Val d'Orcia Vacation Rentals from CA $108: Short-Term Rentals for 2026

Rolling hills, a vineyard, and a historic building on a hill.

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Our top choices for Val d'Orcia vacation rentals

A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

1. Hotel San Gregorio

Pienza

Michael

CA $221 total

includes taxes & fees

Nov 16 - Nov 17

A patio area with outdoor seating, potted plants, and a view of the landscape.

2. Affitacamere Maria Gabriella

Pienza

Janine und Thomas

CA $200 total

includes taxes & fees

Nov 22 - Nov 23

A poolside area with two glasses of water, candles, and a stone pathway.

3. Casanova - Panoramic Rooms and Suites

San Quirico d'Orcia

Oscar

CA $283 total

includes taxes & fees

Nov 18 - Nov 19

A wooden door with a metal handle, a brick archway, a staircase, and a flower pot on the wall.

4. Idolina Guest House

Montalcino

Jaiden

CA $142 total

includes taxes & fees

Dec 9 - Dec 10

A balcony with a metal railing, a small table with a chair, potted plants, and a view of the sea.

5. PienzaLettings Suites

Pienza

Pearlyn

CA $136 total

includes taxes & fees

Dec 10 - Dec 11

A stone-walled room with a large bathtub, a fireplace, and a set of stone steps leading to the tub.

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

San Quirico d'Orcia

Elena

CA $149 total

includes taxes & fees

Nov 26 - Nov 27

A dining table with a bottle of wine, two wine glasses, a candle, and a vase with flowers.

7. B&B Le Scalette di Piazza

Montalcino

Morris

CA $190 total

includes taxes & fees

Nov 16 - Nov 17

A stone building with a courtyard, outdoor seating, and a warm light setting.

8. Sarna Residence

San Quirico d'Orcia

Bokang

CA $189 total

includes taxes & fees

Nov 16 - Nov 17

A restaurant with tables and wicker chairs, large windows, and a view of buildings and greenery.

9. Palazzo Saloni

Montalcino

Michael

CA $414 total

includes taxes & fees

Dec 15 - Dec 16

A rectangular pool with a metal ladder, surrounded by wooden lounge chairs and a stone deck.

10. Corte Francigena - Apartments

Montalcino

Ivan

CA $192 total

includes taxes & fees

Nov 16 - Nov 17

A bedroom with a brick archway, a bed with white linens, a small table with a magazine, and a painting on the wall.

11. TuscanyLettings Studio&Room

Pienza

Lucas

CA $126 total

includes taxes & fees

Dec 9 - Dec 10

A stone building with a wooden door, a staircase, and a small window with a metal grill.

12. Casa Gioia - Casa Olivieri

Pienza

Nancy

CA $134 total

includes taxes & fees

Dec 8 - Dec 9

A two-story building with a stone facade, a wooden door, and shutters on the windows. There are potted plants in front of the entrance.

13. SUITE WINE - Relax and Create in the Heart of Valdorcia

San Quirico d'Orcia

priscilla e.

CA $190 total

includes taxes & fees

Nov 16 - Nov 17

A stone building with a wooden door and two windows with shutters.

14. A Casetta di Brunello, tranquil and with breathtaking views.

Montalcino

MICHAEL H.

CA $293 total

includes taxes & fees

Nov 16 - Nov 17

A narrow stone alley with potted plants and benches.

15. Alice's House, charm and relaxation

Montalcino (SI)

Robert S.

CA $302 total

includes taxes & fees

Nov 16 - Nov 17

A kitchen with a granite countertop, a hanging pendant light, and a brick archway.

16. "Il Focolare" Superior Apartment in Monticchiello

Monticchiello

Dan

CA $181 total

includes taxes & fees

Nov 19 - Nov 20

A stone building with a sign reading "Borgo di Mezzo".

17. Casa Gelda, relax with a view.

Castelnuovo dell'Abate

Lisa K.

CA $212 total

includes taxes & fees

Nov 17 - Nov 18

A swimming pool with lounge chairs and umbrellas, surrounded by stone walls and tall trees.

18. Apartment 'La Casina' with Shared Pool, Wi-Fi and Air Conditioning

Castiglione d'Orcia

Anonymous traveller

CA $247 total

includes taxes & fees

Nov 20 - Nov 21

A bedroom with a bed, a desk, and a chair. There is a wooden ceiling and a window.

19. The house in the village - Apartment Angelica - Val d'Orcia

Monticchiello

Melissa B.

CA $172 total

includes taxes & fees

Nov 16 - Nov 17

A narrow alleyway with stone walls, potted plants, and a wooden door.

20. Apartment 'La Dimora di Pienza in Val d'Orcia' with Wi-Fi

Pienza

CA $223 total

includes taxes & fees

Nov 17 - Nov 18

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Top Val d'Orcia Hotel Reviews

Relais Val d'Orcia

Pienza

10/10 Excellent

MARC-ANDRE

A rustic stone building with a stone wall and a wooden fence.

Vento Dorcia

Pienza

10/10 Excellent

Robert

A person relaxing in a hot tub with a view of a vineyard and mountains in the background.

Villa Le Prata - Residenza del Vescovo

Montalcino

10/10 Excellent

Karen

An outdoor dining area with white tables and chairs, a white canopy, and a view of a hillside with trees and a building in the background.

B&B Porta Castellana

Montalcino

10/10 Excellent

Everything was perfection. Cant say enough about it. Starting mainly with the owners, Annalisa and Duccio. We have travelled to many destinations across the world. We have never had service to this level. They go above and beyond with exceptional service and truly make you feel like you are right at home and in a beautiful setting. Every detail, from the care and service to the accommodations and fresh delicious breakfasts served daily, is truly extraordinary. We would return with our family any...

William

Palazzo Saloni

Montalcino

10/10 Excellent

Daniel

A hotel room with a large bed, a vanity with a mirror, and a green archway.

Hotel Certosa Di Maggiano

Siena

10/10 Excellent

My husband and I were very impressed as soon as we arrived. Benjamin already knew who we were by names without having to show any booking documents. All staff were extremely professional and friendly greeting us with a smile. They were all very helpful with information like providing tour guidances, places to dine, etc. The whole compound is out of the world. We definitely picked the perfect setting for what we were after, a rustic Tuscany environment. Big enough outside the busy Siena town and...

Louisa

A hot tub with a view of a historic building and mountains.

Casa Franci Montalcino

Montalcino

10/10 Excellent

Emilie

A pool with a tree in the center, surrounded by a deck and a view of hills in the background.

La Posta Hotel & Thermal Spa

San Quirico d'Orcia

10/10 Excellent

Gaeun

A modern hotel room with a bed, two mustard-colored armchairs, a floor lamp, and a flat-screen TV mounted on the wall.

Relais Villa Grazianella - UNA Esperienze

Montepulciano

10/10 Excellent

Despite our updated European GPS, it was really painful trying to find the place, it is in Aquaviva, not in the city of Montepulciano but 20 minutes away. If you are looking for "Via Grazianelle" or "Relais Villa Grazianella", you won't find it. It is part of a complex called Fattoria Del Cerro. Look for that or ask for that instead if you get lost. No signs anywhere, so head for Aquaviva and look for the ICM gas station, and make a right at the gas station, continue up the hill and you'll find...

Anonymous traveller

A spa area with a stone wall, wooden beams, a large window with a view, and a hot tub.

Mastrojanni Relais - Small Luxury Hotels of the World

Montalcino

10/10 Excellent

Zachary

Find out more about Val d'Orcia

Everything you need to know about Val d'Orcia vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Val d'Orcia vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Val d'Orcia vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Val d'Orcia vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Val d'Orcia. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Val d'Orcia vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Val d'Orcia vacation rentals we have selected for you start as low as CA $108 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Val d'Orcia rentals

At Expedia, we put the best Val d'Orcia vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Val d'Orcia rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Val d'Orcia vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Val d'Orcia. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Val d'Orcia Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Val d'Orcia vacation rentals

1. Hotel San Gregorio

2. Affitacamere Maria Gabriella

3. Casanova - Panoramic Rooms and Suites

4. Idolina Guest House

5. PienzaLettings Suites

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

7. B&B Le Scalette di Piazza

8. Sarna Residence

9. Palazzo Saloni

10. Corte Francigena - Apartments

11. TuscanyLettings Studio&Room

12. Casa Gioia - Casa Olivieri

13. SUITE WINE - Relax and Create in the Heart of Valdorcia

14. A Casetta di Brunello, tranquil and with breathtaking views.

15. Alice's House, charm and relaxation

16. "Il Focolare" Superior Apartment in Monticchiello

17. Casa Gelda, relax with a view.

18. Apartment 'La Casina' with Shared Pool, Wi-Fi and Air Conditioning

19. The house in the village - Apartment Angelica - Val d'Orcia

20. Apartment 'La Dimora di Pienza in Val d'Orcia' with Wi-Fi

Find vacation rentals that suit your style

Top Val d'Orcia Hotel Reviews

Relais Val d'Orcia

10/10 Excellent

Find out more about Val d'Orcia

Val d'Orcia vacation rentals: An excellent choice for every season

How to find incredible deals on Val d'Orcia rentals

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