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

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3409 Best Vacation Rentals in Montego Bay (Starting from $112)

Montego Bay-106 Sea Lane home
Montego Bay-106 Sea Lane home
House
MD, USA
0.1k from Montego Bay center

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

3 Bedrooms7 Guests
New to Booking
$251
Average price / night
Check Availability
Direct Canal Front w/ Boat Tie up in the Highly sought after Montego Bay Community, Pools, Tennis !
Direct Canal Front w/ Boat Tie up in the Highly sought after Montego Bay Community, Pools, Tennis !
House
Ocean City, MD, 21842, United States
0.1k from Montego Bay center

AC, Dryer, Extra Bed, Internet, Kitchen, Laundry, No Smoking, Patio, Washer

3 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$437
Average price / night
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Montego Bay-Bayside Blues on Beachcomber
Montego Bay-Bayside Blues on Beachcomber
House
Ocean City, MD, USA
0.1k from Montego Bay center

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

1 Bedroom8 Guests
6.8

Good

8 reviews

$538
Average price / night
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Montego Bay Community Canal Front  wrap around porch, boat tie up, Pools, Tennis N. Ocean City MD!
Montego Bay Community Canal Front wrap around porch, boat tie up, Pools, Tennis N. Ocean City MD!
House
Ocean City, MD, 21842, United States
0.1k from Montego Bay center

Dryer, No Smoking, TV, Washer, Washer And Dryer

4 Bedrooms10 Guests
7.8

Good

6 reviews

$397
Average price / night
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Holly Point B5
Holly Point B5
House
Ocean City, MD, USA
0.2k from Montego Bay center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay, Accessible hotels

2 Bedrooms6 Guests
New to Booking
$386
Average price / night
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Relax Here in this quiet Beach house!
Relax Here in this quiet Beach house!
House
Ocean City, MD, 21842, United States
0.1k from Montego Bay center

AC, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

2 Bedrooms7 Guests
9.6

Exceptional

19 reviews

$331
Average price / night
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Montego Bay - Sea Lane
Montego Bay - Sea Lane
House
Ocean City, MD, USA
0.2k from Montego Bay center

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

3 Bedrooms6 Guests
New to Booking
$112
Average price / night
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Canal front home with free WiFi, deck, private dock, shared pool & tennis
Canal front home with free WiFi, deck, private dock, shared pool & tennis
House
Ocean City, MD, 21842, United States
0.1k from Montego Bay center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
8.6

Fabulous

15 reviews

$277
Average price / night
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Oyster Lane Hideout
Oyster Lane Hideout
House
Ocean City, MD, USA
0.3k from Montego Bay center

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

2 Bedrooms6 Guests
8.0

Good

2 reviews

$448
Average price / night
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Renovated waterfront home with dock, bay access, & shared pool/tennis
Renovated waterfront home with dock, bay access, & shared pool/tennis
House
Ocean City, MD, 21842, United States
0.1k from Montego Bay center

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

3 Bedrooms6 Guests
9.4

Superb

23 reviews

$371
Average price / night
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Walk to Maryland Beach Canal-Front Escape with Dock
Walk to Maryland Beach Canal-Front Escape with Dock
House
Ocean City, MD, USA
0.3k from Montego Bay center

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

2 Bedrooms5 Guests
7.6

Good

8 reviews

$349
Average price / night
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Updated dog-friendly home with gas grill, 2 pools, 2 tennis courts, fishing pier
Updated dog-friendly home with gas grill, 2 pools, 2 tennis courts, fishing pier
House
Ocean City, MD, 21842, United States
0.1k from Montego Bay center

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

3 Bedrooms8 Guests
7.0

Good

11 reviews

$444
Average price / night
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Montego Bay - Lola B's Bayside Beach Bungalow
Montego Bay - Lola B's Bayside Beach Bungalow
House
Ocean City, MD, USA
0.3k from Montego Bay center

Parking, Pool, Child Friendly, Internet, Balcony/Terrace, Air Conditioner, Pet Friendly

2 Bedrooms6 Guests
New to Booking
$258
Average price / night
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Spacious waterfront home, Walk to beach, restaurants and more.
Spacious waterfront home, Walk to beach, restaurants and more.
House
Ocean City, MD, 21842, United States
0.2k from Montego Bay center

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

3 Bedrooms13 Guests
10.0

Exceptional

59 reviews

$462
Average price / night
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Twin Tree Road 511 home
Twin Tree Road 511 home
House
Ocean City, MD, USA
0.4k from Montego Bay center

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

3 Bedrooms8 Guests
New to Booking
$439
Average price / night
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Stunning New  3 Bedroom 3800 Sqft Bayside Steps from Beach!
Stunning New 3 Bedroom 3800 Sqft Bayside Steps from Beach!
House
Ocean City, MD, 21842, United States
0.2k from Montego Bay center

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

2 Bedrooms10 Guests
10.0

Exceptional

2 reviews

$640
Average price / night
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Montego Bay - South Ocean Drive 203
Montego Bay - South Ocean Drive 203
House
Ocean City, MD, USA
0.4k from Montego Bay center

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

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$136
Average price / night
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Highly sought after Montego Bay Community, 2 Large Outdoor Community Pools, Tennis, off 130th St.!
Highly sought after Montego Bay Community, 2 Large Outdoor Community Pools, Tennis, off 130th St.!
House
Ocean City, MD, 21842, United States
0.2k from Montego Bay center

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

3 Bedrooms8 Guests
10.0

Exceptional

6 reviews

$224
Average price / night
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Montego Bay
Montego Bay
House
Montego Bay, Ocean City, Maryland, USA
0.4k from Montego Bay center

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

3 Bedrooms5 Guests
9.4

Superb

7 reviews

$453
Average price / night
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Newly renovated home in much sought after  Montego Bay Community. 2 Pools and tennis
Newly renovated home in much sought after Montego Bay Community. 2 Pools and tennis
House
Ocean City, MD, 21842, United States
0.2k from Montego Bay center

AC, Dryer, Extra Bed, Heater, Kitchen, Laundry, Living Area, Microwave, No Smoking

3 Bedrooms8 Guests
9.2

Superb

10 reviews

$317
Average price / night
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Holly Point B5 | Condo in Ocean City
Holly Point B5 | Condo in Ocean City
House
Ocean City, MD, 21842, United States
0.2k from Montego Bay center

AC, Balcony, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
9.4

Superb

3 reviews

$402
Average price / night
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Spacious and beautifully updated 3BR 2Bath Home with community pools and tennis pickelball
Spacious and beautifully updated 3BR 2Bath Home with community pools and tennis pickelball
House
Ocean City, MD, 21842, United States
0.3k from Montego Bay center

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

3 Bedrooms10 Guests
New to Booking
$279
Average price / night
Check Availability
Bayfront mobile home with private dock, shared pools, & tennis court
Bayfront mobile home with private dock, shared pools, & tennis court
House
Ocean City, MD, 21811, United States
0.3k from Montego Bay center

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

2 Bedrooms6 Guests
8.2

Very Good

15 reviews

$253
Average price / night
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Beautiful 3 BR 2 BA Home in Montego Bay - Community Pool
Beautiful 3 BR 2 BA Home in Montego Bay - Community Pool
House
Ocean City, MD, 21842, United States
0.3k from Montego Bay center

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

3 Bedrooms8 Guests
9.8

Exceptional

47 reviews

$353
Average price / night
Check Availability
3 BR 2 BA Home in Montego Bay - Community Pool
3 BR 2 BA Home in Montego Bay - Community Pool
House
Ocean City, MD, 21842, United States
0.3k from Montego Bay center

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

3 Bedrooms6 Guests
9.8

Exceptional

36 reviews

$394
Average price / night
Check Availability
Walk to Maryland Beach: Canal-Front Escape w/ Dock
Walk to Maryland Beach: Canal-Front Escape w/ Dock
House
Ocean City, MD, 21842-5892, United States
0.3k from Montego Bay center

AC, Arcade, Balcony, Crib, Dryer, Elevator, Free Parking, Heater, Kitchen

2 Bedrooms5 Guests
9.8

Exceptional

7 reviews

$326
Average price / night
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Waterfront Getaway-walk to beach and local favorites!
Waterfront Getaway-walk to beach and local favorites!
House
Ocean City, MD, 21842, United States
0.3k from Montego Bay center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
10.0

Exceptional

39 reviews

$604
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.

Stay Near Montego Bay's Top Attractions

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Montego Bay Vacation Rentals on the Map

Frequently Asked Questions

You can explore 3409 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 $112 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, 27 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, Balcony/Terrace, and Laundry. 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.