great time visiting the area. The home is beautiful. "
Legnaia countryside luxury property, shared pool, ideal base to discover Tuscany

Villa Le Tortore Tuscany private luxury pool relax

10.0 out of 10, Exceptional, (88)
"Loved our 10 days staying here couldn’t fault anything! Amazing location, would love to return."
Villa Le Tortore Tuscany private luxury pool relax

Beautiful farmhouse nestled in very sweet hills just a few minutes from Siena

10.0 out of 10, Exceptional, (13)
"The setting is truly incredible! Stunning views, a well kept and comfortable house to stay in. We spent lots of family time in the pool and loved being just 15 minutes outside of Siena yet feeling so removed from everything. I highly recommend staying here!"
Beautiful farmhouse nestled in very sweet hills just a few minutes from Siena

Farmhouse with beautiful pool and jacuzzi, panoramic location in chianti

9.8 out of 10, Exceptional, (60)
"We spent 3 weeks in Europe from Barcelona to Cadaques to Provence to Cannes to Nice to Monaco to Rome and Castellina in Chianti. Our stay in Stella at this location was our absolute favorite. Federico was very kind kind, greeted us upon arrival, helped us with questions, and gave us suggestions around the area. We highly recommend this place and are already making our plans to return."
Farmhouse with beautiful pool and jacuzzi, panoramic location in chianti

Farmhouse in old mill nestled in the beautiful Chianti hills

8.8 out of 10, Excellent, (16)
"A beautiful place to stay and very friendly hosts; Roberto and Rafaella will do anything to make your stay unforgettable. The house has everything you need and the pool is nice and beautiful. Lots of nice places to visit in the neighbourhood. I can surely recommend this Farmhouse!!!!"
Farmhouse in old mill nestled in the beautiful Chianti hills

Domus Nannini SPA - Palazzo Nannini - Loggia Salimbeni

10.0 out of 10, Exceptional, (17)
"The apartment is very large, beautifully decorated, and is in a fantastic location in Siena. Couldn't be better..... Gianluca was the perfect host. We were very happy!!! Will rent again for sure!!!"
Domus Nannini SPA - Palazzo Nannini - Loggia Salimbeni

L'Oliviera by Interhome

9.6 out of 10, Exceptional, (5)
L'Oliviera by Interhome

Exclusive luxury property with private pool in Siena countryside Borgo la Chiusa

10.0 out of 10, Exceptional, (1)
"Our stay at Borgo la Chiusa was fantastic. Our family of 12 all agreed that the home was more than the pictures and the descriptions could show online. We will come back and stay here again and would also refer this home to all of our family and friends. The location was perfect. We did day trips to many of the cities and towns. We had Francesca prepare us a meal in the home which was delicious. The experience that our children and grand children had watching the meal being prepared was an...
Exclusive luxury property with private pool in Siena countryside Borgo la Chiusa

Casa Chianti Classico Panoramic View, Castellina in Chianti, Italy

Casa Chianti Classico Panoramic View, Castellina in Chianti, Italy

Stunning private villa with WIFI, A/C, TV, terrace, pets allowed, panoramic view and parking

10.0 out of 10, Exceptional, (1)
"Petit appartement confortable avec tous les services. Une vue extraordinaire sur le vallée du Chianti. Près de tout. Très propre. Le village de Castellina a été notre coup de coeur avec d'excellents restaurants. Les petits déjeuners sur la terrasse de l'appartement devant la vallée ont été forts appréciés. Merci à notre hôte."
Stunning private villa with WIFI, A/C, TV, terrace, pets allowed, panoramic view and parking
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Siena

Il Battistero Siena - Residenza d'Epoca

9.6 out of 10, Exceptional, (156)
"Wonderful place. Super helpful staff, perfect location, comfortable and safe."
The price is AED 663
AED 745 total
includes taxes & fees
27 May - 28 May
Il Battistero Siena - Residenza d'Epoca

ApartHotel Anghel

8.2 out of 10, Very Good, (314)
"Nice place, quiet and clean!"
The price is AED 335
AED 385 total
includes taxes & fees
14 Jun - 15 Jun
ApartHotel Anghel

Porta Pispini Residence

2.0 star property
9.6 out of 10, Exceptional, (14)
"A fabulous property - well appointed and equipped. Very modern, clean and quiet. We enjoyed our daily walks into Siena via the Porta Pispini. We would love to stay here again."
The price is AED 482
AED 547 total
includes taxes & fees
18 May - 19 May
Porta Pispini Residence
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.