An ancient stone tower with a view of rolling hills and fields in the background.

Roccastrada Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Roccastrada vacation rentals

A courtyard with stone steps leading to a small building, surrounded by lush greenery and stone buildings in the background.

1. Country House il Ciliegio

Country House il Ciliegio
Roccastrada
9.2 out of 10, Wonderful, (7 reviews)
"It was a very pleasant stay, a warm welcome. A beautiful location surrounded by nature."
Netherlands
Maaike
The price is ￥13,624
￥15,338 total
includes taxes & fees
Nov 2 - Nov 3
Country House il Ciliegio
A glass-enclosed structure with a wooden deck, surrounded by various plants and a garden.

2. Agriturismo Benvenuti

Agriturismo Benvenuti
Roccastrada
6.0 out of 10, (3 reviews)
"La stanza era molto grande e tranquilla. C'è anche un giardino abbastanza ampio a disposizione esclusiva di ogni camera/appartamento. Estrema cortesia. Ovviamente si è in aperta campagna, non in vicinanza del mare o dentro un borgo, ma in auto si raggiungo facilmente molte località interessanti del luogo. Su alcuni particolari, potrebbe essere tenuto un po' meglio, ma nel complesso ha un ottimo rapporto qualità/prezzo per la zona."
Italy
Ivano
The price is ￥12,293
￥15,632 total
includes taxes & fees
Oct 27 - Oct 28
Agriturismo Benvenuti
A bedroom with a bed, a bedside table, a TV mounted on the wall, and a sliding glass door leading to a balcony with a view of greenery and hills.

3. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (32 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is ￥9,749
￥13,009 total
includes taxes & fees
Nov 20 - Nov 21
Tuscasì Aparthotel
A narrow hallway with a wooden bench, a radiator, and a wooden cabinet.

4. Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca
Siena City Centre
9.6 out of 10, Exceptional, (222 reviews)
"The room was so unique and convenient for everything we wanted to do. Wish we could have spent more than one night!"
United States
Kellie
The price is ￥17,537
￥19,994 total
includes taxes & fees
Nov 9 - Nov 10
Il Battistero Siena - Residenza d'Epoca
A courtyard with outdoor seating, a building with multiple windows, and a stone wall.

5. Palazzo Saloni

Palazzo Saloni
Montalcino
10.0 out of 10, Exceptional, (14 reviews)
"Excellent location to tour wine country montalcino."
United States
Michael
The price is ￥44,003
￥50,160 total
includes taxes & fees
Nov 1 - Nov 2
Palazzo Saloni
A table set with breakfast items on a balcony overlooking a historic town.

6. Residenza d'Epoca Palazzo Borghesi

Residenza d'Epoca Palazzo Borghesi
Siena City Centre
9.6 out of 10, Exceptional, (135 reviews)
"We had a great stay!"
United States
Suelina
The price is ￥22,046
￥24,954 total
includes taxes & fees
Nov 21 - Nov 22
Residenza d'Epoca Palazzo Borghesi
A table with two wine glasses, a bottle, and a book.

7. Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (101 reviews)
"Very nice place. Nice people, clean and just nice"
Denmark
Leo
The price is ￥10,927
￥12,723 total
includes taxes & fees
Nov 18 - Nov 19
Domus il Palio B&B
A wooden door with a metal handle, a brick archway, a staircase, and a flower pot on the wall.

8. Idolina Guest House

Idolina Guest House
Montalcino
9.6 out of 10, Exceptional, (118 reviews)
"A truly special place!"
United States
Jaiden
The price is ￥13,120
￥15,838 total
includes taxes & fees
Oct 30 - Oct 31
Idolina Guest House
An aerial view of a historic stone building complex with a swimming pool, surrounded by lush greenery and vineyards.

9. Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (187 reviews)
"Very peaceful and scenic. Wish we had stayed longer."
United States
Amir
The price is ￥13,898
￥16,694 total
includes taxes & fees
Nov 1 - Nov 2
Bosco della Spina
A narrow street with buildings on either side, featuring arched windows and a pedestrian walkway.

10. B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (217 reviews)
"Very clean and comfortable, great location and staff"
United States
Heather
The price is ￥11,548
￥13,406 total
includes taxes & fees
Nov 3 - Nov 4
B&B Il Corso
A bathroom with a window view of a historic building and a tiled roof.

11. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (495 reviews)
"Very friendly staff and great location close to the center of town. Breakfast was a nice touch and just what we needed to start the day. Would recommend!"
United States
Jacob
The price is ￥15,722
￥17,997 total
includes taxes & fees
Nov 2 - Nov 3
Siena Vip
A historic building with a clock tower, arched windows, and a shop selling souvenirs.

12. PALAZZO DEL PAPA

PALAZZO DEL PAPA
Siena City Centre
9.6 out of 10, Exceptional, (117 reviews)
"Hamza is so helpful!! Finding the property is a little tricky, but he helped every step of the way! He also provided excellent dining suggestions and a great cooking class!"
United States
Charles
The price is ￥28,360
￥31,899 total
includes taxes & fees
Nov 7 - Nov 8
PALAZZO DEL PAPA
A dining table with a bottle of wine, two wine glasses, a candle, and a vase with flowers.

13. B&B Le Scalette di Piazza

B&B Le Scalette di Piazza
Montalcino
9.4 out of 10, Exceptional, (106 reviews)
"We had a great stay in this conveniently located property. The breakfast was good with many options and staff to assist."
Canada
Morris
The price is ￥18,690
￥21,263 total
includes taxes & fees
Nov 6 - Nov 7
B&B Le Scalette di Piazza
A room with a white wardrobe, a glass-top table, a chair, and a large ornate mirror.

14. B&B Palazzo del Magnifico

B&B Palazzo del Magnifico
Siena City Centre
9.8 out of 10, Exceptional, (76 reviews)
"Wonderful place, great location."
United States
Khaled
The price is ￥15,572
￥17,832 total
includes taxes & fees
Nov 8 - Nov 9
B&B Palazzo del Magnifico
A spacious hotel room with a large bed, a sitting area with chairs, and a view through an arched doorway to another room.

15. La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House
Siena City Centre
9.8 out of 10, Exceptional, (254 reviews)
"Great stay. Thanks for the hospitality and kindness."
United Kingdom
Agnieszka
La Terrazza Sul Campo Rooming House
A large estate with multiple buildings, a swimming pool, and a well-maintained garden.

16. Dimora Santa Margherita - Boutique Hotel

Dimora Santa Margherita - Boutique Hotel
Cinigiano
8.2 out of 10, Very good, (12 reviews)
"We had a great time at this place. The room was spectacular and the views were some of the best on this entire trip. We would definitely come back. The only thing that we didn’t love was the menu at the restaurant is quite limited and there were not many things on the menu that appealed to us, as we were looking for more traditional Tuscan food. Breakfast was great and very traditional. The staff was fantastic and very helpful. Loved it."
Canada
Nicole
The price is ￥47,082
￥52,141 total
includes taxes & fees
Oct 27 - Oct 28
Dimora Santa Margherita - Boutique Hotel
A stone-walled room with a fireplace, a hot tub, candles, and a tray with snacks.

17. Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso

Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
San Quirico d'Orcia
9.0 out of 10, Wonderful, (50 reviews)
"Our stay was great. "
United States
Elena
The price is ￥20,128
￥22,844 total
includes taxes & fees
Nov 9 - Nov 10
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
A pool area with lounge chairs and umbrellas, surrounded by tall cypress trees and a view of distant hills.

18. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.0 out of 10, Wonderful, (103 reviews)
"The variety at the buffet was really good and the coffee machines made really good coffee. The site itself was very nice and well maintained. The problem with this place is the reception for arrival and departure, no service and fast to dismiss you."
Canada
DANIELA
The price is ￥26,710
￥30,084 total
includes taxes & fees
Oct 27 - Oct 28
Casanova - Panoramic Rooms and Suites
A rectangular pool with a metal ladder, surrounded by wooden lounge chairs and a stone deck.

19. Corte Francigena - Apartments

Corte Francigena - Apartments
Montalcino
9.6 out of 10, Exceptional, (22 reviews)
"The unit is very clean, awesome breakfast, beautiful view"
Canada
Ivan
The price is ￥17,873
￥21,066 total
includes taxes & fees
Nov 8 - Nov 9
Corte Francigena - Apartments
An outdoor swimming pool with a wooden pergola, lounge chairs, and a stone wall backdrop.

20. Guild Living Siena Senior Resort & Residence

Guild Living Siena Senior Resort & Residence
Scacciapensieri
8.8 out of 10, Excellent, (60 reviews)
"We booked this last - minute and were really impressed with the whole experience. The property and grounds are beautiful. Staff was so friendly and helpful. The rooms were well appointed and quiet. Beds were too firm for our liking, but it was easy to overlook as the entire stay was really great. Good options in the restaurant too. The block of hotel rooms is in a retirement resort, which I think is a wonderful idea! Very much enjoyed our stay. We had a car and parking was free."
United States
Heidi
The price is ￥18,066
￥20,576 total
includes taxes & fees
Nov 3 - Nov 4
Guild Living Siena Senior Resort & 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.
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Top Roccastrada Hotel Reviews

Palazzo Ravizza

Palazzo Ravizza

10/10 Excellent
"Beautiful hotel close to the historic town center and Il Campo. Nice restaurant, bar, lobby, and beautiful garden area which offers fantastic sunset views. Room was very nice as well. A lovely place to stay in Siena."
James 2-night trip
Posted 6 hours ago
Palazzo Ravizza

Find out more about Roccastrada

Search for holiday rentals in Roccastrada on Expedia! You can easily find your home rentals, villas, holiday apartments in Roccastrada using one of the methods below:

  • View our selection of featured holiday rentals in Roccastrada
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Look no further and take a look at our great range of rental properties in Roccastrada!

Frequently asked questions

Can I find vacation rentals in Roccastrada?

Yes, we give you a choice of vacation rentals close to well known points of interest in Roccastrada, or you can choose a secluded option if you're looking for a relaxing stay.

What are some of the best vacation home rentals that Roccastrada has to offer?

Casa Viale Italia - homely house with direct access to the sandy beach: This vacation home rental near Roccastrada is located near the beach and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Roccastrada?

Choose from 77 Expedia vacation rentals in Roccastrada for a memorable vacation.

What’s there to see and do in Roccastrada?

I Canaloni del Torrente Farma and Val di Merse are a couple of lovely local spots to get outside and enjoy nature. Podere Ristella Vineyards and Winery and Castello del Belagaio are other places to visit while you're in town.

What’s a vacation rental in Roccastrada like?

Vacation rentals are private properties where you can stay for several days or longer in Roccastrada. Vacation rentals provide amenities like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, vacation rentals can provide a sense of privacy away from shared hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a great option for family trips or small group gatherings.