San Leonino Vacation Rentals

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Dec 8 - Dec 9
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Dec 9 - Dec 10
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Dec 12 - Dec 14
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Dec 19 - Dec 21

Vacation Rentals in San Leonino

Aerial view
Relais Villa Olmo

Relais Villa Olmo

Impruneta
9.4 out of 10, Exceptional, (227)
"This is a beautiful Villa with a stunning views. Rooms were large and very clean and the location was wonderful. It was close to Florence and ideal for exploring Tuscany. Restaurant offered delicious buffet breakfast and many other wonderful local dishes for lunch and dinner. I would highly recommend this Villa and would love to stay here again."
United States
Ewa
Relais Villa Olmo
Birthday party area
Siena Vip

Siena Vip

Siena City Centre
9.2 out of 10, Wonderful, (420)
"A great location!"
Canada
Cheryl
Siena Vip
Exterior
PALAZZO DEL PAPA

PALAZZO DEL PAPA

Siena City Centre
9.6 out of 10, Exceptional, (96)
"Hamza was so wonderful and accommodating, would definitely stay here again!"
United States
Elise
The price is ￥18,547
￥21,124 total
includes taxes & fees
Dec 15 - Dec 16
PALAZZO DEL PAPA
32-inch Smart TV with digital channels, TV, streaming services
B&B Il Corso

B&B Il Corso

Siena City Centre
9.8 out of 10, Exceptional, (190)
"Safe, clean, close to all attractions"
Canada
Carlo
B&B Il Corso
Exterior detail
Villa il Fedino

Villa il Fedino

San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (97)
"Great people, great location great service"
Canada
James
The price is ￥22,114
￥25,048 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Villa il Fedino
Balcony
Palazzo al Torrione 2

Palazzo al Torrione 2

San Gimignano City Centre
9.2 out of 10, Wonderful, (107)
"Truly a gem! Our room was beautiful with a lovely view. It is very close to the main road and restaurants. Definitely opt in for the breakfast it was absolutely delicious. "
United States
Leasly
The price is ￥14,549
￥21,430 total
includes taxes & fees
Dec 15 - Dec 16
Palazzo al Torrione 2
Apartment, 2 Bedrooms | Premium bedding, down comforters, in-room safe, blackout drapes
Terre di Baccio

Terre di Baccio

Greve in Chianti
9.8 out of 10, Exceptional, (71)
"Great hotel in a beautiful location with fantastic staff. "
United Kingdom
Mark
Terre di Baccio
Royal Apartment | View from room
Tuscasì Aparthotel

Tuscasì Aparthotel

Sovicille
9.0 out of 10, Wonderful, (24)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is ￥10,906
￥12,540 total
includes taxes & fees
Dec 9 - Dec 10
Tuscasì Aparthotel
Bar (on property)
Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca

Siena City Centre
9.6 out of 10, Exceptional, (191)
"Great location and friendly staff. "
United States
Parissa
Il Battistero Siena - Residenza d'Epoca
Terrace/patio
Casa di Campagna in Toscana

Casa di Campagna in Toscana

Sovicille
9.4 out of 10, Exceptional, (18)
"Fantastic experience with friendly hosts and an excellent breakfast! A little rustic here and there but all part of the charm!"
United Kingdom
Alasdair
Casa di Campagna in Toscana
Standard Double Room (with Toilet) | Living area | 24-inch LED TV with satellite channels, TV
Palazzo Masi

Palazzo Masi

Siena City Centre
8.8 out of 10, Excellent, (84)
"Very friendly and attentive, a very clean place and its location is excellent. "
United States
Gloria
The price is ￥14,797
￥16,999 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Palazzo Masi
Breakfast, lunch, dinner served; Regional cuisine
La Locanda di Pietracupa

La Locanda di Pietracupa

Barberino Tavarnelle
9.4 out of 10, Exceptional, (35)
"Great place, wonderful restaurant"
Germany
Isabell
La Locanda di Pietracupa
Panoramic Suite, City View | View from room
Residenza d'Epoca Palazzo Borghesi

Residenza d'Epoca Palazzo Borghesi

Siena City Centre
9.6 out of 10, Exceptional, (116)
"We enjoyed our stay here. Convenient, clean, central to city center, shops, and restaurants. We would stay here again."
United States
Linda
The price is ￥28,437
￥32,004 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Residenza d'Epoca Palazzo Borghesi
Quadruple Room, City View | Desk, iron/ironing board, free WiFi, bed sheets
Al Mercato B&B

Al Mercato B&B

Siena City Centre
9.0 out of 10, Wonderful, (96)
"Hotel is a one block from main square of the city also have a good restaurant around the corner "
United States
Guillermo
The price is ￥10,124
￥13,449 total
includes taxes & fees
Dec 14 - Dec 15
Al Mercato B&B
Suite | Premium bedding, Select Comfort beds, minibar, in-room safe
La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House

Siena City Centre
9.8 out of 10, Exceptional, (239)
"Huge room! Great location "
Canada
karen
La Terrazza Sul Campo Rooming House
Exterior
Sportland

Sportland

Colle di Val d'Elsa
7.2 out of 10, Good, (5)
"Struttura essenziale ed economica "
Italy
Giorgio
Sportland
Lobby lounge
ApartHotel Anghel

ApartHotel Anghel

Siena
8.4 out of 10, Very Good, (334)
"Would recommend staying here and will hopefully be back!"
Canada
Lisa
The price is ￥10,758
￥12,557 total
includes taxes & fees
Dec 10 - Dec 11
ApartHotel Anghel
Restaurant
B&B Dei Rossi

B&B Dei Rossi

Siena City Centre
8.2 out of 10, Very Good, (18)
"Wonderful stay. Large room, shared kitchen and great location to shops and restaurants. A lot of stairs, but it comes with a beautiful view. "
Canada
Alana
The price is ￥11,985
￥13,907 total
includes taxes & fees
Dec 9 - Dec 10
B&B Dei Rossi
Front of property
L' Eroico

L' Eroico

Gaiole in Chianti
10.0 out of 10, Exceptional, (12)
"Monica was the friendliest most enthusiastic host we’ve stayed with. Everything from her greeting to the amazing breakfast was perfect. She does a lot of baking, so the breakfast was really a treat and you could also get eggs cooked in various ways. The room was a little small but very comfortable. Parking was on the street, but it was fairly close and easy."
United States
Perry
L' Eroico
Exterior detail
B&B Palazzo Tortoli

B&B Palazzo Tortoli

San Gimignano City Centre
9.2 out of 10, Wonderful, (57)
"This is a great B&B its right in the heart of the town. The rooms are very clean and have historical character. The staff are so friendly and helpful. "
United States
April
The price is ￥19,055
￥21,865 total
includes taxes & fees
Jan 2 - Jan 3, 2026
B&B Palazzo Tortoli
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 Italia

Hotel Italia

10/10 Excellent
"This was a short stay for us in Siena. A great hotel. Friendly staff and the best bargain best breakfast we have had in Italy. Highly recommended"
Phil 1-night trip
Posted 3 days ago
Hotel Italia

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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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 a coffee maker. 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 Chianti Sculpture Park. 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.