Default HTG hotel image

Sassofortino Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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 P5,541
P6,236 total
includes taxes & fees
Nov 4 - Nov 5
Country House il Ciliegio
An outdoor dining area with a table set for two, overlooking a lush green landscape and a hill in the distance.

2. 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
Podere Cascatelle & Agriletizia
A wooden interior with a glass-enclosed shower, large windows, and a wooden floor.

3. 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 P4,378
P5,660 total
includes taxes & fees
Oct 23 - Oct 24
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.

4. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (31 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is P3,906
P5,212 total
includes taxes & fees
Nov 2 - Nov 3
Tuscasì Aparthotel
An aerial view of a historic stone building complex with a swimming pool, surrounded by lush greenery and vineyards.

5. Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (179 reviews)
"Lovely stay! I would highly recommend this hotel. The indoor pool was just so enjoyable after a day out sightseeing. "
United Kingdom
Lizl
The price is P5,060
P6,129 total
includes taxes & fees
Oct 27 - Oct 28
Bosco della Spina
A stone courtyard with a bench, potted plants, and a building in the background.

6. Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.6 out of 10, Exceptional, (27 reviews)
"A wonderful stay. "
United States
Sally
The price is P6,156
P6,982 total
includes taxes & fees
Oct 30 - Oct 31
Casa di Campagna in Toscana
An interior with stone walls, wooden doors, and a bar area with stools and bottles.

7. Borgo Il Poggiaccio

Borgo Il Poggiaccio
Sovicille
8.8 out of 10, Excellent, (67 reviews)
"I loved the stay here. A great quiet place with an awesome restaurant and unbelievable staff. "
United States
Louie
The price is P6,774
P7,803 total
includes taxes & fees
Oct 6 - Oct 7
Borgo Il Poggiaccio
Outdoor pool

8. Residence Arianna

Residence Arianna
Sovicille
9.6 out of 10, Exceptional, (9 reviews)
"The place is excellent! The owner and her daughter extremely friendly and kind! They helped us with everything we needed. I will definitely stay here again. I highly recommend this place!"
United States
Violeta
The price is P9,605
P10,777 total
includes taxes & fees
Oct 8 - Oct 9
Residence Arianna
A spacious living area with a dining table, red chairs, and a small round table. Large windows provide natural light and views of greenery outside.

9. Residence Il Boschetto

Residence Il Boschetto
Grosseto
8.6 out of 10, Excellent, (8 reviews)
"The house is gorgeous! The area is very nice and the amenities were great! "
United States
Enrique
The price is P4,808
P5,500 total
includes taxes & fees
Oct 6 - Oct 7
Residence Il Boschetto
A person relaxing in a hot tub with a glass of wine.

10. Botrona B&B

Botrona B&B
Scarlino
9.4 out of 10, Exceptional, (26 reviews)
"Amazing B&B! Beautiful, clean, and very classy! Staff is excellent and friendly… breakfast is superb and staff’s hospitality is heart warming. Our stay was very pleasant. Home away from home… surprisingly beautiful grounds with jacuzzi and a sauna available whenever you want! Thank you!"
United States
Anna
The price is P5,988
P6,586 total
includes taxes & fees
Oct 11 - Oct 12
Botrona B&B
A stone building with a tiled roof, a brick pathway, and a small grassy area.

11. Le Mascie Country House

Le Mascie Country House
Casole d'Elsa
9.2 out of 10, Wonderful, (9 reviews)
"We loved our stay. The property is quiet and private but is in close proximity to a small town. Very charming and the pool was an added bonus. "
United States
Misti
The price is P19,201
P21,262 total
includes taxes & fees
Oct 17 - Oct 18
Le Mascie Country House
A large estate with multiple buildings, a swimming pool, and a well-maintained garden.

12. 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 P16,413
P18,196 total
includes taxes & fees
Oct 25 - Oct 26
Dimora Santa Margherita - Boutique Hotel
A compact kitchen with a gas stove, a refrigerator, and a wooden dining table with chairs.

13. Nido con vista

Nido con vista
Radicondoli
The price is P9,562
P10,518 total
includes taxes & fees
Nov 1 - Nov 2
Nido con vista
A pool area with lounge chairs and umbrellas, surrounded by lush greenery and overlooking a scenic view.

14. BeVedetta - Relais & Glamping - Adult Only

BeVedetta - Relais & Glamping - Adult Only
Scarlino
10.0 out of 10, Exceptional, (12 reviews)
"Loved it here!!!"
United States
Nina
BeVedetta - Relais & Glamping - Adult Only
A building with a tiled roof, a paved walkway, and potted plants.

15. La Residenza del Golfo

La Residenza del Golfo
Scarlino
9.0 out of 10, Wonderful, (19 reviews)
"Nice place. Simple and clean. Beach is 2 mins from the apartments. It’s a dog beach and is nice. Not the best in the area but certainly good enough for a quick escape to the beach. We were there for 2 weeks at the end of July and the beaches weren’t packed. The place is well air conditioned and clean. There are communal bbqs that are well maintained. Most people have dogs which is fine with us but might not be for everyone. Overall a simple, basic but pleasant stay and decent value. It’s near...
United Kingdom
Ashley
The price is P5,705
P11,908 total
includes taxes & fees
Oct 9 - Oct 10
La Residenza del Golfo
A bedroom with a bed, a radiator, a window, a painting, and a bedside table.

16. Belvedere Nada

Belvedere Nada
San Rocco A Pilli
The price is P12,241
P13,465 total
includes taxes & fees
Oct 19 - Oct 20
Belvedere Nada
A rustic stone building with a tiled roof, surrounded by lush greenery and a clear sky.

17. Apartment in Chianti With Pool ID 3939

Apartment in Chianti With Pool ID 3939
Casole d'Elsa
The price is P24,016
P26,558 total
includes taxes & fees
Oct 7 - Oct 8
Apartment in Chianti With Pool ID 3939
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Sassofortino Hotel Reviews

Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

8/10 Good
"Although the property and the staff were great, our room was a bit of a disappointment. Junior Sweet was just a giant room with furniture that was uncomfortable to use. In general the room needs an update. Not exactly what we expected. We unfortunately had a neighbor who opened up the gate outside in between our terrace which should have never happen if it had been locked. He did that because he said my husbands iPad was too loud when in fact, his was too loud and my husband who had headphones on could not hear his show so took them off so he could hear it. Needless to say we avoided our terrace after that. Shout out to Chiara and Samantha who took a desert request seriously and made two of my evenings! Michael and David’s were also wonderful!"
Ellen 5-night trip
Posted 14 hours ago
Castiglion del Bosco, A Rosewood Hotel

Find out more about Sassofortino

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

  • View our selection of featured holiday rentals in Sassofortino
  • Use the map to find apartments and other holiday homes in the Sassofortino neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Sassofortino while they last

Look no further and take a look at our great range of rental properties in Sassofortino!

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.

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.