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Sassofortino Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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

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 CA $121
CA $136 total
includes taxes & fees
Oct 9 - Oct 10
Country House il Ciliegio
A window with a view of a green landscape and a clear sky.

2. Casa Giovy - Relaxation with a view all the way to the sea, in the Tuscan hills

Casa Giovy - Relaxation with a view all the way to the sea, in the Tuscan hills
Roccastrada
The price is CA $123
CA $152 total
includes taxes & fees
Oct 5 - Oct 6
Casa Giovy - Relaxation with a view all the way to the sea, in the Tuscan hills
An outdoor dining area with a table set for two, overlooking a lush green landscape and a hill in the distance.

3. Podere Cascatelle & Agriletizia

Podere Cascatelle & Agriletizia
Massa Marittima
10.0 out of 10, Exceptional, (3 reviews)
"Great for families, convenient parking and facilities, very tranquil."
United States
Ciarán
The price is CA $135
CA $160 total
includes taxes & fees
Oct 1 - Oct 2
Podere Cascatelle & Agriletizia
A serene pool area with lounge chairs and a clear view of the sunset over a hilly landscape.

4. Equipped glamping tent and infinity pool in a Tuscan olive grove

Equipped glamping tent and infinity pool in a Tuscan olive grove
Roccastrada
Equipped glamping tent and infinity pool in a Tuscan olive grove
A tent with a bed, wooden railings, and a view of trees and mountains.

5. Ottagono – Your Elegant Nature Retreat in the Tuscan Olive Grove

Ottagono – Your Elegant Nature Retreat in the Tuscan Olive Grove
Toscana
The price is CA $196
CA $224 total
includes taxes & fees
Oct 1 - Oct 2
Ottagono – Your Elegant Nature Retreat in the Tuscan Olive Grove
A swimming pool with clear water, surrounded by olive trees and a view of distant mountains.

6. Sahara – The Spacious Family Glamping Tent Under the Tuscan Sun

Sahara – The Spacious Family Glamping Tent Under the Tuscan Sun
Toscana
The price is CA $210
CA $263 total
includes taxes & fees
Oct 1 - Oct 2
Sahara – The Spacious Family Glamping Tent Under the Tuscan Sun
An outdoor dining area with stone walls, tables, and chairs.

7. Fragolina di Bosco – Twin Room with Val di Farma View

Fragolina di Bosco – Twin Room with Val di Farma View
Piloni
The price is CA $181
CA $181 total
includes taxes & fees
Oct 5 - Oct 6
Fragolina di Bosco – Twin Room with Val di Farma View
A patio with a wooden table, a blue lounge chair, a striped chair, and a large umbrella.

8. Detached house with garden a few minutes from the abbey of San Galgano

Detached house with garden a few minutes from the abbey of San Galgano
Toscana
10.0 out of 10, Exceptional, (1 review)
"Petite maison cosy et juste parfaite pour deux personnes. La localisation est très bonne, à l’entrée du village de Monticiano. L’accueil a été enthousiaste et la communication très fluide. Merci pour ce beau séjour ! On recommande !"
United States
Julie M.
The price is CA $80
CA $195 total
includes taxes & fees
Oct 1 - Oct 2
Detached house with garden a few minutes from the abbey of San Galgano
A wooden interior with a glass-enclosed shower, large windows, and a wooden floor.

9. 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 CA $100
CA $129 total
includes taxes & fees
Oct 23 - Oct 24
Agriturismo Benvenuti
A backyard with a swimming pool, lounge chairs, and a stone pathway.

10. San Michele - Casa Giano: Oak Grove View, Shared Pool & Wi-Fi

San Michele - Casa Giano: Oak Grove View, Shared Pool & Wi-Fi
Montieri
The price is CA $161
CA $161 total
includes taxes & fees
Oct 5 - Oct 6
San Michele - Casa Giano: Oak Grove View, Shared Pool & Wi-Fi
A swimming pool with clear water, surrounded by olive trees and a view of distant mountains.

11. Stargazer – Your Sky‑View Hideaway in the Tuscan Hills

Stargazer – Your Sky‑View Hideaway in the Tuscan Hills
Toskana
The price is CA $210
CA $263 total
includes taxes & fees
Oct 1 - Oct 2
Stargazer – Your Sky‑View Hideaway in the Tuscan Hills
A stone building with outdoor seating and string lights.

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

Uva Spina – Intimate Double Room with Val di Farma View
Piloni
The price is CA $203
CA $203 total
includes taxes & fees
Oct 5 - Oct 6
Uva Spina – Intimate Double Room with Val di Farma View
A house with a patio, a table with chairs, and a large umbrella.

13. Casetta di campagna indipendente

Casetta di campagna indipendente
Roccastrada
The price is CA $510
CA $608 total
includes taxes & fees
Oct 3 - Oct 4
Casetta di campagna indipendente
An outdoor dining area with stone walls, tables, and chairs.

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

Mora Selvatica – Deluxe Room with Private Balcony and Val di Farma View
Piloni
The price is CA $268
CA $268 total
includes taxes & fees
Oct 7 - Oct 8
Mora Selvatica – Deluxe Room with Private Balcony and Val di Farma View
A patio with a round table and chairs, a window with blinds, and a view of trees and hills.

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

Panorama-Ferien-Toscana Your vacation home in Tuscany
Massa Marittima
10.0 out of 10, Exceptional, (3 reviews)
"Ottima accoglienza, appartamento e giardino come da presentazione Francesco molto gentile e disponibile"
Italy
stefano f.
The price is CA $134
CA $199 total
includes taxes & fees
Oct 14 - Oct 15
Panorama-Ferien-Toscana Your vacation home in Tuscany
A stone building with outdoor seating and string lights.

16. Narciso dei Poeti – Deluxe Double Room with Extra Bed

Narciso dei Poeti – Deluxe Double Room with Extra Bed
Piloni
The price is CA $246
CA $246 total
includes taxes & fees
Oct 5 - Oct 6
Narciso dei Poeti – Deluxe Double Room with Extra Bed
A white building with a solar panel roof, surrounded by green fields and trees.

17. Room 'Oliva' with Shared Garden and Wi-Fi

Room 'Oliva' with Shared Garden and Wi-Fi
Gavorrano
Room 'Oliva' with Shared Garden and Wi-Fi
A stone building with a patio, outdoor seating, and a view of a green landscape.

18. Holiday Home 'San Michele - Capanna Scopi' with Pool & Mountain Views, Wi-Fi, A/C

Holiday Home 'San Michele - Capanna Scopi' with Pool & Mountain Views, Wi-Fi, A/C
Montieri
The price is CA $225
CA $225 total
includes taxes & fees
Oct 1 - Oct 2
Holiday Home 'San Michele - Capanna Scopi' with Pool & Mountain Views, Wi-Fi, A/C
A backyard with a swimming pool, lounge chairs, and a stone pathway.

19. San Michele - Casa Rosa: Valley & Mountain Views, Shared Pool, Wi-Fi

San Michele - Casa Rosa: Valley & Mountain Views, Shared Pool, Wi-Fi
Montieri
The price is CA $225
CA $225 total
includes taxes & fees
Oct 1 - Oct 2
San Michele - Casa Rosa: Valley & Mountain Views, Shared Pool, Wi-Fi
A stone building with wooden shutters, a covered patio, and a garden area.

20. Holiday Home 'San Michele - La Valle' with Valley & Mountain View, Shared Pool, A/C

Holiday Home 'San Michele - La Valle' with Valley & Mountain View, Shared Pool, A/C
Montieri
The price is CA $225
CA $225 total
includes taxes & fees
Oct 1 - Oct 2
Holiday Home 'San Michele - La Valle' with Valley & Mountain View, Shared Pool, A/C
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 Sassofortino Hotel Reviews

Podere Brizio

Podere Brizio

10/10 Excellent
"From the moment we arrived to the time we left was excellent, the staff, the room, Breakfast, and pool were all very good, we reserved a table with them in the evening of which was also a lovely experience, on the whole its a lovely and most relaxing place to be. we definitely will return."
Julie 1-night trip
Posted 20 hours ago
Podere Brizio

Find out more about Sassofortino

Everything you need to know about Sassofortino 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 Sassofortino 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 Sassofortino vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Sassofortino vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Sassofortino. 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 Sassofortino 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 Sassofortino vacation rentals we have selected for you start as low as CA $126 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Sassofortino rentals

At Expedia, we put the best Sassofortino 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 Sassofortino 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 Sassofortino 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 Sassofortino. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.