San Leolino Vacation Rentals from ￥11,163: Search Short-Term Rentals

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 kitchenware. You can relax into your vacation with a garden and a library.

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Our top choices for San Leolino vacation rentals

A pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

1. Villa di Sotto

Castelnuovo Berardenga

Philippe

￥34,079 total

includes taxes & fees

Oct 1 - Oct 2

A villa with a swimming pool, outdoor seating, and a tennis court.

2. Villa Curina Resort

Castelnuovo Berardenga

Deanna

￥26,892 total

includes taxes & fees

Oct 4 - Oct 5

A cozy living room with a stone wall, a wine rack, and two sofas.

3. Villa Cassia di Baccano

Loro Ciuffenna

Ralphvincent

￥29,461 total

includes taxes & fees

Oct 10 - Oct 11

A courtyard with a fountain, a pergola with flowers, and a building with a bell tower.

4. Relais Villa Belpoggio - Residenza d'Epoca

Loro Ciuffenna

Mona

￥26,951 total

includes taxes & fees

Oct 5 - Oct 6

A stone building with a garden in front.

5. Borgo Argenina

Gaiole in Chianti

Tatevik

￥42,615 total

includes taxes & fees

Oct 1 - Oct 2

A compact kitchen with a wooden countertop, stainless steel appliances, and a modern design.

6. Cennano Suite - enter apartment

Montevarchi

Judith T.

￥20,162 total

includes taxes & fees

Oct 5 - Oct 6

An arched stone bridge with a white building on the right, featuring a balcony with plants.

7. 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

￥20,162 total

includes taxes & fees

Oct 1 - Oct 2

A covered patio with a wooden table and chairs, stone walls, and a view of a garden.

8. Villa 'Il Fienile Il Sole Verde' with Shared Pool and Wi-Fi

Bucine

Anonymous traveler

￥74,046 total

includes taxes & fees

Oct 5 - Oct 6

A stone building with a yellow sign reading "b&b erioico".

9. L' Eroico

Gaiole in Chianti

Angela

￥27,013 total

includes taxes & fees

Oct 29 - Oct 30

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

￥21,411 total

includes taxes & fees

Oct 1 - Oct 2

A wooden table with two chairs on a balcony, overlooking a lush green landscape with trees and hills.

11. Casa Vacanze Le Fornaci

Pergine Valdarno

Lisette

￥22,213 total

includes taxes & fees

Oct 1 - Oct 2

A staircase with a wooden handrail, a potted plant, and a chair in a hallway.

12. Villa Fontis Rapolano

Rapolano Terme

Barbara

￥15,707 total

includes taxes & fees

Oct 1 - Oct 2

A courtyard with outdoor seating, a stone building with a tower, and a well-maintained garden.

13. Castello di Gargonza

Monte San Savino

Iain

￥43,089 total

includes taxes & fees

Oct 1 - Oct 2

A spa area with a stone-walled arch, a hot tub, and a small window.

14. DormiVeglia B&B

Monte San Savino

Melissa Hyun Joo

￥18,877 total

includes taxes & fees

Oct 4 - Oct 5

A stone building with a sloped roof, a small porch, and a gravel driveway.

15. Podere La Chiusella

Rapolano Terme

"We enjoyed our stay. Everything was clean and comfortable, and the complex itself was impressive and a stunning place to stay. The location was also a convenient base for seeing Tuscany, and we had a great meal nearby in Rapolano Terme. Overall, it has the potential to be one of the coolest places you'll ever stay, though we did encounter a few technical issues regarding the shower and WiFi (which the hosts were quickly responsive about). I'd still recommend it, but it's helpful if you go in...

Kevin

￥19,007 total

includes taxes & fees

Oct 6 - Oct 7

A pool area with a water slide and a stage for performances.

16. Villa Norcenni Aparthotel

Figline e Incisa Valdarno

Laka

￥12,087 total

includes taxes & fees

Oct 1 - Oct 2

A bedroom with a large bed, bedside tables, a window, a radiator, and a TV.

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

Monteaperti

Ian F.

￥33,544 total

includes taxes & fees

Oct 12 - Oct 13

A stone building with a tiled roof, surrounded by a well-maintained garden with various plants and a cactus in the foreground.

18. La Murata

Rapolano Terme

Elizabeth

￥23,148 total

includes taxes & fees

Oct 7 - Oct 8

A hot tub with two people, surrounded by trees and a wooden deck.

19. 2 Cuori e 1 Yurta Glamping in Toscana

Asciano

￥44,427 total

includes taxes & fees

Oct 18 - Oct 19

An arched brick corridor with gravel flooring, potted plants, and a gate leading to a garden area.

20. Ca' Bianca Tuscany Relais

Siena

Talha

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Top San Leolino Hotel Reviews

Hotel Athena

10/10 Excellent

"The hotel is wonderful! The staff is extremely friendly and helpful. The location is great…jut a short walk to shopping, restaurants, and the cathedral. Our room was very clean and the beds were comfortable. The view from the terrace is stunning."

Hu Norcenni Girasole Village

10/10 Excellent

"My family and I had such a great time. Such a kid friendly place and at check in they even had a little playground while you waiting and gave the kids bubbles. So great to be in nature and all of the amenities were lovely. The waterparks that were padded on the ground were genius and we did a family wine tasting which was such a lovely memory. Our stay was so nice with the deck and the grocery store is so affordable for dinners in. Love love love! My toddler played all day and there were so many times we got to relax because they had everything that we wanted or needed right on property."

Find out more about San Leolino

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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 kitchenware. 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 Terme Antica Querciolaia. 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. Villa Curina Resort

3. Villa Cassia di Baccano

4. Relais Villa Belpoggio - Residenza d'Epoca

5. Borgo Argenina

6. Cennano Suite - enter apartment

7. Locanda Antico Borgo

8. Villa 'Il Fienile Il Sole Verde' with Shared Pool and Wi-Fi

9. L' Eroico

10. Palazzo Tarlati Residenza d'Epoca

11. Casa Vacanze Le Fornaci

12. Villa Fontis Rapolano

13. Castello di Gargonza

14. DormiVeglia B&B

15. Podere La Chiusella

16. Villa Norcenni Aparthotel

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

18. La Murata

19. 2 Cuori e 1 Yurta Glamping in Toscana

20. Ca' Bianca Tuscany Relais

Find vacation rentals that suit your style

Top San Leolino Hotel Reviews

Hotel Athena

La Certosa di Pontignano

Hotel Minerva

Borgo Scopeto Wine & Country Relais

Hu Norcenni Girasole Village

Grand Hotel Continental Siena – Starhotels Collezione

Hotel Chiusarelli

Villa Ermellina Siena, a Tribute Portfolio Hotel

Castello di Leonina Relais

Find out more about San Leolino

Frequently asked questions

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