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

Vacation Rentals in Province of Siena

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Our top choices for Province of Siena vacation rentals

Exterior

1. Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (139 reviews)
"Wonderful place - clean, comfortable, quiet with excellent hosts. Perfect location near everything in town including the parking. Can’t wait to return!"
United States
Shelly
The price is NT$4,157
NT$4,722 total
includes taxes & fees
Aug 6 - Aug 7
Bed & Breakfast Vicolo dell'Oste
Food court

2. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (146 reviews)
"Lucca was the perfect host, very accommodating to any queries we had and was always willing to help during our stay Couldn’t recommend staying here highly enough - we had a great time staying here and would highly recommend if you are in the area definitely book here"
United Kingdom
Jonathan
The price is NT$4,561
NT$5,167 total
includes taxes & fees
Aug 26 - Aug 27
La Locanda di San Francesco
Interior

3. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.6 out of 10, Exceptional, (115 reviews)
"It was very well located ."
Canada
Marlenne
The price is NT$5,324
NT$6,006 total
includes taxes & fees
Aug 11 - Aug 12
Meublé Il Riccio
Food and drink

4. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (152 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is NT$7,660
NT$8,650 total
includes taxes & fees
Aug 25 - Aug 26
Hotel San Gregorio
Property entrance

5. Il Tosco

Il Tosco
Montepulciano
10.0 out of 10, Exceptional, (130 reviews)
"Beautiful hotel in the best location. We so enjoyed our stay, especially the amazing breakfast and sweets they had available all day long."
United States
Margaret
The price is NT$9,881
NT$11,019 total
includes taxes & fees
Aug 6 - Aug 7
Il Tosco
Terrace/patio

6. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (100 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is NT$3,701
NT$4,146 total
includes taxes & fees
Sep 2 - Sep 3
Palazzo Pacini
Romantic Double Room, 1 Bedroom, Non Smoking | View from room

7. B&B Palazzo Tortoli

B&B Palazzo Tortoli
San Gimignano City Centre
9.2 out of 10, Wonderful, (64 reviews)
"In the center of town overlooking a plaza (other rooms overlook the valley). Multiple museums, and dining and shopping options within very easy walking distance. The town and surroundings are beautiful."
United States
Harold
The price is NT$4,550
NT$5,192 total
includes taxes & fees
Aug 6 - Aug 7
B&B Palazzo Tortoli
Suite Aria | Terrace/patio

8. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (39 reviews)
"Time transported to the Renaissance at this beautiful, well-kept palazzo… Riccardo’s family did a truly amazing job restoring this place and the facilities are modern & without any discomfort."
American Samoa
Melissa Hyun Joo
The price is NT$5,707
NT$6,427 total
includes taxes & fees
Aug 6 - Aug 7
Delcorto Suites
Terrace/patio

9. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (178 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is NT$6,372
NT$7,121 total
includes taxes & fees
Aug 7 - Aug 8
Abbadia Sicille Relais
Standard Double Room (La Piazza) | Desk, soundproofing, WiFi (free), bed sheets

10. B&B Le Scalette di Piazza

B&B Le Scalette di Piazza
Montalcino
9.4 out of 10, Exceptional, (99 reviews)
"Great location, nice room, and great host!"
United States
Chris
The price is NT$4,524
NT$5,126 total
includes taxes & fees
Aug 7 - Aug 8
B&B Le Scalette di Piazza
Exterior

11. Idolina Guest House

Idolina Guest House
Montalcino
9.6 out of 10, Exceptional, (117 reviews)
"This is a wonderful B&B that is part of the historic district. Sloping uneven floors, which is the charm of having the chance to stay in a piece of history. A very comfortable room, with breakfast at a cafe nearby. Parking option is nearby, just talk with your host who is so helpful. Wonderful location to walk and enjoy all the town has to offer."
United States
Sophie
The price is NT$3,026
NT$3,628 total
includes taxes & fees
Aug 18 - Aug 19
Idolina Guest House
Aerial view

12. Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (176 reviews)
"Lovely stay! I would highly recommend this hotel. The indoor pool was just so enjoyable after a day out sightseeing. "
United Kingdom
Lizl
The price is NT$5,190
NT$6,008 total
includes taxes & fees
Aug 31 - Sep 1
Bosco della Spina
Premium bedding, down comforters, pillowtop beds, desk

13. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (29 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is NT$2,427
NT$3,156 total
includes taxes & fees
Aug 9 - Aug 10
Tuscasì Aparthotel
Front of property

14. Podere La Chiusella

Podere La Chiusella
Rapolano Terme
9.4 out of 10, Exceptional, (31 reviews)
"Et sjarmerende lite B&B. Har nok vært utrolig vakkert i sine glansdager, men områdene rundt bærer preg av lite vedlikehold. Leiligheten var helt grei for en overnatting. Gulvet på badet var ikke rent. Når vi tørket opp etter oss ble håndkleet møkkete. Men overnattingen var helt grei alt i alt. Når vi skulle sjekke ut var det ikke et menneske å se, resepsjonen var stengt. Endte med å sette nøklene i døra og dra da alt var betalt ved bestilling."
Norway
Elisabeth
The price is NT$4,899
NT$5,539 total
includes taxes & fees
Aug 25 - Aug 26
Podere La Chiusella
Property entrance

15. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (104 reviews)
"Staff was great, and they even scheduled transportation to and from the train station for us. Great location on the main strip of Montepluciano!"
United States
Nicholas
The price is NT$2,667
NT$3,084 total
includes taxes & fees
Aug 18 - Aug 19
Residenza Fabroni
Lounge

16. Mariani Bed & Breakfast

Mariani Bed & Breakfast
Castellina in Chianti
9.8 out of 10, Exceptional, (17 reviews)
"Very nice and quiet neighbourhood. Close to city centre. The host is very kind."
Japan
Chie
The price is NT$2,975
NT$3,422 total
includes taxes & fees
Aug 6 - Aug 7
Mariani Bed & Breakfast
Suite Bernardo, Panoramica al terzo piano senza ascensore | Terrace/patio

17. PienzaLettings Suites

PienzaLettings Suites
Pienza
10.0 out of 10, Exceptional, (5 reviews)
"Clean room with friendly and helpful staff. Thank you so much for the wonderful stay"
United States
Pearlyn
The price is NT$3,731
NT$4,254 total
includes taxes & fees
Aug 25 - Aug 26
PienzaLettings Suites
Balcony

18. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (109 reviews)
"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "
United States
Angel
The price is NT$3,496
NT$4,966 total
includes taxes & fees
Sep 3 - Sep 4
Palazzo al Torrione 2
Porch

19. Donna Nobile

Donna Nobile
San Gimignano City Centre
8.2 out of 10, Very Good, (166 reviews)
"Very easy checkin, friendly staff. Loved the kitchen area!"
Canada
Treena
The price is NT$2,887
NT$3,363 total
includes taxes & fees
Aug 6 - Aug 7
Donna Nobile
1 treatment room, massages

20. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (93 reviews)
"Very good accommodation in the heart of Val’d’Orcia. Reasonably priced"
Finland
Jarkko
The price is NT$5,991
NT$6,739 total
includes taxes & fees
Aug 31 - Sep 1
Casanova - Panoramic Rooms and Suites
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

Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais

10/10 Excellent
"We spent a wonderful week at Borgo Scopeto and thoroughly enjoyed every minute. It has everything you'd hope for from a luxury Tuscan retreat: beautiful historic buildings, immaculately kept grounds, and a peaceful atmosphere full of character. The staff were warm, attentive and genuinely welcoming without ever feeling intrusive, and the food was consistently excellent. One of the biggest advantages is its location. Siena is only a short drive away - you can even see the city's campanile while having breakfast - so it was easy to combine days by the pool with exploring one of Tuscany's most beautiful cities (and, inevitably, a bit of shopping to keep our teenage daughter happy). A fantastic place to stay, and one we'd happily recommend."
Nicholas 7-night trip
Posted 1 hour ago
Borgo Scopeto Wine & Country Relais

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