San Leolino Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in San Leolino

ApartHotel Anghel

Siena
8.4 out of 10, Very good, (331)
"Would recommend staying here and will hopefully be back!"
Canada
Lisa
The price is NZ$144
includes taxes & fees
24 Nov - 25 Nov
ApartHotel Anghel

Il Battistero Siena - Residenza d'Epoca

Siena City Centre
9.6 out of 10, Exceptional, (188)
"Great location and friendly staff. "
United States
Parissa
Il Battistero Siena - Residenza d'Epoca

Farmhouse in the heart of the real chiantishire

Castellina in Chianti
10.0 out of 10, Exceptional, (147)
"We loved our stay! The Farmhouse is really lovely and the view out the back is exceptional. We enjoyed a lot of home cooked meals with the most stunning view. Daniele was amazing to communicate with as well. Definitely hope to be back one day! "
Australia
Rebekah T.
Farmhouse in the heart of the real chiantishire

Regis Condo

Siena City Centre
9.4 out of 10, Exceptional, (65)
"This was one of our favorite stays in Italy. It was spacious, clean, and in a great part of the city."
United States
Ben
Regis Condo

Relais Villa Belvedere

Figline e Incisa Valdarno
9.2 out of 10, Wonderful, (69)
"Very nice place"
United States
Maria
The price is NZ$195
includes taxes & fees
25 Nov - 26 Nov
Relais Villa Belvedere

Villa with large garden in the Chianti hills

Siena
9.6 out of 10, Exceptional, (75)
"Our group enjoyed staying in this location. It was comfortable and a perfect central location for exploring Tuscany."
United States
Jessica P.
Villa with large garden in the Chianti hills

Residenza d'Epoca Palazzo Borghesi

Siena City Centre
9.6 out of 10, Exceptional, (116)
"We enjoyed our stay here. Convenient, clean, central to city center, shops, and restaurants. We would stay here again."
United States
Linda
The price is NZ$321
includes taxes & fees
19 Nov - 20 Nov
Residenza d'Epoca Palazzo Borghesi

Camping Siena Colleverde

3.0 star property
Scacciapensieri
8.2 out of 10, Very good, (159)
"Safe, great proximity to Siena without being too close, nice pool."
United States
Martha
Camping Siena Colleverde

Il Poggio dell'Eremita

Sinalunga
10.0 out of 10, Exceptional, (58)
"Amazing property! Could not recommend more."
United States
Annika P.
The price is NZ$282
includes taxes & fees
19 Nov - 20 Nov
Il Poggio dell'Eremita

17th century farmhouse with private pool and Wi-Fi and air conditioning

Arezzo
9.2 out of 10, Wonderful, (39)
"We stayed as a family of 10 and had a great time. The accommodation is definitely rustic and traditional. It won’t suit everyone but if you’re looking to get back to basics look no further! For us as an Australian family it could have cleaner and we ended up doing cleaning ourselves to make it more comfortable. The bed linen and towels are also ready for a refresh. The host was great and provided a good summary of the local area and sights. Arezzo is a lovely day out. "
Australia
Anonymous traveller
17th century farmhouse with private pool and Wi-Fi and air conditioning

Borgo Argiano

Castelnuovo Berardenga
10.0 out of 10, Exceptional, (73)
"Borgo Argiano is a beautiful property, very well run by Dario and staff. We highly recommend staying there if you are interested in exploring the Tuscan region. The apartments are large and they stock the kitchen for convenience It is also a winery and you could get a tour was well as a tasting of the delicious wines."
United States
Aurora
Borgo Argiano

ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

Castellina in Chianti
10.0 out of 10, Exceptional, (64)
"We had a company retreat at this amazing location. Everyone was in love with the place and the facilities!"
Netherlands
Jochem G.
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

Wonderful Villa - Air Bubble Massage Pool - WiFi - max.14peopl

Greve in Chianti (Firenze)
10.0 out of 10, Exceptional, (42)
"Elena and her staff were excellent. They provided us with a welcome dinner which was great after our long trip in, as well as breakfast the next morning. Property is beautiful up in top of a hill overlooking the beautiful landscape. We had 9 people with more than enough room for all of us. Highly recommended!"
United States
Ryan F.
Wonderful Villa - Air Bubble Massage Pool - WiFi - max.14peopl

Villa Il Palagio

Rignano sull'Arno
8.6 out of 10, Excellent, (60)
"We stayed 2 nights and loved it! We have a 2 bedroom , 2 bath apartment and it was so spacious. We enjoyed the kind staff and the breakfast had a lot of choices. It was great"
United States
Rebekkah
Villa Il Palagio

Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!

Siena
10.0 out of 10, Exceptional, (9)
"Fabulous place to stay with a big group of family and friends. Very easy walk to town and the beautiful treasures of Siena."
United Kingdom
Marc K.
Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!

PICTURESQUE VIEWS OLIVE VINEYARDS EAT DRINK PURE RECREATION

Ruffoli
9.8 out of 10, Exceptional, (58)
"Great location in the heart Chianti. The host was very welcoming and the apartment was perfect. very comfortable bed and very quiet location. Nice terrace and pool but unfortunately the weather wasnt warm enough for us to enjoy the pool. There is a dirt road to get to the apartment but very easy to navigate so dont be worried about it. Thank you Babette, we hope to have the pleasure of going back sometime."
United States
Andre P.
PICTURESQUE VIEWS OLIVE VINEYARDS EAT DRINK PURE RECREATION

A Panoramic Tuscan Luxury - Villa Maria in Fronzano

Reggello
10.0 out of 10, Exceptional, (75)
"Walk 5 minutes to a village with grocery store or simply sit by the pool to enjoy the view. This villa has it all! Our family of 10 (adults and kids) spent 2 weeks at Villa Maria and would recommend it for its amenities and location. The host, Tomasso, and chef, Donato, were the ultimate guides and helpers. Take the train into Florence to avoid parking a car. Experience Borroncino Restaurant in Reggello for a gastronomic treat. We would certainly return to this heavenly spot for touring...
United States
Maralin G.
A Panoramic Tuscan Luxury - Villa Maria in Fronzano

Charming 2Br Flat - City Center Siena Close To Piazza Del Campo

Siena City Centre
9.4 out of 10, Exceptional, (61)
"Very relaxing property in a great location close to il Campo. "
United States
David N.
Charming 2Br Flat - City Center Siena Close To Piazza Del Campo

Romantic house in the middle of the Chianti vineyards in the heart of Tuscany.

Greve in Chianti
9.0 out of 10, Wonderful, (24)
"Wonderful house with all the facilities you need for self-catering. Although we used it as a base to visit all around the area, we also spent a few days just relaxing in the garden and going to the pool.Well equipped kitchen including a dishwasher and washing machine.Very peacefu, would love to come back one day."
United States
Robert H.
Romantic house in the middle of the Chianti vineyards in the heart of Tuscany.

BEAUTIFUL VILLA with private Pool in the heart of Chianti

castelnuovo berardenga
10.0 out of 10, Exceptional, (27)
"Great villa great view fantastic hostage "
Germany
Markus B.
BEAUTIFUL VILLA with private Pool in the heart of Chianti
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.
Save an average of 15% on thousands of hotels when you're signed in

Top San Leolino Hotel Reviews

Find out more about San Leolino

Everything you need to know about San Leolino holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the San Leolino holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 San Leolino holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

San Leolino holiday rentals: An excellent choice for every season

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

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A San Leolino holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of San Leolino holiday rentals we have selected for you start as low as NZ$144 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on San Leolino rentals

At Expedia, we put the best San Leolino holiday 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 San Leolino 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 San Leolino holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around San Leolino. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in San Leolino?

Yes, there are holiday rentals close to the most popular sights in San Leolino, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that San Leolino has to offer?

Borgo Argiano: This holiday home rental outside of San Leolino is located on a river, and has a balcony, a terrace and a BBQ 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 holiday with a garden and a library.

What’s there to see and do in San Leolino?

Explore the area and family-friendly sights such as Siena Circuit, or get out into nature at a spot like Chianti Sculpture Park. In the wider area, you’ll find Villa a Sesta Polo Club and Cantalici Winery.

What’s a holiday rental in San Leolino like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in San Leolino. Holiday rentals feature amenities such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from shared hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for a family trip.