Bossi holiday rentals

We found 1,193 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Bossi to find one that's perfect for your trip. Whether you’re staying in a holiday home with a group or just with your pet, you'll have the best amenities for spending time at your home away from home, including Wi-Fi and parking. Whatever you're looking for, you'll be able to choose a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Bossi

Showing deals for:13 Nov - 20 Nov

Villa west garden
Outdoor banquet area
main hall
Villa entry
Exceptional
(14 reviews)

Exclusive Villa 18th century, with pool. Fine winery in Chianti central Tuscany

Bucine

26% off
AU$23,221
for 7 nights, 1 home
AU$3,317 per night
includes taxes & fees
Exclusive Villa 18th century, with pool. Fine winery in Chianti central Tuscany
Living area
Pool
Private kitchen
Living area
Exceptional
(5 reviews)

Private villa in the heart of chianti with view of siena

Castellina in Chianti

5% off
AU$5,043
for 7 nights, 1 villa
AU$720 per night
includes taxes & fees
Private villa in the heart of chianti with view of siena
Living area
Private kitchen
Dining
Interior
Exceptional
(44 reviews)

Le Redi: sustainable geothermal country villa, amazing views over Chianti hills

Castelnuovo Berardenga

9% off
AU$3,184
for 7 nights, 1 villa
AU$455 per night
includes taxes & fees
Le Redi: sustainable geothermal country villa, amazing views over Chianti hills
Pool
Dining
Property grounds
Living area
Exceptional
(54 reviews)

Portion Farmhouse nestled in the heart of Chianti with private pool,

Gaiole in Chianti

9% off
AU$3,266
for 7 nights, 1 home
AU$467 per night
includes taxes & fees
Portion Farmhouse nestled in the heart of Chianti with private pool,
Living room
Dining
Room
Interior
Exceptional
(29 reviews)

Palazzo Pannilini-Historical residence

Siena

7% off
AU$8,571
for 7 nights, 1 apartment
AU$1,224 per night
includes taxes & fees
Palazzo Pannilini-Historical residence
Interior
Property grounds
Room
Property grounds
Exceptional
(7 reviews)

Charming relais in Siena at the gates of Chianti

Siena

11% off
AU$1,501
for 7 nights, 1 apartment
AU$214 per night
includes taxes & fees
Charming relais in Siena at the gates of Chianti
Interior
Outdoor dining
Room
Private kitchen
Exceptional
(10 reviews)

Apartment in renovated farmhouse in typical Chianti Tuscan village

Castelnuovo Berardenga

7% off
AU$1,792
for 7 nights, 1 home
AU$256 per night
includes taxes & fees
Apartment in renovated farmhouse in typical Chianti Tuscan village
Private kitchen
Property grounds
Living area
Exterior
Exceptional
(16 reviews)

Beautiful farmhouse nestled in very sweet hills just a few minutes from Siena

Siena

9% off
AU$9,011
for 7 nights, 1 home
AU$1,287 per night
includes taxes & fees
Beautiful farmhouse nestled in very sweet hills just a few minutes from Siena
Interior
Outdoor dining
Second bed room - detail
modern and bright kitchen with balcony
Exceptional
(69 reviews)

Family apartment with magical view on the old city, balcony, wifi & parking

Siena

7% off
AU$2,360
for 7 nights, 1 apartment
AU$337 per night
includes taxes & fees
Family apartment with magical view on the old city, balcony, wifi & parking
Living area
Room
Bathroom
Room
Exceptional
(13 reviews)

Il Casato, beautiful apartment in the heart of Siena

Siena

11% off
AU$1,732
for 7 nights, 1 apartment
AU$247 per night
includes taxes & fees
Il Casato, beautiful apartment in the heart of Siena

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    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Choose a holiday rental for your Bossi getaway

Learn about the unique charm of Bossi with a stay in a holiday home rental. This city has something for everyone. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in and around Bossi

Do you want to discover top things to see and do while you're in town? Venture out of your holiday home and check out everything that makes Bossi a fun spot to go on holiday. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Siena Circuit (4.5 mi / 7.3 km)
  • Cantalici Winery (4.8 mi / 7.8 km)
  • Terra di Seta (6.3 mi / 10.2 km)
  • Badia a Coltibuono (8.4 mi / 13.6 km)
  • San Giovanni Terme Rapolano (9.5 mi / 15.3 km)
  • Castello di Radda Winery (9.5 mi / 15.3 km)

Exploring the natural features in Bossi

Whether you're an adventurous traveller or just want to take in the scenery, Bossi is a great place to spend some time outside. Here are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Terme Antica Querciolaia (9.5 mi / 15.4 km)
  • Alta Val d'Elsa River Park (15.9 mi / 25.7 km)
  • Val di Merse (17.6 mi / 28.4 km)
  • Val di Chiana (27.3 mi / 43.9 km)
  • Arno River (28.9 mi / 46.4 km)
  • Chianti Sculpture Park (3.8 mi / 6 km)

Frequently asked questions

What is the best area to stay in Bossi when booking a holiday rental?
When considering a holiday rental in the charming area of Bossi, Tuscany, the surrounding neighbourhoods offer a delightful blend of scenic beauty and cultural richness. One of the best areas to stay is near the historic centre, where you can immerse yourself in the local atmosphere and enjoy easy access to breathtaking landscapes.This region is known for its picturesque vineyards and olive groves, making it an ideal spot for those who wish to explore the Tuscan countryside. A short drive or leisurely stroll can lead you to remarkable attractions such as the stunning medieval castles and the renowned wine estates that offer tastings and tours. Additionally, nearby towns boast historical architecture and quaint shops, providing a wonderful opportunity to experience authentic Tuscan life.While the exact number of holiday rental properties can vary, you will find a range of options from charming villas to cosy apartments, ensuring that there is something to suit different tastes and budgets.
What are the top attractions in Bossi?
In Bossi, Tuscany, visitors can experience firsthand the picturesque countryside and experience the charm of traditional Tuscan life. The area is known for its beautiful vineyards and olive groves, making it a great destination for those interested in wine tasting and culinary experiences. Nearby, the historic city of Siena is just a short drive away, renowned for its stunning medieval architecture, the famous Piazza del Campo, and the stunning Siena Cathedral.Additionally, the scenic landscapes of the Chianti region offer ample opportunities for hiking and exploring quaint villages like Castellina in Chianti and Radda in Chianti, both of which are easily accessible from Bossi. For art lovers, the city of Florence, with its world-class museums and art galleries, is within reach, allowing guests to enjoy the cultural richness of Tuscany.
Are all fees included in the Bossi holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Bossi holiday homes with parking?
Stayz offers a wide selection of holiday homes in Bossi with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Bossi holiday homes?
You can find great discounts on holiday homes in Bossi on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Bossi holiday home booking on Stayz?
To find Bossi holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Bossi?
A long-stay holiday home in Bossi is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Bossi holiday home?
Book your Bossi holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Bossi?
Prices for holiday homes in Bossi vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Bossi to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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