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San Leonino Holiday Rentals

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Check prices for these dates

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

Our top choices for San Leonino holiday 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, (33 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is AU$118
includes taxes & fees
20 Nov - 21 Nov
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 AU$306
includes taxes & fees
31 Oct - 1 Nov
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
The price is AU$149
includes taxes & fees
29 Oct - 30 Oct
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 AU$164
includes taxes & fees
1 Nov - 2 Nov
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 AU$173
includes taxes & fees
30 Oct - 31 Oct
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 AU$213
includes taxes & fees
2 Nov - 3 Nov
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 AU$212
includes taxes & fees
30 Oct - 31 Oct
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 AU$94
includes taxes & fees
27 Nov - 28 Nov
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 AU$136
includes taxes & fees
28 Nov - 29 Nov
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 AU$255
includes taxes & fees
29 Oct - 30 Oct
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 AU$188
includes taxes & fees
11 Nov - 12 Nov
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, (82 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
The price is AU$217
includes taxes & fees
29 Oct - 30 Oct
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 AU$135
includes taxes & fees
15 Nov - 16 Nov
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 AU$204
includes taxes & fees
13 Nov - 14 Nov
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 AU$158
includes taxes & fees
9 Nov - 10 Nov
Guild Living Siena Senior Resort & Residence
A view through a window of a stone staircase leading to a building with arched windows and a tower, overlooking a hilly landscape.

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 AU$235
includes taxes & fees
1 Nov - 2 Nov
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 AU$175
includes taxes & fees
9 Nov - 10 Nov
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 AU$169
includes taxes & fees
30 Oct - 31 Oct
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 traveller
The price is AU$81
includes taxes & fees
29 Oct - 30 Oct
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 AU$125
includes taxes & fees
29 Oct - 30 Oct
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

Hotel Minerva

Hotel Minerva

10/10 Excellent
"Clean, great breakfast, lovely view!"
Tracy 2-night trip
Posted 2 days ago
Hotel Minerva

Find out more about San Leonino

Everything you need to know about San Leonino 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 Leonino holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, 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 Leonino holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

San Leonino holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A San Leonino 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 Leonino holiday rentals we have selected for you start as low as AU$81 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on San Leonino rentals

At Expedia, we put the best San Leonino 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 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 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 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 holiday rentals in San Leonino?

Yes, there are holiday rentals close to the most popular sights in San Leonino, 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 Leonino has to offer?

Borgo Argiano: This holiday home rental outside of San Leonino 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 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 wider area.

What’s a holiday rental in San Leonino like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in San Leonino. Holiday rentals offer extras such as hot tubs, fire pits and patios so you'll feel right at home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from public hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for family trips.