A historic town with a prominent tower and a rainbow arching over it.

Vacation Homes in Province of Siena

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sep - 13 Sep
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Top Cities in Province of Siena

A historic square with a prominent tower and statues.
Vacation HomesVacation Homes

Pienza

Pienza

Our top choices for Province of Siena vacation homes

Deluxe Apartment | Premium bedding, down comforters, in-room safe, desk

Borgo Argiano

Borgo Argiano
Castelnuovo Berardenga
10.0 out of 10, Exceptional, (85 reviews)
"Amazing staff, clean room, amazing pool!"
United States
Blake
Borgo Argiano
Premium Apartment, 2 Bedrooms, 2 Bathrooms, Annex Building | Lanai

Il Palazzetto

Il Palazzetto
Siena
9.6 out of 10, Exceptional, (7 reviews)
"Endroit agréable, idéal pour visiter Sienne à moins de 10mns en voiture et rayonner dans la région."
France
Francois
Il Palazzetto
TV, fireplace, DVD player, table tennis

Idyllic guest house in Tuscan country house style with swimming pool

Idyllic guest house in Tuscan country house style with swimming pool
Sinalunga
10.0 out of 10, Exceptional, (28 reviews)
"Great place to be, lovely dogs"
Germany
Holger M.
Idyllic guest house in Tuscan country house style with swimming pool
Property grounds

The House of Alice, charm and relaxation

The House of Alice, charm and relaxation
Montalcino (SI)
9.8 out of 10, Exceptional, (75 reviews)
"Lovely charming home and town"
United States
Dana S.
The House of Alice, charm and relaxation
Property grounds

Old Tuscan house in the medieval village of Castiglione d'Orcia

Old Tuscan house in the medieval village of Castiglione d'Orcia
Castiglione d'Orcia
9.2 out of 10, Wonderful, (21 reviews)
"Great location"
United States
Bei
Old Tuscan house in the medieval village of Castiglione d'Orcia
Interior

Esclusivo per te

Esclusivo per te
COLLE VAL D' ELSA
9.8 out of 10, Exceptional, (15 reviews)
"All you need is available, peacefull and quiet."
Netherlands
Emile G.
Esclusivo per te
Outdoor dining

HOUSE WOW panoramic terrace *.*

HOUSE WOW panoramic terrace *.*
Siena City Centre
10.0 out of 10, Exceptional, (23 reviews)
"Amazing place! Amazing view! Amazing host!"
United States
Mollie H.
HOUSE WOW panoramic terrace *.*
Interior

Sweet home, the home of the small village

Sweet home, the home of the small village
Colle di Val d'Elsa
9.6 out of 10, Exceptional, (11 reviews)
"It is a lovely place to stay and discover Tuscany. The house is clean, big and the pool is great to have a refeshing dive. We enjoyed our stay a lot."
United States
Djip d.
Sweet home, the home of the small village
Smart TV, books

Historic center of Siena: Castellare residence with TV, WI-FI and AIR CONDITION

Historic center of Siena: Castellare residence with TV, WI-FI and AIR CONDITION
Siena City Centre
10.0 out of 10, Exceptional, (25 reviews)
"This place was a dream. The location is outstanding and the quality of everything is superb. The suite is a nice blend of new updates with classic design. I would very happily stay there again. "
Canada
Peter H.
Historic center of Siena: Castellare residence with TV, WI-FI and AIR CONDITION
Exterior

Farmhouse in the heart of the real chiantishire

Farmhouse in the heart of the real chiantishire
Castellina in Chianti
10.0 out of 10, Exceptional, (155 reviews)
"Great farmhouse, wonderful scenery in the vineyards. Great and always helpful host."
United States
Charlotte S.
Farmhouse in the heart of the real chiantishire
Property grounds

Spacious house between Siena e Firenze with private swimming pool, A/C and Wi-Fi

Spacious house between Siena e Firenze with private swimming pool, A/C and Wi-Fi
Radicondoli
9.2 out of 10, Wonderful, (38 reviews)
"Wonderful location. Interesting villa. Beautiful views. Generous owner/manager."
United States
Carol L.
Spacious house between Siena e Firenze with private swimming pool, A/C and Wi-Fi
Smart TV, fireplace

Entire Historic Residence in Tuscany (Val d'Orcia),in the Heart of Montepulciano

Entire Historic Residence in Tuscany (Val d'Orcia),in the Heart of Montepulciano
Montepulciano
9.8 out of 10, Exceptional, (9 reviews)
"Great place great location "
United States
Paul R.
Entire Historic Residence in Tuscany (Val d'Orcia),in the Heart of Montepulciano
Property grounds

Splendid farmhouse in Val d'Orcia with private swimming pool and sauna

Splendid farmhouse in Val d'Orcia with private swimming pool and sauna
Radicofani
10.0 out of 10, Exceptional, (12 reviews)
The price is AED 4,212
AED 5,282 total
includes taxes & fees
15 Aug - 16 Aug
Splendid farmhouse in Val d'Orcia with private swimming pool and sauna
Interior

Domus Nannini SPA - Palazzo Nannini - Loggia Salimbeni

Domus Nannini SPA - Palazzo Nannini - Loggia Salimbeni
Siena City Centre
10.0 out of 10, Exceptional, (25 reviews)
"Perfect location!"
United States
Brent F.
Domus Nannini SPA - Palazzo Nannini - Loggia Salimbeni
Outdoor pool

Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.2 out of 10, Wonderful, (10 reviews)
"Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10. "
United States
Jackie
The price is AED 474
AED 542 total
includes taxes & fees
2 Aug - 3 Aug
Casa Vacanze Le Case
Property grounds

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

Beautiful farmhouse nestled in very sweet hills just a few minutes from Siena
Siena
10.0 out of 10, Exceptional, (16 reviews)
"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!"
United States
Mark C.
Beautiful farmhouse nestled in very sweet hills just a few minutes from Siena
Outdoor pool

Casa Rossella,charming house in historical Chianti Estate ,private pool

Casa Rossella,charming house in historical Chianti Estate ,private pool
San Gusme
10.0 out of 10, Exceptional, (53 reviews)
"Beautiful property. Great for a relaxing time in Tuscany"
United States
Peggy R.
Casa Rossella,charming house in historical Chianti Estate ,private pool
Property grounds

A historic, cozy, quiet, and bright 16th-century house

A historic, cozy, quiet, and bright 16th-century house
Montalcino
10.0 out of 10, Exceptional, (9 reviews)
"Excellent host, clean home, beautifully appointed, and located in the heart of Montalcino. Walkable to grocery store and many restaurants."
United States
Staci L.
A historic, cozy, quiet, and bright 16th-century house
Outdoor dining

Tuscan village in SIena. farmhouse surrounded by garden,pool and panoramic view

Tuscan village in SIena. farmhouse surrounded by garden,pool and panoramic view
Asciano
10.0 out of 10, Exceptional, (44 reviews)
"It was a great location for day trips throughout Tuscany. The pool was awesome addition. Would definitely recommend the place."
United States
Derrick W.
Tuscan village in SIena. farmhouse surrounded by garden,pool and panoramic view
Exterior

Spacious apartment strategically located for visiting Siena and province

Spacious apartment strategically located for visiting Siena and province
Sovicille
9.2 out of 10, Wonderful, (5 reviews)
"Molto simpatico ed accogliente, richieste evase velocemente e molto bene."
Italy
gianluigi v.
Spacious apartment strategically located for visiting Siena and province
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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Top Province of Siena Hotel Reviews

Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent
"Gorgeous hotel, amazing views. Fabulous staff. They made our stay in Siena extra special."
Seth 2-night trip
Posted 1 day ago
Grand Hotel Continental Siena – Starhotels Collezione