Sassofortino Vacation Rentals

Dates

November 2026

December 2026

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Our top choices for Sassofortino 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

Roccastrada

Maaike

AED 363 total

includes taxes & fees

8 Nov - 9 Nov

A mountainous landscape during sunset with a clear sky.

2. Casa Giovy - A family-friendly village nestled among the hills, the sea, and hot springs in the Tuscan Maremma

Roccastrada

AED 357 total

includes taxes & fees

8 Nov - 9 Nov

An outdoor dining area with stone walls, tables, and chairs.

3. Giacinto – Classic Double Room

Piloni

AED 464 total

includes taxes & fees

9 Nov - 10 Nov

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.

4. Tuscasì Aparthotel

Sovicille

Sergey

AED 305 total

includes taxes & fees

20 Nov - 21 Nov

A person relaxing in a hot tub with a glass of wine.

5. Botrona B&B

Scarlino

Anna

AED 321 total

includes taxes & fees

1 Dec - 2 Dec

A patio with a round table and chairs, a window with blinds, and a view of trees and hills.

6. Panorama-Ferien-Toscana Your vacation home in Tuscany

Massa Marittima

stefano f.

AED 447 total

includes taxes & fees

8 Nov - 9 Nov

A patio with a wooden table, a blue lounge chair, a striped chair, and a large umbrella.

7. Detached house with a garden, just a few minutes from the Abbey of San Galgano

Toscana

Julie M.

AED 467 total

includes taxes & fees

19 Nov - 20 Nov

A stone patio with metal chairs and a table, surrounded by greenery and a stone wall.

8. Holiday Apartment 'Lavanda' with Mountain View, Shared Pool & Wi-Fi

Montieri

AED 642 total

includes taxes & fees

8 Nov - 9 Nov

A restaurant with wooden beams, arched ceilings, and multiple tables with chairs.

9. Room 'Erbe Aromatiche - Poggio Alla Luna' with Wi-Fi

Gerfalco

AED 445 total

includes taxes & fees

8 Nov - 9 Nov

A tree with a swing chair, a clear sky, and a distant tree.

10. Room 'Ghianda' with Shared Garden, Balcony and Wi-Fi

Gavorrano

Anonymous traveler

AED 333 total

includes taxes & fees

8 Nov - 9 Nov

A stone courtyard with a bench, potted plants, and a building in the background.

11. Casa di Campagna in Toscana

Sovicille

Sally

AED 350 total

includes taxes & fees

15 Nov - 16 Nov

A stone building with outdoor seating and string lights.

12. Uva Spina – Intimate Double Room with Val di Farma View

Piloni

AED 520 total

includes taxes & fees

9 Nov - 10 Nov

13. Residence Arianna

Sovicille

Violeta

AED 551 total

includes taxes & fees

9 Nov - 10 Nov

14. Deluxe Room 'Narciso Dei Poeti' with Extra Bed

Piloni

AED 631 total

includes taxes & fees

9 Nov - 10 Nov

A kitchen with a wooden ceiling, a central island with bar stools, a fireplace, and a bookshelf.

15. Holiday Apartment 'Glicine' with Mountain View, Shared Pool & Wi-Fi

Montieri

AED 838 total

includes taxes & fees

8 Nov - 9 Nov

16. Villa Pianosa, Botri dei Lumachi

Toscana

AED 1,142 total

includes taxes & fees

7 Dec - 8 Dec

An infinity pool with a clear view of the sunset and distant mountains.

17. Villa Giglio, Botri dei Lumachi

Toscana

AED 1,142 total

includes taxes & fees

7 Dec - 8 Dec

An outdoor dining area with stone walls and tables, surrounded by potted plants and string lights.

18. Mora Selvatica – Deluxe Room with Private Balcony and Val di Farma View

Piloni

AED 687 total

includes taxes & fees

9 Nov - 10 Nov

A building with arched windows and columns, potted plants on the balcony, and a stone wall.

19. Palazzo Malfatti - Two-room apartment for two people

Massa Marittima

AED 422 total

includes taxes & fees

8 Nov - 9 Nov

An outdoor patio with a wooden floor, a covered seating area, and a view of a green landscape.

20. Farmhouse 'Le Gerlette - La Stalla' with Shared Pool, Wi-Fi and Air Conditioning

Braccagni

AED 465 total

includes taxes & fees

8 Nov - 9 Nov

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Find vacation rentals that suit your style

Top Sassofortino Hotel Reviews

A spacious dining area with a large table and chairs, stone walls, and a view of the mountains.

Valdonica Winery & Vineyard Residence

Roccastrada

10/10 Excellent

Josh

An outdoor dining area with stone buildings, tables with orange tablecloths, and string lights.

Historic Farmhouse Casa del Chiodo

Roccastrada

10/10 Excellent

The Casa Del Chiodo was the perfect Tuscan B&B experience for us. From the moment Marco greeted us to the amazing multiple course evening meal that owner/chef Paola prepared to the breakfast served by Irene, it was the epitome of Italian hospitality. While the evening meal was extra, it was definitely worth it as it showcased local farm grown and hunted/gathered foods (such as mushrooms, venison and roasted chestnuts). Our room was clean, true to historical construction with modern amenities....

Nita Marie

A restaurant with outdoor seating, a bar area, and a view of the landscape.

B&B da Nada Locanda Toscana

Roccastrada

10/10 Excellent

We stayed here for three nights and had an incredible experience. The room was clean, offered a beautiful view, and had reliable Wi-Fi. The location is perfect for exploring, only an hour's drive to Montalcino and incredibly close to several fantastic wineries. The restaurant itself is absolutely fantastic: The panoramic views are amazing, the food is to die for (home cooking style), and the wine selection is excellent. Laura, her husband, and their son, Leonardo, are wonderful, welcoming...

Alexandre

A balcony with a view of a green landscape and a sunset. There are two lounge chairs and a small table with a glass of wine.

Conti di San Bonifacio Wine Resort

Gavorrano

10/10 Excellent

Paul

A rectangular swimming pool with a clear blue water, surrounded by a well-maintained lawn and several lounge chairs.

Antico Casale L'Impostino

Civitella Paganico

10/10 Excellent

Mason

A swimming pool with a waterfall feature, large windows, and a lounge chair.

Montebelli Agriturismo & Country Hotel

Gavorrano

10/10 Excellent

G&J

A stone building with multiple windows and a balcony, surrounded by lush greenery and trees.

Relais Le Macine di Stigliano

Sovicille

10/10 Excellent

Nicholas

A pool with a modern water feature and a stone structure.

Mercure Petriolo Siena Terme Spa Hotel

Civitella Paganico

10/10 Excellent

Anonymous traveler

An outdoor patio with wooden tables and chairs, large windows offering a view of a mountainous landscape.

Agriturismo Giù al Pozzo

Gavorrano

10/10 Excellent

Micaiah

A stone wall with a view of rolling hills and mountains.

Castello Banfi - Il Borgo - Relais et Chateaux

Montalcino

10/10 Excellent

Castello Banfi - Il Borgo is either a great place to anchor your restoration or to invigorate your exploration. There's plenty to do on property: a wine tour through the high-tech wine production facility; wine tasting overlooking the Tuscan landscape (you have a substantial selection to choose from); lounging by the pool overlooking the many acres of grape vines, olive and plum trees, and the hills beyond; a visit to their glass museum; an intimate cooking class with one of the top Chefs in...

Greg

A villa with a swimming pool, surrounded by trees and hills.

Castiglion del Bosco, A Rosewood Hotel

Montalcino

10/10 Excellent

KEDARNATH

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

Valentin Y.

A bedroom with a bed, a chair, a table, and a stone wall.

Dimora delle Muse

Montalcino

10/10 Excellent

Anonymous traveler

A stone building with a pool, lounge chairs, and a garden with flowers.

Podere Brizio

Montalcino

10/10 Excellent

Wonderful, beautiful property! The rooms are immaculate and nicely decorated. Breakfast is bountiful with wonderful homemade tarts, breads, frittatas. Do not miss dining in the restaurant for dinner. We had several dinners among the best of our 3 week trip to Italy. The staff is very professional, friendly and passionate about their job. Thank you Vito and Caterina for going above and beyond expectations and making our stay one I will never forget. We are already planning our return.

Sharon

A large, multi-story residential building with multiple balconies, surrounded by well-maintained lawns and trees.

Il Pelagone Hotel & Golf Resort Toscana

Gavorrano

10/10 Excellent

Matthew

A poolside area with two lounge chairs and a woven ottoman.

Il Burellino Wine & Resort

Montalcino

10/10 Excellent

Tami

Frequently Asked Questions

Can I find a vacation rental in Sassofortino?

Yes, there are vacation rentals close to well known sights in Sassofortino, or you can go with a more secluded option if you're looking for relaxation.

What are some of the best vacation rentals in Sassofortino?

Spacious house between Siena e Firenze with private swimming pool, A/C and Wi-Fi: Visitors like this Sassofortino vacation home rental. It is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill 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. It offers a private balcony, a terrace, and a selection of books so you can immerse yourself in your vacation.

How many vacation rentals will I find in Sassofortino?

Choose from 3 Expedia vacation rentals in Sassofortino for a memorable vacation.

What can I see and do in Sassofortino?

Explore the area and family-friendly sights such as Terme Petriolo, or get out into nature at a spot like I Canaloni del Torrente Farma. Podere Ristella Vineyards and Winery and Abbazia di San Galgano are a couple of places you'll find in the larger area.

What are vacation rentals like in Sassofortino?

Vacation rentals are privately owned properties you can reserve for a few days or a quick weekend in Sassofortino. Vacation rentals feature extras such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a clean environment, vacation rentals can offer a sense of privacy away from shared hotel elevators and busy reception areas 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 a great choice for families.

Sassofortino Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Sassofortino vacation rentals

1. Country House il Ciliegio

2. Casa Giovy - A family-friendly village nestled among the hills, the sea, and hot springs in the Tuscan Maremma

3. Giacinto – Classic Double Room

4. Tuscasì Aparthotel

5. Botrona B&B

6. Panorama-Ferien-Toscana Your vacation home in Tuscany

7. Detached house with a garden, just a few minutes from the Abbey of San Galgano

8. Holiday Apartment 'Lavanda' with Mountain View, Shared Pool & Wi-Fi

9. Room 'Erbe Aromatiche - Poggio Alla Luna' with Wi-Fi

10. Room 'Ghianda' with Shared Garden, Balcony and Wi-Fi

11. Casa di Campagna in Toscana

12. Uva Spina – Intimate Double Room with Val di Farma View

13. Residence Arianna

14. Deluxe Room 'Narciso Dei Poeti' with Extra Bed

15. Holiday Apartment 'Glicine' with Mountain View, Shared Pool & Wi-Fi

16. Villa Pianosa, Botri dei Lumachi

17. Villa Giglio, Botri dei Lumachi

18. Mora Selvatica – Deluxe Room with Private Balcony and Val di Farma View

19. Palazzo Malfatti - Two-room apartment for two people

20. Farmhouse 'Le Gerlette - La Stalla' with Shared Pool, Wi-Fi and Air Conditioning

Find vacation rentals that suit your style

Top Sassofortino Hotel Reviews

Valdonica Winery & Vineyard Residence

10/10 Excellent

Frequently Asked Questions

Can I find a vacation rental in Sassofortino?

What are some of the best vacation rentals in Sassofortino?

How many vacation rentals will I find in Sassofortino?

What can I see and do in Sassofortino?

What are vacation rentals like in Sassofortino?