Vacation Rentals with Pool in Montalcino, Tuscany: Compare 10+ Sites & Save

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Vacation Rentals with Pool
  3.  Italy
  4.  Tuscany
  5.  Montalcino

Refine your search

Price per night

Amenity Filter

Rating

130 Best Vacation Rentals with Pool in Montalcino (Starting from $65)

Agriturismo Villa Paradisino MUSICO
Agriturismo Villa Paradisino MUSICO
House
Montalcino, Italy
1.0k from Montalcino center

Cheap, Accommodations, Pools, Farm stays, Parking, Cottages, Lodgings, Places to stay, Family

4 Bedrooms8 Guests
9.5

Superb

4 reviews

$194
Average price / night
Check Availability
Villa La Fortezza in the heart of the historic center of Montalcino with Jacuzzi
Villa La Fortezza in the heart of the historic center of Montalcino with Jacuzzi
House
Montalcino, 53024, Italy
0.2k from Montalcino center

AC, Free Parking, Internet, No Smoking, Pool

3 Bedrooms7 Guests
10.0

Exceptional

4 reviews

$1042
Average price / night
Check Availability
il burellino
il burellino
House
Montalcino, Italy
1.2k from Montalcino center

Accommodations, Pools, Farm stays, Parking, Cottages, Lodgings, Vacation rentals, Places to stay, Family

3 Bedrooms7 Guests
9.6

Exceptional

298 reviews

$183
Average price / night
Check Availability
Villa in Montalcino with 11 bedrooms sleeps 22
Villa in Montalcino with 11 bedrooms sleeps 22
Villa
Montalcino, 53024, Italy
0.5k from Montalcino center

AC, Balcony, Barbecue, Breakfast Available, Crib, Dryer, Fireplace, Free Parking, Heater

11 Bedrooms22 Guests
New to Booking
$13245
Average price / night
Check Availability
Tenuta Canina
Tenuta Canina
House
Montalcino, Italy
1.2k from Montalcino center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings

3 Bedrooms10 Guests
9.8

Exceptional

21 reviews

$307
Average price / night
Check Availability
Villa Montalcino - Montalcino ,Tuscany
Villa Montalcino - Montalcino ,Tuscany
Villa
Montalcino, 53024, Italy
1.2k from Montalcino center

Dryer, Fireplace, Free Parking, Internet, Kitchen, Laundry, No Smoking, Outdoor Space, Pool

3 Bedrooms8 Guests
New to Booking
$524
Average price / night
Check Availability
Borgo Canalicchio Di Sopra Relais
Borgo Canalicchio Di Sopra Relais
House
Montalcino, Italy
1.4k from Montalcino center

Cheap, Accommodations, Pools, Farm stays, Parking, Romantic, Cottages, Lodgings, Vacation rentals

8 Bedrooms16 Guests
9.5

Superb

325 reviews

$199
Average price / night
Check Availability
Classic, Private Villa with Breathtaking Views - Private Pool
Classic, Private Villa with Breathtaking Views - Private Pool
Villa
montalcino, 99999, Italy
2.2k from Montalcino center

AC, Arcade, Barbecue, Crib, Fireplace, Free Parking, Heater, Internet, Kitchen

4 Bedrooms6 Guests
10.0

Exceptional

25 reviews

$660
Average price / night
Check Availability
Croce di mezzo
Croce di mezzo
House
Montalcino, Italy
2.2k from Montalcino center

Cheap, Accommodations, Pools, Farm stays, Parking, Cottages, Pet-friendly, Lodgings, Vacation rentals

10 Bedrooms31 Guests
8.7

Fabulous

104 reviews

$65
Average price / night
Check Availability
Holiday apartment with pool
Holiday apartment with pool
Apartment
Montalcino, 53024, Italy
2.5k from Montalcino center

Free Parking, Internet, No Smoking, Pool

1 Bedroom2 Guests
New to Booking
$360
Average price / night
Check Availability
agriturismo l'arte dei semplici
agriturismo l'arte dei semplici
House
Montalcino, Italy
2.2k from Montalcino center

Cheap, Accommodations, Pools, Farm stays, Parking, Cottages, Pet-friendly, Lodgings, Vacation rentals

7 Bedrooms18 Guests
8.5

Very Good

269 reviews

$122
Average price / night
Check Availability
Holiday flat with pool and parking
Holiday flat with pool and parking
Apartment
Montalcino, 53024, Italy
2.5k from Montalcino center

Free Parking, Internet, No Smoking, Pool

2 Bedrooms5 Guests
New to Booking
$419
Average price / night
Check Availability
Villa Le Prata - Residenza Del Vescovo
Villa Le Prata - Residenza Del Vescovo
Resort
Montalcino, Italy
2.3k from Montalcino center

Cheap, Accommodations, Pools, Resorts, Parking, Lodgings, Hot tubs, Places to stay

15 Bedrooms30 Guests
9.7

Exceptional

116 reviews

$377
Average price / night
Check Availability
Holiday flat with balcony and view
Holiday flat with balcony and view
Apartment
Montalcino, 53024, Italy
2.5k from Montalcino center

Balcony, Free Parking, Internet, No Smoking, Pool

1 Bedroom2 Guests
New to Booking
$482
Average price / night
Check Availability
Agriturismo Podere La Casa
Agriturismo Podere La Casa
Apartment
Montalcino, Italy
2.4k from Montalcino center

Pet Friendly, Pool, Parking, Kitchen, Child Friendly

8 Bedrooms14 Guests
8.8

Fabulous

77 reviews

$335
Average price / night
Check Availability
Holiday apartment with pool and balcony
Holiday apartment with pool and balcony
Apartment
Montalcino, 53024, Italy
2.5k from Montalcino center

Balcony, Free Parking, Internet, No Smoking, Pool

1 Bedroom2 Guests
New to Booking
$382
Average price / night
Check Availability
Le Ragnaie
Le Ragnaie
House
Montalcino, Italy
2.5k from Montalcino center

Cheap, Accommodations, Pools, Farm stays, Parking, Romantic, Cottages, Lodgings, Vacation rentals

13 Bedrooms20 Guests
9.1

Superb

674 reviews

$118
Average price / night
Check Availability
Holiday flat with breakfast buffet
Holiday flat with breakfast buffet
Apartment
Montalcino, 53024, Italy
2.5k from Montalcino center

Free Parking, Internet, No Smoking, Pool

2 Bedrooms5 Guests
New to Booking
$434
Average price / night
Check Availability
Casanova di Neri Relais
Casanova di Neri Relais
House
Montalcino, Italy
2.6k from Montalcino center

Cheap, Accommodations, Pools, Farm stays, Parking, Cottages, Lodgings, Vacation rentals, Places to stay

10 Bedrooms20 Guests
9.2

Superb

149 reviews

$284
Average price / night
Check Availability
Holiday flat with direct access to the pool
Holiday flat with direct access to the pool
Apartment
Montalcino, 53024, Italy
2.5k from Montalcino center

Free Parking, Internet, No Smoking, Pool

1 Bedroom3 Guests
New to Booking
$296
Average price / night
Check Availability
Capanna Suites
Capanna Suites
House
Montalcino, Italy
3.1k from Montalcino center

Cheap, Accommodations, Pools, Farm stays, Parking, Spa, Cottages, Lodgings, Vacation rentals

11 Bedrooms8 Guests
9.5

Superb

630 reviews

$536
Average price / night
Check Availability
Wonderful new villa in Maremma, near Montalcino and Castiglione della Pescaia
Wonderful new villa in Maremma, near Montalcino and Castiglione della Pescaia
Villa
Montalcino, 53024, Italy
2.6k from Montalcino center

AC, Barbecue, Fireplace, Free Parking, Heater, Housekeeping, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
9.6

Exceptional

25 reviews

$609
Average price / night
Check Availability
Antico Convento I Cappuccini - Villa & Wedding Venue
Antico Convento I Cappuccini - Villa & Wedding Venue
Villa
Montalcino, 53024, Italy
3.0k from Montalcino center

Fireplace, Kitchen, Laundry, Pool

14 Bedrooms26 Guests
10.0

Exceptional

3 reviews

$3297
Average price / night
Check Availability
Holiday home with air conditioning, pool and private garden
Holiday home with air conditioning, pool and private garden
House
castell dell´piano, 58033, Italy
4.3k from Montalcino center

Fireplace, Free Parking, Internet, Laundry, Living Area, Microwave, No Smoking, Outdoor Space, Pool

7 Bedrooms17 Guests
New to Booking
$750
Average price / night
Check Availability
VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24
VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24
Villa
Montalcino, 53024, Italy
4.4k from Montalcino center

AC, Elevator, Free Parking, Heater, Internet, No Smoking, Outdoor Space, Pool, Toys

12 Bedrooms24 Guests
New to Booking
$7371
Average price / night
Check Availability
Cordella in Montalcino Wine Resort
Cordella in Montalcino Wine Resort
House
Podere Meleto 27, Montalcino, 53024, Italy
5.4k from Montalcino center

AC, Free Parking, Heater, Housekeeping, Internet, Laundry, No Smoking, Outdoor Space, Pool

8.4

Very Good

25 reviews

$67
Average price / night
Check Availability
Cerretalta - Country villa with private pool
Cerretalta - Country villa with private pool
Villa
San Quirico D'orcia, 53024, Italy
5.9k from Montalcino center

AC, Balcony, Barbecue, Crib, Fireplace, Free Parking, Heater, Internet, Kitchen

7 Bedrooms14 Guests
10.0

Exceptional

9 reviews

$816
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals with Pool in Montalcino.

Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods

Stay Near Montalcino's Top Attractions

VacationByOwnerRentals can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.

Montalcino Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 130 verified vacation rentals with a pool in Montalcino. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Montalcino vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $65 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Montalcino offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Montalcino welcome pets. Currently, 51 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Montalcino often include additional outdoor features such as Pool, Fireplace/Heating, and Kitchen. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Montalcino offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.