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Villastrada Vacation Rentals

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Our top choices for Villastrada vacation rentals

1. La Piccola Locanda

La Piccola Locanda
Chiusi
8.0 out of 10, Very good, (13 reviews)
"Very homey and wonderful people! We loved the restaurant below."
United States
autumn
The price is CA $158
CA $177 total
includes taxes & fees
Oct 9 - Oct 10
La Piccola Locanda

2. Borgo Dolciano

Borgo Dolciano
Chiusi
9.0 out of 10, Wonderful, (26 reviews)
"Lovely restored Tuscan villa and farmhouse. Very comfortable stay. Felt that the people who run it do so with a lot of heart and style. Great value too. "
Canada
Carla
The price is CA $206
CA $230 total
includes taxes & fees
Sep 10 - Sep 11
Borgo Dolciano

3. Casa Roda – Your Home by Lake Trasimeno, Between Umbria and Tuscany

Casa Roda – Your Home by Lake Trasimeno, Between Umbria and Tuscany
Castiglione del Lago
10.0 out of 10, Exceptional, (1 review)
"Great location in beautiful Tuscany. Very nice host and hospitallity. Would come back again!"
United States
Bin L.
The price is CA $159
CA $232 total
includes taxes & fees
Sep 10 - Sep 11
Casa Roda – Your Home by Lake Trasimeno, Between Umbria and Tuscany

4. Scenic Farmhouse with Pool

Scenic Farmhouse with Pool
Città Della Pieve
9.4 out of 10, Exceptional, (34 reviews)
"Great place for a getaway! The views from the terrace are stunning, and the pool is a real treat"
United States
Anonymous traveller
Scenic Farmhouse with Pool

5. La Locanda Di Cetona

La Locanda Di Cetona
Cetona
8.8 out of 10, Excellent, (8 reviews)
"We arrived quite late, but the staff were friendly, responsive, and very helpful with the self-check-in process. Their support made our arrival easy and stress-free. The room was charming, clean, and well cared for. We also really enjoyed the location and the atmosphere of this little town. Having a café just downstairs for breakfast was a nice bonus. We had a great stay and would be happy to return."
Canada
Ruby
The price is CA $197
CA $216 total
includes taxes & fees
Sep 13 - Sep 14
La Locanda Di Cetona

6. Boutique Apartment Natura

Boutique Apartment Natura
Chiusi
10.0 out of 10, Exceptional, (1 review)
"Great location and very clean!"
Canada
Shelley
The price is CA $119
CA $145 total
includes taxes & fees
Sep 10 - Sep 11
Boutique Apartment Natura

7. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (65 reviews)
"I had a fantastic experience with this place. Great people!!!"
South Korea
Young Rok
The price is CA $155
CA $211 total
includes taxes & fees
Oct 4 - Oct 5
Affitacamere Maria Gabriella

8. Boutique Apartment Eleganza

Boutique Apartment Eleganza
Chiusi Scalo
9.6 out of 10, Exceptional, (5 reviews)
"Amazing apartment!So close to the train!"
United States
Ryan W.
The price is CA $120
CA $146 total
includes taxes & fees
Sep 13 - Sep 14
Boutique Apartment Eleganza

9. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (109 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 CA $117
CA $135 total
includes taxes & fees
Sep 13 - Sep 14
Residenza Fabroni

10. Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (140 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 CA $185
CA $210 total
includes taxes & fees
Sep 11 - Sep 12
Bed & Breakfast Vicolo dell'Oste

11. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.6 out of 10, Exceptional, (117 reviews)
"It was very well located ."
Canada
Marlenne
The price is CA $228
CA $258 total
includes taxes & fees
Sep 19 - Sep 20
Meublé Il Riccio

12. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (147 reviews)
"Incredible views from our room"
United Kingdom
Isabelle
The price is CA $302
CA $339 total
includes taxes & fees
Oct 8 - Oct 9
La Locanda di San Francesco

13. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (43 reviews)
"Room, location, staff - it was perfection. We can not wait to return."
United States
Denise
The price is CA $244
CA $275 total
includes taxes & fees
Sep 10 - Sep 11
Delcorto Suites

14. Spacious apartment with all amenities - short distance from Castiglione del Lago

Spacious apartment with all amenities - short distance from Castiglione del Lago
Macchie
9.0 out of 10, Wonderful, (2 reviews)
"The apartment was just like the website. The family were welcoming and helpful. Communication with Veronica was quick. Overall we were extremely satisfied and would definitely stay there again "
Canada
Lisa S.
The price is CA $128
CA $192 total
includes taxes & fees
Sep 29 - Sep 30
Spacious apartment with all amenities - short distance from Castiglione del Lago

15. Villa on the Umbria-Tuscany border—for families and friends—with a private pool

Villa on the Umbria-Tuscany border—for families and friends—with a private pool
Città della Pieve
10.0 out of 10, Exceptional, (57 reviews)
"Stunning views and great location to see so much. The villa housed all my 16 guests comfortably. The large shared kitchen and the terrace were our favorites spots, plus the dimly lit living area was also a great gathering area. MariaLaura was very responsive to any issues we had. Would definitely stay again"
United States
Kim B.
The price is CA $962
CA $1,082 total
includes taxes & fees
Oct 6 - Oct 7
Villa on the Umbria-Tuscany border—for families and friends—with a private pool

16. Renovated flat with panoramic view-Casa Olivazzo

Renovated flat with panoramic view-Casa Olivazzo
Chiusi
The price is CA $182
CA $222 total
includes taxes & fees
Oct 3 - Oct 4
Renovated flat with panoramic view-Casa Olivazzo

17. Il Tosco

Il Tosco
Montepulciano
10.0 out of 10, Exceptional, (131 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 CA $422
CA $471 total
includes taxes & fees
Sep 24 - Sep 25
Il Tosco

18. Eagle House

Eagle House
CHIANCIANO
10.0 out of 10, Exceptional, (3 reviews)
"Paolo and Monica were such gracious and enthusiastic hosts. The property is beautiful, and the hospitality was great. Paolo and Monica helped plan our itinerary each day which made for a stress-free week. The highlight was the interaction with owls, eagles, and other animals, as well as the wine cave and the history behind it. Thanks again, Paolo and Monica! "
United States
Rob C.
The price is CA $317
CA $455 total
includes taxes & fees
Sep 10 - Sep 11
Eagle House

19. Casale dell'Assiolo

Casale dell'Assiolo
Castiglione del Lago
The price is CA $168
CA $191 total
includes taxes & fees
Sep 13 - Sep 14
Casale dell'Assiolo

20. 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 CA $194
CA $218 total
includes taxes & fees
Oct 4 - Oct 5
Abbadia Sicille Relais
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 Villastrada Hotel Reviews

Find out more about Villastrada

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Villastrada. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Villastrada?

Yes, we give you a choice of vacation rentals close to popular attractions in Villastrada, or you can go with a more remote option if you're looking for relaxation.

What are some of the best vacation home rentals in Villastrada?

Villa with private pool, air conditioning in Val d'Orcia. Very quiet place!!!: This vacation home rental outside of Villastrada is located in a rural location and has an outdoor pool, a patio, and air-conditioning to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the garden in this rental home to help you unwind.

What’s there to see and do in Villastrada?

Explore the area and family-friendly sights such as Centro Servizi Turistici Citta della Pieve, or get out into nature at a spot like Lake Trasimeno. In the larger area, you’ll find Terme Sant'Elena and Isola Maggiore.

What’s a vacation rental in Villastrada like?

A vacation rental is a private property you can stay in for several days or longer in Villastrada. Vacation rentals feature extras such as patios, hot tubs, and fire pits to help you enjoy your stay. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from shared hotel elevators and busy front desks while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for family gatherings.