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
14 Aug - 16 Aug
In two months
25 Sep - 27 Sep
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 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, (86 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)
"A truly beautiful place. It's quiet and idyllic and feels just like living in Italy. You can spend the day going to places that might have tons of tourists and then come back here to a peaceful beautiful house."
United States
Dean B.
Idyllic guest house in Tuscan country house style with swimming pool
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

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
Interior

Palazzo Tamanti - 4 King BR 6 Bath Estate Home in Montalcino Center

Palazzo Tamanti - 4 King BR 6 Bath Estate Home in Montalcino Center
Montalcino
10.0 out of 10, Exceptional, (3 reviews)
"Absolutely the most stunning VRBO we have ever stayed at. Majestic In both stature and comfort. Every need anticipated and met. Communication with host and Valentina perfect. The standard of luxury located in a fairy tale setting! A must visit - we did not want to leave!! Cannot say enough about this special villa."
United States
Robert K.
The price is AED 2,084
AED 3,700 total
includes taxes & fees
1 Aug - 2 Aug
Palazzo Tamanti - 4 King BR 6 Bath Estate Home in Montalcino Center
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, (156 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
Exterior

Villa Banditello, secluded, panoramic view over Montepulciano valley.

Villa Banditello, secluded, panoramic view over Montepulciano valley.
torrita di siena, fraz. montefollonico
10.0 out of 10, Exceptional, (26 reviews)
"Just amazing. From views of the countryside, to the peaceful surroundings, this home is a one of a kind. We absolutely loved our stay. Highly recommend to ALL!! "
United States
Nicol A.
Villa Banditello, secluded, panoramic view over Montepulciano valley.
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
Outdoor pool

Villa with private pool, air conditioning in Val d'Orcia. Very quiet place!!!

Villa with private pool, air conditioning in Val d'Orcia. Very quiet place!!!
Sarteano
10.0 out of 10, Exceptional, (29 reviews)
"Our stay at the Villa was absolutely perfect for our family and friends. The hosts went above and beyond to make us feel welcome, even surprising us with delightful treats throughout our stay. The Villa's remote location offers breathtaking views and unparalleled privacy, making it an ideal retreat. We can't imagine a better place to stay and wholeheartedly recommend this Villa to anyone looking for a truly exceptional experience!"
Canada
Satish P.
Villa with private pool, air conditioning in Val d'Orcia. Very quiet place!!!
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
Outdoor dining

INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING

INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING
Montepulciano
9.6 out of 10, Exceptional, (89 reviews)
"Loved this property. Right at the edge of town. Beautiful views"
United States
Celya F.
INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING
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)
"We enjoyed a relaxing time at you house. Close to a lot of nearby activities. "
United States
Michael B.
The price is AED 4,176
AED 5,266 total
includes taxes & fees
15 Aug - 16 Aug
Splendid farmhouse in Val d'Orcia with private swimming pool and sauna
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

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
9.4 out of 10, Exceptional, (11 reviews)
"Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10. "
United States
Jackie
The price is AED 453
AED 520 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
3 bedrooms, in-room safe, desk, iron/ironing board

detached villa with private pool and garden

detached villa with private pool and garden
Castellina in Chianti
8.8 out of 10, Excellent, (29 reviews)
"Brilliant location, very easy access to village. Fantastic pool and garden for relaxation both of a very high standard. Check in was easy, kitchen and interior facilities were adequate. "
United Kingdom
Elaine D.
detached villa with private pool and garden
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
"What a wonderful stay right in the cent of siena historic district. really recommend this hotel. Staff are very kind and welcoming."
Suresh 2-night trip
Posted 1 day ago
Grand Hotel Continental Siena – Starhotels Collezione

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