San Leonino holiday rentals

We found 1,517 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in San Leonino to find one that's perfect for your trip. Whether you're going on holiday with family or friends, holiday rentals have the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a washer and dryer. What you'll find is a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – San Leonino

Showing deals for:20 Nov - 27 Nov

Private kitchen
Pool
Living area
Living area
Exceptional
(5 reviews)

Private villa in the heart of chianti with view of siena

Castellina in Chianti

5% off
AU$5,026
for 7 nights, 1 villa
AU$718 per night
includes taxes & fees
Private villa in the heart of chianti with view of siena
Pool
House and loggia, seen from the garden
View from the kitchen
House and parking
Exceptional
(58 reviews)

Quiet and Beautiful Property, Large Pool, Airco in bedrooms

Castellina in Chianti

9% off
AU$6,954
for 7 nights, 1 villa
AU$993 per night
includes taxes & fees
Quiet and Beautiful Property, Large Pool, Airco in bedrooms
Outdoor dining
Pool
Property grounds
Exterior
Exceptional
(21 reviews)

Borgo dei Fondi / Il Forno – Ground Floor/ Modern Comfort and Tuscan Charm

Siena

6% off
AU$2,001
for 7 nights, 1 home
AU$286 per night
includes taxes & fees
Borgo dei Fondi / Il Forno – Ground Floor/ Modern Comfort and Tuscan Charm
Property grounds
Dining
Living area
Pool
Exceptional
(55 reviews)

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

Gaiole in Chianti

9% off
AU$3,194
for 7 nights, 1 home
AU$456 per night
includes taxes & fees
Portion Farmhouse nestled in the heart of Chianti with private pool,
Living area
Private kitchen
Dining
Living area
Exceptional
(44 reviews)

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

Castelnuovo Berardenga

9% off
AU$3,113
for 7 nights, 1 villa
AU$445 per night
includes taxes & fees
Le Redi: sustainable geothermal country villa, amazing views over Chianti hills
Living room
Dining
Room
Dining
Exceptional
(29 reviews)

Palazzo Pannilini-Historical residence

Siena

7% off
AU$8,442
for 7 nights, 1 apartment
AU$1,206 per night
includes taxes & fees
Palazzo Pannilini-Historical residence
Interior
Property grounds
Property grounds
Room
Exceptional
(7 reviews)

Charming relais in Siena at the gates of Chianti

Siena

11% off
AU$1,486
for 7 nights, 1 apartment
AU$212 per night
includes taxes & fees
Charming relais in Siena at the gates of Chianti
Interior
Property grounds
Interior
Exterior
Exceptional
(8 reviews)

The Bartaline hut

Greve in Chianti

9% off
AU$1,430
for 7 nights, 1 home
AU$204 per night
includes taxes & fees
The Bartaline hut
Pool
Exterior
Room
Interior
Exceptional
(22 reviews)

Legnaia countryside luxury property, shared pool, ideal base to discover Tuscany

Siena

14% off
AU$3,592
for 7 nights, 1 villa
AU$513 per night
includes taxes & fees
Legnaia countryside luxury property, shared pool, ideal base to discover Tuscany
Exterior
Property grounds
Private kitchen
Private kitchen
Exceptional
(16 reviews)

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

Siena

9% off
AU$8,847
for 7 nights, 1 home
AU$1,264 per night
includes taxes & fees
Beautiful farmhouse nestled in very sweet hills just a few minutes from Siena
Property grounds
Exterior detail
Interior
Interior
Wonderful
(11 reviews)

Lovely country house in the Chianti region, for 4 persons, near Siena

Castellina in Chianti

13% off
AU$1,965
for 7 nights, 1 home
AU$281 per night
includes taxes & fees
Lovely country house in the Chianti region, for 4 persons, near Siena
Pool
Property grounds
Interior
Property grounds
Exceptional
(81 reviews)

Villa with large garden in the Chianti hills

Castellina in Chianti

9% off
AU$905
for 7 nights, 1 home
AU$129 per night
includes taxes & fees
Villa with large garden in the Chianti hills
Private kitchen
Living area
Property grounds
Dining
Exceptional
(116 reviews)

Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany

Siena

14% off
AU$7,983
for 7 nights, 1 villa
AU$1,140 per night
includes taxes & fees
Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany
modern and bright kitchen with balcony
Outdoor dining
Interior
Second bed room - detail
Exceptional
(69 reviews)

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

Siena

7% off
AU$2,327
for 7 nights, 1 apartment
AU$332 per night
includes taxes & fees
Family apartment with magical view on the old city, balcony, wifi & parking
Living area
Room
Dining
Room
Exceptional
(13 reviews)

Il Casato, beautiful apartment in the heart of Siena

Siena

11% off
AU$1,731
for 7 nights, 1 apartment
AU$247 per night
includes taxes & fees
Il Casato, beautiful apartment in the heart of Siena
Interior
Outdoor dining
Interior
Dining
Exceptional
(46 reviews)

Period residence located in the heart of Siena

Siena

5% off
AU$1,522
for 7 nights, 1 apartment
AU$217 per night
includes taxes & fees
Period residence located in the heart of Siena
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Book a holiday rental for your San Leonino getaway

Learn about the unique charm of San Leonino with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Sightseeing in and around San Leonino

Do you want to find top things to see and do during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that San Leonino has to offer. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Terra di Seta (4.2 mi / 6.7 km)
  • Castello di Radda Winery (6.4 mi / 10.3 km)
  • Isole e Olena Winery (6.7 mi / 10.9 km)
  • Il Molino di Grace Winery (7.1 mi / 11.5 km)
  • Borgo di Vescine - Tenute di Castelvecchi (7.2 mi / 11.5 km)
  • Castello della Paneretta (7.4 mi / 11.9 km)

Exploring the natural features in San Leonino

Whether you're looking for adventure or just want to appreciate the scenery, San Leonino is a great place to get out in nature. Here are some of the area’s most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Alta Val d'Elsa River Park (8.5 mi / 13.7 km)
  • Val di Merse (17.2 mi / 27.7 km)
  • Arno River (24 mi / 38.6 km)
  • Chianti Sculpture Park (4.6 mi / 7.4 km)
  • Sentierelsa Trail (8.4 mi / 13.5 km)
  • Le Caldane Thermal Baths (8.4 mi / 13.6 km)

Travelling to and around San Leonino

Fly into Peretola Airport (FLR), the closest airport, located 26.8 mi (43.2 km) from the city centre.

Frequently asked questions

What is the most popular type of holiday home accommodation in San Leonino?
The most in-demand types of holiday homes in San Leonino are farmhouses. Want something different? Stayz offers a variety of options to match our guests' needs, so you'll see holiday homes in all shapes and sizes. The ideal fit is waiting for you — get hold of yours today.
How much does it cost to rent a holiday home in San Leonino?
Different factors can affect the price of a holiday home in San Leonino, such as the type of property, season and length of stay. However, all Stayz homes have something in common — unbeatable value. Just enter your travel dates to find your perfect match.
How much does it cost to rent a beach house in San Leonino?
The average price for a holiday home by the beach in San Leonino will depend on when you'll be there and the size and style of property you're searching for. You can easily find prices on Stayz by entering your destination and preferred travel dates. Then make use of the filter tool to choose the number of bedrooms and amenities important to you, such as air conditioning, WiFi and a hot tub.
Are there pet-friendly holiday homes in San Leonino?
Good news. There are. You can choose from two holiday homes that welcome pets in San Leonino on Stayz. Our furry friends need to get away from it all too, so simply use our search function for pet-friendly holiday homes to book a perfect pad where Spot can share in the good times.
Can I rent a house with a pool in San Leonino?
Add a new level of fun to your trip by booking your group into one of the two houses with a private pool in San Leonino. Use our search filter to find the kind of property you want on Stayz, and then spend your downtime frolicking in a swimming pool that's for your use only.
What are popular home amenities in San Leonino?
Some of the most popular home amenities people are looking for in San Leonino include a fireplace, a garden and a swimming pool. Whether you're taking a trip with family, your besties or even pets, Stayz holiday homes provide the best amenities for ultimate relaxation with your loved ones.
Are there holiday homes in San Leonino that welcome kids?
San Leonino has two family-friendly holiday homes. And discovering a stay that welcomes children is a cinch with Stayz's "Properties good for families" filter. Besides having the entire place to yourselves, you can also look forward to perks and amenities like multiple bedrooms, kitchens and private pools.
What are the top attractions for families in San Leonino?
Treat the kiddos to a day out at these top family-friendly attractions in San Leonino:
  • Archaeological Museum of Chianti
  • Walls of Monteriggioni
Are there holiday homes with WiFi in San Leonino?
You'll have a choice of two holiday homes with WiFi in San Leonino. If you'd like to disconnect from the world while on holiday, but still need to be connected to the internet, these getaways have just what you need. Narrow your search by applying the WiFi filter on Stayz.
How old do you have to be to rent a holiday home in San Leonino?
The minimum age is typically 16, 18 or 21. It can differ across properties on Stayz, so check the rules of your chosen San Leonino stay before booking.
How long can I rent a holiday home in San Leonino for?
The length of time you can book a holiday home in San Leonino is down to the property. Just enter your chosen dates to see a list of options offering extended stays. With lots of creature comforts such as full kitchens and air conditioning, as well as some offering weekly or monthly discounts, you're sure to discover somewhere perfect to call your home away from home in San Leonino.