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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
The price is AU$175 per night from 19 May to 20 May
AU$175
19 May - 20 May
includes taxes & fees
Located in Rosignano Marittimo, Antico Podere San Francesco Hotel is within a 15-minute drive of Acqua Village and Parco Gallorose.
Opens in a new windowAntico Podere San Francesco Hotel
Holiday house with private pool and fenced garden

Holiday house with private pool and fenced garden

Volterra Toskana
Located in Volterra, this vacation home is on a river, within a 15-minute drive of Balze di Volterra and Palazzo Incontri Viti.
Opens in a new windowHoliday house with private pool and fenced garden
Le Macine, a wonderful ancient restored watermill with Pool

Le Macine, a wonderful ancient restored watermill with Pool

Volterra Tuscany
Located in Volterra, this vacation home is in a rural location, within a 10-minute drive of Medici Fortress and Porta all'Arco.
Opens in a new windowLe Macine, a wonderful ancient restored watermill with Pool
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Sensationall tuscan property with uptown furnishing

Sensationall tuscan property with uptown furnishing

Chianni Toscana
Located in Chianni, this vacation home is in a rural location, within a 15-minute drive of Casciana Thermal Baths and Azienda Agricola Castelvecchio.
Opens in a new windowSensationall tuscan property with uptown furnishing
Villa in the green with private garden and panoramic balcony, 10 minutes from the sea

Villa in the green with private garden and panoramic balcony, 10 minutes from the sea

San Vincenzo (Li) Tuscany
When you stay at this vacation home in San Vincenzo, you'll be by the sea, within a 5-minute drive of Parco Archeominerario di San Silvestro and Marina di San ...
Opens in a new windowVilla in the green with private garden and panoramic balcony, 10 minutes from the sea
house in the historic village in the Tuscan hills

house in the historic village in the Tuscan hills

Chianni Toscana
Located in Chianni, this vacation home is in a rural location, within a 10-minute drive of Azienda Agricola Castelvecchio and Casciana Thermal Baths.
Opens in a new windowhouse in the historic village in the Tuscan hills
Charming Villa with spectacular view on the etruscan coast

Charming Villa with spectacular view on the etruscan coast

Castellina Marittima Tuscany
Located in Castellina Marittima, this vacation home is by the sea, within a 10-minute drive of Lama Tzong Khapa Institute and Cantina Etrusca.
Opens in a new windowCharming Villa with spectacular view on the etruscan coast
Country House & Spa - Inside Nature with panoramic views, Art Surrounded

Country House & Spa - Inside Nature with panoramic views, Art Surrounded

Volterra Italy
Located in Volterra, this vacation home is in a rural location, within a 15-minute drive of Medici Fortress and Cathedral of Volterra.
Opens in a new windowCountry House & Spa - Inside Nature with panoramic views, Art Surrounded
Villa with 2 spacious apartments for 2 x 7 people and swimming pool near Pisa and the sea

Villa with 2 spacious apartments for 2 x 7 people and swimming pool near Pisa and the sea

Fauglia Tuscany
With a stay at this vacation home in Fauglia, you'll be within a 15-minute drive of Pasta Martelli and Castello dei Vicari.
Opens in a new windowVilla with 2 spacious apartments for 2 x 7 people and swimming pool near Pisa and the sea
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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
929 Holiday Homes
Lowest Price
AU$152
Highest Price
AU$1,594
Popular accommodation
Antico Podere San Francesco Hotel, Holiday house with private pool and fenced garden, Le Macine, a wonderful ancient restored watermill with Pool, Sensationall tuscan property with uptown furnishing, Villa in the green with private garden and panoramic balcony, 10 minutes from the sea, house in the historic village in the Tuscan hills, Charming Villa with spectacular view on the etruscan coast, Country House & Spa - Inside Nature with panoramic views, Art Surrounded, Villa with 2 spacious apartments for 2 x 7 people and swimming pool near Pisa and the sea

Top trending hotels in Montescudaio

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 Archaeological Park of Villa Romana of San Vincenzino and Parco ...
Opens in a new windowHu 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$152 per night from 21 May to 22 May
AU$152
21 May - 22 May
includes taxes & fees
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.
Opens in a new windowMax Hotel Livorno
Tombolo Talasso & Beach Resort

Tombolo Talasso & Beach Resort

5 out of 5
Via Del Corallo 3 Castagneto Carducci LI
Fully refundableReserve now, pay when you stay
The price is AU$507 per night from 21 May to 22 May
AU$507
21 May - 22 May
includes taxes & fees
A stay at Tombolo Talasso & Beach Resort places you in the heart of Castagneto Carducci, a 2-minute drive from Cavallino Matto and 12 minutes from Marina di ...
Opens in a new windowTombolo Talasso & Beach Resort
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Castelfalfi

Castelfalfi

5 out of 5
Loc. Castelfalfi Montaione FI
The price is AU$1,594 per night from 25 May to 26 May
AU$1,594
25 May - 26 May
includes taxes & fees
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.
Opens in a new windowCastelfalfi
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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.