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

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  2. Vacation Rentals with Pool
  3.  USA

  4.  Florida
  5.  Orlando
  6.  Montego Bay

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7702 Best Vacation Rentals with Pool in Montego Bay (Starting from $89)

Amazing Blue Private Pool 4BR House Near Disney
Amazing Blue Private Pool 4BR House Near Disney
House
Kissimmee, FL, USA
0.1k from Montego Bay center

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

4 Bedrooms7 Guests
9.8

Exceptional

12 reviews

$267
Average price / night
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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
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6 Mi to Disney World Lake-View Retreat with Pool!
6 Mi to Disney World Lake-View Retreat with Pool!
House
Kissimmee, FL, USA
0.1k from Montego Bay center

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

3 Bedrooms8 Guests
New to Booking
$174
Average price / night
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Look at This, too!  Fun in the Sun for Everyone!
Look at This, too! Fun in the Sun for Everyone!
Condo
Kissimmee, FL, 34746, United States
0.1k from Montego Bay center

AC, Arcade, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
9.2

Superb

52 reviews

$116
Average price / night
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4820 Private Paradise
4820 Private Paradise
House
Kissimmee, FL, USA
0.2k from Montego Bay center

Pool, Air Conditioner, Guest Services, Barbecue/Outdoor Cooking, Oceanfront, Ocean View, Security/Safety

4 Bedrooms7 Guests
New to Booking
$180
Average price / night
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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
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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
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Cozivill
Cozivill
Apartment
Kissimmee, FL, USA
0.3k from Montego Bay center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Places to stay, Family, Self-catering

3 Bedrooms6 Guests
9.1

Superb

22 reviews

$110
Average price / night
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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
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Your home away from Home!
Your home away from Home!
House
Kissimmee, FL, USA
0.3k from Montego Bay center

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

3 Bedrooms8 Guests
New to Booking
$414
Average price / night
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Charming 3-bedroom pool home is just few minutes away from Disney.
Charming 3-bedroom pool home is just few minutes away from Disney.
House
Kissimmee, FL, 34746, United States
0.3k from Montego Bay center

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

3 Bedrooms6 Guests
8.0

Good

1 reviews

$192
Average price / night
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3111-102RD CONDO 2 BEDS/2 BATHS (SANITIZED)
3111-102RD CONDO 2 BEDS/2 BATHS (SANITIZED)
Apartment
Kissimmee, FL, USA
0.3k from Montego Bay center

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

2 Bedrooms6 Guests
New to Booking
$334
Average price / night
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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
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3111-302HM STOREY LAKE, CONDO 2/2 LAKE VIEW
3111-302HM STOREY LAKE, CONDO 2/2 LAKE VIEW
Apartment
Montego Bay, Kissimmee, Florida, USA
0.3k from Montego Bay center

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

2 Bedrooms6 Guests
8.8

Fabulous

4 reviews

$89
Average price / night
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Stylish, first floor 3 bedroom condo minutes to Disney parks, shopping and more
Stylish, first floor 3 bedroom condo minutes to Disney parks, shopping and more
Condo
Kissimmee, FL, 34746, United States
0.3k from Montego Bay center

AC, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms6 Guests
New to Booking
$224
Average price / night
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Sweet
Sweet
Apartment
Kissimmee, FL, USA
0.3k from Montego Bay center

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

3 Bedrooms6 Guests
New to Booking
$192
Average price / night
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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
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Kissimmee Vacation Rental with Pool about 6 Mi to Disney
Kissimmee Vacation Rental with Pool about 6 Mi to Disney
House
Kissimmee, FL, USA
0.4k from Montego Bay center

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

4 Bedrooms10 Guests
New to Booking
$322
Average price / night
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Beautiful Homely Vacation Condominium
Beautiful Homely Vacation Condominium
Condo
Kissimmee, FL, 34746, United States
0.3k from Montego Bay center

AC, Arcade, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub

3 Bedrooms6 Guests
9.8

Exceptional

61 reviews

$119
Average price / night
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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
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Modern and Cozy Condo close to Disney & Universal!!
Modern and Cozy Condo close to Disney & Universal!!
Condo
Kissimmee, FL, 34746, United States
0.3k from Montego Bay center

AC, Balcony, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms6 Guests
New to Booking
$170
Average price / night
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Chatham House
Chatham House
Villa
Kissimmee, FL, USA
0.4k from Montego Bay center

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

4 Bedrooms12 Guests
9.7

Exceptional

19 reviews

$187
Average price / night
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⭐Special ⭐Open Plan Villa Close To ALL Attractions!!!
⭐Special ⭐Open Plan Villa Close To ALL Attractions!!!
Condo
Kissimmee, FL, 34746, United States
0.3k from Montego Bay center

AC, Balcony, Barbecue, Dryer, Extra Bed, Fitness Equipment, Free Parking, Heater, Hot Tub

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$152
Average price / night
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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
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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
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945 Sweet retreat 4 bedrooms with pool and spa
945 Sweet retreat 4 bedrooms with pool and spa
Condo
kissimmee, FL, 34746, United States
0.3k from Montego Bay center

AC, Dryer, Fitness Equipment, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms6 Guests
New to Booking
$165
Average price / night
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“Parkside Paradise 3 BR Condo by Disney, Epcot & Universal”
“Parkside Paradise 3 BR Condo by Disney, Epcot & Universal”
Condo
Kissimmee, FL, 34746, United States
0.4k from Montego Bay center

AC, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$182
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 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 Pool on the Map

Frequently Asked Questions

You can explore 7702 verified vacation rentals with a pool in Montego Bay. 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 Montego Bay vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $89 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Montego Bay 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 Montego Bay welcome pets. Currently, 20 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 Montego Bay often include additional outdoor features such as Pool, Child Friendly, and Fireplace/Heating. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Montego Bay 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.