San Leonino Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for San Leonino vacation rentals

B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (82 reviews)
"It was a wonderful stay the bed was comfortable and the view was beautiful. "
United States
Ruben
The price is CA $171
CA $194 total
includes taxes & fees
May 25 - May 26
B&B La Fonte del Machiavelli

Villa Montecastello

Villa Montecastello
Monteriggioni
The price is CA $261
CA $292 total
includes taxes & fees
Jun 4 - Jun 5
Villa Montecastello

Relais Villa Olmo

Relais Villa Olmo
Impruneta
9.4 out of 10, Exceptional, (243 reviews)
"We had an excellent stay, the staff is very friendly, stunning location and easy but windy road into Florence "
United States
Juliana
The price is CA $261
CA $292 total
includes taxes & fees
May 25 - May 26
Relais Villa Olmo

Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (30 reviews)
"The view was so incredible and the pool just like a dream. "
Canada
Sarah
The price is CA $306
CA $339 total
includes taxes & fees
May 27 - May 28
Riserva di Fizzano Residence

Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (32 reviews)
"Beautiful villa, very spacious, gorgeous property and great restaurant on the property to have a delicious meal. Staff very welcoming. Close to other main cities, like Siena, for day trips. We loved sitting by the pool, although it wasn’t heated, so too cold to use in April. We did love using the indoor heated pool and hot tub each day. We had a fabulous time and hope to go back someday! "
Canada
Jeremy
The price is CA $208
CA $229 total
includes taxes & fees
May 24 - May 25
Villa di Sotto

Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.4 out of 10, Exceptional, (24 reviews)
"A wonderful stay. "
United States
Sally
The price is CA $165
CA $186 total
includes taxes & fees
May 24 - May 25
Casa di Campagna in Toscana

Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (171 reviews)
"Lovely stay! I would highly recommend this hotel. The indoor pool was just so enjoyable after a day out sightseeing. "
United Kingdom
Lizl
The price is CA $169
CA $199 total
includes taxes & fees
May 24 - May 25
Bosco della Spina

Villa Norcenni Aparthotel

Villa Norcenni Aparthotel
2.0 star property
Figline e Incisa Valdarno
7.4 out of 10, Good, (21 reviews)
"It was clean and safe."
United Kingdom
Laka
The price is CA $76
CA $89 total
includes taxes & fees
May 24 - May 25
Villa Norcenni Aparthotel

Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (100 reviews)
"This is a lovely gem. Includes parking which is hard to find. Family owned and its a truly beautiful place. Breakfast was amazing as well!! Recommend!! "
United States
rose
The price is CA $304
CA $341 total
includes taxes & fees
May 27 - May 28
Villa il Fedino

Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.0 out of 10, Wonderful, (26 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is CA $126
CA $159 total
includes taxes & fees
Jun 8 - Jun 9
Tuscasì Aparthotel

Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (72 reviews)
"The stay was great, and the staff were wonderful. "
United States
SYDNEY
The price is CA $432
CA $481 total
includes taxes & fees
Jun 4 - Jun 5
Terre di Baccio

Villa Rosa Panzano

Villa Rosa Panzano
Greve in Chianti
8.2 out of 10, Very good, (53 reviews)
"The facilities were great, including access to the swimming pool. The staff were very friendly and helpful. Breakfast options were good. Parking on site. Villa is a 10 minute drive to two lovely Tuscan towns (Greve and Panzano). Would stay here again - it was so atmospheric! "
United Kingdom
Rachel
The price is CA $175
CA $198 total
includes taxes & fees
May 25 - May 26
Villa Rosa Panzano

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 CA $142
CA $162 total
includes taxes & fees
May 25 - May 26
Il Pozzo di Sant'Andrea

Antico Borgo Poggiarello

Antico Borgo Poggiarello
2.0 star property
Monteriggioni
9.0 out of 10, Wonderful, (20 reviews)
"We had an absolutely wonderful time staying here. Our kids had fun on their playground and my wife and I enjoyed the views, the hospitality. And the entire experience. The food was outstanding. "
United States
James Bakley
The price is CA $242
CA $271 total
includes taxes & fees
May 24 - May 25
Antico Borgo Poggiarello

Borgo Il Poggiaccio

Borgo Il Poggiaccio
Sovicille
8.8 out of 10, Excellent, (65 reviews)
"Beautiful place, great position in the countryside, truly relaxing place, wish we could stay longer, definitely will return A***"
United States
Dean
The price is CA $207
CA $235 total
includes taxes & fees
May 30 - May 31
Borgo Il Poggiaccio

Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (88 reviews)
"Hotel clean comfortable. No elevator, no reception desk. "
United States
Karin
The price is CA $113
CA $131 total
includes taxes & fees
Jun 7 - Jun 8
Domus il Palio B&B

Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (113 reviews)
"Front desk was very helpful and very comfortable room. "
United States
Chris
The price is CA $116
CA $131 total
includes taxes & fees
May 24 - May 25
Chianti Village Morrocco

Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (448 reviews)
"It’s very close to the historical center but feels quiet and like you are separate from it. I loved our stay"
United States
David
The price is CA $199
CA $225 total
includes taxes & fees
Jun 4 - Jun 5
Siena Vip

Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (23 reviews)
"Such a beautiful place to stay! The cottage was amazing, very spacious and clean. The grounds themselves were picturesque, was well above our expectations and the host was very welcoming and accommodating."
United Kingdom
Sasha
The price is CA $458
CA $516 total
includes taxes & fees
Jun 7 - Jun 8
Borgo Argenina

B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes

B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes
San Casciano in Val di Pesa
9.4 out of 10, Exceptional, (26 reviews)
"The beautiful place, very comfortable, the incredible attention, the breakfast felt like in Homewith a lot of love We hope to return one day"
Mexico
Raymundo
The price is CA $160
CA $183 total
includes taxes & fees
Jun 4 - Jun 5
B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes
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.
Save an average of 15% on thousands of hotels when you're signed in

Top San Leonino Hotel Reviews

Find out more about San Leonino

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with San Leonino. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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 an electric kettle. 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 Terra di Seta 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.