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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for San Leolino holiday rentals

A villa with a swimming pool, outdoor seating, and a tennis court.

1. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (81 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
The price is £113
includes taxes & fees
24 Oct - 25 Oct
Villa Curina Resort
A hot tub with two glasses of a beverage.

2. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (40 reviews)
"Great spot"
Canada
Philippe
The price is £146
includes taxes & fees
29 Oct - 30 Oct
Villa di Sotto
A courtyard with outdoor seating, a stone building with a tower, and a well-maintained garden.

3. Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.4 out of 10, Exceptional, (48 reviews)
"Roberto, his wife and his staff were all round great. Very friendly helpful and great service. We were very happy to find this authentic castle/village to stay in Tuscany."
Canada
Iain
The price is £203
includes taxes & fees
23 Oct - 24 Oct
Castello di Gargonza
A wooden table with two chairs on a balcony, overlooking a lush green landscape with trees and hills.

4. Casa Vacanze Le Fornaci

Casa Vacanze Le Fornaci
Pergine Valdarno
9.8 out of 10, Exceptional, (7 reviews)
"Very nice hotel with friendly stad"
Denmark
Lisette
The price is £101
includes taxes & fees
23 Oct - 24 Oct
Casa Vacanze Le Fornaci
A cozy living room with a stone wall, a wine rack, and two sofas.

5. Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (27 reviews)
The price is £95
includes taxes & fees
27 Oct - 28 Oct
Villa Cassia di Baccano
A stone building with a garden in front.

6. Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (28 reviews)
"What an amazing place. We enjoyed it so much."
United States
Tatevik
The price is £147
includes taxes & fees
27 Oct - 28 Oct
Borgo Argenina
A courtyard with a fountain, a pergola with flowers, and a building with a bell tower.

7. Relais Villa Belpoggio - Residenza d'Epoca

Relais Villa Belpoggio - Residenza d'Epoca
Loro Ciuffenna
9.8 out of 10, Exceptional, (36 reviews)
"We had fantastic time here! The property is so beautiful and special! The views are stunning and the breakfast was very delicious! Hope we will come again! Special thanks to Tania who was very friendly and nice all the time!"
Germany
Kristina
The price is £117
includes taxes & fees
28 Oct - 29 Oct
Relais Villa Belpoggio - Residenza d'Epoca
An arched stone bridge with a white building on the right, featuring a balcony with plants.

8. Locanda Antico Borgo

Locanda Antico Borgo
Civitella in Val di Chiana
9.2 out of 10, Wonderful, (21 reviews)
"What an absolutely beautiful stay, in a stunning place. Our host was attentive and kind, and the food was wonderful. The hotel and rooms were spotlessly clean, and particularly for my needs on a road trip with my 18 year old son, the accommodation offering two adjoining bedrooms was perfect, and we could park outside. Also very good value in my opinion. I would definitely return, it’s also ideal for couples and I would love to bring my wife here. "
United Kingdom
Mr Andy
The price is £88
includes taxes & fees
28 Oct - 29 Oct
Locanda Antico Borgo
A stone building with a yellow sign reading "b&b erioico".

9. L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (15 reviews)
"Monica is a very gracious host. We very much enjoyed our stay. The village is also very quaint and within walking distance. We appreciate the hospitality and highly recommend staying here if you’re coming to the area."
United States
Angela
The price is £113
includes taxes & fees
2 Nov - 3 Nov
L' Eroico
An outdoor dining setup with a pool and lounge chairs in the background.

10. DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (30 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
The price is £89
includes taxes & fees
8 Nov - 9 Nov
DormiVeglia B&B
A stone building with a sloped roof, a small porch, and a gravel driveway.

11. Podere La Chiusella

Podere La Chiusella
Rapolano Terme
9.2 out of 10, Wonderful, (33 reviews)
"We enjoyed our stay. Everything was clean and comfortable, and the complex itself was impressive and a stunning place to stay. The location was also a convenient base for seeing Tuscany, and we had a great meal nearby in Rapolano Terme. Overall, it has the potential to be one of the coolest places you'll ever stay, though we did encounter a few technical issues regarding the shower and WiFi (which the hosts were quickly responsive about). I'd still recommend it, but it's helpful if you go in...
United Kingdom
Kevin
The price is £86
includes taxes & fees
22 Nov - 23 Nov
Podere La Chiusella
Property entrance

12. Palazzo Tarlati Residenza d'Epoca

Palazzo Tarlati Residenza d'Epoca
Civitella in Val di Chiana
8.0 out of 10, Very good, (3 reviews)
"Small family-owned inn located in center of Civitella in Val di Chiana. Room was comfortable and included all we needed. It was cold upon check-in which the co-owner tried to remedy with a space heater. It took a while. The room warmed up after the first night. The other co-owner kindly offered me our first night complimentary. (Thank you again.). The breakfast was simple and included fruit, juice, yogurt, sliced cheese and cold cut, packages sweets, tea, coffee and water. The owners were...
United States
Marco
The price is £134
includes taxes & fees
23 Oct - 24 Oct
Palazzo Tarlati Residenza d'Epoca
A staircase with a wooden handrail, a potted plant, and a chair in a hallway.

13. Villa Fontis Rapolano

Villa Fontis Rapolano
Rapolano Terme
10.0 out of 10, Exceptional, (1 review)
"Bella struttura, nuova, pulita in posizione comoda"
Italy
Barbara
The price is £71
includes taxes & fees
23 Oct - 24 Oct
Villa Fontis Rapolano
Pool

14. iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (41 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
The price is £66
includes taxes & fees
17 Nov - 18 Nov
iConic Wellness Resort
A narrow street with buildings on both sides, featuring arched doorways and windows with shutters.

15. Limehome Arezzo Duomo

Limehome Arezzo Duomo
Arezzo Centro Storico
9.0 out of 10, Wonderful, (4 reviews)
"I really liked the brand new room. Nice design and super comfy bed. Plus free coffee is a nice addition to the experience there. Loved it. Plus my personal highlight were the nice views into the historical center of Arezzo."
Germany
Florian
The price is £76
includes taxes & fees
25 Oct - 26 Oct
Limehome Arezzo Duomo
A stone building with a tiled roof, surrounded by a well-maintained garden with various plants and a cactus in the foreground.

16. La Murata

La Murata
Rapolano Terme
9.2 out of 10, Wonderful, (13 reviews)
"Amazingly beautiful place! Wish i could have stayed longer to enjoy the view but was just passing through. The apartment was so cute and clean. Any family would enjoy staying here. I would stay here again if i were in the area."
United States
Elizabeth
The price is £109
includes taxes & fees
23 Oct - 24 Oct
La Murata
An aerial view of a historic castle complex with multiple buildings, including a large central structure with a tower, surrounded by well-maintained gardens and pathways.

17. Castello di Modanella

Castello di Modanella
Rapolano Terme
8.0 out of 10, Very good, (17 reviews)
"To far out"
United States
Dennis
The price is £108
includes taxes & fees
23 Oct - 24 Oct
Castello di Modanella
A bedroom with a stone wall, a large mirror, a bed with white linens, a potted plant, and a view through a window with curtains.

18. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (80 reviews)
"Amazing property and room, only issue is it’s very understaffed so it’s hard to get anything without chasing down workers. They also don’t stay on the property so after like 11pm you’re on your own. Besides that it was a wonderful location and very peaceful."
United States
Gage
The price is £244
includes taxes & fees
31 Oct - 1 Nov
Terre di Baccio
A white table with a bowl of snacks, two glasses of orange drink, and a small potted plant on a balcony.

19. RESIDENCE LECCIO

RESIDENCE LECCIO
Asciano
9.4 out of 10, Exceptional, (8 reviews)
"Very nice, affordable place in beautiful area"
United States
Corey
The price is £72
includes taxes & fees
28 Oct - 29 Oct
RESIDENCE LECCIO
A swimming pool with lounge chairs and umbrellas, surrounded by stone walls and a landscaped area with trees.

20. Relais Villa Belvedere

Relais Villa Belvedere
Figline e Incisa Valdarno
9.0 out of 10, Wonderful, (77 reviews)
"True Tuscan style, beautiful views and a lovely breakfast."
Canada
Janet
The price is £78
includes taxes & fees
23 Oct - 24 Oct
Relais Villa Belvedere
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

Fattoria di Vegi

Fattoria di Vegi

10/10 Excellent
"Excellent staff and beautiful hotel"
Xinyi 2-night trip
Posted 10 hours ago
Fattoria di Vegi

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, apart-hotels, 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 £50 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 kitchenware. 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 Terme Antica Querciolaia. 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.