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Featured Holiday Homes in Montescudaio

Antico Podere San Francesco Hotel

Antico Podere San Francesco Hotel

Stradone del Lupo, 13, Rosignano Marittimo, LI
Fully refundableReserve now, pay when you stay
The price is AU$130 per night from 14 May to 15 May
AU$130
includes taxes & fees
14 May - 15 May
Located in Rosignano Marittimo, Antico Podere San Francesco Hotel is within a 15-minute drive of Acqua Village and Parco Gallorose.
Antico Podere San Francesco Hotel
LUXURY COTTAGE WITH POOL & BREATHTAKING VIEW - NEXT TO A GOLF COURSE (PENDOLINO)

LUXURY COTTAGE WITH POOL & BREATHTAKING VIEW - NEXT TO A GOLF COURSE (PENDOLINO)

Ghizzano
When you stay at this vacation home in Peccioli, you'll be next to a golf course and 14 minutes by car from Castelfalfi Golf Course.
LUXURY COTTAGE WITH POOL & BREATHTAKING VIEW - NEXT TO A GOLF COURSE (PENDOLINO)
Two-room apartment in a country house with park and swimming pool, near the sea.

Two-room apartment in a country house with park and swimming pool, near the sea.

Bibbona
Located in Bibbona, this vacation home is by the sea, within a 5-minute drive of Golf Club Le Capanne and Viale dei Cipressi.
Two-room apartment in a country house with park and swimming pool, near the sea.
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Old house with garden in the center of Bibbona, with a view to

Old house with garden in the center of Bibbona, with a view to

Bibbona
With a stay at this vacation home, you'll be centrally located in Bibbona, within a 10-minute drive of Parco Gallorose and Golf Club Le Capanne.
Old house with garden in the center of Bibbona, with a view to
Wonderful apartment with pool on the etruscan coast, only 3km far from the beach

Wonderful apartment with pool on the etruscan coast, only 3km far from the beach

Rosignano marittima
Located in Rosignano Marittimo, this vacation home is by the ocean, within a 15-minute drive of Hermann Geiger Cultural Foundation and Archaeological Park of ...
Wonderful apartment with pool on the etruscan coast, only 3km far from the beach
Charming Villa with spectacular view on the etruscan coast

Charming Villa with spectacular view on the etruscan coast

Castellina Marittima
Located in Castellina Marittima, this vacation home is by the sea, within a 10-minute drive of Lama Tzong Khapa Institute and Cantina Etrusca.
Charming Villa with spectacular view on the etruscan coast
Volterra Countryside House

Volterra Countryside House

Volterra
A stay at this vacation home places you in the heart of Volterra, within a 5-minute walk of Cathedral of Volterra and Rossi Alabastri Volterra.
Volterra Countryside House
Apartment with 3 bedrooms, 1 bathroom and garden with furniture and bbc

Apartment with 3 bedrooms, 1 bathroom and garden with furniture and bbc

Toscana
With a stay at this vacation home, you'll be centrally located in Fauglia, within a 15-minute drive of Pasta Martelli and Cantina Delle Colline Pisane.
Apartment with 3 bedrooms, 1 bathroom and garden with furniture and bbc
Holiday house with private pool and fenced garden

Holiday house with private pool and fenced garden

Volterra
Located in Volterra, this vacation home is on a river, within a 15-minute drive of Palazzo Incontri Viti and Pinacoteca e Museo Civico.
Holiday house with private pool and fenced garden
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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.

Montescudaio Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Montescudaio vacation homes are the perfect way for you to wing it.

Holiday houses in Montescudaio let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Montescudaio in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Montescudaio adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Montescudaio with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Montescudaio vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Montescudaio Holiday Homes essential information

Accommodation
900 Holiday Homes
Lowest Price
AU$130
Highest Price
AU$1,632
Popular accommodation
Antico Podere San Francesco Hotel, LUXURY COTTAGE WITH POOL & BREATHTAKING VIEW - NEXT TO A GOLF COURSE (PENDOLINO), Two-room apartment in a country house with park and swimming pool, near the sea., Old house with garden in the center of Bibbona, with a view to, Wonderful apartment with pool on the etruscan coast, only 3km far from the beach, Charming Villa with spectacular view on the etruscan coast, Volterra Countryside House, Apartment with 3 bedrooms, 1 bathroom and garden with furniture and bbc, Holiday house with private pool and fenced garden

Top trending hotels in Montescudaio

Fattoria La Steccaia

Fattoria La Steccaia

Località Pianetto, 8, Montescudaio, PI
Located in Montescudaio, Fattoria La Steccaia is connected to a shopping center, within a 15-minute drive of La Regola Azienda Vitivinicola and Hermann Geiger ...
Fattoria La Steccaia
Hu Montescudaio Village

Hu Montescudaio Village

3 out of 5
Via Del Poggetto Montescudaio, Montescudaio, PI
When you stay at Hu Montescudaio Village in Montescudaio, you'll be within a 10-minute drive of Hermann Geiger Cultural Foundation and Archaeological Park of ...
Hu Montescudaio Village
Max Hotel Livorno

Max Hotel Livorno

4 out of 5
Via Giotto Ciardi, 28, Livorno, LI
Fully refundableReserve now, pay when you stay
The price is AU$200 per night from 19 May to 20 May
AU$200
includes taxes & fees
19 May - 20 May
With a stay at Max Hotel Livorno in Livorno, you'll be within a 10-minute drive of Port of Livorno and Stabilimento termale Acque della Salute.
Max Hotel Livorno
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Castelfalfi

Castelfalfi

5 out of 5
Loc. Castelfalfi, Montaione, FI
The price is AU$1,632 per night from 16 May to 17 May
AU$1,632
includes taxes & fees
16 May - 17 May
Located in Montaione, Castelfalfi is in a rural location, a 4-minute drive from Castelfalfi Golf Course and 7 minutes from Monastery of San Vivaldo.
Castelfalfi
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See all available properties in Montescudaio
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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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^Subject to availability and chosen travel dates.