Default HTG hotel image

Search Vacation Homes in Montescudaio

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Montescudaio holiday homes

A swimming pool with lounge chairs and umbrellas, surrounded by a stone wall and a building with large windows.

1. San Francesco Country Resort

San Francesco Country Resort
Rosignano Marittimo
9.4 out of 10, Exceptional, (53 reviews)
"Loved the resort and excellent service."
United Kingdom
PIETRO
The price is HK$490
HK$563 total
includes taxes & fees
30 Oct - 31 Oct
San Francesco Country Resort
A rustic outdoor dining area with wooden chairs and a table, overlooking a scenic landscape with fields and a distant mountain.

2. Fattoria Podere i Luoghi

Fattoria Podere i Luoghi
Casale Marittimo
The price is HK$599
HK$694 total
includes taxes & fees
27 Oct - 28 Oct
Fattoria Podere i Luoghi
An outdoor patio with a glass table and chairs, surrounded by a garden with trees and a clear sky.

3. Beautiful private villa for 2 guests with A/C, WIFI, TV, patio and pets allowed

Beautiful private villa for 2 guests with A/C, WIFI, TV, patio and pets allowed
Montescudaio
The price is HK$1,678
HK$2,124 total
includes taxes & fees
27 Oct - 28 Oct
Beautiful private villa for 2 guests with A/C, WIFI, TV, patio and pets allowed
A bedroom with a bed, nightstands, a dresser, a mirror, and a chandelier.

4. Holiday Home 'Casa Cardelli - A due passi dal Mare'

Holiday Home 'Casa Cardelli - A due passi dal Mare'
Cecina
The price is HK$1,518
HK$2,599 total
includes taxes & fees
27 Oct - 28 Oct
Holiday Home 'Casa Cardelli - A due passi dal Mare'
A room with a bed, a chair, and a staircase leading to an upper level.

5. Holiday Home 'La Casetta' with Private Terrace, Garden & Wi-Fi

Holiday Home 'La Casetta' with Private Terrace, Garden & Wi-Fi
Volterra
6.0 out of 10, (1 review)
"This unit is clean but way too cluttered with stuff. There is no clear surfaces anywhere! The neighbors definitely don’t want people staying there and 3 different neighbors said things we couldn’t understand but were clearly not welcoming us. Might be better for Italians only!"
United States
Christine W.
The price is HK$750
HK$892 total
includes taxes & fees
2 Nov - 3 Nov
Holiday Home 'La Casetta' with Private Terrace, Garden & Wi-Fi
A wooden table with a lantern, potted plants, and a hanging red flower arrangement.

6. Holiday Home 'Mare Colline Città D'Arte' with Private Garden

Holiday Home 'Mare Colline Città D'Arte' with Private Garden
Rosignano Marittimo
The price is HK$914
HK$1,458 total
includes taxes & fees
27 Oct - 28 Oct
Holiday Home 'Mare Colline Città D'Arte' with Private Garden
An aerial view of a property with a central swimming pool, surrounded by manicured gardens and a few buildings.

7. Bungalow 'Stella 2' with Shared Pool, Private Terrace and Air Conditioning

Bungalow 'Stella 2' with Shared Pool, Private Terrace and Air Conditioning
Bibbona
The price is HK$1,562
HK$1,696 total
includes taxes & fees
28 Oct - 29 Oct
Bungalow 'Stella 2' with Shared Pool, Private Terrace and Air Conditioning
A pool with lounge chairs and a pink chair, surrounded by greenery and a clear sky.

8. Holiday Home 'Casetta Maya' with Sea View, Wi-Fi and Air Conditioning

Holiday Home 'Casetta Maya' with Sea View, Wi-Fi and Air Conditioning
Riparbella
9.6 out of 10, Exceptional, (5 reviews)
"War echt eine klasse Unterkunft. Auf dem Anwesen wohnen nur noch die Besitzer, die sehr freundlich und hilfsbereit waren. Den Pool hatten wir während dem gesamten Aufenthalt für uns alleine. Die Besitzer nutzen ihn vermutlich nur bei unserer Abwesenheit. Immer wieder gerne. Können die Unterkunft und die Umgebung sowie als Ausgangspunkt zu vielen Sehenswürdigkeiten und Wanderwege im vollen Umfang weiterempfehlen."
United States
Thomas K.
The price is HK$3,865
HK$4,832 total
includes taxes & fees
31 Oct - 1 Nov
Holiday Home 'Casetta Maya' with Sea View, Wi-Fi and Air Conditioning
A rectangular swimming pool with blue water, surrounded by lounge chairs and umbrellas, with trees and a clear sky in the background.

9. Apartment 'Podere Nuti – 4 Lauro' with Private Gazebo, Shared Pool and Garden

Apartment 'Podere Nuti – 4 Lauro' with Private Gazebo, Shared Pool and Garden
Cecina
The price is HK$1,940
HK$2,405 total
includes taxes & fees
1 Nov - 2 Nov
Apartment 'Podere Nuti – 4 Lauro' with Private Gazebo, Shared Pool and Garden
An aerial view of a property with a swimming pool, multiple villas, and surrounding greenery.

10. Lido Toscano, Private Garden, Pool and Pet Friendly

Lido Toscano, Private Garden, Pool and Pet Friendly
Castellina Marittima
The price is HK$2,237
HK$3,005 total
includes taxes & fees
27 Oct - 28 Oct
Lido Toscano, Private Garden, Pool and Pet Friendly
A stone building with a flat roof, multiple windows, and a small porch area.

11. Podere Cagnesi: Relaxation in the Heart of Nature

Podere Cagnesi: Relaxation in the Heart of Nature
Podere Cagnesi
The price is HK$949
HK$1,789 total
includes taxes & fees
27 Oct - 28 Oct
Podere Cagnesi: Relaxation in the Heart of Nature
A stone building with a wooden balcony, a covered patio with a table and chairs, and potted plants.

12. Holiday Home 'La Cantinetta' with Wi-Fi

Holiday Home 'La Cantinetta' with Wi-Fi
Chianni
The price is HK$1,636
HK$1,653 total
includes taxes & fees
27 Oct - 28 Oct
Holiday Home 'La Cantinetta' with Wi-Fi
A stone building with arches, surrounded by lush greenery and hills.

13. Caravan 'Gitano Pavone Blu' with Private Terrace, Shared Garden and Air Conditioning

Caravan 'Gitano Pavone Blu' with Private Terrace, Shared Garden and Air Conditioning
Suvereto
The price is HK$750
HK$999 total
includes taxes & fees
1 Nov - 2 Nov
Caravan 'Gitano Pavone Blu' with Private Terrace, Shared Garden and Air Conditioning
A courtyard with a round table, potted plants, a wooden door, and stone walls.

14. 'Piccola Corte' Holiday Home with Wi-Fi

'Piccola Corte' Holiday Home with Wi-Fi
Chianni
The price is HK$2,044
HK$2,062 total
includes taxes & fees
27 Oct - 28 Oct
'Piccola Corte' Holiday Home with Wi-Fi
A wooden deck leading to a yellow building with a covered porch, a fenced garden, and a clear sky.

15. Bungalow 'Sole2' with Shared Pool, Private Terrace and Air Conditioning

Bungalow 'Sole2' with Shared Pool, Private Terrace and Air Conditioning
Bibbona
The price is HK$1,601
HK$1,734 total
includes taxes & fees
27 Oct - 28 Oct
Bungalow 'Sole2' with Shared Pool, Private Terrace and Air Conditioning
An aerial view of a property with a central swimming pool, surrounded by manicured gardens and a few buildings.

16. Bungalow 'Sole1' with Shared Pool, Private Terrace and Air Conditioning

Bungalow 'Sole1' with Shared Pool, Private Terrace and Air Conditioning
Bibbona
The price is HK$1,601
HK$1,734 total
includes taxes & fees
28 Oct - 29 Oct
Bungalow 'Sole1' with Shared Pool, Private Terrace and Air Conditioning
Outdoor dining

17. Cozy 2-bedroom house in charming Usigliano with breathtaking views

Cozy 2-bedroom house in charming Usigliano with breathtaking views
Usigliano
The price is HK$1,318
HK$1,511 total
includes taxes & fees
27 Oct - 28 Oct
Cozy 2-bedroom house in charming Usigliano with breathtaking views
An aerial view of a property with a central swimming pool, surrounded by manicured gardens and a few buildings.

18. Bungalow 'Stella 1' with Shared Pool, Private Terrace and Air Conditioning

Bungalow 'Stella 1' with Shared Pool, Private Terrace and Air Conditioning
Bibbona
10.0 out of 10, Exceptional, (1 review)
"Kleines mobile Home mit allem was man braucht.Terrasse ist supi. Zum Pool sind es ca 100m.Pool ist sauber und groß genug zum schwimmen, hat allerdings nur von 10-19 Uhr auf. Ruhige Umgebung. Man ist schnell im Hinterland mit Bergen und Wasserfällen oder am Meer. Für alle was dabei. Gerne wieder "
Germany
Michael W.
The price is HK$1,639
HK$1,773 total
includes taxes & fees
28 Oct - 29 Oct
Bungalow 'Stella 1' with Shared Pool, Private Terrace and Air Conditioning
An outdoor balcony with a table set for two, surrounded by chairs, overlooking a scenic landscape with trees and hills.

19. A beautiful "Tuscan"-style cottage overlooking a magical landscape welcomes families.

A beautiful "Tuscan"-style cottage overlooking a magical landscape welcomes families.
Crespina Lorenzana
10.0 out of 10, Exceptional, (2 reviews)
"Absolutely fabulous property and lovely owners! Spotless, comfortable, spacious and a gorgeous view. We had a fantastic holiday."
United Kingdom
Julie A.
The price is HK$1,142
HK$1,827 total
includes taxes & fees
31 Oct - 1 Nov
A beautiful "Tuscan"-style cottage overlooking a magical landscape welcomes families.
A rectangular swimming pool with blue water, surrounded by lounge chairs and umbrellas, with trees and a clear sky in the background.

20. Apartment 'Podere Nuti – 3 Vallino' with Private Gazebo, Shared Pool & Garden

Apartment 'Podere Nuti – 3 Vallino' with Private Gazebo, Shared Pool & Garden
Cecina
The price is HK$2,080
HK$2,546 total
includes taxes & fees
1 Nov - 2 Nov
Apartment 'Podere Nuti – 3 Vallino' with Private Gazebo, Shared Pool & Garden
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Montescudaio Hotel Reviews

Villa Nencini

Villa Nencini

10/10 Excellent
"I will start by saying that we will be back to Villa Nencini next year, and for a full week's stay. Does that tell you something? The location is perfect for the walking trips; the owners/managers are on site; the grandfather is the chef, taking time to hunt the boar and deer for the larder! The rooms are clean and well-appointed, with marvelous views over the ancient Etruscan walls, down the Cessine valley to the Tyreenean Sea. Breakfast and dinner are in what was once the Villa's stable, now spotless and convivial rooms with patio access for dining. Parking is free and right beside the Villa. We'd stayed in five small Tuscan cities on this trip, and Voltera was our favorite, in large part due to our hosts and the Villa Nencini!"
John 2-night trip
Posted 8 hours ago
Villa Nencini

Find out more about Montescudaio

Montescudaio Vacation Homes information

Number of reviews
62
Accommodation
890 Vacation Homes
Lowest Price
HK$563
Highest Price
HK$4,832

Explore a world of travel with Expedia