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Bossi Vacation Rentals

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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 Bossi vacation 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, (80 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
$110 nightly
The price is $125
Oct 13 - Oct 14
Total with taxes and fees
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
$171 nightly
The price is $197
Oct 15 - Oct 16
Total with taxes and fees
Borgo Argenina
A pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

3. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (40 reviews)
"Great spot"
Canada
Philippe
$168 nightly
The price is $185
Oct 12 - Oct 13
Total with taxes and fees
Villa di Sotto
An arched brick corridor with gravel flooring, potted plants, and a gate leading to a garden area.

4. Ca' Bianca Tuscany Relais

Ca' Bianca Tuscany Relais
Siena
10.0 out of 10, Exceptional, (46 reviews)
"Clean room, amazing staff"
Canada
Talha
$240 nightly
The price is $269
Oct 8 - Oct 9
Total with taxes and fees
Ca' Bianca Tuscany Relais
An outdoor swimming pool with a wooden pergola, lounge chairs, and a stone wall backdrop.

5. Guild Living Siena Senior Resort & Residence

Guild Living Siena Senior Resort & Residence
Scacciapensieri
8.8 out of 10, Excellent, (53 reviews)
"Amazing! Thank you!"
United Kingdom
Lucy
$106 nightly
The price is $121
Nov 1 - Nov 2
Total with taxes and fees
Guild Living Siena Senior Resort & Residence
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.

6. 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
$72 nightly
The price is $83
Nov 2 - Nov 3
Total with taxes and fees
Tuscasì Aparthotel
A bedroom with a bed, bedside table, and a window with a view of greenery.

7. 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
$135 nightly
The price is $153
Oct 26 - Oct 27
Total with taxes and fees
La Coroncina Lodging
A courtyard with outdoor seating, a stone building with a tower, and a well-maintained garden.

8. Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.2 out of 10, Wonderful, (44 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
$242 nightly
The price is $271
Oct 7 - Oct 8
Total with taxes and fees
Castello di Gargonza
A stone building with a yellow sign reading "b&b erioico".

9. 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
$136 nightly
The price is $159
Nov 2 - Nov 3
Total with taxes and fees
L' Eroico
A modern lobby with white leather sofas, a glass coffee table, and potted plants.

10. ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very good, (349 reviews)
"Humming noise in the room. Slow internet. Fine bed. Good location."
Netherlands
Lauro
$66 nightly
The price is $78
Nov 5 - Nov 6
Total with taxes and fees
ApartHotel Anghel
A stone building with a sloped roof, a small porch, and a gravel driveway.

11. 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
$88 nightly
The price is $101
Oct 7 - Oct 8
Total with taxes and fees
Podere La Chiusella
A rustic stone building with a courtyard.

12. Fullino Nero

Fullino Nero
Siena
9.6 out of 10, Exceptional, (56 reviews)
"Great stay! Clean rooms with air conditioning. Beautiful grounds "
United States
Christian
$107 nightly
The price is $122
Oct 7 - Oct 8
Total with taxes and fees
Fullino Nero
A spacious hotel room with a large bed, a sitting area with chairs, and a view through an arched doorway to another room.

13. La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House
Siena City Centre
9.8 out of 10, Exceptional, (251 reviews)
"Great stay. Thanks for the hospitality and kindness."
United Kingdom
Agnieszka
$100 nightly
The price is $115
Nov 2 - Nov 3
Total with taxes and fees
La Terrazza Sul Campo Rooming House
A stone building with a tiled roof, surrounded by a well-maintained garden with various plants and a cactus in the foreground.

14. La Murata

La Murata
Rapolano Terme
9.2 out of 10, Wonderful, (13 reviews)
"Amazingly beautiful place! Wish i could have stayed longer to enjoy the view but was just passing through. The apartment was so cute and clean. Any family would enjoy staying here. I would stay here again if i were in the area."
United States
Elizabeth
$127 nightly
The price is $144
Oct 7 - Oct 8
Total with taxes and fees
La Murata
A staircase with a wooden handrail, a potted plant, and a chair in a hallway.

15. 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
$79 nightly
The price is $91
Oct 7 - Oct 8
Total with taxes and fees
Villa Fontis Rapolano
A wine cellar with stone walls, wine racks, and tables with glasses and candles.

16. Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca
Siena City Centre
9.6 out of 10, Exceptional, (221 reviews)
"The room was so unique and convenient for everything we wanted to do. Wish we could have spent more than one night!"
United States
Kellie
$133 nightly
The price is $150
Nov 5 - Nov 6
Total with taxes and fees
Il Battistero Siena - Residenza d'Epoca
A table set with breakfast items on a balcony overlooking a historic town.

17. Residenza d'Epoca Palazzo Borghesi

Residenza d'Epoca Palazzo Borghesi
Siena City Centre
9.6 out of 10, Exceptional, (132 reviews)
"We had a great experience Property is perfectly located."
United States
Roman
$141 nightly
The price is $159
Nov 4 - Nov 5
Total with taxes and fees
Residenza d'Epoca Palazzo Borghesi
A bathroom with a window view of a historic building and a tiled roof.

18. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (485 reviews)
"Great location right in the heart of everything and next to an escalator that takes you to the main plaza. Very comfortable bed, friendly staff. Convenient parking option very close by."
United States
Heather
$93 nightly
The price is $107
Nov 4 - Nov 5
Total with taxes and fees
Siena Vip
A hotel room with a bed, a bedside table with a lamp, a potted plant, and a view of the outside through the window.

19. PALAZZO DEL PAPA

PALAZZO DEL PAPA
Siena City Centre
9.6 out of 10, Exceptional, (116 reviews)
"The setup was more like a guest house/Bed and Breakfast. It was impeccably clean and newly renovated, which made it very cozy and comfortable. Everything needed was provided. The location was half a block from the Piazza del Campo. And last but not least, Hamza was one of the most welcoming and gracious hosts imaginable, directing us to a magical Trattoria, Pappei’s, that felt like you were visiting your own Nonna! Wonderful!!!"
United States
Walter
$181 nightly
The price is $204
Nov 3 - Nov 4
Total with taxes and fees
PALAZZO DEL PAPA
A building with a sign for 'Residence Leccio' and a café named 'La Rumba Café'.

20. RESIDENCE LECCIO

RESIDENCE LECCIO
Asciano
9.4 out of 10, Exceptional, (8 reviews)
"Very nice, affordable place in beautiful area"
United States
Corey
$75 nightly
The price is $89
Oct 14 - Oct 15
Total with taxes and fees
RESIDENCE LECCIO
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

Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent
"Beautiful hotel and very helpful staff. Excellent location in the heart of Siena. Disappointed with our hotel room. Not up to our expectations."
JOHN 3-night trip
Posted 8 hours ago
Grand Hotel Continental Siena – Starhotels Collezione

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 $78 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.

Explore a world of travel with Expedia

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 kitchenware. You can relax into your vacation with a garden and a library.

How many vacation rentals are there in Bossi?

Expedia has 5 vacation 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 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.