Family-Friendly Vacation Rentals in Montego Bay, FL: Compare 10+ Sites & Save

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5790 Best Family Vacation Rentals 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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Family-Friendly Home with Lanai about 6 Mi to Disney
Family-Friendly Home with Lanai about 6 Mi to Disney
House
Kissimmee, FL, USA
0.2k from Montego Bay center

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

4 Bedrooms12 Guests
New to Booking
$195
Average price / night
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Private Paradise! Stunning south-facing pool home
Private Paradise! Stunning south-facing pool home
House
Kissimmee, FL, 34746, United States
0.2k from Montego Bay center

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

4 Bedrooms10 Guests
7.8

Good

11 reviews

$252
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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4820 JAMAICA LANE 4BED
4820 JAMAICA LANE 4BED
House
Kissimmee, FL, USA
0.2k from Montego Bay center

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

1 Bedroom8 Guests
New to Booking
$292
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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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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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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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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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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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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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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2492-3-SW-Spacious Condo
2492-3-SW-Spacious Condo
Apartment
Kissimmee, FL, USA
0.3k from Montego Bay center

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

1 Bedroom6 Guests
New to Booking
$1271
Average price / night
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SW40 - 3BR Tropical Oasis Near Disney & Pool
SW40 - 3BR Tropical Oasis Near Disney & Pool
Apartment
Kissimmee, FL, 34746, United States
0.3k from Montego Bay center

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

4 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$172
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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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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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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Florida Escape -Award Winning -Pet Friendly - Pool
Florida Escape -Award Winning -Pet Friendly - Pool
House
Kissimmee, FL, 34746, United States
0.4k from Montego Bay center

AC, Arcade, Balcony, Crib, Dryer, Heater, Internet, Kitchen, Laundry

4 Bedrooms12 Guests
New to Booking
$488
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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“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
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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
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 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

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 Family Vacation Rentals 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 Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 5790 verified family-friendly vacation rentals in Montego Bay. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Montego Bay vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $89 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Montego Bay offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in Montego Bay are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in Montego Bay often include amenities such as Child Friendly, Fireplace/Heating, and Pool. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.