Holiday Rentals in San Leolino

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Our top choices for San Leolino holiday rentals

Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (23 reviews)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is €153
includes taxes & fees
22 Apr - 23 Apr
Villa Cassia di Baccano

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 €98
includes taxes & fees
16 Apr - 17 Apr
Il Pozzo di Sant'Andrea

Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti

Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti
Monteaperti
10.0 out of 10, Exceptional, (2 reviews)
"We loved this place. Modern cabin set in a rustic Tuscan setting. Beautiful property, very comfortable stay, and very attentive staff. Family owned and operated. Amazing restaurant just steps away. A perfect place for respite"
United States
Ian F.
The price is €171
includes taxes & fees
16 Apr - 17 Apr
Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti

Villa La Ginestra

Villa La Ginestra
Subbiano
9.6 out of 10, Exceptional, (5 reviews)
"Le charme de l'endroit, l'attention de l'hôte, le confort, le déjeuner delicieux."
Canada
Philippe
The price is €126
includes taxes & fees
16 Apr - 17 Apr
Villa La Ginestra

Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.2 out of 10, Wonderful, (40 reviews)
"Beautiful area and friendly staff. We stayed here several years ago and were so excited to return."
United States
David
The price is €275
includes taxes & fees
16 Apr - 17 Apr
Castello di Gargonza

Fullino Nero

Fullino Nero
Siena
9.6 out of 10, Exceptional, (50 reviews)
"Great stay! Clean rooms with air conditioning. Beautiful grounds "
United States
Christian
The price is €109
includes taxes & fees
16 Apr - 17 Apr
Fullino Nero

Artisti del Cavallo Tourism

Artisti del Cavallo Tourism
Foiano della Chiana
8.4 out of 10, Very good, (24 reviews)
"Good house for one night. "
Germany
Heiner
The price is €82
includes taxes & fees
16 Apr - 17 Apr
Artisti del Cavallo Tourism

La Coroncina Lodging

La Coroncina Lodging
Siena
10.0 out of 10, Exceptional, (42 reviews)
"Fantastic place, and I highly recommend it."
United States
Hassan
The price is €118
includes taxes & fees
16 Apr - 17 Apr
La Coroncina Lodging

Tolletta 10 e Lode - One Bedroom House, Sleeps 4

Tolletta 10 e Lode - One Bedroom House, Sleeps 4
Arezzo Centro Storico
10.0 out of 10, Exceptional, (1 review)
" La casa pulitissima è molto bella, l’host molto disponibile e gentile, risponde sempre e anche subito. La posizione ottimale per fare il giro dei mercatini e di tutta la città. Consigliatissima "
Italy
Maria Gemma
The price is €153
includes taxes & fees
19 Apr - 20 Apr
Tolletta 10 e Lode - One Bedroom House, Sleeps 4

Ca' Bianca Tuscany Relais

Ca' Bianca Tuscany Relais
Siena
10.0 out of 10, Exceptional, (43 reviews)
"Great time, perfect property and location."
United States
Christopher
The price is €214
includes taxes & fees
16 Apr - 17 Apr
Ca' Bianca Tuscany Relais

Il Poggio dell'Eremita

Il Poggio dell'Eremita
Sinalunga
10.0 out of 10, Exceptional, (59 reviews)
"Fantastic place! Great location. "
Canada
Paul Q.
The price is €159
includes taxes & fees
18 Apr - 19 Apr
Il Poggio dell'Eremita

Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.8 out of 10, Exceptional, (25 reviews)
"Perfect location on the top of a hill surrounded by the beautiful vineyards of Chianti. Enjoy the view by the pool or the fabulous sunset with a glass of wine. The staff were friendly and the restaurant was 5 star. I highly recommend a stay to fulfill all your Tuscan dreams. "
United States
Eileen
The price is €193
includes taxes & fees
13 May - 14 May
Riserva di Fizzano Residence

Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (29 reviews)
"Lovely relaxation options and wonderful restaurant attached to the property! Great for a stay where you are travelling through Tuscany by car! Do not recommend travelling by public transport or taxi as it is very expensive."
Australia
Amelia
The price is €152
includes taxes & fees
19 Apr - 20 Apr
Villa di Sotto

House Il Cipresso in the heart of Chianti with swimming pool

House Il Cipresso in the heart of Chianti with swimming pool
Castellina in Chianti
10.0 out of 10, Exceptional, (1 review)
"Beautiful setting with a rustic and friendly vibe. The place was clean and well-kept. We enjoyed every minute! A bonus was that the nights were cool (did t need the AC), and we slept with the windows open, despite the heat during the day."
Canada
Jon M.
House Il Cipresso in the heart of Chianti with swimming pool

DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (28 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
The price is €101
includes taxes & fees
19 Apr - 20 Apr
DormiVeglia B&B

L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (13 reviews)
"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
The price is €164
includes taxes & fees
20 Apr - 21 Apr
L' Eroico

Mariani Bed & Breakfast

Mariani Bed & Breakfast
Castellina in Chianti
9.8 out of 10, Exceptional, (17 reviews)
"Very nice and quiet neighbourhood. Close to city centre. The host is very kind."
Japan
Chie
The price is €90
includes taxes & fees
21 Apr - 22 Apr
Mariani Bed & Breakfast

Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (22 reviews)
"It is an amazing location nested among wineries and rolling hills. If you like a quiet and sophisticated location this is your ideal place. You will need a car to move around but, you will be rewarded by the view and the opportunities for wine tastings and small villages visits. "
United States
Massimo
The price is €195
includes taxes & fees
26 Apr - 27 Apr
Borgo Argenina

B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (199 reviews)
"Excellent location, rooms, staff."
United States
Mario Humberto
The price is €115
includes taxes & fees
29 Apr - 30 Apr
B&B Il Corso

San Michele al Borgo

San Michele al Borgo
Castiglion Fiorentino
9.8 out of 10, Exceptional, (9 reviews)
"Excellent staff and tasty breakfast!"
United States
Vern
The price is €108
includes taxes & fees
16 Apr - 17 Apr
San Michele al Borgo
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 Leolino Hotel Reviews

Find out more about San Leolino

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

San Leolino holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in San Leolino. 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A San Leolino 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 Leolino holiday rentals we have selected for you start as low as €64 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on San Leolino rentals

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

Can I find a holiday rental in San Leolino?

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

Borgo Argiano: This holiday home rental outside of San Leolino 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 an espresso maker. You can relax into your holiday with a garden and a library.

What’s there to see and do in San Leolino?

Explore the area and family-friendly sights such as Siena Circuit, or get out into nature at a spot like Chianti Sculpture Park. In the wider area, you’ll find Villa a Sesta Polo Club and Cantalici Winery.

What’s a holiday rental in San Leolino like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in San Leolino. Holiday rentals feature amenities such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from shared hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for a family trip.