Bossi Vacation Rentals

Check prices for these dates

In two weeks
May 22 - May 24
In two months
Jul 3 - Jul 5
In three months
Jul 31 - Aug 2
In four months
Aug 28 - Aug 30

Our top choices for Bossi vacation rentals

Villa, Air conditioning, Courtyard View | Exterior

Villa Montecastello

Villa Montecastello
Monteriggioni
$169 nightly
The price is $189
May 14 - May 15
Total with taxes and fees
Villa Montecastello
Premium bedding, down comforters, pillowtop beds, minibar

Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
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
$78 nightly
The price is $89
May 10 - May 11
Total with taxes and fees
Tuscasì Aparthotel
Exterior

Il Pozzo di Sant'Andrea

Il Pozzo di Sant'Andrea
Siena
9.8 out of 10, Exceptional, (16 reviews)
"Great host, lovely place near Siena"
United Kingdom
Prem
$102 nightly
The price is $116
May 17 - May 18
Total with taxes and fees
Il Pozzo di Sant'Andrea
Lobby

Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (23 reviews)
"The staff were great and the villa was amazing"
United States
Ralphvincent
$153 nightly
The price is $168
May 11 - May 12
Total with taxes and fees
Villa Cassia di Baccano
Seasonal outdoor pool, sun loungers

Residence Arianna

Residence Arianna
Sovicille
9.6 out of 10, Exceptional, (4 reviews)
"We had a 4 night’s stay here and used it as our base for tours around Toscany. It is located in a quiet area outside Siena. The apartment was nice and clean. We used the kitchen for minor cooking and that worked well. There is a supermarket close by and small restaurants in the town. The AC was working great. The host was very keen to share information on good places to see and was eager to make our stay as pleasant as possible. The breakfast was very nice and they also have a restaurant where...
Denmark
Gitte Harrits
$154 nightly
The price is $173
May 9 - May 10
Total with taxes and fees
Residence Arianna
1 bedroom, free WiFi, bed sheets

Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti

Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti
Monteaperti
10.0 out of 10, Exceptional, (2 reviews)
"We loved this place. Modern cabin set in a rustic Tuscan setting. Beautiful property, very comfortable stay, and very attentive staff. Family owned and operated. Amazing restaurant just steps away. A perfect place for respite"
United States
Ian F.
$212 nightly
The price is $218
May 12 - May 13
Total with taxes and fees
Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti
Studio, Patio, Ground Floor | Terrace/patio

Fullino Nero

Fullino Nero
Siena
9.6 out of 10, Exceptional, (51 reviews)
"Great stay! Clean rooms with air conditioning. Beautiful grounds "
United States
Christian
$102 nightly
The price is $117
May 18 - May 19
Total with taxes and fees
Fullino Nero
Romantic Double Room, 1 Queen Bed, Hot Tub, Ground Floor | Private spa tub

DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (28 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
$95 nightly
The price is $109
May 17 - May 18
Total with taxes and fees
DormiVeglia B&B
Hair dryer, bidet, towels, soap

Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Toscana
$137 nightly
The price is $141
May 11 - May 12
Total with taxes and fees
Rooster House, cooking classes and opera
Food court

Antico Borgo Poggiarello

Antico Borgo Poggiarello
2.0 star property
Monteriggioni
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
$163 nightly
The price is $183
May 10 - May 11
Total with taxes and fees
Antico Borgo Poggiarello
Exterior

Villa Norcenni Aparthotel

Villa Norcenni Aparthotel
2.0 star property
Figline e Incisa Valdarno
7.4 out of 10, Good, (21 reviews)
"It was clean and safe."
United Kingdom
Laka
$50 nightly
The price is $59
May 10 - May 11
Total with taxes and fees
Villa Norcenni Aparthotel
Terrace/patio

Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (99 reviews)
"A nice blend of old world charm and modern conveniences. It is far from "
United States
John
$116 nightly
The price is $130
May 11 - May 12
Total with taxes and fees
Palazzo Pacini
Seasonal outdoor pool, pool umbrellas, sun loungers

Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Tavarnelle
8.4 out of 10, Very Good, (41 reviews)
"Conveniently situated between Florence and Siena in the heart of the Chianti region with stunning views. Friendly relaxed hosts who provide a substantial breakfast. Beautiful large swimming pool to cool off at the end of the day."
United Kingdom
Andrew
$61 nightly
The price is $74
May 13 - May 14
Total with taxes and fees
Villa San Filippo
Interior

Villa Fontis Rapolano

Villa Fontis Rapolano
Rapolano Terme
$81 nightly
The price is $93
May 11 - May 12
Total with taxes and fees
Villa Fontis Rapolano
View from room

Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (112 reviews)
"Front desk was very helpful and very comfortable room. "
United States
Chris
$73 nightly
The price is $83
May 9 - May 10
Total with taxes and fees
Chianti Village Morrocco
Interior detail

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
$158 nightly
The price is $178
May 19 - May 20
Total with taxes and fees
La Coroncina Lodging
Exterior

L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (13 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
$164 nightly
The price is $190
May 23 - May 24
Total with taxes and fees
L' Eroico
Exterior

Colle di Val d'Elsa - Siena - Apt Pink - B

Colle di Val d'Elsa - Siena - Apt Pink - B
Colle di Val d'Elsa
10.0 out of 10, Exceptional, (2 reviews)
"The host is excellent. Perfect English and Italian. Thoughtful and great communication. Parking instructions were accurate. The apartment was beautiful and the bed was comfortable. The apartment is walkable to dining and shopping. The street is steep and the nearby medievale hill town is steeper. While we loved walking up to the hill town everyday, we liked the variety of dining and shopping near the apartment."
United States
Tamara C.
$164 nightly
The price is $166
May 12 - May 13
Total with taxes and fees
Colle di Val d'Elsa - Siena - Apt Pink - B
Interior

Chianti Craft House Badia a Passignano

Chianti Craft House Badia a Passignano
Barberino Tavarnelle
9.8 out of 10, Exceptional, (10 reviews)
"Great food in the area. Beautiful church tour and a fantastic host for our stay!"
United States
Craig & Conny M.
$211 nightly
The price is $216
May 18 - May 19
Total with taxes and fees
Chianti Craft House Badia a Passignano
Terrace/patio

Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.4 out of 10, Exceptional, (22 reviews)
"Fantastic experience with friendly hosts and an excellent breakfast! A little rustic here and there but all part of the charm!"
United Kingdom
Alasdair
$106 nightly
The price is $120
May 17 - May 18
Total with taxes and fees
Casa di Campagna in Toscana
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

Palazzo Ravizza

Palazzo Ravizza

10/10 Excellent
"Great place to stay in Siena."
John L 2-night trip
Posted 1 hour ago
Palazzo Ravizza

Find out more about Bossi

Everything you need to know about Bossi 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 Bossi vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 Bossi vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Bossi vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Bossi. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Bossi in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $57 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Bossi rentals

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

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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 an electric kettle. 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 Borgo di Vescine - Tenute di Castelvecchi, or get outside and enjoy nature at Terme Antica Querciolaia. 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.