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Our top choices for Bossi holiday rentals

Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (422)
"A great location!"
Canada
Cheryl
The price is ฿4,387
฿4,973 total
includes taxes & fees
4 Jan - 5 Jan 2026
Siena Vip

B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (192)
"Safe, clean, close to all attractions"
Canada
Carlo
B&B Il Corso

Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (23)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is ฿4,529
฿4,982 total
includes taxes & fees
7 Jan - 8 Jan 2026
Villa Cassia di Baccano

La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House
Siena City Centre
9.8 out of 10, Exceptional, (239)
"Huge room! Great location "
Canada
karen
La Terrazza Sul Campo Rooming House

Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.4 out of 10, Exceptional, (19)
"Fantastic experience with friendly hosts and an excellent breakfast! A little rustic here and there but all part of the charm!"
United Kingdom
Alasdair
Casa di Campagna in Toscana

Villa le Camelie Siena

Villa le Camelie Siena
Petriccio
8.6 out of 10, Excellent, (8)
"Personal people are very good. "
Switzerland
Wenjuan
The price is ฿2,858
฿3,291 total
includes taxes & fees
23 Dec - 24 Dec
Villa le Camelie Siena

Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (81)
"Convenient for parking, clean and relatively easy access to the town. The rooms were functional, getting into the place after hours was easy ( check in). No breakfast but a supermarket was 300 meters away"
Canada
Marcus
Domus il Palio B&B

ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very good, (335)
"Would recommend staying here and will hopefully be back!"
Canada
Lisa
The price is ฿1,954
฿2,297 total
includes taxes & fees
24 Dec - 25 Dec
ApartHotel Anghel

PALAZZO DEL PAPA

PALAZZO DEL PAPA
Siena City Centre
9.6 out of 10, Exceptional, (96)
"Hamza was so wonderful and accommodating, would definitely stay here again!"
United States
Elise
The price is ฿6,018
฿6,767 total
includes taxes & fees
27 Dec - 28 Dec
PALAZZO DEL PAPA

B&B Palazzo del Magnifico

B&B Palazzo del Magnifico
Siena City Centre
9.8 out of 10, Exceptional, (63)
"Great location. Room spacious and clean. Personnel friendly and great service walkable to best historic places. Could find something better "
United States
Rodolfo
B&B Palazzo del Magnifico

Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (25)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is ฿2,343
฿3,055 total
includes taxes & fees
25 Dec - 26 Dec
Tuscasì Aparthotel

Al Mercato B&B

Al Mercato B&B
Siena City Centre
9.0 out of 10, Wonderful, (96)
"Hotel is a one block from main square of the city also have a good restaurant around the corner "
United States
Guillermo
The price is ฿2,307
฿3,008 total
includes taxes & fees
11 Jan - 12 Jan 2026
Al Mercato B&B

Sportland

Sportland
Colle di Val d'Elsa
7.2 out of 10, Good, (5)
"Struttura essenziale ed economica "
Italy
Giorgio
Sportland

Il Pozzo di Sant'Andrea

Il Pozzo di Sant'Andrea
Siena
9.8 out of 10, Exceptional, (16)
"Great host, lovely place near Siena"
United Kingdom
Prem
Il Pozzo di Sant'Andrea

B&B Dei Rossi

B&B Dei Rossi
Siena City Centre
8.2 out of 10, Very good, (18)
"Wonderful stay. Large room, shared kitchen and great location to shops and restaurants. A lot of stairs, but it comes with a beautiful view. "
Canada
Alana
The price is ฿2,437
฿2,828 total
includes taxes & fees
23 Dec - 24 Dec
B&B Dei Rossi

Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (108)
"Front desk was very helpful and very comfortable room. "
United States
Chris
Chianti Village Morrocco

La Coroncina Lodging

La Coroncina Lodging
Siena
10.0 out of 10, Exceptional, (42)
"Fantastic place, and I highly recommend it."
United States
Hassan
The price is ฿3,849
฿4,381 total
includes taxes & fees
14 Jan - 15 Jan 2026
La Coroncina Lodging

La Locanda di Pietracupa

La Locanda di Pietracupa
Barberino Tavarnelle
9.4 out of 10, Exceptional, (35)
"Great place, wonderful restaurant"
Germany
Isabell
La Locanda di Pietracupa

DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (27)
"This was our favourite B&B. The owner Simona was absolutely wonderful. The hot tub in our room was out of this world. If you have the chance to visite this gem…DO IT!!"
Canada
Claude
DormiVeglia B&B

L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (12)
"Monica was the friendliest most enthusiastic host we’ve stayed with. Everything from her greeting to the amazing breakfast was perfect. She does a lot of baking, so the breakfast was really a treat and you could also get eggs cooked in various ways. The room was a little small but very comfortable. Parking was on the street, but it was fairly close and easy."
United States
Perry
L' Eroico
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

Find out more about Bossi

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

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

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.

What are some of the best holiday rentals that Bossi has to offer?

Borgo Argiano: This holiday home rental outside of Bossi is located on a river, and has a balcony, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and an electric kettle. You can relax into your holiday with a garden and a library.

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 Chianti Sculpture Park. 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.