San Leolino Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Vacation Rentals in San Leolino

Lobby lounge
ApartHotel Anghel

Apartment in Siena

8.4 out of 10, Very Good, (334)
"Would recommend staying here and will hopefully be back!"
Canada
Lisa
The price is ￥10,758
￥12,557 total
includes taxes & fees
Dec 10 - Dec 11
ApartHotel Anghel
Bar (on property)
Il Battistero Siena - Residenza d'Epoca

Residence in Siena City Centre

9.6 out of 10, Exceptional, (191)
"Great location and friendly staff. "
United States
Parissa
Il Battistero Siena - Residenza d'Epoca
Exterior
Farmhouse in the heart of the real chiantishire

Vacation Home in Castellina in Chianti

10.0 out of 10, Exceptional, (148)
"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
Grand Apartment with Garden | Private kitchen | Full-size fridge, microwave, oven, stovetop
Regis Condo

Apartment in 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
Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
Relais Villa Belvedere

Aparthotel in Figline e Incisa Valdarno

9.0 out of 10, Wonderful, (70)
"Very nice place"
United States
Maria
The price is ￥14,348
￥16,054 total
includes taxes & fees
Dec 9 - Dec 10
Relais Villa Belvedere
Exterior
Il Poggio dell'Eremita

Villa in Sinalunga

10.0 out of 10, Exceptional, (59)
"Amazing property! Could not recommend more."
United States
Annika P.
The price is ￥21,973
￥25,590 total
includes taxes & fees
Dec 9 - Dec 10
Il Poggio dell'Eremita
Panoramic Suite, City View | View from room
Residenza d'Epoca Palazzo Borghesi

Residence in 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 ￥28,437
￥32,004 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Residenza d'Epoca Palazzo Borghesi
Exterior
Camping Siena Colleverde

Camping in Scacciapensieri

3.0 star property
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
Outdoor pool
17th century farmhouse with private pool and Wi-Fi and air conditioning

Villa in 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 traveler
17th century farmhouse with private pool and Wi-Fi and air conditioning
Outdoor dining
Villa with large garden in the Chianti hills

Vacation Home in 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
Outdoor dining
PICTURESQUE VIEWS OLIVE VINEYARDS EAT DRINK PURE RECREATION

Apartment in Ruffoli

9.8 out of 10, Exceptional, (59)
"This is the most special place I’ve ever been. It’s breathtakingly beautiful. The house itself it’s stunning but the outside terrace and pool area is a dream. I will absolutely come back here again if I get the chance. The host was very helpful, communicative and kind."
United States
Alexandra E.
PICTURESQUE VIEWS OLIVE VINEYARDS EAT DRINK PURE RECREATION
Exterior
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

Villa in Castellina in Chianti

10.0 out of 10, Exceptional, (64)
"Gorgeous property - we had a wonderful stay "
United Kingdom
Michelle D.
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Pool
Beautiful villa for 6 guests with private pool, A/C, WIFI, TV, patio and pets allowed

Vacation Home in Cavriglia

10.0 out of 10, Exceptional, (13)
"Really great stay here.The villa is absolutely beautiful on the outside and inside.Parking was easy (right in front of property).Location was beautiful and hosts were great."
United States
Mohammed S.
Beautiful villa for 6 guests with private pool, A/C, WIFI, TV, patio and pets allowed
Front of property - evening/night
Villa Il Palagio

Apartment in Rignano sull'Arno

8.6 out of 10, Excellent, (60)
"The best place in the region"
United Kingdom
Kamen
Villa Il Palagio
Suite | Premium bedding, Select Comfort beds, minibar, in-room safe
La Terrazza Sul Campo Rooming House

Residence in Siena City Centre

9.8 out of 10, Exceptional, (239)
"Huge room! Great location "
Canada
karen
La Terrazza Sul Campo Rooming House
Terrace/patio
Borgo Argiano

Vacation Home in 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
Outdoor dining
A Panoramic Tuscan Luxury - Villa Maria in Fronzano

Villa in 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
Outdoor pool, pool umbrellas, sun loungers
Riserva di Fizzano Residence

Residence in Castellina in Chianti

3.0 star property
9.8 out of 10, Exceptional, (24)
"Perfect location on the top of a hill surrounded by the beautiful vineyards of Chianti. Enjoy the view by the pool or the fabulous sunset with a glass of wine. The staff were friendly and the restaurant was 5 star. I highly recommend a stay to fulfill all your Tuscan dreams. "
United States
Eileen
Riserva di Fizzano Residence
Interior
Romantic house in the middle of the Chianti vineyards in the heart of Tuscany.

Vacation Home in 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.
Daily cooked-to-order breakfast (EUR 15 per person)
La Coroncina Lodging

Aparthotel in Siena

10.0 out of 10, Exceptional, (42)
"Fantastic place, and I highly recommend it."
United States
Hassan
The price is ￥12,810
￥14,814 total
includes taxes & fees
Dec 11 - Dec 12
La Coroncina Lodging
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 San Leolino Hotel Reviews

Hotel Italia

Hotel Italia

10/10 Excellent
"This was a short stay for us in Siena. A great hotel. Friendly staff and the best bargain best breakfast we have had in Italy. Highly recommended"
Phil 1-night trip
Posted 4 days ago
Hotel Italia

Find out more about San Leolino

Search for holiday rentals in San Leolino on Expedia! You can easily find your home rentals, villas, holiday apartments in San Leolino using one of the methods below:

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Frequently asked questions

Can I find a vacation rental in San Leolino?

Yes, you can find vacation rentals near the most popular sights in San Leolino, or you can go with a more remote option if you want a relaxing place to stay.

What are some of the best vacation home rentals in San Leolino?

Borgo Argiano: You might want to consider this vacation home rental near San Leolino, which 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 a coffee maker. You can relax into your vacation 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 larger area, you’ll find Villa a Sesta Polo Club and Cantalici Winery.

What’s a vacation rental in San Leolino like?

Vacation rentals are private properties where you can stay for a few weeks or just a few days in San Leolino. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll have all the conveniences of home. If you're concerned about cleanliness, a vacation rental can offer a sense of safety away from shared hotel elevators and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for a family trip.