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San Leonino Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for San Leonino vacation rentals

A stone building with a courtyard, a swimming pool, and vineyard fields in the background.

1. Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (40 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
$164 nightly
The price is $182
Oct 8 - Oct 9
Total with taxes and fees
Riserva di Fizzano Residence
A kitchen with wooden cabinets, a glass display case, and a dining area with a table and chairs.

2. Mariani Bed & Breakfast

Mariani Bed & Breakfast
Castellina in Chianti
9.8 out of 10, Exceptional, (18 reviews)
"Beautiful view, very clean and everything in great condition. Friendly service. We will definitely stay again."
United States
Frank
$88 nightly
The price is $101
Oct 13 - Oct 14
Total with taxes and fees
Mariani Bed & Breakfast
A stone building with a garden in front.

3. Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (27 reviews)
"What an amazing place. We enjoyed it so much."
United States
Tatevik
$214 nightly
The price is $245
Oct 5 - Oct 6
Total with taxes and fees
Borgo Argenina
A rustic stone building with a courtyard.

4. Fullino Nero

Fullino Nero
Siena
9.6 out of 10, Exceptional, (56 reviews)
"Great stay! Clean rooms with air conditioning. Beautiful grounds "
United States
Christian
$108 nightly
The price is $123
Oct 5 - Oct 6
Total with taxes and fees
Fullino Nero
A villa with a swimming pool, outdoor seating, and a tennis court.

5. 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
$139 nightly
The price is $158
Oct 4 - Oct 5
Total with taxes and fees
Villa Curina Resort
A bakery display with pastries and a coffee station.

6. B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (211 reviews)
"We enjoyed our stay very much. Staff was very friendly and offered great advise on places to eat. The rooms had great charm to them. We were delighted with our selection of where to stay."
United States
Enrique
$114 nightly
The price is $130
Oct 31 - Nov 1
Total with taxes and fees
B&B Il Corso
A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

7. Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi
Castellina in Chianti
9.0 out of 10, Wonderful, (4 reviews)
"Staff was very helpful. Was a bit bummed the pool was closed as that was part of the reason for choosing the hotel. "
United States
Jeffrey
$131 nightly
The price is $146
Oct 20 - Oct 21
Total with taxes and fees
Casa Vacanze Squarcialupi
A pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

8. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (40 reviews)
"Great spot"
Canada
Philippe
$167 nightly
The price is $184
Oct 8 - Oct 9
Total with taxes and fees
Villa di Sotto
A bathroom with a window view of a historic building and a tiled roof.

9. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (484 reviews)
"Fantastic location and very friendly staff, we will definitely be back"
United Kingdom
Luis
$99 nightly
The price is $113
Nov 1 - Nov 2
Total with taxes and fees
Siena Vip
An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

10. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (102 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
$111 nightly
The price is $125
Nov 1 - Nov 2
Total with taxes and fees
Palazzo Pacini
A table with two wine glasses, a bottle, and a book.

11. Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (98 reviews)
"Everything was very clean and modern, working perfect. We didn’t meet anyone from the staff. And it would be nice if they leave some bottle of water for each room. We like the place a lot. People have to consider that it is outside Siena walls and it’s a pretty steep and long distance walk"
United States
María
$67 nightly
The price is $78
Oct 29 - Oct 30
Total with taxes and fees
Domus il Palio B&B
An outdoor swimming pool with a wooden pergola, lounge chairs, and a stone wall backdrop.

12. Guild Living Siena Senior Resort & Residence

Guild Living Siena Senior Resort & Residence
Scacciapensieri
8.8 out of 10, Excellent, (51 reviews)
"Amazing! Thank you!"
United Kingdom
Lucy
$108 nightly
The price is $123
Nov 1 - Nov 2
Total with taxes and fees
Guild Living Siena Senior Resort & Residence
A building with a sign reading 'Villa Le Camelie' and multiple flags.

13. Villa le Camelie Siena

Villa le Camelie Siena
Petriccio
8.6 out of 10, Excellent, (8 reviews)
"Nice for the price. Would stay there again."
United States
Mark
$82 nightly
The price is $95
Oct 29 - Oct 30
Total with taxes and fees
Villa le Camelie Siena
A bedroom with a bed, a bedside table, a TV mounted on the wall, and a sliding glass door leading to a balcony with a view of greenery and hills.

14. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (31 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
$77 nightly
The price is $89
Oct 31 - Nov 1
Total with taxes and fees
Tuscasì Aparthotel
A table with breakfast items and a view of rolling hills.

15. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Tavarnelle Val di Pesa
8.6 out of 10, Excellent, (121 reviews)
"It’s seen its best day a while ago. Basic necessities for an overnight, but I wouldn’t choose it again."
United States
Winonah
$73 nightly
The price is $82
Oct 13 - Oct 14
Total with taxes and fees
Chianti Village Morrocco
A table set with breakfast items on a balcony overlooking a historic town.

16. Residenza d'Epoca Palazzo Borghesi

Residenza d'Epoca Palazzo Borghesi
Siena City Centre
9.6 out of 10, Exceptional, (131 reviews)
"We had a great experience Property is perfectly located."
United States
Roman
$190 nightly
The price is $213
Oct 28 - Oct 29
Total with taxes and fees
Residenza d'Epoca Palazzo Borghesi
A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building.

17. Residenzia del Sogno

Residenzia del Sogno
Castellina in Chianti
9.6 out of 10, Exceptional, (15 reviews)
"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "
Canada
Katherine
$127 nightly
The price is $144
Oct 6 - Oct 7
Total with taxes and fees
Residenzia del Sogno
A stone building with a sign reading "Reception Antica Fonte".

18. Antica Fonte Residenza di Siena

Antica Fonte Residenza di Siena
Siena
6.0 out of 10, (2 reviews)
"Not very good hosts. They don’t speak English and they don’t help accomodate guests for issues out of their control. I would stay away very poor customer service "
Australia
Geoffrey
$86 nightly
The price is $99
Oct 16 - Oct 17
Total with taxes and fees
Antica Fonte Residenza di Siena
A spacious hotel room with a large bed, a sitting area with chairs, and a view through an arched doorway to another room.

19. La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House
Siena City Centre
9.8 out of 10, Exceptional, (251 reviews)
"Great stay. Thanks for the hospitality and kindness."
United Kingdom
Agnieszka
$125 nightly
The price is $142
Oct 29 - Oct 30
Total with taxes and fees
La Terrazza Sul Campo Rooming House
A stone building with outdoor seating and a view of the countryside.

20. 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
$160 nightly
The price is $179
Oct 18 - Oct 19
Total with taxes and fees
Antico Borgo Poggiarello
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

Villa I Barronci Resort & Spa

Villa I Barronci Resort & Spa

8/10 Good
"Under renovation so it could have been better"
Kimberli 1-night trip
Posted 12 hours ago
Villa I Barronci Resort & Spa

Find out more about San Leonino

Everything you need to know about San Leonino 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 Leonino 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 Leonino vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

San Leonino vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in San Leonino. 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 Leonino 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 $55 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 Leonino rentals

At Expedia, we put the best San Leonino 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 Leonino 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 Leonino 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 Leonino. 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

Are there vacation rentals in San Leonino?

Yes, there are vacation rentals near top sights in San Leonino, or you can select a secluded option if you're looking for a relaxing stay.

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

Borgo Argiano: This vacation home rental outside of San Leonino 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 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 Val di Merse. City Hall Castellina In Chianti and Monteriggioni Castle are a couple of places you'll find in the larger area.

What’s a vacation rental in San Leonino like?

A vacation rental is a private property you can stay in for several days or longer in San Leonino. Vacation rentals provide amenities such as WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a sanitized environment, vacation rentals can provide a sense of privacy away from public hotel elevators and busy front desks while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for a family trip or a small group gathering.