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San Leonino Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for San Leonino vacation rentals

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.

1. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (32 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is P3,953
P5,274 total
includes taxes & fees
Nov 20 - Nov 21
Tuscasì Aparthotel
A stone building with a garden in front.

2. 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 P11,321
P13,023 total
includes taxes & fees
Oct 31 - Nov 1
Borgo Argenina
A room with a window featuring sheer curtains, a radiator below, and a view of a green landscape.

3. 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
Mariani Bed & Breakfast
A rustic stone building with a courtyard.

4. Fullino Nero

Fullino Nero
Siena
9.6 out of 10, Exceptional, (59 reviews)
"Very nice place close to"
Canada
Annie
The price is P6,175
P7,078 total
includes taxes & fees
Oct 27 - Oct 28
Fullino Nero
A balcony with a view of rolling hills, a table with a book and a bottle, and a chair.

5. Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Val d'Elsa
8.6 out of 10, Excellent, (57 reviews)
"This place was beautiful, quiet like a picture you’d see in the movies"
Canada
Nadia
The price is P7,127
P8,267 total
includes taxes & fees
Oct 28 - Oct 29
Villa San Filippo
A stone building with a yellow sign reading "b&b erioico".

6. 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 P8,207
P9,597 total
includes taxes & fees
Nov 2 - Nov 3
L' Eroico
A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building.

7. Residenzia del Sogno

Residenzia del Sogno
Castellina in Chianti
9.8 out of 10, Exceptional, (16 reviews)
"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "
Canada
Katherine
The price is P8,420
P9,547 total
includes taxes & fees
Oct 30 - Oct 31
Residenzia del Sogno
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, (355 reviews)
"Great stay highly recommend!!"
United States
jon
The price is P3,693
P4,348 total
includes taxes & fees
Nov 5 - Nov 6
ApartHotel Anghel
A table with breakfast items and a view of rolling hills.

9. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Tavarnelle Val di Pesa
8.6 out of 10, Excellent, (121 reviews)
"Superb property. Nice and quiet atmosphere. We enjoyed a lot. Definitely will come again."
United States
Nirav
The price is P5,398
P6,081 total
includes taxes & fees
Oct 27 - Oct 28
Chianti Village Morrocco
A hot tub with two glasses of a beverage.

10. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (40 reviews)
"Great spot"
Canada
Philippe
The price is P10,438
P11,482 total
includes taxes & fees
Oct 27 - Oct 28
Villa di Sotto
A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

11. 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
The price is P7,694
P8,891 total
includes taxes & fees
Nov 6 - Nov 7
Casa Vacanze Squarcialupi
A villa with a swimming pool, outdoor seating, and a tennis court.

12. 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 P9,304
P10,519 total
includes taxes & fees
Oct 28 - Oct 29
Villa Curina Resort
A stone courtyard with a bench, potted plants, and a building in the background.

13. 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
The price is P5,899
P6,703 total
includes taxes & fees
Nov 16 - Nov 17
Casa di Campagna in Toscana
A traditional interior with stone arches, a staircase, and a cozy seating area with a table.

14. Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
9.4 out of 10, Exceptional, (9 reviews)
"Very nice agriturismo. "
United States
Ruth
The price is P8,152
P9,252 total
includes taxes & fees
Nov 8 - Nov 9
Agriturismo La Ferrozzola
An outdoor swimming pool with a wooden pergola, lounge chairs, and a stone wall backdrop.

15. Guild Living Siena Senior Resort & Residence

Guild Living Siena Senior Resort & Residence
Scacciapensieri
8.8 out of 10, Excellent, (60 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
The price is P7,876
P8,948 total
includes taxes & fees
Nov 2 - Nov 3
Guild Living Siena Senior Resort & Residence
A traditional room with a wooden sofa, two chairs, a round table, and a patterned rug.

16. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.6 out of 10, Exceptional, (103 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is P8,891
P9,922 total
includes taxes & fees
Oct 27 - Oct 28
Palazzo Pacini
A bedroom with a bed, bedside table, and a window with a view of greenery.

17. 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 P7,365
P8,387 total
includes taxes & fees
Nov 23 - Nov 24
La Coroncina Lodging
A traditional stone building with a courtyard, a staircase, and potted plants.

18. 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 P6,867
P7,838 total
includes taxes & fees
Oct 27 - Oct 28
Il Pozzo di Sant'Andrea
A white mobile home with blue shutters, a red roof, and a small deck with white chairs.

19. Camping Boschetto Di Piemma

Camping Boschetto Di Piemma
3.0 star property
San Gimignano
8.8 out of 10, Excellent, (91 reviews)
"Great experience, close to a beautiful city and castle on a hill. "
New Zealand
Anonymous traveler
The price is P3,381
P3,933 total
includes taxes & fees
Oct 28 - Oct 29
Camping Boschetto Di Piemma
A building with a sign reading 'Villa Le Camelie' and multiple flags.

20. 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
The price is P5,182
P5,984 total
includes taxes & fees
Nov 8 - Nov 9
Villa le Camelie Siena
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

La Certosa di Pontignano

La Certosa di Pontignano

10/10 Excellent
"Beautiful property, staff was always helpful. Food was excellent."
Anita 5-night trip
Posted 8 hours ago
La Certosa di Pontignano

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 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.