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Check prices for these dates

In two weeks
5 Jun - 7 Jun
In two months
17 Jul - 19 Jul
In three months
14 Aug - 16 Aug
In four months
11 Sep - 13 Sep

Our top choices for San Leonino holiday rentals

Villa, Air conditioning, Courtyard View | Exterior

Villa Montecastello

Villa Montecastello
Monteriggioni
The price is ฿6,984
฿7,796 total
includes taxes & fees
19 May - 20 May
Villa Montecastello
Premium bedding, down duvets, pillow-top beds, minibar

Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.0 out of 10, Wonderful, (26 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is ฿2,280
฿3,002 total
includes taxes & fees
22 May - 23 May
Tuscasì Aparthotel
Aerial view

Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (30 reviews)
"The view was so incredible and the pool just like a dream. "
Canada
Sarah
The price is ฿6,964
฿7,736 total
includes taxes & fees
25 May - 26 May
Riserva di Fizzano Residence
Exterior

Il Pozzo di Sant'Andrea

Il Pozzo di Sant'Andrea
Siena
9.8 out of 10, Exceptional, (16 reviews)
"Great host, lovely place near Siena"
United Kingdom
Prem
The price is ฿3,455
฿3,952 total
includes taxes & fees
25 May - 26 May
Il Pozzo di Sant'Andrea
Food court

Antico Borgo Poggiarello

Antico Borgo Poggiarello
2.0 star property
Monteriggioni
9.0 out of 10, Wonderful, (20 reviews)
"We had an absolutely wonderful time staying here. Our kids had fun on their playground and my wife and I enjoyed the views, the hospitality. And the entire experience. The food was outstanding. "
United States
James Bakley
The price is ฿5,745
฿6,434 total
includes taxes & fees
16 Jun - 17 Jun
Antico Borgo Poggiarello
Studio, Patio, Ground Floor | Terrace/patio

Fullino Nero

Fullino Nero
Siena
9.6 out of 10, Exceptional, (51 reviews)
"Great stay! Clean rooms with air conditioning. Beautiful grounds "
United States
Christian
The price is ฿3,606
฿4,118 total
includes taxes & fees
19 May - 20 May
Fullino Nero
Indoor pool, seasonal outdoor pool, pool umbrellas, pool loungers

Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (32 reviews)
"Beautiful villa, very spacious, gorgeous property and great restaurant on the property to have a delicious meal. Staff very welcoming. Close to other main cities, like Siena, for day trips. We loved sitting by the pool, although it wasn’t heated, so too cold to use in April. We did love using the indoor heated pool and hot tub each day. We had a fabulous time and hope to go back someday! "
Canada
Jeremy
The price is ฿5,254
฿5,780 total
includes taxes & fees
29 May - 30 May
Villa di Sotto
Outdoor dining

B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (82 reviews)
"It was a wonderful stay the bed was comfortable and the view was beautiful. "
United States
Ruben
The price is ฿4,261
฿4,839 total
includes taxes & fees
19 May - 20 May
B&B La Fonte del Machiavelli
Aerial view

Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (171 reviews)
"Lovely stay! I would highly recommend this hotel. The indoor pool was just so enjoyable after a day out sightseeing. "
United Kingdom
Lizl
The price is ฿3,695
฿4,369 total
includes taxes & fees
21 May - 22 May
Bosco della Spina
Aerial view

Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (65 reviews)
"Pros: 1. Beautiful property with an amazing view. 2. Spacious family suite 3. Comfortable bed 4. Quiet, waking up to birds singing in the morning. Cons: 1. Stink bugs in the suite; once we understood they are common this time of year and easy to capture and release outside, it was ok. 2. Showers are very small. 3. A/C not turned on this time of year; was not offered fans until the last day. 4. Minimal amenities. 5. Few outlets The villa is beautiful, just be prepared for a “rustic”...
United States
Niyo
The price is ฿5,719
฿6,595 total
includes taxes & fees
20 May - 21 May
Villa Curina Resort
Terrace/patio

Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.4 out of 10, Exceptional, (23 reviews)
"Fantastic experience with friendly hosts and an excellent breakfast! A little rustic here and there but all part of the charm!"
United Kingdom
Alasdair
The price is ฿3,913
฿4,418 total
includes taxes & fees
24 May - 25 May
Casa di Campagna in Toscana
Exterior

Villa Norcenni Aparthotel

Villa Norcenni Aparthotel
2.0 star property
Figline e Incisa Valdarno
7.4 out of 10, Good, (21 reviews)
"It was clean and safe."
United Kingdom
Laka
The price is ฿1,964
฿2,275 total
includes taxes & fees
19 May - 20 May
Villa Norcenni Aparthotel
Exterior

Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (23 reviews)
"Such a beautiful place to stay! The cottage was amazing, very spacious and clean. The grounds themselves were picturesque, was well above our expectations and the host was very welcoming and accommodating."
United Kingdom
Sasha
The price is ฿5,040
฿5,847 total
includes taxes & fees
21 May - 22 May
Borgo Argenina
Food court

Borgo Il Poggiaccio

Borgo Il Poggiaccio
Sovicille
8.8 out of 10, Excellent, (65 reviews)
"Beautiful place, great position in the countryside, truly relaxing place, wish we could stay longer, definitely will return A***"
United States
Dean
The price is ฿5,450
฿6,185 total
includes taxes & fees
22 May - 23 May
Borgo Il Poggiaccio
Apartment, 1 Bedroom, Garden View | View from room

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
The price is ฿5,600
฿6,312 total
includes taxes & fees
19 May - 20 May
La Coroncina Lodging
Property entrance

Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (100 reviews)
"This is a lovely gem. Includes parking which is hard to find. Family owned and its a truly beautiful place. Breakfast was amazing as well!! Recommend!! "
United States
rose
The price is ฿8,525
฿9,529 total
includes taxes & fees
28 May - 29 May
Villa il Fedino
Deluxe Double or Twin Room | 2 bedrooms, Frette Italian sheets, hypo-allergenic bedding, down duvets

Residence Il Connubio

Residence Il Connubio
3.0 star property
Impruneta
8.8 out of 10, Excellent, (32 reviews)
"Such a cute little place! Very clean and easy to get around! Would highly recommend!"
United States
Desiree
The price is ฿3,147
฿3,575 total
includes taxes & fees
21 May - 22 May
Residence Il Connubio
Business Room, 1 Bedroom | Down duvets, desk, cots/infant beds, rollaway beds

Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (88 reviews)
"Hotel clean comfortable. No elevator, no reception desk. "
United States
Karin
The price is ฿2,754
฿3,181 total
includes taxes & fees
7 Jun - 8 Jun
Domus il Palio B&B
Room amenity

Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (442 reviews)
"It’s very close to the historical center but feels quiet and like you are separate from it. I loved our stay"
United States
David
The price is ฿4,717
฿5,340 total
includes taxes & fees
15 Jun - 16 Jun
Siena Vip
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 Leonino Hotel Reviews

Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais

10/10 Excellent
"We had a lovely stay for a weekend. Excellent, high quality suite, great restaurant and pleasant team. Spa was very relaxing and a great place to chill out. "
Mike 2-night trip
Posted 17 hours ago
Borgo Scopeto Wine & Country Relais

Find out more about San Leonino

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

  • View our selection of featured holiday rentals in San Leonino
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  • Enter your travel dates to view the best deals on holiday rentals in San Leonino while they last

Look no further and take a look at our great range of rental properties in San Leonino!

Frequently asked questions

Are there holiday rentals in San Leonino?

Yes, there are holiday rentals close to the most popular sights in San Leonino, 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 Leonino has to offer?

Borgo Argiano: This holiday home rental outside of San Leonino 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 an electric kettle. You can relax into your holiday with a garden and a library.

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

Explore the area and family-friendly sights such as Borgo di Vescine - Tenute di Castelvecchi, or get out into nature at a spot like Chianti Sculpture Park. City Hall Castellina In Chianti and Terra di Seta are a couple of places you'll find in the wider area.

What’s a holiday rental in San Leonino like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in San Leonino. Holiday rentals offer extras such as hot tubs, fire pits and patios so you'll feel right at home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from public hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for family trips.