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Featured Holiday Homes in Montalcino

Beautiful stone house with garden and private pool.

Beautiful stone house with garden and private pool.

Sovicille - Siena
Stay at this vacation home in Siena. Enjoy free WiFi, private pools, and a garden. Popular attractions Piazza del Campo and San Leonardo al Lago are located ...
Beautiful stone house with garden and private pool.
Il Palazzetto

Il Palazzetto

Strada del Lucherino, 31, Siena, SI
Stay at this vacation home in Siena. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Piazza del Campo and Porta Tufi are located ...
Il Palazzetto
Borgo Argiano

Borgo Argiano

Loc. Argiano, Pianella, Castelnuovo Berardenga, SI
Book a stay at this business-friendly vacation home in Castelnuovo Berardenga. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Piazza ...
Borgo Argiano
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Your dream home! In harmony with nature!  Priv. Pool - fantastic views!

Your dream home! In harmony with nature! Priv. Pool - fantastic views!

Arcidosso
Book a stay at this family-friendly vacation home in Arcidosso. Enjoy free WiFi, private pools, and a garden. Popular attractions Monte Amiata and Mount Amiata ...
Your dream home! In harmony with nature! Priv. Pool - fantastic views!
The House of Alice, charm and relaxation

The House of Alice, charm and relaxation

Montalcino (SI)
The price is NZ$465 per night from 24 July to 25 July
NZ$465
24 July - 25 July
includes taxes & fees
Stay at this vacation home in Montalcino. Enjoy a garden, laundry facilities, and cable/satellite TV service. Popular attractions Abbazia di Sant'Antimo and ...
The House of Alice, charm and relaxation
Villa Le Tortore Tuscany private luxury pool relax

Villa Le Tortore Tuscany private luxury pool relax

Siena
Stay at this vacation home in Siena. Enjoy free WiFi, private pools, and a garden. Popular attractions Piazza del Campo and Porta Romana are located nearby.
Villa Le Tortore Tuscany private luxury pool relax
Villa il Giuggiolo, ancient country house with pool at Azienda Fontelunga

Villa il Giuggiolo, ancient country house with pool at Azienda Fontelunga

cortona
Stay at this vacation home in Cortona. Enjoy free WiFi, private pools, and a garden. Popular attractions Parterre Garden and Santa Maria delle Grazie are located ...
Villa il Giuggiolo, ancient country house with pool at Azienda Fontelunga
Casa Bacco - private house with a remarkable garden in the centre of Cortona

Casa Bacco - private house with a remarkable garden in the centre of Cortona

Cortona
Stay at this vacation home in Cortona. Enjoy a garden, laundry facilities, and cable/satellite TV service. Popular attractions Signorelli Theatre and Museum ...
Casa Bacco - private house with a remarkable garden in the centre of Cortona
Porcilaia tiny countryside property, shared pool, ideal base to discover Tuscany

Porcilaia tiny countryside property, shared pool, ideal base to discover Tuscany

Siena
Stay at this vacation home in Siena. Enjoy free WiFi, private pools, and a garden. Popular attractions Piazza del Campo and San Leonardo al Lago are located ...
Porcilaia tiny countryside property, shared pool, ideal base to discover Tuscany
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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.

Montalcino 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 Montalcino vacation homes are the perfect way for you to wing it.

Holiday houses in Montalcino 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 Montalcino 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 Montalcino adventures, obvs.

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

Montalcino Holiday Homes essential information

Accommodation
1362 Holiday Homes
Lowest Price
NZ$465
Highest Price
NZ$3,565
Popular accommodation
Beautiful stone house with garden and private pool., Il Palazzetto, Borgo Argiano, Your dream home! In harmony with nature! Priv. Pool - fantastic views!, The House of Alice, charm and relaxation, Villa Le Tortore Tuscany private luxury pool relax, Villa il Giuggiolo, ancient country house with pool at Azienda Fontelunga, Casa Bacco - private house with a remarkable garden in the centre of Cortona, Porcilaia tiny countryside property, shared pool, ideal base to discover Tuscany

Top trending hotels in Montalcino

Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery

5 out of 5
Località Velona, Castelnuovo dell'Abate, Montalcino, SI
Fully refundableReserve now, pay when you stay
The price is NZ$1,559 per night from 28 July to 29 July
NZ$1,559
28 July - 29 July
includes taxes & fees
Stay at this 5-star luxury hotel in Montalcino. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Abbazia di Sant'Antimo and Museum of Brunello ...
Castello di Velona Resort Thermal SPA & Winery
Rosewood Castiglion del Bosco

Rosewood Castiglion del Bosco

5 out of 5
Localita Castiglion del Bosco, Montalcino, SI
Fully refundableReserve now, pay when you stay
The price is NZ$3,565 per night from 2 Aug to 3 Aug
NZ$3,565
2 Aug - 3 Aug
includes taxes & fees
Stay at this 5-star luxury hotel in Montalcino. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Castiglion del Bosco Winery and Corte ...
Rosewood Castiglion del Bosco
SI Montalcino Hotel

SI Montalcino Hotel

3 out of 5
Via Osticcio 21, Montalcino, SI
Fully refundableReserve now, pay when you stay
Stay at this 3-star hotel in Montalcino. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
SI Montalcino Hotel
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Castello Banfi - Il Borgo

Castello Banfi - Il Borgo

5 out of 5
Castello di Poggio alle Mura s.n.c., Montalcino, SI
The price is NZ$1,699 per night from 7 Aug to 8 Aug
NZ$1,699
7 Aug - 8 Aug
includes taxes & fees
Stay at this 5-star luxury hotel in Montalcino. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Castello Banfi and Poggio Antico are ...
Castello Banfi - Il Borgo
Don't see what you're looking for?
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.