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

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

Refine your search

Price per night

Amenity Filter

Rating

365 Best Vacation Rentals with Pool in Montespertoli (Starting from $65)

Le Mandrie di Ripalta
Le Mandrie di Ripalta
House
Montespertoli, Italy
1.2k from Montespertoli center

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

6 Bedrooms23 Guests
8.9

Fabulous

1035 reviews

$118
Average price / night
Check Availability
Locanda del podestà: 17th century mansion in Chianti
Locanda del podestà: 17th century mansion in Chianti
Villa
Montespertoli, 50025, Italy
0.9k from Montespertoli center

Balcony, Barbecue, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Outdoor Space

5 Bedrooms12 Guests
9.8

Exceptional

60 reviews

$262
Average price / night
Check Availability
Podere Villabassa
Podere Villabassa
House
Montespertoli, Tuscany, Italy
1.4k from Montespertoli center

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

6 Bedrooms20 Guests
New to Booking
$328
Average price / night
Check Availability
Apartment with Swimming Pool and Tennis
Apartment with Swimming Pool and Tennis
Apartment
Montespertoli, 50025, Italy
1.1k from Montespertoli center

AC, Barbecue, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking, Pool

1 Bedroom5 Guests
10.0

Exceptional

1 reviews

$165
Average price / night
Check Availability
Agriturismo Le Ginestruzze
Agriturismo Le Ginestruzze
House
Montespertoli, Italy
1.6k from Montespertoli center

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

15 Bedrooms32 Guests
7.7

Good

14 reviews

$363
Average price / night
Check Availability
Villa Ginestruzze – Villa with Private Pool and Exclusive Suites in Tuscany
Villa Ginestruzze – Villa with Private Pool and Exclusive Suites in Tuscany
Villa
Montespertoli, 50025, Italy
1.6k from Montespertoli center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Outdoor Space

5 Bedrooms10 Guests
New to Booking
$548
Average price / night
Check Availability
Borgo Filicardo
Borgo Filicardo
Apartment
Montespertoli, Italy
1.8k from Montespertoli center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Jacuzzis, Places to stay

16 Bedrooms5 Guests
9.5

Superb

20 reviews

$80
Average price / night
Check Availability
Limonaia – Elegant Tuscan Apartment with Spacious Rooms, Pool, and Relaxation
Limonaia – Elegant Tuscan Apartment with Spacious Rooms, Pool, and Relaxation
Apartment
Montespertoli, 50025, Italy
1.8k from Montespertoli center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Outdoor Space

3 Bedrooms6 Guests
New to Booking
$255
Average price / night
Check Availability
Nido di Rondine
Nido di Rondine
Apartment
Montespertoli, Italy
1.8k from Montespertoli center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay, Family

1 Bedroom2 Guests
9.2

Superb

7 reviews

$65
Average price / night
Check Availability
Panorama – Apartment with Terrace and Views of the Tuscan Countryside
Panorama – Apartment with Terrace and Views of the Tuscan Countryside
Apartment
Montespertoli, 50025, Italy
1.8k from Montespertoli center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Outdoor Space

2 Bedrooms5 Guests
New to Booking
$238
Average price / night
Check Availability
Villa Caterina 2 by Falcony apartments
Villa Caterina 2 by Falcony apartments
Villa
Montespertoli, Italy
2.1k from Montespertoli center

Ocean View, Oceanfront, Pool, Guest Services, Air Conditioner, Security/Safety, Pet Friendly

1 Bedroom6 Guests
New to Booking
$231
Average price / night
Check Availability
Casina – Tuscan Apartment with Pool among Vineyards and Olive Groves
Casina – Tuscan Apartment with Pool among Vineyards and Olive Groves
Apartment
Montespertoli, 50025, Italy
1.9k from Montespertoli center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Outdoor Space

1 Bedroom3 Guests
New to Booking
$149
Average price / night
Check Availability
Villa Caterina 1 by falcony apartments
Villa Caterina 1 by falcony apartments
Apartment
Montespertoli, Italy
2.1k from Montespertoli center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay, Self-catering

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$161
Average price / night
Check Availability
Cipressina – Spacious Tuscan Apartment with Pool for Families and Groups
Cipressina – Spacious Tuscan Apartment with Pool for Families and Groups
Apartment
Montespertoli, 50025, Italy
1.9k from Montespertoli center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Outdoor Space

4 Bedrooms8 Guests
New to Booking
$376
Average price / night
Check Availability
Fattoria La Gigliola
Fattoria La Gigliola
Resort
Montespertoli, Tuscany, Italy
2.1k from Montespertoli center

Sports/Activities, Guest Services, Ocean View, Pool, Balcony/Terrace, Toiletries, Accessibility

29 Bedrooms65 Guests
5.8

Review score

5 reviews

$179
Average price / night
Check Availability
Elegant 7 bedrooms villa in Tuscany
Elegant 7 bedrooms villa in Tuscany
Villa
Toscana, 50025, Italy
2.2k from Montespertoli center

Arcade, Free Parking, Heater, Internet, Kitchen, Laundry, No Smoking, Outdoor Space, Pool

7 Bedrooms16 Guests
New to Booking
$1018
Average price / night
Check Availability
Fattoria la Gigliola - Il Frantoio
Fattoria la Gigliola - Il Frantoio
House
Montespertoli, Italy
2.1k from Montespertoli center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

1 Bedroom5 Guests
7.7

Good

3 reviews

$130
Average price / night
Check Availability
Villa Paola Private Pool Gym in Chianti, Montespertoli, Italy
Villa Paola Private Pool Gym in Chianti, Montespertoli, Italy
House
Montespertoli, 50025, Italy
2.5k from Montespertoli center

AC, Barbecue, Fireplace, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

5 Bedrooms11 Guests
10.0

Exceptional

1 reviews

$581
Average price / night
Check Availability
Fattoria la Gigliola - Il Fattore
Fattoria la Gigliola - Il Fattore
House
Montespertoli, Italy
2.1k from Montespertoli center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms9 Guests
5.5

Review score

4 reviews

$232
Average price / night
Check Availability
ANCIENT AIR-CND PRIVATE VILLA POOL & JACUZZI ON  FLORENCE HILLS FAMILY FRIENDLY
ANCIENT AIR-CND PRIVATE VILLA POOL & JACUZZI ON FLORENCE HILLS FAMILY FRIENDLY
Villa
Montespertoli, 50025, Italy
2.5k from Montespertoli center

Barbecue, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

5 Bedrooms12 Guests
9.6

Exceptional

13 reviews

$500
Average price / night
Check Availability
Fattoria la Gigliola - La Limonaia
Fattoria la Gigliola - La Limonaia
House
Montespertoli, Italy
2.1k from Montespertoli center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

2 Bedrooms6 Guests
5.3

Review score

3 reviews

$244
Average price / night
Check Availability
Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!
Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!
Villa
Montespertoli, 50025, Italy
2.6k from Montespertoli center

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

9 Bedrooms22 Guests
10.0

Exceptional

12 reviews

$2087
Average price / night
Check Availability
Cozy apartment for 4/5 pax in a cottage in Chianti,Wifi,Swimmingpool,AIR-CO,Chef
Cozy apartment for 4/5 pax in a cottage in Chianti,Wifi,Swimmingpool,AIR-CO,Chef
Apartment
Poppiano, 50025, Italy
2.7k from Montespertoli center

AC, Breakfast Available, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

2 Bedrooms5 Guests
8.0

Good

3 reviews

$452
Average price / night
Check Availability
Tuscan Apart for 4/5 persons, WIFI, AIR-CO, SW-POOL, all comforts in the country
Tuscan Apart for 4/5 persons, WIFI, AIR-CO, SW-POOL, all comforts in the country
Apartment
Montespertoli, 50025, Italy
2.7k from Montespertoli center

AC, Breakfast Available, Crib, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen

2 Bedrooms5 Guests
10.0

Exceptional

22 reviews

$452
Average price / night
Check Availability
Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites
Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites
Villa
Montespertoli, 50025, Italy
2.7k from Montespertoli center

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

9 Bedrooms22 Guests
10.0

Exceptional

38 reviews

$2087
Average price / night
Check Availability
Villa Lola In Montespertoli, Tuscany
Villa Lola In Montespertoli, Tuscany
Villa
Montespertoli, 50025, Italy
2.8k from Montespertoli center

AC, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, No Smoking

6 Bedrooms12 Guests
9.0

Fabulous

2 reviews

$696
Average price / night
Check Availability
Villa La Torre 16, Montespertoli, Florence and Chianti
Villa La Torre 16, Montespertoli, Florence and Chianti
Villa
Montespertoli, 50025, Italy
2.8k from Montespertoli center

Barbecue, Dryer, Heater, Kitchen, Laundry, Living Area, Microwave, No Smoking, Outdoor Space

8 Bedrooms16 Guests
New to Booking
$980
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 Montespertoli.

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

Stay Near Montespertoli's Top Attractions

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

Montespertoli Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 365 verified vacation rentals with a pool in Montespertoli. 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 Montespertoli 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 Montespertoli 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 Montespertoli welcome pets. Currently, 52 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 Montespertoli often include additional outdoor features such as Pool, Fireplace/Heating, and Balcony/Terrace. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Montespertoli 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.