Vacation Rentals with Private Pool in Montego Bay, FL: Compare 10+ Sites & Save

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Vacation Rentals with Private Pool
  3.  USA

  4.  Florida
  5.  Orlando
  6.  Montego Bay

Refine your search

Price per night

Amenity Filter

Rating

3637 Best Vacation Rentals with Private Pool in Montego Bay (Starting from $111)

Private Paradise! Stunning south-facing pool home
Private Paradise! Stunning south-facing pool home
House
Kissimmee, FL, USA
0.2k from Montego Bay center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

4 Bedrooms10 Guests
New to Booking
$256
Average price / night
Check Availability
6 Mi to Disney World: Lake-View Retreat w/ Pool!
6 Mi to Disney World: Lake-View Retreat w/ Pool!
House
Kissimmee, FL, 34746, United States
0.1k from Montego Bay center

AC, Dryer, Fireplace, Free Parking, Heater, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$227
Average price / night
Check Availability
Brittany - Perfect 3 BR Pool Home
Brittany - Perfect 3 BR Pool Home
House
Kissimmee, FL, USA
0.4k from Montego Bay center

Cheap, Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Places to stay

3 Bedrooms6 Guests
7.5

Good

4 reviews

$111
Average price / night
Check Availability
Family Home in Kissimmee Florida - Near All Attractions !
Family Home in Kissimmee Florida - Near All Attractions !
House
Kissimmee, FL, 34746, United States
0.1k from Montego Bay center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms15 Guests
9.0

Fabulous

4 reviews

$346
Average price / night
Check Availability
Luxury Getaway 3BR Apartment near Disney Parks
Luxury Getaway 3BR Apartment near Disney Parks
Apartment
Kissimmee, FL, USA
1.1k from Montego Bay center

Apartments, Luxury, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Places to stay, Accessible hotels

3 Bedrooms7 Guests
New to Booking
$130
Average price / night
Check Availability
Grand Laguna 3BR Penthouse Near Disney Parks
Grand Laguna 3BR Penthouse Near Disney Parks
Apartment
Kissimmee, FL, USA
1.2k from Montego Bay center

Apartments, Accommodations, Pools, Parking, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$148
Average price / night
Check Availability
Your Own 3BR Private Home w/ Heated Pool • Quiet Family Retreat Near Disney
Your Own 3BR Private Home w/ Heated Pool • Quiet Family Retreat Near Disney
House
Kissimmee, FL, 34746, United States
0.2k from Montego Bay center

AC, Arcade, Barbecue, Crib, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

3 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$328
Average price / night
Check Availability
Sunkissed Oasis: 5-bed Villa Pool Games Room
Sunkissed Oasis: 5-bed Villa Pool Games Room
Villa
Kissimmee, FL, USA
1.3k from Montego Bay center

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

1 Bedroom10 Guests
New to Booking
$261
Average price / night
Check Availability
Comfy 3 bedroom with pool
Comfy 3 bedroom with pool
House
Kissimmee, FL, 34746, United States
0.3k from Montego Bay center

AC, Dryer, Free Parking, Internet, Living Area, Microwave, No Smoking, Pool, TV

3 Bedrooms8 Guests
6.0

Review score

1 reviews

$255
Average price / night
Check Availability
Grand Luxury 3BR Penthouse near Disney Parks
Grand Luxury 3BR Penthouse near Disney Parks
Apartment
Kissimmee, FL, USA
1.3k from Montego Bay center

Apartments, Luxury, Cheap, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Places to stay

3 Bedrooms6 Guests
9.3

Superb

4 reviews

$126
Average price / night
Check Availability
3 Bed Home, Close to Disney, some pets considered, 4904
3 Bed Home, Close to Disney, some pets considered, 4904
House
Kissimmee, FL, 34746, United States
0.3k from Montego Bay center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms6 Guests
9.2

Superb

57 reviews

$225
Average price / night
Check Availability
Storey Lake Resort 5 Bedroom Vacation Home with Pool 2307
Storey Lake Resort 5 Bedroom Vacation Home with Pool 2307
House
Kissimmee, FL, USA
1.4k from Montego Bay center

Accommodations, Pools, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Vacation rentals

5 Bedrooms14 Guests
7.4

Good

5 reviews

$216
Average price / night
Check Availability
Beautiful private 3 bed villa with spa and amazing south facing lake view
Beautiful private 3 bed villa with spa and amazing south facing lake view
Villa
Kissimmee, FL, 34746, United States
0.3k from Montego Bay center

AC, Arcade, Barbecue, Crib, Dryer, Free Parking, Heater, Hot Tub, Internet

3 Bedrooms8 Guests
9.4

Superb

70 reviews

$245
Average price / night
Check Availability
New Home at Storey Lake8 Bedrooms and 5 Bathrooms
New Home at Storey Lake8 Bedrooms and 5 Bathrooms
House
Kissimmee, FL, USA
1.5k from Montego Bay center

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

8 Bedrooms20 Guests
New to Booking
$652
Average price / night
Check Availability
KISSIMMEE 3/2 home, 10 minutes to Disney, with pool & BBQ included!
KISSIMMEE 3/2 home, 10 minutes to Disney, with pool & BBQ included!
House
Kissimmee, FL, 34746, United States
0.3k from Montego Bay center

AC, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

3 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$312
Average price / night
Check Availability
Storey Lake Resort 679 - Hosted by Top Villas
Storey Lake Resort 679 - Hosted by Top Villas
Villa
Kissimmee, FL, USA
1.5k from Montego Bay center

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

5 Bedrooms13 Guests
New to Booking
$485
Average price / night
Check Availability
Cozy 3BR Family Home Minutes from Disney
Cozy 3BR Family Home Minutes from Disney
House
Kissimmee, FL, 34746, United States
0.4k from Montego Bay center

AC, Crib, Dryer, Heater, Internet, Kitchen, Microwave, No Smoking, Pool

3 Bedrooms7 Guests
10.0

Exceptional

3 reviews

$191
Average price / night
Check Availability
Magic Marvel Getaway
Magic Marvel Getaway
Villa
Kissimmee, FL, USA
1.5k from Montego Bay center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Hot tubs

9 Bedrooms24 Guests
8.0

Good

3 reviews

$646
Average price / night
Check Availability
Bright 3BR pool home with screened lanai, Jacuzzi & near Disney parks
Bright 3BR pool home with screened lanai, Jacuzzi & near Disney parks
House
Kissimmee, FL, 34746, United States
0.4k from Montego Bay center

AC, Arcade, Barbecue, Dryer, Free Parking, Internet, Kitchen, Living Area, Microwave

3 Bedrooms10 Guests
8.0

Good

1 reviews

$201
Average price / night
Check Availability
Disney Close: Cozy Club Cortile Apartment
Disney Close: Cozy Club Cortile Apartment
Apartment
Kissimmee, FL, USA
1.5k from Montego Bay center

Apartments, Accommodations, Pools, Parking, Spa, Lodgings, Places to stay

1 Bedroom8 Guests
New to Booking
$355
Average price / night
Check Availability
Pet friendly 3 Bed Villa with Private Pool
Pet friendly 3 Bed Villa with Private Pool
Villa
Kissimmee, FL, 34746, United States
0.4k from Montego Bay center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
8.0

Good

54 reviews

$206
Average price / night
Check Availability
 Helen's Disney Dream Home - Chatham Park
Helen's Disney Dream Home - Chatham Park
House
Kissimmee, FL, 34746, United States
0.4k from Montego Bay center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms5 Guests
10.0

Exceptional

90 reviews

$195
Average price / night
Check Availability
Amazing Blue Private Pool - 4BR House Near Disney
Amazing Blue Private Pool - 4BR House Near Disney
House
Kissimmee, FL, 34746, United States
0.4k from Montego Bay center

AC, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms7 Guests
8.8

Fabulous

5 reviews

$274
Average price / night
Check Availability
Kissimmee Vacation Rental w/ Pool ~ 6 Mi to Disney
Kissimmee Vacation Rental w/ Pool ~ 6 Mi to Disney
House
Kissimmee, FL, 34746, United States
0.4k from Montego Bay center

AC, Crib, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

4 Bedrooms10 Guests
7.4

Good

3 reviews

$347
Average price / night
Check Availability
Lakeview, massage spa, tropical classic decor, quiet and secure neighborhood!
Lakeview, massage spa, tropical classic decor, quiet and secure neighborhood!
Villa
Kissimmee, FL, 34746, United States
0.5k from Montego Bay center

AC, Arcade, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen

4 Bedrooms8 Guests
9.2

Superb

109 reviews

$198
Average price / night
Check Availability
2711 House Overlooking Lake
2711 House Overlooking Lake
Villa
Kissimmee, FL, 34746, United States
0.5k from Montego Bay center

AC, Dryer, Heater, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

3 Bedrooms6 Guests
9.0

Fabulous

52 reviews

$115
Average price / night
Check Availability
The Den! Private Pool and Pond Views, 5 Miles to Disney
The Den! Private Pool and Pond Views, 5 Miles to Disney
House
Kissimmee, FL, 34746, United States
0.5k from Montego Bay center

AC, Arcade, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

68 reviews

$224
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 Private Pool in Montego Bay.

Stay Near Montego Bay's Top Attractions

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

Montego Bay Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 3637 verified vacation rentals with a private pool in Montego Bay. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Montego Bay vary depending on the property size, location, and travel season. Rates typically start from around $111 per night, with higher prices for larger homes, prime locations, or peak travel periods.

Yes, properties listed with private pools are intended for the exclusive use of guests staying at that home. You can review listing photos and descriptions to better understand the layout and level of privacy offered.

Yes, some vacation rentals with private pools in Montego Bay also welcome pets. Currently, 18 listings allow pets, although policies may vary. It’s a good idea to review any rules related to pets and outdoor areas before booking.

Private pool properties are often in high demand, especially during holidays and warmer months, so booking 90 to 120 days in advance is recommended. During quieter periods, you may still find availability closer to your travel dates.

Vacation rentals with private pools in Montego Bay often include additional features such as Pool, Private Pool, and Internet. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Montego Bay include safety features such as pool fences, covers, or screened enclosures. It’s recommended to check the property details to confirm whether a specific rental meets your safety preferences.