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San Leolino Vacation Rentals

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for San Leolino vacation rentals

A pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

1. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (40 reviews)
"Great spot"
Canada
Philippe
$162 nightly
The price is $179
Oct 20 - Oct 21
Total with taxes and fees
Villa di Sotto
A villa with a swimming pool, outdoor seating, and a tennis court.

2. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (80 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
$121 nightly
The price is $137
Oct 20 - Oct 21
Total with taxes and fees
Villa Curina Resort
A stone building with a yellow sign reading "b&b erioico".

3. 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
$128 nightly
The price is $149
Nov 5 - Nov 6
Total with taxes and fees
L' Eroico
A cozy living room with a stone wall, a wine rack, and two sofas.

4. Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (27 reviews)
"The staff were great and the villa was amazing"
United States
Ralphvincent
$129 nightly
The price is $142
Oct 18 - Oct 19
Total with taxes and fees
Villa Cassia di Baccano
A courtyard with a fountain, a pergola with flowers, and a building with a bell tower.

5. Relais Villa Belpoggio - Residenza d'Epoca

Relais Villa Belpoggio - Residenza d'Epoca
Loro Ciuffenna
9.8 out of 10, Exceptional, (35 reviews)
"Excellent getaway- beautiful property - great staff - extremely clean - I give it a 100"
United Kingdom
Mona
$139 nightly
The price is $153
Oct 25 - Oct 26
Total with taxes and fees
Relais Villa Belpoggio - Residenza d'Epoca
An arched stone bridge with a white building on the right, featuring a balcony with plants.

6. 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
$105 nightly
The price is $115
Oct 24 - Oct 25
Total with taxes and fees
Locanda Antico Borgo
A wooden table with two chairs on a balcony, overlooking a lush green landscape with trees and hills.

7. 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
$117 nightly
The price is $132
Oct 19 - Oct 20
Total with taxes and fees
Casa Vacanze Le Fornaci
A compact kitchen with a wooden countertop, stainless steel appliances, and a modern design.

8. Cennano Suite - enter apartment

Cennano Suite - enter apartment
Montevarchi
10.0 out of 10, Exceptional, (3 reviews)
"After and before the tourist rushes of Florence. I enjoyed a few very quiet and relaxing days in a beautiful and spacious place. "
Germany
Judith T.
$108 nightly
The price is $108
Nov 1 - Nov 2
Total with taxes and fees
Cennano Suite - enter apartment
A stone building with a garden in front.

9. 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
$180 nightly
The price is $207
Oct 19 - Oct 20
Total with taxes and fees
Borgo Argenina
A spa area with a stone-walled arch, a hot tub, and a small window.

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
$101 nightly
The price is $116
Nov 8 - Nov 9
Total with taxes and fees
DormiVeglia B&B
A staircase with a wooden handrail, a potted plant, and a chair in a hallway.

11. 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
$85 nightly
The price is $98
Oct 19 - Oct 20
Total with taxes and fees
Villa Fontis Rapolano
A courtyard with outdoor seating, a stone building with a tower, and a well-maintained garden.

12. 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
$234 nightly
The price is $262
Oct 28 - Oct 29
Total with taxes and fees
Castello di Gargonza
A stone building with a tiled roof, surrounded by a well-maintained garden with various plants and a cactus in the foreground.

13. 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
$115 nightly
The price is $131
Oct 29 - Oct 30
Total with taxes and fees
La Murata
A stone building with a large arched entrance, two potted plants, and a small clock above the door.

14. 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
$94 nightly
The price is $108
Oct 21 - Oct 22
Total with taxes and fees
Podere La Chiusella
Property entrance

15. 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
$163 nightly
The price is $179
Oct 16 - Oct 17
Total with taxes and fees
Palazzo Tarlati Residenza d'Epoca
Pool

16. 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
$84 nightly
The price is $99
Nov 15 - Nov 16
Total with taxes and fees
iConic Wellness Resort
An arched stone gateway leading to a pathway lined with potted plants and lights.

17. Castello di Modanella

Castello di Modanella
Rapolano Terme
8.0 out of 10, Very good, (17 reviews)
"To far out"
United States
Dennis
$121 nightly
The price is $138
Oct 25 - Oct 26
Total with taxes and fees
Castello di Modanella
A building with a sign for 'Residence Leccio' and a café named 'La Rumba Café'.

18. RESIDENCE LECCIO

RESIDENCE LECCIO
Asciano
9.4 out of 10, Exceptional, (8 reviews)
"Very nice, affordable place in beautiful area"
United States
Corey
$75 nightly
The price is $88
Oct 29 - Oct 30
Total with taxes and fees
RESIDENCE LECCIO
A dining area with a brick archway, wooden dining table, chairs, and a chandelier.

19. Holiday Home 'Poggio Loccano' with Private Garden and Balcony

Holiday Home 'Poggio Loccano' with Private Garden and Balcony
Montevarchi
$373 nightly
The price is $373
Nov 2 - Nov 3
Total with taxes and fees
Holiday Home 'Poggio Loccano' with Private Garden and Balcony
A stone building with arched windows and a gravel driveway.

20. Villa La Ginestra

Villa La Ginestra
Subbiano
9.6 out of 10, Exceptional, (5 reviews)
"Le charme de l'endroit, l'attention de l'hôte, le confort, le déjeuner delicieux."
Canada
Philippe
$100 nightly
The price is $113
Oct 18 - Oct 19
Total with taxes and fees
Villa La Ginestra
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

La Certosa di Pontignano

La Certosa di Pontignano

10/10 Excellent
"Absolutely amazing stay! The room was clean, large with a great view. The staff was always willing to help. Could not have asked for more. Highly recommend!"
Virginia 2-night trip
Posted 2 hours ago
La Certosa di Pontignano

Find out more about San Leolino

Everything you need to know about San Leolino vacation rentals

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

San Leolino vacation 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 low season months. For more hustle and bustle, you may prefer to visit San Leolino in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $73 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on San Leolino rentals

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

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.

Explore a world of travel with Expedia

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: Visitors like this San Leolino vacation home rental. It 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 kitchenware. 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 Terme Antica Querciolaia. 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.