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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for San Leolino holiday rentals

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

1. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (38 reviews)
"Great spot"
Canada
Philippe
The price is 4.187.404 ₫
4.606.144 ₫ total
includes taxes & fees
10 Sept - 11 Sept
Villa di Sotto
Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas

2. Borgo di Erboli

Borgo di Erboli
Cavriglia
The price is 3.373.583 ₫
3.771.439 ₫ total
includes taxes & fees
27 Aug - 28 Aug
Borgo di Erboli
Exterior

3. Locanda Antico Borgo

Locanda Antico Borgo
Civitella in Val di Chiana
9.2 out of 10, Wonderful, (20 reviews)
"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. "
United Kingdom
Mr Andy
The price is 3.107.372 ₫
3.418.110 ₫ total
includes taxes & fees
26 Aug - 27 Aug
Locanda Antico Borgo
Exterior

4. L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (14 reviews)
"Monica is a very gracious host. We very much enjoyed our stay. The village is also very quaint and within walking distance. We appreciate the hospitality and highly recommend staying here if you’re coming to the area."
United States
Angela
The price is 3.942.884 ₫
4.579.162 ₫ total
includes taxes & fees
24 Aug - 25 Aug
L' Eroico
Aerial view

5. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (73 reviews)
"Beautiful property"
Canada
Mary
The price is 4.949.797 ₫
5.565.771 ₫ total
includes taxes & fees
23 Aug - 24 Aug
Villa Curina Resort
Lobby

6. Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (24 reviews)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is 5.224.785 ₫
5.747.263 ₫ total
includes taxes & fees
15 Sept - 16 Sept
Villa Cassia di Baccano
Family Apartment, 2 Bedrooms, Hill View, Tower | View from room

7. Casa Vacanze Le Fornaci

Casa Vacanze Le Fornaci
Pergine Valdarno
9.8 out of 10, Exceptional, (7 reviews)
"We absolutely loved our stay at this hotel. The suite was perfect and the restaurant had probably the best food I have had in Tuscany. We definitely plan to stay there again."
United States
Gregory
The price is 4.355.821 ₫
4.882.149 ₫ total
includes taxes & fees
31 Aug - 1 Sept
Casa Vacanze Le Fornaci
Front of property

8. Relais Villa Belpoggio - Residenza d'Epoca

Relais Villa Belpoggio - Residenza d'Epoca
Loro Ciuffenna
9.8 out of 10, Exceptional, (35 reviews)
"Excellent getaway- beautiful property - great staff - extremely clean - I give it a 100"
United Kingdom
Mona
The price is 4.647.419 ₫
5.112.040 ₫ total
includes taxes & fees
2 Sept - 3 Sept
Relais Villa Belpoggio - Residenza d'Epoca
Property entrance

9. Palazzo Tarlati Residenza d'Epoca

Palazzo Tarlati Residenza d'Epoca
Civitella in Val di Chiana
8.0 out of 10, Very good, (3 reviews)
"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...
United States
Marco
The price is 3.299.837 ₫
3.629.851 ₫ total
includes taxes & fees
17 Aug - 18 Aug
Palazzo Tarlati Residenza d'Epoca
Interior

10. Villa Fontis Rapolano

Villa Fontis Rapolano
Rapolano Terme
10.0 out of 10, Exceptional, (1 review)
"Bella struttura, nuova, pulita in posizione comoda"
Italy
Barbara
The price is 2.326.405 ₫
2.680.040 ₫ total
includes taxes & fees
21 Aug - 22 Aug
Villa Fontis Rapolano
Romantic Double Room, 1 Queen Bed, Hot Tub, Ground Floor | Private spa tub

11. DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (29 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
The price is 3.369.986 ₫
3.827.980 ₫ total
includes taxes & fees
17 Aug - 18 Aug
DormiVeglia B&B
Exterior

12. Hu Norcenni Girasole Village

Hu Norcenni Girasole Village
4.0 star property
Figline e Incisa Valdarno
8.6 out of 10, Excellent, (329 reviews)
"We all loved this place. It is conveniently close to Florence or Sienna so you can take a day trips if you get bored but there are plenty of activities on site. We wished we have reserved more days to stay but we will do that next year."
United States
Kalinka
The price is 5.407.653 ₫
6.039.164 ₫ total
includes taxes & fees
19 Aug - 20 Aug
Hu Norcenni Girasole Village
Lunch and dinner served

13. Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.2 out of 10, Wonderful, (44 reviews)
"Beautiful historic fortress / castle with tastefully updated rooms, great amenities that maintains the old character "
Canada
Ariel
The price is 6.530.981 ₫
7.305.074 ₫ total
includes taxes & fees
17 Aug - 18 Aug
Castello di Gargonza
Front of property

14. Podere La Chiusella

Podere La Chiusella
Rapolano Terme
9.4 out of 10, Exceptional, (32 reviews)
"Merci à Michele pour son accueil et la qualité de son hébergement. Tout était parfait. Localisation parfaite pour les Crete Sienese et Val d’Orcia. Très recommandé pour les familles. Nous reviendrons au Pozzo avec grand plaisir."
France
François
The price is 2.819.411 ₫
3.222.347 ₫ total
includes taxes & fees
15 Sept - 16 Sept
Podere La Chiusella
Exterior

15. Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (24 reviews)
"A very peaceful and relaxing B&B that I highly recommend, spacious rooms , clean and well maintained! Host were very pleasing and helpful… definitely recommend!!"
Canada
Sabatino
The price is 6.844.469 ₫
7.770.905 ₫ total
includes taxes & fees
23 Aug - 24 Aug
Borgo Argenina
Seasonal outdoor pool, open 7:30 AM to 7:30 PM, pool umbrellas

16. Podere Vesta

Podere Vesta
3.0 star property
Asciano
9.2 out of 10, Wonderful, (20 reviews)
"This was the best stay and experience during our 20 days trip to italy. Beautiful property 20min from Siena. It had everything we needed. The apartment is stocked with everything you could need for a long stay. My son had so much fun, and the free bikes were a plus. Make sure to pass by a grocery store before arriving, you won’t want to leave the property"
United States
Katerine
The price is 2.453.144 ₫
5.209.104 ₫ total
includes taxes & fees
22 Aug - 23 Aug
Podere Vesta
Front of property

17. RESIDENCE LECCIO

RESIDENCE LECCIO
Asciano
9.4 out of 10, Exceptional, (8 reviews)
"Very nice, affordable place in beautiful area"
United States
Corey
The price is 2.338.779 ₫
2.723.901 ₫ total
includes taxes & fees
6 Sept - 7 Sept
RESIDENCE LECCIO
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

Villa Scacciapensieri Boutique Hotel

Villa Scacciapensieri Boutique Hotel

8/10 Good
"All in all a lovely property with lovely staff. Good location, easy bus ride to Siena town."
Natalia 2-night trip
Posted 5 hours ago
Villa Scacciapensieri Boutique Hotel

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’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.