San Leolino Vacation Rentals from CA $146: Short-Term Rentals for 2026

Q: 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.

Check prices for these dates

In two weeks

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Our top choices for San Leolino vacation rentals

Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers

1. Villa di Sotto

Castelnuovo Berardenga

Philippe

CA $244 total

includes taxes & fees

Sep 10 - Sep 11

Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas

2. Borgo di Erboli

Cavriglia

CA $192 total

includes taxes & fees

Aug 27 - Aug 28

3. Locanda Antico Borgo

Civitella in Val di Chiana

"What an absolutely beautiful stay, in a stunning place. Our host was attentive and kind, and the food was wonderful. The hotel and rooms were spotlessly clean, and particularly for my needs on a road trip with my 18 year old son, the accommodation offering two adjoining bedrooms was perfect, and we could park outside. Also very good value in my opinion. I would definitely return, it’s also ideal for couples and I would love to bring my wife here. "

Mr Andy

CA $181 total

includes taxes & fees

Aug 26 - Aug 27

4. L' Eroico

Gaiole in Chianti

Angela

CA $243 total

includes taxes & fees

Aug 24 - Aug 25

5. Villa Curina Resort

Castelnuovo Berardenga

Mary

CA $275 total

includes taxes & fees

Aug 25 - Aug 26

6. Villa Cassia di Baccano

Loro Ciuffenna

Ralphvincent

CA $305 total

includes taxes & fees

Sep 15 - Sep 16

7. Holiday Home 'Poggio Loccano' with Private Garden and Balcony

Montevarchi

CA $464 total

includes taxes & fees

Aug 17 - Aug 18

Family Apartment, 2 Bedrooms, Hill View, Tower | View from room

8. Casa Vacanze Le Fornaci

Pergine Valdarno

Gregory

CA $259 total

includes taxes & fees

Aug 31 - Sep 1

9. Relais Villa Belpoggio - Residenza d'Epoca

Loro Ciuffenna

Mona

CA $269 total

includes taxes & fees

Sep 2 - Sep 3

10. Palazzo Tarlati Residenza d'Epoca

Civitella in Val di Chiana

"Small family-owned inn located in center of Civitella in Val di Chiana. Room was comfortable and included all we needed. It was cold upon check-in which the co-owner tried to remedy with a space heater. It took a while. The room warmed up after the first night. The other co-owner kindly offered me our first night complimentary. (Thank you again.). The breakfast was simple and included fruit, juice, yogurt, sliced cheese and cold cut, packages sweets, tea, coffee and water. The owners were...

Marco

CA $193 total

includes taxes & fees

Aug 17 - Aug 18

11. Villa Fontis Rapolano

Rapolano Terme

Barbara

CA $137 total

includes taxes & fees

Aug 21 - Aug 22

Romantic Double Room, 1 Queen Bed, Hot Tub, Ground Floor | Private spa tub

12. DormiVeglia B&B

Monte San Savino

Melissa Hyun Joo

CA $193 total

includes taxes & fees

Aug 19 - Aug 20

13. Hu Norcenni Girasole Village

Figline e Incisa Valdarno

Kalinka

CA $298 total

includes taxes & fees

Aug 19 - Aug 20

14. Castello di Gargonza

Monte San Savino

Ariel

CA $376 total

includes taxes & fees

Aug 17 - Aug 18

15. Podere La Chiusella

Rapolano Terme

François

CA $171 total

includes taxes & fees

Sep 15 - Sep 16

16. Borgo Argenina

Gaiole in Chianti

Sabatino

CA $412 total

includes taxes & fees

Aug 23 - Aug 24

Seasonal outdoor pool, open 7:30 AM to 7:30 PM, pool umbrellas

17. Podere Vesta

Asciano

Katerine

CA $276 total

includes taxes & fees

Aug 22 - Aug 23

18. RESIDENCE LECCIO

Asciano

Corey

CA $145 total

includes taxes & fees

Sep 6 - Sep 7

19. Apartment Casale Rosennano - Riserva with Shared Garden & Wi-Fi

Rosennano

CA $443 total

includes taxes & fees

Aug 21 - Aug 22

20. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

Ruffoli

"This is truly a unique and special property providing incredible value . One of the most beautiful views in a spectacular setting hidden away in the Tuscan hills above Panzano. A perfect location for day trips to vinyards, restaurants and the Chianti area. Our apartment was extremely well appointed and beautifully decorated. Spacious and varied outdoor sitting areas and patios with a very nice pool area. Our hostess Babette was extremely accomodating and informative which added to our overall...

James

CA $255 total

includes taxes & fees

Aug 17 - Aug 18

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Top San Leolino Hotel Reviews

Villa Scacciapensieri Boutique Hotel

8/10 Good

"All in all a lovely property with lovely staff. Good location, easy bus ride to Siena town."

Villa Casagrande Resort & SPA

10/10 Excellent

"What a wonderful 3 night break at Villa Casagrande! My wife and I had a beautiful stay in this historic villa. There’s a little steep walk up to the pool and restaurant next to it which were perfect and where we spent most of our time relaxing and sunbathing with the view of the trees and the Tuscan mountains. The staff were incredible, so kind, quick to help and made our stay even more pleasant. We both had lovely massages and relaxed in the spa area and one evening did the historic tour and wine tasting which was exceptional. The guides and sommeliers were so knowledgeable and so lovely and the organic Chianti wines they produce are an absolute must to taste and buy. The hotel’s main restaurant was the best in Filigne (the local town) and the food was incredible. One of the nights we had a live musician who was fantastic. We had dinner twice there; mushroom tagliatelle, the lamb, the wild boar gnocchi and paccheri carbonara were to die for! It’s only 50 mins on the train to Florence which is one of our favourite cities to explore in one day and we picked this place especially because it’s only a 12 minute walk from the Filigne Valdarno station and avoids the need to hire a car. We went for the comfort room which was spacious and clean and the air con was great and important for us it had a powerful shower. We truly had a wonderful time and absolutely cannot wait to go back next year! Grazie Villa Casagrande!"

Borgo Scopeto Wine & Country Relais

10/10 Excellent

"We spent a wonderful week at Borgo Scopeto and thoroughly enjoyed every minute. It has everything you'd hope for from a luxury Tuscan retreat: beautiful historic buildings, immaculately kept grounds, and a peaceful atmosphere full of character. The staff were warm, attentive and genuinely welcoming without ever feeling intrusive, and the food was consistently excellent. One of the biggest advantages is its location. Siena is only a short drive away - you can even see the city's campanile while having breakfast - so it was easy to combine days by the pool with exploring one of Tuscany's most beautiful cities (and, inevitably, a bit of shopping to keep our teenage daughter happy). A fantastic place to stay, and one we'd happily recommend."

Castello di Leonina Relais

8/10 Good

"The view from the dining area was perfect. The included breakfast was amazing and the complimentary ebike rentals were perfect to get around outside of the hotel to catch more amazing views! The food at dinner was perfect. The only thing that was lacking was the bathroom showers. Ours was leaking. Other than that it was a perfect stay."

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, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of San Leolino vacation rentals we have selected for you start as low as CA $146 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 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.

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.

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Check prices for these dates

Our top choices for San Leolino vacation rentals

1. Villa di Sotto

2. Borgo di Erboli

3. Locanda Antico Borgo

4. L' Eroico

5. Villa Curina Resort

6. Villa Cassia di Baccano

7. Holiday Home 'Poggio Loccano' with Private Garden and Balcony

8. Casa Vacanze Le Fornaci

9. Relais Villa Belpoggio - Residenza d'Epoca

10. Palazzo Tarlati Residenza d'Epoca

11. Villa Fontis Rapolano

12. DormiVeglia B&B

13. Hu Norcenni Girasole Village

14. Castello di Gargonza

15. Podere La Chiusella

16. Borgo Argenina

17. Podere Vesta

18. RESIDENCE LECCIO

19. Apartment Casale Rosennano - Riserva with Shared Garden & Wi-Fi

20. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

Find vacation rentals that suit your style

Top San Leolino Hotel Reviews

Villa Scacciapensieri Boutique Hotel

Villa Casagrande Resort & SPA

Hotel Chiusarelli

Hotel Athena

Borgo Scopeto Wine & Country Relais

Castello di Spaltenna- Small Luxury Hotels of the World

La Certosa di Pontignano

Castello di Leonina Relais

Fattoria di Vegi

Find out more about San Leolino

Frequently asked questions

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