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

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8346 Best 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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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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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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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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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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Cozy 4BR Family Home Near Disney at Montego Bay
Cozy 4BR Family Home Near Disney at Montego Bay
House
Kissimmee, FL, 34746, United States
0.2k from Montego Bay center

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

4 Bedrooms8 Guests
New to Booking
$224
Average price / night
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Spacious 4BR/3BA Home Near Disney
Spacious 4BR/3BA Home Near Disney
House
Kissimmee, FL, 34746, United States
0.2k from Montego Bay center

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

4 Bedrooms12 Guests
New to Booking
$228
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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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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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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Montego Bay 4BR Villa near Disney
Montego Bay 4BR Villa near Disney
Villa
Kissimmee, FL, 34746, United States
0.2k from Montego Bay center

AC, Balcony, Dryer, Free Parking, Kitchen, Living Area, Microwave, No Smoking, TV

5 Bedrooms8 Guests
New to Booking
$195
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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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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Guest Suite w/ Private Pool Near Disney - Kissimmee
Guest Suite w/ Private Pool Near Disney - Kissimmee
Apartment
Kissimmee, FL, 34746, United States
0.3k from Montego Bay center

AC, Fitness Equipment, No Smoking

1 Bedroom2 Guests
New to Booking
$192
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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Lake View 3BR Villa w/ Private Pool – 15 Min to Disney
Lake View 3BR Villa w/ Private Pool – 15 Min to Disney
House
Kissimmee, FL, 34746, United States
0.3k from Montego Bay center

AC, Heater, No Smoking

3 Bedrooms8 Guests
New to Booking
$214
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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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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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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Brittany - Perfect 3 BR Pool Home
Brittany - Perfect 3 BR Pool Home
House
Kissimmee, FL, 34746, United States
0.4k from Montego Bay center

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

3 Bedrooms6 Guests
8.0

Good

1 reviews

$491
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 in Montego Bay.

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Montego Bay Vacation Rentals on the Map

Frequently Asked Questions

You can explore 8346 verified vacation rentals in Montego Bay. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Montego Bay vary depending on the season, property size, and location. Rates typically start from around $89 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Montego Bay include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Montego Bay welcome pets. Currently, 24 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Montego Bay often include amenities such as Fireplace/Heating, Pool, and Internet. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.