Bossi 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
Mar 20 - Mar 22
In two months
May 1 - May 3
In three months
May 29 - May 31
In four months
Jun 26 - Jun 28

Our top choices for Bossi vacation rentals

Exterior

Condo resort in Trequanda

Luxury resort in the Tuscan countryside
Luxury resort in the Tuscan countryside
Lobby

Townhouse in Loro Ciuffenna

Villa Cassia di Baccano
9.4 out of 10, Exceptional, (23 reviews)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is P9,930
P10,922 total
includes taxes & fees
Mar 8 - Mar 9
Villa Cassia di Baccano
Exterior

Townhouse in Siena

Il Pozzo di Sant'Andrea
9.8 out of 10, Exceptional, (16 reviews)
"Great host, lovely place near Siena"
United Kingdom
Prem
Il Pozzo di Sant'Andrea
Premium bedding, down comforters, pillowtop beds, minibar

Aparthotel in Sovicille

Tuscasì Aparthotel
9.0 out of 10, Wonderful, (26 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is P4,062
P5,352 total
includes taxes & fees
Mar 21 - Mar 22
Tuscasì Aparthotel
Lunch and dinner served, local cuisine

Residence in Monte San Savino

Castello di Gargonza
3.0 star property
9.2 out of 10, Wonderful, (39 reviews)
"Beautiful area and friendly staff. We stayed here several years ago and were so excited to return."
United States
David
Castello di Gargonza
Terrace/patio

Residence in Montalcino

Borgo Lucignanello Bandini
9.4 out of 10, Exceptional, (12 reviews)
"Beautiful stay "
United States
Marc
The price is P19,791
P22,314 total
includes taxes & fees
Mar 8 - Mar 9
Borgo Lucignanello Bandini
Free daily buffet breakfast

Townhouse in Greve in Chianti

Terre di Baccio
9.8 out of 10, Exceptional, (72 reviews)
"The stay was great, and the staff were wonderful. "
United States
SYDNEY
Terre di Baccio
Seasonal outdoor pool

Aparthotel in Asciano

Albergo Diffuso Borgo Santo
The price is P14,967
P16,804 total
includes taxes & fees
Mar 27 - Mar 28
Albergo Diffuso Borgo Santo
Food court

Residence in Monteriggioni

Antico Borgo Poggiarello
2.0 star property
9.0 out of 10, Wonderful, (20 reviews)
"We had an absolutely wonderful time staying here. Our kids had fun on their playground and my wife and I enjoyed the views, the hospitality. And the entire experience. The food was outstanding. "
United States
James Bakley
The price is P15,029
P16,736 total
includes taxes & fees
Mar 27 - Mar 28
Antico Borgo Poggiarello
Breakfast area

Townhouse in Civitella in Val di Chiana

Locanda Antico Borgo
9.2 out of 10, Wonderful, (20 reviews)
"What an absolutely beautiful stay, in a stunning place. Our host was attentive and kind, and the food was wonderful. The hotel and rooms were spotlessly clean, and particularly for my needs on a road trip with my 18 year old son, the accommodation offering two adjoining bedrooms was perfect, and we could park outside. Also very good value in my opinion. I would definitely return, it’s also ideal for couples and I would love to bring my wife here. "
United Kingdom
Mr Andy
The price is P6,989
P7,688 total
includes taxes & fees
Mar 9 - Mar 10
Locanda Antico Borgo
Exterior

Villa in Monteriggioni

Villa Montecastello
The price is P17,297
P19,231 total
includes taxes & fees
Mar 15 - Mar 16
Villa Montecastello
Front of property

Townhouse in Castelnuovo Berardenga

Villa Curina Resort
9.6 out of 10, Exceptional, (64 reviews)
"This was our second stay. The property is beautiful and our room was lovely. The breakfast was one of the best on our trip in Italy."
Canada
Dr Anne
Villa Curina Resort
Room amenity

Townhouse in Siena City Centre

Siena Vip
9.2 out of 10, Wonderful, (429 reviews)
"Nice place!"
United States
Pavel
The price is P5,951
P6,819 total
includes taxes & fees
Mar 9 - Mar 10
Siena Vip
Reception

Townhouse in Colle di Val d'Elsa

Sportland
7.2 out of 10, Good, (5 reviews)
"Struttura essenziale ed economica "
Italy
Giorgio
Sportland
Exterior

Townhouse in Gaiole in Chianti

L' Eroico
10.0 out of 10, Exceptional, (12 reviews)
"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
Terrace/patio

Cottage in Siena

Fullino Nero
9.6 out of 10, Exceptional, (50 reviews)
"Great stay! Clean rooms with air conditioning. Beautiful grounds "
United States
Christian
The price is P6,735
P7,681 total
includes taxes & fees
Mar 9 - Mar 10
Fullino Nero
Property grounds

Townhouse in Ravacciano

Domus il Palio B&B
9.2 out of 10, Wonderful, (83 reviews)
"Hotel clean comfortable. No elevator, no reception desk. "
United States
Karin
Domus il Palio B&B
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 Bossi Hotel Reviews

Hotel Santa Caterina

Hotel Santa Caterina

10/10 Excellent
"Very beautiful hotel by the city wall,friendly staff and a good breakfast."
gary 3-night trip
Posted 2 days ago
Hotel Santa Caterina

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:

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

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

Frequently asked questions

Can I find vacation rentals in Bossi?

Yes, we offer vacation rentals near popular attractions in Bossi, or you can choose a more remote option if you're looking for a relaxing stay.

What's the top vacation rental in Bossi?

Borgo Argiano: Visitors like this Bossi vacation home rental. It is located on a river and has a balcony, a terrace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a coffee maker. You can relax into your vacation 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 larger area, you’ll find Castle of Brolio and Cantalici Winery.

What’s a vacation rental in Bossi like?

Vacation rentals are private properties where you can stay for a couple of days or more in Bossi. Vacation rentals feature amenities such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a great option for a small group gathering.