Montalcino Holiday Rentals
Apartment
- Tuscany
- ·
- Montalcino
- 0.36 mi to center
10.0Exceptional
(56 Reviews)
3 Bedrooms
2 Baths
6 Guests
1615 ft²
Parking
Balcony/Terrace
Kitchen
Air Conditioner
US $456/Night
7 Nights - US $3,191
House
- Tuscany
- ·
- Montalcino
- 4.66 mi to center
10.0Exceptional
(18 Reviews)
3 Bedrooms
3 Baths
6 Guests
269.1 ft²
- Parking
- Balcony/Terrace
View- Kitchen
US $114/Night
7 Nights - US $798
Bed & Breakfast
- Montalcino
- ·
- Sant'Angelo In Colle
- 0.11 mi to center
10.0Exceptional
(71 Reviews)
1 Bedroom
1 Bath
Breakfast- Parking
- Air Conditioner
Internet
US $235/Night
7 Nights - US $1,648
Cottage
- Montalcino
- ·
- Camigliano
- 0.45 mi to center
10.0Exceptional
(49 Reviews)
3 Bedrooms
2 Baths
6 Guests
1292 ft²
Private Pool- Parking
Pool
Ocean View
US $571/Night
7 Nights - US $3,999
Villa
- Tuscany
- ·
- Montalcino
- 0.18 mi to center
10.0Exceptional
(13 Reviews)
4 Bedrooms
6 Baths
8 Guests
4305.56 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $684/Night
7 Nights - US $4,785
House
- Montalcino
- ·
- Montisi
- 0.46 mi to center
10.0Exceptional
(46 Reviews)
3 Bedrooms
4 Baths
10 Guests
2583 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $507/Night
7 Nights - US $3,550
Villa
10.0Exceptional
(46 Reviews)
2 Bedrooms
1 Bath
6 Guests
915 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $236/Night
7 Nights - US $1,652
Apartment
10.0Exceptional
(32 Reviews)
3 Bedrooms
2 Baths
6 Guests
Hot Tub- Parking
- Balcony/Terrace
- Kitchen
US $264/Night
7 Nights - US $1,850
Villa
- Tuscany
- ·
- Montalcino
- 1.38 mi to center
10.0Exceptional
(25 Reviews)
4 Bedrooms
3 Baths
6 Guests
3250 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $797/Night
7 Nights - US $5,580
Luxury Holiday Rentals in Montalcino
Over 807+ Luxury Holiday Rentals in or Near Montalcino
Villa
- Montalcino
- ·
- Argiano
- 0.63 mi to center
1 Bedroom
1 Bath
- Pool
- Air Conditioner
Child Friendly
Laundry
US $8,431/Night
7 Nights - US $59,019
Villa
- Tuscany
- ·
- Montalcino
- 2.76 mi to center
12 Bedrooms
1 Bath
24 Guests
5920 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $7,319/Night
7 Nights - US $51,235
House
9.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
1528 ft²
- Breakfast
- Parking
- Pool
- Ocean View
US $6,497/Night
7 Nights - US $45,479
House
3 Bedrooms
1 Bath
6 Guests
1679 ft²
- Breakfast
- Pool
- Balcony/Terrace
- Kitchen
US $6,438/Night
7 Nights - US $45,063
House
3 Bedrooms
3 Baths
6 Guests
1679 ft²
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $6,381/Night
7 Nights - US $44,667
House
2 Bedrooms
2 Baths
4 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $6,365/Night
7 Nights - US $44,555
House
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
- Pool
- Balcony/Terrace
- Kitchen
Pet Friendly
US $6,359/Night
7 Nights - US $44,511
Resort
8.0Excellent
(1 Review)
3 Baths
6 Guests
1679 ft²
- Breakfast
- Parking
- Pool
- Ocean View
US $6,303/Night
7 Nights - US $44,118
House
- Tuscany
- ·
- Montalcino
- 3.92 mi to center
12 Bedrooms
12 Baths
24 Guests
5802 ft²
- Breakfast
- Parking
- Kitchen
- Air Conditioner
US $4,290/Night
7 Nights - US $30,030
Top-Rated Holiday Rentals with a Pool in Montalcino
Over 498+ The Best Private Villas and Holiday Rentals in Montalcino with a Pool
Hotel
- Montalcino
- ·
- Poggio alle Mura
- 0.13 mi to center
10.0Exceptional
(130 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
Spa
US $1,183/Night
7 Nights - US $8,279
Hotel
- Tuscany
- ·
- Montalcino
- 1.39 mi to center
10.0Exceptional
(86 Reviews)
1 Bath
- Hot Tub
- Breakfast
- Parking
- Pool
US $588/Night
7 Nights - US $4,119
Other
- Tuscany
- ·
- Montalcino
- 0.66 mi to center
10.0Exceptional
(81 Reviews)
1 Bedroom
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $272/Night
7 Nights - US $1,905
Hotel
- Montalcino
- ·
- Castiglione del Bosco
- 0.05 mi to center
10.0Exceptional
(77 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Spa
US $2,543/Night
7 Nights - US $17,799
Other
- Tuscany
- ·
- Montalcino
- 4.25 mi to center
10.0Exceptional
(74 Reviews)
1 Bedroom
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $567/Night
7 Nights - US $3,971
Hotel
- Tuscany
- ·
- Montalcino
- 3.91 mi to center
10.0Exceptional
(23 Reviews)
26 Baths
1204.36 ft²
Oceanfront- Hot Tub
EV Charge Station- Parking
US $260/Night
7 Nights - US $1,821
House
- Montalcino
- ·
- Vergelle
- 0.37 mi to center
10.0Exceptional
(20 Reviews)
2 Bedrooms
2 Baths
4 Guests
969 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $247/Night
7 Nights - US $1,732
Villa
- Montalcino
- ·
- San Giovanni d'Asso
- 0.46 mi to center
10.0Exceptional
(13 Reviews)
6 Bedrooms
8 Baths
12 Guests
8374 ft²
- Private Pool
- Breakfast
- Parking
- Pool
US $2,814/Night
7 Nights - US $19,700
Villa
10.0Exceptional
(13 Reviews)
5 Bedrooms
6 Baths
10 Guests
2583 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $864/Night
7 Nights - US $6,046
Pet-Friendly Holiday Rentals in Montalcino
Over 481+ Pet-Friendly Holiday Rentals in or Near Montalcino
Villa
- Tuscany
- ·
- Montalcino
- 3.70 mi to center
10.0Exceptional
(11 Reviews)
7 Bedrooms
11 Baths
14 Guests
4844 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $752/Night
7 Nights - US $5,263
Apartment
- Tuscany
- ·
- Montalcino
- 3.31 mi to center
10.0Exceptional
(9 Reviews)
3 Bedrooms
2 Baths
9 Guests
1076.39 ft²
- Parking
- Balcony/Terrace
- View
- Internet
US $58/Night
7 Nights - US $406
Bed & Breakfast
- Tuscany
- ·
- Montalcino
- 0.13 mi to center
10.0Exceptional
(24 Reviews)
1 Bedroom
1 Bath
- Breakfast
- Kitchen
- Internet
- Pet Friendly
US $234/Night
7 Nights - US $1,635
Villa
Private Villa with private pool, WIFI, A/C, TV, pets allowed, panoramic view, close to Montepulciano
10.0Exceptional
(9 Reviews)
5 Bedrooms
6 Baths
10 Guests
2583 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $811/Night
7 Nights - US $5,677
House
10.0Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
5 Guests
1130.21 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $219/Night
7 Nights - US $1,534
Villa
- Tuscany
- ·
- Montalcino
- 3.65 mi to center
10.0Exceptional
(9 Reviews)
7 Bedrooms
8 Baths
14 Guests
5382 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $693/Night
7 Nights - US $4,853
Apartment
- Tuscany
- ·
- Montalcino
- 1.49 mi to center
10.0Exceptional
(8 Reviews)
2 Bedrooms
2 Baths
3 Guests
861 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $349/Night
7 Nights - US $2,440
Apartment
- Tuscany
- ·
- Montalcino
- 1.49 mi to center
10.0Exceptional
(7 Reviews)
2 Bedrooms
2 Baths
4 Guests
969 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $364/Night
7 Nights - US $2,546
Apartment
- Tuscany
- ·
- Montalcino
- 1.41 mi to center
10.0Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
3 Guests
861 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $335/Night
7 Nights - US $2,345
Large Holiday Rentals and Private Villas in Montalcino
Over 211+ Large Holiday Rentals and Private Villas in or Near Montalcino
Villa
- Tuscany
- ·
- Montalcino
- 0.03 mi to center
10.0Exceptional
(24 Reviews)
3 Bedrooms
3 Baths
6 Guests
1615 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $1,333/Night
7 Nights - US $9,329
House
- Montalcino
- ·
- Montisi
- 0.14 mi to center
10.0Exceptional
(4 Reviews)
5 Bedrooms
6 Baths
10 Guests
3444.45 ft²
- Oceanfront
- Breakfast
- Parking
- Ocean View
US $470/Night
7 Nights - US $3,293
Villa
1 Bedroom
1 Bath
- Parking
- Pool
- Balcony/Terrace
- Internet
US $412/Night
7 Nights - US $2,882
Villa
- Montalcino
- ·
- Camigliano
- 0.51 mi to center
10.0Exceptional
(9 Reviews)
5 Bedrooms
3 Baths
9 Guests
3229 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $1,360/Night
7 Nights - US $9,521
Apartment
10.0Exceptional
(3 Reviews)
9 Bedrooms
7 Baths
18 Guests
663.77 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $169/Night
7 Nights - US $1,184
Villa
- Tuscany
- ·
- Montalcino
- 1.88 mi to center
10.0Exceptional
(3 Reviews)
14 Bedrooms
9 Baths
26 Guests
- Pool
- Kitchen
- Pet Friendly
- Child Friendly
US $3,665/Night
7 Nights - US $25,652
Villa
- Montalcino
- ·
- Castelnuovo dell'Abate
- 0.31 mi to center
10.0Exceptional
(3 Reviews)
4 Bedrooms
3 Baths
8 Guests
3229 ft²
- Private Pool
- Breakfast
- Parking
- Pool
US $933/Night
7 Nights - US $6,528
Villa
- Tuscany
- ·
- Montalcino
- 3.67 mi to center
10.0Exceptional
(2 Reviews)
7 Bedrooms
8 Baths
14 Guests
4844 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $677/Night
7 Nights - US $4,739
Villa
10.0Exceptional
(1 Review)
11 Bedrooms
9 Baths
22 Guests
- Private Pool
- Breakfast
- Parking
- Pool
US $1,849/Night
7 Nights - US $12,945
Wheelchair Accessible Holiday Homes in Montalcino
Over 18+ Wheelchair Accessible Holiday Homes in or Near Montalcino
House
9.9Exceptional
(282 Reviews)
8 Bedrooms
8 Baths
24 Guests
344.45 ft²
- Oceanfront
- Breakfast
- EV Charge Station
- Parking
US $345/Night
7 Nights - US $2,417
Resort
- Tuscany
- ·
- Montalcino
- 0.17 mi to center
10.0Exceptional
(1 Review)
1 Bath
2 Guests
- Breakfast
- Parking
- Balcony/Terrace
- Kitchen
US $343/Night
7 Nights - US $2,404
House
- Montalcino
- ·
- Tavernelle
- 0.05 mi to center
9.4Exceptional
(668 Reviews)
12 Bedrooms
3 Baths
6 Guests
269.1 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $311/Night
7 Nights - US $2,180
House
- Tuscany
- ·
- Montalcino
- 2.76 mi to center
9.8Exceptional
(160 Reviews)
1 Bedroom
1 Bath
- Hot Tub
- Breakfast
- Parking
- Pool
US $253/Night
7 Nights - US $1,770
House
- Tuscany
- ·
- Montalcino
- 1.94 mi to center
9.3Exceptional
(482 Reviews)
11 Bedrooms
4 Baths
8 Guests
419.79 ft²
- Oceanfront
- Hot Tub
- Breakfast
- EV Charge Station
US $570/Night
7 Nights - US $3,989
Other
- Tuscany
- ·
- Montalcino
- 3.83 mi to center
9.2Exceptional
(5 Reviews)
1 Bedroom
1 Bath
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $96/Night
7 Nights - US $671
Apartment
- Tuscany
- ·
- Montalcino
- 3.82 mi to center
9.2Exceptional
(210 Reviews)
17 Bedrooms
17 Baths
32 Guests
862.46 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $91/Night
7 Nights - US $637
House
9.1Exceptional
(709 Reviews)
28 Bedrooms
23 Baths
68 Guests
411.86 ft²
- Oceanfront
- Breakfast
- EV Charge Station
- Parking
US $481/Night
7 Nights - US $3,367
House
- Montalcino
- ·
- Vergelle
- 0.02 mi to center
9.1Exceptional
(63 Reviews)
7 Bedrooms
6 Baths
24 Guests
699.65 ft²
- Oceanfront
- Breakfast
- Parking
- Pool
US $646/Night
7 Nights - US $4,522
Montalcino Private Villas and Holiday Homes Under $200
Over 251+ Montalcino Private Villas and Holiday Homes Under $200
House
- Tuscany
- ·
- Montalcino
- 0.15 mi to center
10.0Exceptional
(5 Reviews)
1 Bedroom
1 Bath
2 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $160/Night
7 Nights - US $1,119
Villa
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
914.93 ft²
- Parking
- Pool
- View
- Internet
US $174/Night
7 Nights - US $1,219
Bed & Breakfast
- Tuscany
- ·
- Montalcino
- 0.29 mi to center
10.0Exceptional
(40 Reviews)
1 Bedroom
1 Bath
- Breakfast
- Parking
- Balcony/Terrace
- Kitchen
US $197/Night
7 Nights - US $1,379
Apartment
- Tuscany
- ·
- Montalcino
- 0.29 mi to center
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
4 Guests
538 ft²
- Parking
- Ocean View
- View
- Kitchen
US $168/Night
7 Nights - US $1,177
Apartment
- Montalcino
- ·
- San Giovanni d'Asso
- 0.24 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
861.11 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $138/Night
7 Nights - US $967
Apartment
- Montalcino
- ·
- Torrenieri
- 0.20 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Breakfast
- Parking
- Balcony/Terrace
- Kitchen
US $120/Night
7 Nights - US $839
Apartment
- Tuscany
- ·
- Montalcino
- 0.31 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
269 ft²
- Breakfast
- Balcony/Terrace
- Kitchen
- Internet
US $196/Night
7 Nights - US $1,375
Apartment
- Montalcino
- ·
- San Giovanni d'Asso
- 0.21 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
1 Bath
8 Guests
1292 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $163/Night
7 Nights - US $1,141
House
- Montalcino
- ·
- Sant'Angelo In Colle
- 0.15 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
US $159/Night
7 Nights - US $1,113
Instantly Bookable Holiday Homes in Montalcino
Over 372+ Instantly Bookable Holiday Homes in or Near Montalcino
House
- Tuscany
- ·
- Montalcino
- 0.18 mi to center
10.0Exceptional
(3 Reviews)
4 Bedrooms
5 Baths
8 Guests
4306 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,027/Night
7 Nights - US $7,188
Apartment
- Tuscany
- ·
- Montalcino
- 0.04 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
753 ft²
- Balcony/Terrace
- Kitchen
- Internet
- Child Friendly
US $174/Night
7 Nights - US $1,216
Villa
- Montalcino
- ·
- Montisi
- 0.17 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
3 Baths
6 Guests
1830 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $650/Night
7 Nights - US $4,553
Apartment
- Tuscany
- ·
- Montalcino
- 3.47 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
915 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $422/Night
7 Nights - US $2,957
House
Beautiful private villa with A/C, WIFI, private pool, TV, patio, panoramic view, close to Montalcino
- Montalcino
- ·
- San Giovanni d'Asso
- 0.28 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
3 Baths
5 Guests
1399 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $406/Night
7 Nights - US $2,842
Apartment
- Tuscany
- ·
- Montalcino
- 0.27 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $262/Night
7 Nights - US $1,833
Apartment
- Tuscany
- ·
- Montalcino
- 0.41 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
194 ft²
- Breakfast
- Balcony/Terrace
- Kitchen
- Internet
US $157/Night
7 Nights - US $1,102
Apartment
- Montalcino
- ·
- San Giovanni d'Asso
- 0.06 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
1 Bath
8 Guests
1292 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $152/Night
7 Nights - US $1,065
Apartment
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
4 Guests
786 ft²
- Parking
- Kitchen
- Internet
- Child Friendly
US $129/Night
7 Nights - US $902
Book a Last Minute Place to Stay in Montalcino
About Casai's Private Villas and Holiday Rentals in Montalcino
Discover more than 816 vacation rentals available in Montalcino. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Montalcino.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Montalcino, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Montalcino. On average, places to stay near Montalcino offer 1102.36 ft², with nightly prices averaging US $505.
With Casai, finding and comparing holiday rentals in Montalcino is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Montalcino
| Type | Count |
|---|---|
| Holiday Apartments | 310 |
| Vacation Homes | 246 |
| Villas | 148 |
| Cottages | 2 |
Use these Quick Filters to Find a Holiday Rental in Montalcino
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Montalcino.
Top Attractions Around Montalcino, IT
Casai offers a large selection of top attractions around Montalcino . Research things to do on your vacation before you visit Montalcino.
Other Places to Stay in Montalcino, IT
Frequently Asked Questions About Montalcino?
What are the top holiday rentals in Montalcino?
With numerous options available in Montalcino, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Montalcino:
- Castello Banfi - Il Borgo - Relais et Chateaux
- Villa Le Prata - Residenza del Vescovo
- Il Burellino Wine & Resort
- Castiglion del Bosco, A Rosewood Hotel
- Mastrojanni Relais - Small Luxury Hotels of the World
- Dimora delle Muse
- Unique Views From Inside The Town Of Montalcino
- Charming farmhouse with private pool among Brunello vineyards A real Escape!
- Colombiao di Momo: A Large 17th Century Farmhouse overlooking Tuscan hills
- Castelmuzio - Detached house with private pool
How many holiday rentals have private pools in Montalcino?
Discover a selection of holiday rentals with private pools near Montalcino with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
- Beautiful private villa with WIFI, private pool, TV, veranda, panoramic view, close to Montepulciano
- Castello di Velona Resort, Thermal SPA & Winery
- Holiday apartment with terrace, air conditioning and internet
- Wonderful new villa in Maremma, near Montalcino and Castiglione della Pescaia
Which holiday homes in Montalcino are best for families?
If you're searching for a family-friendly holiday home in Montalcino, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Montalcino:
- Brunello di Montalcino Apartment Farmhouse Bonacchi
- Podere Gli Oppi Toscana
- Corte Francigena - Apartments
How many Casai.com holiday rentals are available in Montalcino?
As of 2026, Casai boasts over 816 properties listed in the Montalcino area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Montalcino.
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