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

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1247 Best Villa Rentals in Montego Bay (Starting from $115)

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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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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Elegant Villa Pool Fun Game Room Near Disney
Elegant Villa Pool Fun Game Room Near Disney
Villa
Kissimmee, FL, USA
0.7k from Montego Bay center

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

4 Bedrooms8 Guests
6.4

Good

17 reviews

$366
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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Deluxe 4 bedrooms Villa at Seven Dwrafs Resort - Close to Disney
Deluxe 4 bedrooms Villa at Seven Dwrafs Resort - Close to Disney
Villa
Kissimmee, FL, USA
1.0k from Montego Bay center

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

4 Bedrooms8 Guests
New to Booking
$218
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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Villas Standard Seven Dwrafs Resort - Close to Disney
Villas Standard Seven Dwrafs Resort - Close to Disney
Villa
Kissimmee, FL, USA
1.0k from Montego Bay center

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

6 Bedrooms6 Guests
8.8

Fabulous

5 reviews

$197
Average price / night
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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
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Kissimmee 3bed Villa Near Disney
Kissimmee 3bed Villa Near Disney
Villa
Kissimmee, FL, USA
1.1k from Montego Bay center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, 4-star, Lodgings

3 Bedrooms10 Guests
8.9

Fabulous

52 reviews

$131
Average price / night
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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
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Villas at Seven Dwarfs - Close to Disney
Villas at Seven Dwarfs - Close to Disney
Villa
Montego Bay, Kissimmee, Florida, USA
1.1k from Montego Bay center

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

21 Bedrooms28 Guests
7.8

Good

518 reviews

$140
Average price / night
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4413 Luxury 12 B.R 11.5BA 19 B.D in upscale community Pool/Game Close to Disney
4413 Luxury 12 B.R 11.5BA 19 B.D in upscale community Pool/Game Close to Disney
Villa
Kissimmee, FL, 34746, United States
0.6k from Montego Bay center

AC, Arcade, Balcony, Crib, Dryer, Fitness Equipment, Heater, Internet, Kitchen

12 Bedrooms32 Guests
New to Booking
$906
Average price / night
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Villas at Seven Dwarfs Resort - Near to Disney
Villas at Seven Dwarfs Resort - Near to Disney
Villa
Kissimmee, FL, USA
1.2k from Montego Bay center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Spa, Cottages, Onsen

3 Bedrooms7 Guests
8.7

Fabulous

38 reviews

$221
Average price / night
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223 Luxury 12 B.R 11.5BA 15 B.D in upscale community Pool/Game Close to Disney
223 Luxury 12 B.R 11.5BA 15 B.D in upscale community Pool/Game Close to Disney
Villa
Kissimmee, FL, 34746, United States
0.6k from Montego Bay center

AC, Dryer, Fitness Equipment, Heater, Internet, Laundry, No Smoking, Washer

12 Bedrooms30 Guests
New to Booking
$1149
Average price / night
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Stylish Resort Villa w Pool Near Disney Gated 5BR
Stylish Resort Villa w Pool Near Disney Gated 5BR
Villa
Kissimmee, FL, USA
1.2k from Montego Bay center

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

5 Bedrooms12 Guests
7.9

Good

14 reviews

$388
Average price / night
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219 Luxury 12 B.R 11.5BA 15 B.D in upscale community Pool/Game Close to Disney\n
219 Luxury 12 B.R 11.5BA 15 B.D in upscale community Pool/Game Close to Disney\n
Villa
Kissimmee, FL, 34746, United States
0.6k from Montego Bay center

AC, Arcade, Balcony, Crib, Dryer, Fitness Equipment, Heater, Internet, Kitchen

12 Bedrooms30 Guests
7.6

Good

4 reviews

$1149
Average price / night
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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
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Disney Pool Retreat | Modern Home • Sleeps 8
Disney Pool Retreat | Modern Home • Sleeps 8
Villa
Kissimmee, FL, 34746, United States
0.7k from Montego Bay center

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

4 Bedrooms8 Guests
New to Booking
$250
Average price / night
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Waterfront 8Br5Ba Game Room/Pool/Spa/Office Space
Waterfront 8Br5Ba Game Room/Pool/Spa/Office Space
Villa
Kissimmee, FL, USA
1.4k from Montego Bay center

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

8 Bedrooms16 Guests
9.0

Fabulous

1 reviews

$512
Average price / night
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Beautiful 4 Bed Vacation Pool Home Near Disney/Universal
Beautiful 4 Bed Vacation Pool Home Near Disney/Universal
Villa
Kissimmee, FL, 34746, United States
0.8k from Montego Bay center

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

4 Bedrooms8 Guests
New to Booking
$215
Average price / night
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4716 Windwood Magic Villa & pool
4716 Windwood Magic Villa & pool
Villa
Kissimmee, FL, USA
1.4k from Montego Bay center

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

4 Bedrooms9 Guests
6.8

Good

9 reviews

$177
Average price / night
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Family Friendly Resort Near Disney with many amenities to enjoy onsite
Family Friendly Resort Near Disney with many amenities to enjoy onsite
Villa
Kissimmee, FL, 34746, United States
0.8k from Montego Bay center

AC, Arcade, Dryer, Extra Bed, Fitness Equipment, Free Parking, Internet, Laundry, No Smoking

2 Bedrooms4 Guests
New to Booking
$141
Average price / night
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🌟 Brand New Luxury 12 BR 11.5 BA Pool Villa / Near Disney / Sleep 30
🌟 Brand New Luxury 12 BR 11.5 BA Pool Villa / Near Disney / Sleep 30
Villa
Kissimmee, FL, 34746, United States
0.8k from Montego Bay center

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

12 Bedrooms26 Guests
9.2

Superb

5 reviews

$887
Average price / night
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2500 Luxury 12 B.R 11.5BA 19 B.D in upscale community Pool/Game Close to Disney
2500 Luxury 12 B.R 11.5BA 19 B.D in upscale community Pool/Game Close to Disney
Villa
Kissimmee, FL, 34746, United States
0.9k from Montego Bay center

AC, Arcade, Balcony, Dryer, Fitness Equipment, Heater, Internet, Laundry, No Smoking

12 Bedrooms30 Guests
New to Booking
$1076
Average price / night
Check Availability
3BR Home at Seven Dwarfs Resort w/ Pool
3BR Home at Seven Dwarfs Resort w/ Pool
Villa
Kissimmee, FL, 34746, United States
0.9k from Montego Bay center

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

4 Bedrooms8 Guests
New to Booking
$208
Average price / night
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🌟Themed 12BR 11.5BA Pool Villa / Spa / Close Disney/ 26 PPl
🌟Themed 12BR 11.5BA Pool Villa / Spa / Close Disney/ 26 PPl
Villa
Kissimmee, FL, 34746, United States
0.9k from Montego Bay center

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

12 Bedrooms26 Guests
8.8

Fabulous

3 reviews

$831
Average price / night
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🌟 Luxury 12 BR/11.5 BA Villa / Sleep 26
🌟 Luxury 12 BR/11.5 BA Villa / Sleep 26
Villa
Kissimmee, FL, 34746, United States
0.9k from Montego Bay center

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

12 Bedrooms26 Guests
New to Booking
$821
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 Villa 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 Villa Rentals on the Map

Frequently Asked Questions

You can currently explore 1247 verified villa rentals in Montego Bay. Our listings are sourced from multiple leading booking platforms, giving you a broad and up-to-date selection of luxury and private villas in one place.

Villa prices in Montego Bay vary depending on the season, location, and amenities. Rates typically start from around $115 per night, with premium properties costing more during peak travel periods. Comparing options across different platforms can help you find the best value for your dates.

Many villas in Montego Bay are designed for privacy and comfort, and a large number of them feature private pools. You can easily filter your search to find villas with pools, helping you choose the perfect stay for relaxation or group travel in Montego Bay.

Yes, Montego Bay offers a wide range of villas ideal for group stays. Many properties include 5 or more bedrooms, making them well-suited for family gatherings, events, or trips with friends. You can filter by bedroom count to quickly find options that match your group size.

For popular travel periods, it’s generally recommended to book your Montego Bay villa around 60 to 90 days in advance to secure the best selection. However, since we compare 10+ sites, it’s still possible to find great last-minute options even 2 to 4 weeks before your trip.

Villas in Montego Bay often include highly sought-after amenities such as Wellness Facilities, Pool, and Fireplace/Heating. These features enhance comfort and convenience, making them especially popular among travelers visiting Montego Bay.

To discover top-rated villas in Montego Bay, you can sort listings by guest ratings and reviews. Our platform aggregates feedback from multiple trusted sources, helping you identify highly rated properties based on real guest experiences. Use the "Rating" filter above to start your search.