Montalcino Vacation Rentals

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Sep 30 - Oct 1
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Vacation Rentals in Montalcino

Private and cozy retreat in Montalcino with private pool surrounded by vineyards
Pool

Private and cozy retreat in Montalcino with private pool surrounded by vineyards

9.4 out of 10, Exceptional, (65)
"If you like a 360-degree view from the top of the hill, this is the place. Amazing views, out in the country with little traffic (more tractors than cars). Very private. We wanted to sit on the patio all day.The house is very comfortable and a good home base for sampling Brunello and visiting the Montalcino vineyards.Camilla was easy to communicate with before and during our stay."
Private and cozy retreat in Montalcino with private pool surrounded by vineyards
Villa in Montalcino, exclusive for you, stunning view!!!
Outdoor pool

Villa in Montalcino, exclusive for you, stunning view!!!

10.0 out of 10, Exceptional, (84)
"Lovely villa in a beautiful location. "
Villa in Montalcino, exclusive for you, stunning view!!!
Hilltop house in the heart of Tuscany with private pool
Outdoor dining

Hilltop house in the heart of Tuscany with private pool

9.8 out of 10, Exceptional, (92)
"Wonderful, quiet, beautiful. Everything you could want in country stay near a small village."
Hilltop house in the heart of Tuscany with private pool
The House of Alice, charm and relaxation
Exterior detail

The House of Alice, charm and relaxation

9.8 out of 10, Exceptional, (66)
"Unbelievable ambience and beauty of the region and the house. Francesco was super helpful. "
The price is ￥27,883
￥37,642 total
includes taxes & fees
Oct 14 - Oct 15
The House of Alice, charm and relaxation
Montalcino: Private villa in the heart of Tuscany, private pool,panoramic view!
Outdoor pool

Montalcino: Private villa in the heart of Tuscany, private pool,panoramic view!

10.0 out of 10, Exceptional, (56)
"Beautiful property comfortable beds. Amazing views room two sit outside and enjoy sunsets."
Montalcino: Private villa in the heart of Tuscany, private pool,panoramic view!
Corte Francigena
Deluxe Condo | Private kitchen | Full-size fridge, microwave, stovetop, dishwasher

Corte Francigena

9.8 out of 10, Exceptional, (6)
"Loved everything about my stay"
The price is ￥24,809
￥29,381 total
includes taxes & fees
Oct 15 - Oct 16
Corte Francigena
Recently restored Villa in Tuscany, sleeps 12, sw.pool, big garden, olive grove.
Outdoor pool

Recently restored Villa in Tuscany, sleeps 12, sw.pool, big garden, olive grove.

10.0 out of 10, Exceptional, (13)
"Impeccable property. Property manager was simply amazing, welcoming, caring, friendly and always willing to help. We would love to come back! "
Recently restored Villa in Tuscany, sleeps 12, sw.pool, big garden, olive grove.
Antico Brunello
Outdoor pool

Antico Brunello

The price is ￥1,150,182
￥1,266,943 total
includes taxes & fees
Oct 9 - Oct 10
Antico Brunello
Casanova - Panoramic Rooms and Suites
Front of property - evening/night

Casanova - Panoramic Rooms and Suites

3.0 star property
9.0 out of 10, Wonderful, (68)
"My fiancée and I enjoyed ourselves! It’s a beautiful place and I adored walking around in the nearby town. "
Casanova - Panoramic Rooms and Suites
Hotel San Gregorio
Breakfast, lunch, dinner served; local cuisine

Hotel San Gregorio

3.0 star property
9.4 out of 10, Exceptional, (129)
"Such friendly staff, loved Pienza and the property was such a good location! "
The price is ￥23,329
￥26,708 total
includes taxes & fees
Oct 29 - Oct 30
Hotel San Gregorio
ApartHotel Anghel
Lobby lounge

ApartHotel Anghel

8.4 out of 10, Very Good, (327)
"Enough space for a family. We were able to walk to restaurants, grocery and old city Siena. "
The price is ￥14,544
￥16,696 total
includes taxes & fees
Oct 30 - Oct 31
ApartHotel Anghel
Il Battistero Siena - Residenza d'Epoca
Bar (on property)

Il Battistero Siena - Residenza d'Epoca

9.6 out of 10, Exceptional, (180)
"Great location. Convenient to attractions, restaurants. "
The price is ￥23,098
￥26,104 total
includes taxes & fees
Oct 21 - Oct 22
Il Battistero Siena - Residenza d'Epoca
Abbadia Sicille Relais
View from room

Abbadia Sicille Relais

4.0 star property
8.8 out of 10, Excellent, (159)
"Great Historical location."
The price is ￥15,331
￥17,389 total
includes taxes & fees
Oct 22 - Oct 23
Abbadia Sicille Relais
Bosco della Spina
Aerial view

Bosco della Spina

9.6 out of 10, Exceptional, (162)
"We enjoyed the scenery and service! Clean and comfortable. "
Bosco della Spina
Country house, really private pool A.C. 20 mn beaches facing Elba Island
Outdoor pool

Country house, really private pool A.C. 20 mn beaches facing Elba Island

7.6 out of 10, Good, (9)
"Die Unterkuinft entsprach unseren Erwartungen. Es war sehr ruhig und sehr sauber. Alles war gepflegt. Die Natur ums Grundstück war sehr präsent aber auch das war Erwartungsgemäß."
Country house, really private pool A.C. 20 mn beaches facing Elba Island
Farmhouse in the hills with panoramic view and swimming pool
Pool

Farmhouse in the hills with panoramic view and swimming pool

9.6 out of 10, Exceptional, (74)
"We‘ve spent two wonderful weeks with our two year old daughter and our dog. The house is beautifully located in the hills with no direct neighbours. The view is fantastic and we felt immediately at home in this beautiful house. We had a wonderful time and our hosts were just lovely. (We cannot say anything about the pool - except that it is huge - because we were there out of season in March when the pool was closed.)"
Farmhouse in the hills with panoramic view and swimming pool
Tuscasì Aparthotel
Royal Apartment | View from room

Tuscasì Aparthotel

9.2 out of 10, Wonderful, (21)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
The price is ￥12,011
￥13,735 total
includes taxes & fees
Oct 1 - Oct 2
Tuscasì Aparthotel
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
Outdoor dining

Sun-Soaked Private View Terrace in the Historical Centre of Cortona.

9.6 out of 10, Exceptional, (71)
"My husband and I loved our stay here! It was so close to town and the terrace was absolutely stunning. Would definitely stay here again! "
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
Camping Siena Colleverde
Exterior

Camping Siena Colleverde

3.0 star property
8.2 out of 10, Very Good, (155)
"Safe, great proximity to Siena without being too close, nice pool."
Camping Siena Colleverde
agriturismo la roggiola
Banquet hall

agriturismo la roggiola

9.6 out of 10, Exceptional, (112)
"Beautiful situation, close to Siena and Orcia valley. Three days very well spent, merci Simonetta !"
agriturismo la roggiola
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 Montalcino Hotel Reviews

Private and cozy retreat in Montalcino with private pool surrounded by vineyards

Private and cozy retreat in Montalcino with private pool surrounded by vineyards

10/10 Excellent
"We absolutely loved this darling villa...the accommodations were all very comfortable and the views & sunsets were spectacular! It's about a 15 min drive from the village of Montalcino but also sits in the midst of several wineries worth visiting. Must have a vehicle to commute to town and the surrounding wineries but enjoying the setting & pool without going anywhere is also recommended ! Camilla is a terrific hostess"
Gina C. 7-night trip
Posted 16 hours ago
Private and cozy retreat in Montalcino with private pool surrounded by vineyards

Find out more about Montalcino

Find out more about Montalcino

Search for holiday rentals in Montalcino on Expedia! You can easily find your home rentals, villas, holiday apartments in Montalcino using one of the methods below:

  • View our selection of featured holiday rentals in Montalcino
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Look no further and take a look at our great range of rental properties in Montalcino!

Explore a world of travel with Expedia

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Frequently asked questions

Are there vacation rentals in Montalcino?

Yes, you can find vacation rentals in Montalcino close to Bosco della Ragnaia, or you can choose a more secluded option if you're looking for a relaxing stay. Discover why Montalcino is known for its spas and countryside. While you're here, grab a bite or have a drink at the wineries.

What's the top vacation rental that Montalcino has to offer?

Borgo Argiano: You might want to consider this vacation home rental near Montalcino, which is located on a river and has a balcony, a terrace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and an espresso maker. You can relax into your vacation with a garden and a library. Another good choice for your trip to Montalcino is The House of Alice, charm and relaxation.

How many vacation rentals are there in Montalcino?

With 38 Expedia vacation rentals, you're sure to find just the right place for your Montalcino stay.

What’s there to see and do in Montalcino?

Enjoy the outdoors at Val di Chiana and Val di Merse, or simply take in cultural attractions like Museum of Brunello and Civic and Diocesan Museum of Sacred Art of Montalcino. Other places in town to visit include Fortress of Montalcino and Tenuta Greppo Franco Biondi Santi.

What’s a vacation rental in Montalcino like?

Vacation rentals are privately owned properties you can book for several days or longer in Montalcino. Vacation rentals offer amenities like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a clean environment, vacation rentals can offer a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for family trips or small group gatherings.