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San Leonino Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for San Leonino vacation rentals

An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

1. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.6 out of 10, Exceptional, (104 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
$114 nightly
The price is $128
Dec 2 - Dec 3
Total with taxes and fees
Palazzo Pacini
An outdoor swimming pool with a wooden pergola, lounge chairs, and a stone wall backdrop.

2. Guild Living Siena Senior Resort & Residence

Guild Living Siena Senior Resort & Residence
Scacciapensieri
8.8 out of 10, Excellent, (62 reviews)
"We booked this last - minute and were really impressed with the whole experience. The property and grounds are beautiful. Staff was so friendly and helpful. The rooms were well appointed and quiet. Beds were too firm for our liking, but it was easy to overlook as the entire stay was really great. Good options in the restaurant too. The block of hotel rooms is in a retirement resort, which I think is a wonderful idea! Very much enjoyed our stay. We had a car and parking was free."
United States
Heidi
$96 nightly
The price is $110
Nov 16 - Nov 17
Total with taxes and fees
Guild Living Siena Senior Resort & Residence
A traditional interior with stone arches, a staircase, and a cozy seating area with a table.

3. Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
9.4 out of 10, Exceptional, (9 reviews)
"Very nice agriturismo. "
United States
Ruth
$126 nightly
The price is $143
Nov 16 - Nov 17
Total with taxes and fees
Agriturismo La Ferrozzola
A rustic stone building with a courtyard.

4. Fullino Nero

Fullino Nero
Siena
9.6 out of 10, Exceptional, (60 reviews)
"Very nice place close to"
Canada
Annie
$100 nightly
The price is $115
Nov 17 - Nov 18
Total with taxes and fees
Fullino Nero
A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

5. Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi
Castellina in Chianti
9.2 out of 10, Wonderful, (5 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
$117 nightly
The price is $131
Nov 16 - Nov 17
Total with taxes and fees
Casa Vacanze Squarcialupi
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.

6. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (34 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
$72 nightly
The price is $82
Nov 19 - Nov 20
Total with taxes and fees
Tuscasì Aparthotel
A stone building with a yellow sign reading "b&b erioico".

7. 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
$127 nightly
The price is $148
Nov 16 - Nov 17
Total with taxes and fees
L' Eroico
A modern lobby with white leather sofas, a glass coffee table, and potted plants.

8. ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very good, (356 reviews)
"The staff were very friendly and helpful. I would recommend this hotel to any traveler"
United States
clifford
$47 nightly
The price is $56
Dec 1 - Dec 2
Total with taxes and fees
ApartHotel Anghel
A bedroom with a bed, bedside table, and a window with a view of greenery.

9. La Coroncina Lodging

La Coroncina Lodging
Siena
9.8 out of 10, Exceptional, (44 reviews)
"Fantastic place, and I highly recommend it."
United States
Hassan
$81 nightly
The price is $93
Nov 16 - Nov 17
Total with taxes and fees
La Coroncina Lodging
A stone courtyard with a bench, potted plants, and a building in the background.

10. Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.6 out of 10, Exceptional, (27 reviews)
"A wonderful stay. "
United States
Sally
$67 nightly
The price is $77
Nov 16 - Nov 17
Total with taxes and fees
Casa di Campagna in Toscana
A table with breakfast items and a view of rolling hills.

11. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Tavarnelle Val di Pesa
8.6 out of 10, Excellent, (122 reviews)
"Superb property. Nice and quiet atmosphere. We enjoyed a lot. Definitely will come again."
United States
Nirav
$56 nightly
The price is $64
Nov 20 - Nov 21
Total with taxes and fees
Chianti Village Morrocco
An aerial view of a hotel with a swimming pool, outdoor seating area, and well-maintained gardens.

12. Antica Pieve B&B

Antica Pieve B&B
Tavarnelle Val di Pesa
9.4 out of 10, Exceptional, (15 reviews)
"Very nice stay here! Great breakfast and coffee every morning. Great location to tour around to different wineries and towns. Free parking. "
Canada
Jessica
$105 nightly
The price is $120
Dec 9 - Dec 10
Total with taxes and fees
Antica Pieve B&B
Outdoor pool

13. Residence Arianna

Residence Arianna
Sovicille
9.6 out of 10, Exceptional, (10 reviews)
"The place is excellent! The owner and her daughter extremely friendly and kind! They helped us with everything we needed. I will definitely stay here again. I highly recommend this place!"
United States
Violeta
$131 nightly
The price is $147
Nov 16 - Nov 17
Total with taxes and fees
Residence Arianna
A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

14. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (82 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
$235 nightly
The price is $263
Nov 24 - Nov 25
Total with taxes and fees
Terre di Baccio
A dining area with a table set for two, featuring a view of greenery through a window.

15. La Locanda di Pietracupa

La Locanda di Pietracupa
Tavarnelle Val di Pesa
9.4 out of 10, Exceptional, (40 reviews)
"Great place, wonderful restaurant"
Germany
Isabell
$143 nightly
The price is $161
Nov 21 - Nov 22
Total with taxes and fees
La Locanda di Pietracupa
A bathroom with a window view of a historic building and a tiled roof.

16. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (498 reviews)
"The room was modern and clean. Enjoyed the breakfast."
Australia
John
$88 nightly
The price is $101
Nov 16 - Nov 17
Total with taxes and fees
Siena Vip
A bakery display with pastries and a coffee station.

17. B&B Il Corso

B&B Il Corso
Siena City Centre
9.6 out of 10, Exceptional, (219 reviews)
"Very clean and comfortable, great location and staff"
United States
Heather
$72 nightly
The price is $84
Dec 10 - Dec 11
Total with taxes and fees
B&B Il Corso
A bathroom with a sink, bidet, toilet, and shower area.

18. 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
$75 nightly
The price is $87
Nov 16 - Nov 17
Total with taxes and fees
Villa le Camelie Siena
A wine cellar with stone walls, wine racks, and tables with glasses and candles.

19. Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca
Siena City Centre
9.6 out of 10, Exceptional, (227 reviews)
"Very nice hotel with wonderful staff. Very accommodating. Would highly recommend."
United States
Anthony
$121 nightly
The price is $138
Dec 1 - Dec 2
Total with taxes and fees
Il Battistero Siena - Residenza d'Epoca
A table with two wine glasses, a bottle, and a book.

20. Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (102 reviews)
"Very nice place. Nice people, clean and just nice"
Denmark
Leo
$60 nightly
The price is $70
Nov 18 - Nov 19
Total with taxes and fees
Domus il Palio B&B
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
"We enjoyed the quiet atmosphere and the amazing staff who were very helpful and kind."
Keith 3-night trip
Posted 6 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 $56 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.