San Leolino Vacation Rentals

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Check prices for these dates

In two weeks
May 1 - May 3
In two months
Jun 12 - Jun 14
In three months
Jul 10 - Jul 12
In four months
Aug 7 - Aug 9

Our top choices for San Leolino vacation rentals

Lobby

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
$163 nightly
The price is $180
May 18 - May 19
Total with taxes and fees
Villa Cassia di Baccano
Front of property

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
$126 nightly
The price is $138
May 14 - May 15
Total with taxes and fees
Villa La Ginestra
Lunch and dinner served, local cuisine

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
$244 nightly
The price is $273
May 10 - May 11
Total with taxes and fees
Castello di Gargonza
Exterior

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
$102 nightly
The price is $117
May 17 - May 18
Total with taxes and fees
Il Pozzo di Sant'Andrea
1 bedroom, free WiFi, bed sheets

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.
$216 nightly
The price is $222
Apr 29 - Apr 30
Total with taxes and fees
Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti
Interior detail

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
$136 nightly
The price is $154
Apr 19 - Apr 20
Total with taxes and fees
La Coroncina Lodging
Studio, Patio, Ground Floor | Terrace/patio

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
$103 nightly
The price is $118
May 6 - May 7
Total with taxes and fees
Fullino Nero
Tasting room

Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca
Siena City Centre
9.6 out of 10, Exceptional, (201 reviews)
"Room was excellent, location was perfect for seeing Siena and restaurant was also excellent"
United Kingdom
John
$120 nightly
The price is $137
May 14 - May 15
Total with taxes and fees
Il Battistero Siena - Residenza d'Epoca
Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers

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
$157 nightly
The price is $173
May 18 - May 19
Total with taxes and fees
Villa di Sotto
Exterior

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
$180 nightly
The price is $180
Apr 19 - Apr 20
Total with taxes and fees
Tolletta 10 e Lode - One Bedroom House, Sleeps 4
Property grounds

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
$246 nightly
The price is $275
Apr 18 - Apr 19
Total with taxes and fees
Ca' Bianca Tuscany Relais
Property grounds

Il Poggio dell'Eremita

Il Poggio dell'Eremita
Sinalunga
10.0 out of 10, Exceptional, (59 reviews)
"Fantastic place! Great location. "
Canada
Paul Q.
$181 nightly
The price is $184
Apr 19 - Apr 20
Total with taxes and fees
Il Poggio dell'Eremita
Property grounds

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
Exterior

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
$159 nightly
The price is $184
Apr 25 - Apr 26
Total with taxes and fees
L' Eroico
Aerial view

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
$197 nightly
The price is $219
May 13 - May 14
Total with taxes and fees
Riserva di Fizzano Residence
Exterior

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
$188 nightly
The price is $216
Apr 26 - Apr 27
Total with taxes and fees
Borgo Argenina
Courtyard

Fontelunga Hotel & Villas

Fontelunga Hotel & Villas
Foiano della Chiana
10.0 out of 10, Exceptional, (5 reviews)
"Amazing stay at this hotel I would recommend it. Great hospitality, clean and picture postcard views. "
United Kingdom
Liam
$283 nightly
The price is $313
Apr 20 - Apr 21
Total with taxes and fees
Fontelunga Hotel & Villas
Deluxe Apartment | Premium bedding, down comforters, in-room safe, desk

Borgo Argiano

Borgo Argiano
Castelnuovo Berardenga
10.0 out of 10, Exceptional, (76 reviews)
"Very comfortable stay. "
United States
Victor
$282 nightly
The price is $320
May 12 - May 13
Total with taxes and fees
Borgo Argiano
Romantic Double Room, 1 Queen Bed, Hot Tub, Ground Floor | Private spa tub

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
$95 nightly
The price is $110
Apr 19 - Apr 20
Total with taxes and fees
DormiVeglia 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, (240 reviews)
"Huge room! Great location "
Canada
karen
$117 nightly
The price is $133
May 12 - May 13
Total with taxes and fees
La Terrazza Sul Campo Rooming House
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

Castello Vicchiomaggio

Castello Vicchiomaggio

10/10 Excellent
"LOVED our stay. I can’t describe how perfect our stay was. It was more beautiful than the pics we’d seen on hotels.com. Beautiful spacious room/apartment. Fabulous dinner in the restaurant, wine tour & tasting. Very helpful staff. Absolutely stunning views. Convenient parking, close to Greve, the town. Perfection. "
Hether 2-night trip
Posted 3 hours ago
Castello Vicchiomaggio

Find out more about San Leolino

Everything you need to know about San Leolino 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 Leolino 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 Leolino vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

San Leolino vacation 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 low season months. For more hustle and bustle, you may prefer to visit San Leolino 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 $68 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 Leolino rentals

At Expedia, we put the best San Leolino 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 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 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 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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in San Leolino?

Yes, you can find vacation rentals near the most popular sights in San Leolino, or you can go with a more remote option if you want a relaxing place to stay.

What are some of the best vacation home rentals in San Leolino?

Borgo Argiano: Visitors like this San Leolino vacation home rental. It 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 an espresso maker. You can relax into your vacation 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 larger area, you’ll find Villa a Sesta Polo Club and Cantalici Winery.

What’s a vacation rental in San Leolino like?

Vacation rentals are private properties where you can stay for a few weeks or just a few days in San Leolino. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll have all the conveniences of home. If you're concerned about cleanliness, a vacation rental can offer a sense of safety away from shared hotel elevators and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for a family trip.