A cobblestone street with historic buildings, a wooden chair, and potted plants.

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Check prices for these dates

In two weeks
4 Sep - 6 Sep
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Casole d'Elsa villas

Exterior

1. Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills

Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills
Gambassi Terme
The price is AED 17,299
AED 17,312 total
includes taxes & fees
14 Sep - 15 Sep
Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills
Exterior

2. The San Leonino House

The San Leonino House
Castellina in Chianti
The price is AED 2,870
AED 5,628 total
includes taxes & fees
23 Aug - 24 Aug
The San Leonino House
Villa, Air conditioning, Courtyard View | Exterior

3. Villa Montecastello

Villa Montecastello
Monteriggioni
8.0 out of 10, Very Good, (3 reviews)
"Amazing stay! Teh apartment is HUGE and GORGEOUS. The whole villa is amazing. The view , unbeatable. The host , super warm. Highly recommend!"
United States
Alvaro
The price is AED 704
AED 787 total
includes taxes & fees
25 Aug - 26 Aug
Villa Montecastello
Exterior

4. Nice apartment in villa with A/C, WIFI, pool, TV, terrace and panoramic view, close to San Gimig...

Nice apartment in villa with A/C, WIFI, pool, TV, terrace and panoramic view, close to San Gimig...
Montaione
10.0 out of 10, Exceptional, (5 reviews)
"We spend a great time, marvellous place and people"
United States
Carole G.
The price is AED 612
AED 698 total
includes taxes & fees
19 Aug - 20 Aug
Nice apartment in villa with A/C, WIFI, pool, TV, terrace and panoramic view, close to San Gimig...
Exterior

5. Villa "Arnilù" with Private Pool & Wi-Fi

Villa "Arnilù" with Private Pool & Wi-Fi
San Gimignano
The price is AED 20,989
AED 22,565 total
includes taxes & fees
19 Aug - 20 Aug
Villa "Arnilù" with Private Pool & Wi-Fi
Property grounds

6. Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Toscana
The price is AED 467
AED 557 total
includes taxes & fees
19 Aug - 20 Aug
Rooster House, cooking classes and opera
Property grounds

7. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Siena
The price is AED 18,453
AED 20,578 total
includes taxes & fees
19 Aug - 20 Aug
VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Outdoor dining

8. Villa Mami: A Tuscan Retreat of Elegance and Charm

Villa Mami: A Tuscan Retreat of Elegance and Charm
Toscana
10.0 out of 10, Exceptional, (1 review)
The price is AED 14,873
AED 18,728 total
includes taxes & fees
16 Sep - 17 Sep
Villa Mami: A Tuscan Retreat of Elegance and Charm
Outdoor dining

9. Villa Marina with private pool, Borgo del Silenzio

Villa Marina with private pool, Borgo del Silenzio
Lajatico
"L’hébergement est situé au milieu de champs, superbe vue pour admirer le lever et coucher du soleil! La route en cailloux pour y accéder, dommage. C’est parfait pour les gens qui recherchent le calme! Maison propre. La literie pourrait être améliorée; matelas un peu durs. La piscine parfaite avec les enfants! L’accueil de Ludovica est agréable, très à l’écoute de nos besoins! Nous avons passé une belle semaine de vacances!"
Switzerland
Loic
Villa Marina with private pool, Borgo del Silenzio
Exterior

10. GuestHost - Porta Romana Elegant House with Private Parking!

GuestHost - Porta Romana Elegant House with Private Parking!
Siena
9.0 out of 10, Wonderful, (4 reviews)
"Excellent location 15 mi minute walk to the center of town. Towels and linens were fresh and fragrant. On site parking was super convenient because of limited parking around the town. The property manager was immediately available by phone and delivered an extra blanket which in 5 minutes of our request."
United States
Kathleen M.
The price is AED 793
AED 1,474 total
includes taxes & fees
7 Sep - 8 Sep
GuestHost - Porta Romana Elegant House with Private Parking!
Outdoor dining

11. Villa Ludovica with private pool, Borgo del Silenzio

Villa Ludovica with private pool, Borgo del Silenzio
Lajatico
10.0 out of 10, Exceptional, (1 review)
"Mooie villa met alle accommodatie op een unieke ligging"
Netherlands
Carl P.
Villa Ludovica with private pool, Borgo del Silenzio
Exterior

12. Villetta Leonardo: Independence, Garden & Relaxation in Tuscany

Villetta Leonardo: Independence, Garden & Relaxation in Tuscany
Montaione
The price is AED 1,088
AED 1,504 total
includes taxes & fees
28 Aug - 29 Aug
Villetta Leonardo: Independence, Garden & Relaxation in Tuscany
Exterior

13. Villa 'Eleonora' with Private Pool, Private Garden and Wi-Fi

Villa 'Eleonora' with Private Pool, Private Garden and Wi-Fi
San Vivaldo
The price is AED 5,697
AED 7,070 total
includes taxes & fees
19 Aug - 20 Aug
Villa 'Eleonora' with Private Pool, Private Garden and Wi-Fi
Terrace/patio

14. Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany

Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
Certaldo - Firenze
2.0 out of 10, (1 review)
"House is very nice and clean , but not equipped for rental, kitchen is poorly equipped, towels are like napkins , no toilet paper, no soap , nothing "
United States
Kelly C.
The price is AED 2,006
AED 2,524 total
includes taxes & fees
19 Aug - 20 Aug
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
Pool

15. "A Casa di Franca Villa con piscina"

"A Casa di Franca Villa con piscina"
Gambassi Terme
10.0 out of 10, Exceptional, (1 review)
"Pros: La estancia en la casa fue muy bonita. Estaba cerca de Florencia, Siena, Sant Gimigano, etc. Viajamos toda la familia y los propietarios fueron muy acogedores. La piscina es un sitio perfecto para relajarse y bañarse después de ver la Toscana. Nuestros hijos y sobrinos jugaron porque tenían de todo. La casa muy equipada y limpia con televisión en todas las habitaciones. Los propietarios además nos ayudaron con un pequeño contratiempo que tuvimos. Nos sentimos como en casa, muchas...
Spain
Anonymous traveler
The price is AED 2,215
AED 3,783 total
includes taxes & fees
24 Aug - 25 Aug
"A Casa di Franca Villa con piscina"
Exterior detail

16. Villa Duomo Mare – Entire House with Garden & Terrace, Walk to Center

Villa Duomo Mare – Entire House with Garden & Terrace, Walk to Center
Massa Marittima
The price is AED 1,817
AED 2,242 total
includes taxes & fees
23 Aug - 24 Aug
Villa Duomo Mare – Entire House with Garden & Terrace, Walk to Center
Pool

17. Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Radda in Chianti
10.0 out of 10, Exceptional, (2 reviews)
"A dream property come true. Breathtaking views, most accommodating hosts, Perfect Tuscan location."
United States
Amber M.
The price is AED 2,282
AED 4,327 total
includes taxes & fees
17 Sep - 18 Sep
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Exterior

18. Villa 'La Casa Nel Bosco - Antiche Dimore' with Shared Pool, Wi-Fi & Air Conditioning

Villa 'La Casa Nel Bosco - Antiche Dimore' with Shared Pool, Wi-Fi & Air Conditioning
Siena
The price is AED 1,700
AED 1,708 total
includes taxes & fees
15 Sep - 16 Sep
Villa 'La Casa Nel Bosco - Antiche Dimore' with Shared Pool, Wi-Fi & Air Conditioning
Pool

19. VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

VILLA CHIGI - Seven Bedroom Villa, Sleeps 14
Siena
The price is AED 23,196
AED 23,196 total
includes taxes & fees
19 Aug - 20 Aug
VILLA CHIGI - Seven Bedroom Villa, Sleeps 14
Property grounds

20. Villa Bonriposo with Private Pool, Wi-Fi, and Air Conditioning

Villa Bonriposo with Private Pool, Wi-Fi, and Air Conditioning
Legoli
The price is AED 10,369
AED 11,644 total
includes taxes & fees
16 Sep - 17 Sep
Villa Bonriposo with Private Pool, Wi-Fi, and Air Conditioning
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 Casole d'Elsa Hotel Reviews

Hotel Athena

Hotel Athena

10/10 Excellent
"We had a superior room, which was very comfortable. We had dinner in the restaurant several times, and the food and drink was excellent. One evening we just enjoyed the cocktail bar, and the staff were fun! Breakfast buffet has everything one could want, and was always fresh. Free parking! You will have an uphill walk to the town centre, but no matter where you go in Siena it’s either up or down. Highly recommended."
Christopher 7-night trip
Posted 9 hours ago
Hotel Athena

Frequently asked questions

How much do villas in Casole d'Elsa cost?
You can expect to pay between AED 787 and AED 5,238 per night for a villa in Casole d'Elsa. No matter your budget, an ideal stay is only clicks away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many villas are there in Casole d'Elsa?
Reclaim your vacation days and choose from 1604 villas in Casole d'Elsa. For a family escape, a weekend getaway and everything in between, Expedia will help you find the perfect place in a few simple clicks.
Why book your villa in Casole d'Elsa with Expedia?
Reserving a villa in Casole d'Elsa is as simple as deciding on your travel dates and choosing the option that meets your needs. Want something affordable or upmarket, or a stay that also features a pool? Use Expedia's search filters to narrow your results and find your perfect match.
How can I find cheap villas in Casole d'Elsa?
The quickest way to compare cheap villas in Casole d'Elsa is with Expedia's helpful filter tool. Refine your search by budget, star rating and amenities to land unbeatable deals in only a few clicks.