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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Bossi holiday rentals

A villa with a swimming pool, outdoor seating, and a tennis court.

1. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (83 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
The price is 3.396.518 ₫
3.851.765 ₫ total
includes taxes & fees
31 Oct - 1 Nov
Villa Curina Resort
A stone building with a garden in front.

2. Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (28 reviews)
"What an amazing place. We enjoyed it so much."
United States
Tatevik
The price is 4.866.806 ₫
5.584.676 ₫ total
includes taxes & fees
31 Oct - 1 Nov
Borgo Argenina
A hot tub with two glasses of a beverage.

3. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (40 reviews)
"Great spot"
Canada
Philippe
The price is 4.818.138 ₫
5.299.952 ₫ total
includes taxes & fees
31 Oct - 1 Nov
Villa di Sotto
A stone building with a yellow sign reading "b&b erioico".

4. L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (15 reviews)
"Monica is a very gracious host. We very much enjoyed our stay. The village is also very quaint and within walking distance. We appreciate the hospitality and highly recommend staying here if you’re coming to the area."
United States
Angela
The price is 3.320.613 ₫
3.883.288 ₫ total
includes taxes & fees
9 Nov - 10 Nov
L' Eroico
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.

5. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (33 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is 1.603.303 ₫
2.139.317 ₫ total
includes taxes & fees
20 Nov - 21 Nov
Tuscasì Aparthotel
A bedroom with a bed, bedside table, and a window with a view of greenery.

6. La Coroncina Lodging

La Coroncina Lodging
Siena
10.0 out of 10, Exceptional, (43 reviews)
"Fantastic place, and I highly recommend it."
United States
Hassan
The price is 2.466.795 ₫
2.829.070 ₫ total
includes taxes & fees
16 Nov - 17 Nov
La Coroncina Lodging
An aerial view of a historic castle complex with multiple buildings, including a large central structure with a tower, surrounded by well-maintained gardens and pathways.

7. Castello di Modanella

Castello di Modanella
Rapolano Terme
8.0 out of 10, Very good, (17 reviews)
"To far out"
United States
Dennis
The price is 3.868.034 ₫
5.234.950 ₫ total
includes taxes & fees
31 Oct - 1 Nov
Castello di Modanella
An outdoor swimming pool with a wooden pergola, lounge chairs, and a stone wall backdrop.

8. Guild Living Siena Senior Resort & Residence

Guild Living Siena Senior Resort & Residence
Scacciapensieri
8.8 out of 10, Excellent, (60 reviews)
"We booked this last - minute and were really impressed with the whole experience. The property and grounds are beautiful. Staff was so friendly and helpful. The rooms were well appointed and quiet. Beds were too firm for our liking, but it was easy to overlook as the entire stay was really great. Good options in the restaurant too. The block of hotel rooms is in a retirement resort, which I think is a wonderful idea! Very much enjoyed our stay. We had a car and parking was free."
United States
Heidi
The price is 2.509.431 ₫
2.875.681 ₫ total
includes taxes & fees
2 Nov - 3 Nov
Guild Living Siena Senior Resort & Residence
A traditional interior with stone arches, a staircase, and a cozy seating area with a table.

9. Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
9.4 out of 10, Exceptional, (9 reviews)
"Very nice agriturismo. "
United States
Ruth
The price is 3.298.580 ₫
3.743.745 ₫ total
includes taxes & fees
8 Nov - 9 Nov
Agriturismo La Ferrozzola
A white table with a bowl of snacks, two glasses of orange drink, and a small potted plant on a balcony.

10. RESIDENCE LECCIO

RESIDENCE LECCIO
Asciano
9.4 out of 10, Exceptional, (8 reviews)
"Very nice, affordable place in beautiful area"
United States
Corey
The price is 1.723.677 ₫
2.040.539 ₫ total
includes taxes & fees
12 Nov - 13 Nov
RESIDENCE LECCIO
A modern lobby with white leather sofas, a glass coffee table, and potted plants.

11. ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very good, (355 reviews)
"Great stay highly recommend!!"
United States
jon
The price is 1.404.477 ₫
1.660.520 ₫ total
includes taxes & fees
15 Nov - 16 Nov
ApartHotel Anghel
A staircase with a wooden handrail, a potted plant, and a chair in a hallway.

12. Villa Fontis Rapolano

Villa Fontis Rapolano
Rapolano Terme
10.0 out of 10, Exceptional, (1 review)
"Bella struttura, nuova, pulita in posizione comoda"
Italy
Barbara
The price is 2.382.142 ₫
2.735.663 ₫ total
includes taxes & fees
11 Nov - 12 Nov
Villa Fontis Rapolano
A stone building with a sloped roof, a small porch, and a gravel driveway.

13. Podere La Chiusella

Podere La Chiusella
Rapolano Terme
9.2 out of 10, Wonderful, (33 reviews)
"We enjoyed our stay. Everything was clean and comfortable, and the complex itself was impressive and a stunning place to stay. The location was also a convenient base for seeing Tuscany, and we had a great meal nearby in Rapolano Terme. Overall, it has the potential to be one of the coolest places you'll ever stay, though we did encounter a few technical issues regarding the shower and WiFi (which the hosts were quickly responsive about). I'd still recommend it, but it's helpful if you go in...
United Kingdom
Kevin
The price is 2.693.577 ₫
3.078.529 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Podere La Chiusella
A stone courtyard with a bench, potted plants, and a building in the background.

14. 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 2.153.532 ₫
2.455.581 ₫ total
includes taxes & fees
15 Nov - 16 Nov
Casa di Campagna in Toscana
A rustic stone building with a courtyard.

15. Fullino Nero

Fullino Nero
Siena
9.6 out of 10, Exceptional, (59 reviews)
"Very nice place close to"
Canada
Annie
The price is 2.610.999 ₫
2.987.838 ₫ total
includes taxes & fees
2 Nov - 3 Nov
Fullino Nero
A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building.

16. Residenzia del Sogno

Residenzia del Sogno
Castellina in Chianti
9.8 out of 10, Exceptional, (16 reviews)
"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "
Canada
Katherine
The price is 3.406.805 ₫
3.862.792 ₫ total
includes taxes & fees
31 Oct - 1 Nov
Residenzia del Sogno
A room with a window featuring sheer curtains, a radiator below, and a view of a green landscape.

17. Mariani Bed & Breakfast

Mariani Bed & Breakfast
Castellina in Chianti
9.8 out of 10, Exceptional, (18 reviews)
"Beautiful view, very clean and everything in great condition. Friendly service. We will definitely stay again."
United States
Frank
The price is 2.371.008 ₫
2.723.704 ₫ total
includes taxes & fees
31 Oct - 1 Nov
Mariani Bed & Breakfast
A stone-paved courtyard with a wrought iron gate, a brick building, and a tree.

18. B&B Le Logge Di Sopra

B&B Le Logge Di Sopra
Asciano
The price is 2.688.756 ₫
3.072.938 ₫ total
includes taxes & fees
24 Nov - 25 Nov
B&B Le Logge Di Sopra
A courtyard with outdoor seating, a stone building with a tower, and a well-maintained garden.

19. Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.4 out of 10, Exceptional, (49 reviews)
"Roberto, his wife and his staff were all round great. Very friendly helpful and great service. We were very happy to find this authentic castle/village to stay in Tuscany."
Canada
Iain
The price is 7.113.024 ₫
7.939.921 ₫ total
includes taxes & fees
7 Nov - 8 Nov
Castello di Gargonza
An aerial view of a historic stone building complex with a swimming pool, surrounded by lush greenery and vineyards.

20. Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (188 reviews)
"Very peaceful and scenic. Wish we had stayed longer."
United States
Amir
The price is 2.309.392 ₫
2.770.945 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Bosco della Spina
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 Bossi Hotel Reviews

Hotel Athena

Hotel Athena

8/10 Good
"Hotel was fine, the staff need to communicate through what port to enter to avoid ZTL fine!! We got fined since we didn’t know. A lady staff was kind enough to email police department not to fine but it didn’t work. The hotel is on the edge of the ZTL zone and you need to enter through “San Marco” port!!"
ALLEN 2-night trip
Posted 20 hours ago
Hotel Athena

Frequently asked questions

Can I find holiday rentals in Bossi?

Yes, there are holiday rentals close to the most popular sights in Bossi, or you can select a more secluded option if you're looking for a relaxing stay.

How many holiday rentals are there in Bossi?

Expedia has 5 holiday rentals for your stay in Bossi.

What’s there to see and do in Bossi?

While exploring the area, visit family-friendly sights like Siena Circuit, or get outside and enjoy nature at Terme Antica Querciolaia. In the wider area, you’ll find Castle of Brolio and Cantalici Winery.

What’s a holiday rental in Bossi like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Bossi. Holiday rentals offer amenities like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can offer a sense of security away from shared hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a popular option for a small group gathering.