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

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  2. Vacation Rentals with Private Pool
  3.  USA

  4.  Maryland

  5.  Ocean City
  6.  Montego Bay

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

Waves 102
Waves 102
Apartment
Ocean City, MD, USA
0.8k from Montego Bay center

Apartments, Accommodations, Pools, Lodgings, Places to stay, Accessible hotels

3 Bedrooms10 Guests
New to Booking
$486
Average price / night
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Beautiful Bay Views *  2 Kayaks To Explore The Bay * Private Dock For Boat!* NEW MASTER BATH in 2022
Beautiful Bay Views * 2 Kayaks To Explore The Bay * Private Dock For Boat!* NEW MASTER BATH in 2022
House
Ocean City, MD, 21842, United States
0.5k from Montego Bay center

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

3 Bedrooms8 Guests
10.0

Exceptional

70 reviews

$619
Average price / night
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Waves
Waves
Apartment
Montego Bay, Ocean City, Maryland, USA
0.8k from Montego Bay center

Apartments, Cheap, Accommodations, Pools, Lodgings, Places to stay, Self-catering, Accessible hotels

5 Bedrooms17 Guests
8.6

Fabulous

5 reviews

$419
Average price / night
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 Ocean View Top Floor, Pool Elevator, steps to the beach Full kitchen, sleeps 4.
Ocean View Top Floor, Pool Elevator, steps to the beach Full kitchen, sleeps 4.
Condo
Ocean City, MD, 21842, United States
0.7k from Montego Bay center

AC, Balcony, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

1 Bedroom4 Guests
10.0

Exceptional

40 reviews

$197
Average price / night
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The Waves Condo Unit 106
The Waves Condo Unit 106
Apartment
Ocean City, USA
0.8k from Montego Bay center

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

3 Bedrooms9 Guests
5.7

Review score

3 reviews

$89
Average price / night
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Ocean calling & country concert availability!
Ocean calling & country concert availability!
Condo
Ocean City, MD, 21842, United States
0.8k from Montego Bay center

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

1 Bedroom6 Guests
9.0

Fabulous

35 reviews

$204
Average price / night
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Waves 307
Waves 307
Apartment
Montego Bay, Ocean City, Maryland, USA
0.8k from Montego Bay center

Apartments, Accommodations, Pools, Lodgings, Places to stay, Accessible hotels

2 Bedrooms6 Guests
6.3

Good

8 reviews

$207
Average price / night
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Ocean City Escape, Waterfront,  Pool,  Dock, Beach, Walk to Restaurants
Ocean City Escape, Waterfront, Pool, Dock, Beach, Walk to Restaurants
House
Ocean City, MD, 21842, United States
0.9k from Montego Bay center

AC, Crib, Dryer, Free Parking, Heater, Hot Tub, Internet, Laundry, No Smoking

3 Bedrooms10 Guests
9.0

Fabulous

2 reviews

$392
Average price / night
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Waves #104
Waves #104
Apartment
Ocean City, MD, USA
0.8k from Montego Bay center

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

2 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$274
Average price / night
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Oceanfront, huge balcony,  New Remodel in North Ocean City
Oceanfront, huge balcony, New Remodel in North Ocean City
Condo
Ocean City, MD, 21842, United States
0.9k from Montego Bay center

AC, Balcony, Dryer, Elevator, Free Parking, Heater, Internet, Kitchen, Laundry

1 Bedroom3 Guests
10.0

Exceptional

139 reviews

$317
Average price / night
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Just Imagine! Newly Renovated Ocean View 1BR-1 Ba Condo
Just Imagine! Newly Renovated Ocean View 1BR-1 Ba Condo
Apartment
Ocean City, MD, USA
1.0k from Montego Bay center

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

1 Bedroom5 Guests
New to Booking
$415
Average price / night
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Ocean Front, North Ocean City, Maryland
Ocean Front, North Ocean City, Maryland
Condo
Ocean City, MD, 21842, United States
0.9k from Montego Bay center

AC, Arcade, Balcony, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Internet

2 Bedrooms6 Guests
10.0

Exceptional

46 reviews

$487
Average price / night
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Holiday Inn Express & Suites - Ocean City by IHG
Holiday Inn Express & Suites - Ocean City by IHG
Resort
Ocean City, MD, USA
1.0k from Montego Bay center

Cheap, Accommodations, Pools, Resorts, Parking, Holiday inn , 3-star, Lodgings, Places to stay

122 Bedrooms56 Guests
8.6

Fabulous

597 reviews

$238
Average price / night
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Hidden Harbour 2BR/2BA – Bayside Condo w/ Pool, Steps to Sand & Northside Park!
Hidden Harbour 2BR/2BA – Bayside Condo w/ Pool, Steps to Sand & Northside Park!
Condo
Ocean City, MD, 21842, United States
0.9k from Montego Bay center

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

2 Bedrooms6 Guests
10.0

Exceptional

14 reviews

$230
Average price / night
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Marylander Condominiums, 90 steps from the beach
Marylander Condominiums, 90 steps from the beach
Apartment
Ocean City, MD, USA
1.0k from Montego Bay center

Apartments, Accommodations, Pools, Parking, Serviced apartments, Lodgings, Vacation rentals, Beach, Places to stay

14 Bedrooms6 Guests
8.6

Fabulous

154 reviews

$340
Average price / night
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Stunning Ocean Front Renovated 2BR, 1 Bonus Rm , 2BA , Pool/Pickleball-North OCM
Stunning Ocean Front Renovated 2BR, 1 Bonus Rm , 2BA , Pool/Pickleball-North OCM
Condo
Ocean City, MD, 21842, United States
0.9k from Montego Bay center

AC, Balcony, Dryer, Elevator, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
9.8

Exceptional

25 reviews

$452
Average price / night
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Avalon 507 condo
Avalon 507 condo
Apartment
Ocean City, MD, USA
1.1k from Montego Bay center

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

3 Bedrooms10 Guests
New to Booking
$199
Average price / night
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Serene Canal front condo w/Balcony, WiFi, AC & community pool access
Serene Canal front condo w/Balcony, WiFi, AC & community pool access
Condo
Ocean City, MD, 21842, United States
1.1k from Montego Bay center

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

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$329
Average price / night
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Avalon 406
Avalon 406
Apartment
Montego Bay, Ocean City, Maryland, USA
1.1k from Montego Bay center

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

3 Bedrooms8 Guests
New to Booking
$224
Average price / night
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Stroll to North Ocean City Beaches, cozy 1-bedroom condo awaits
Stroll to North Ocean City Beaches, cozy 1-bedroom condo awaits
Condo
Ocean City, MD, 21842, United States
1.1k from Montego Bay center

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

2 Bedrooms4 Guests
9.8

Exceptional

132 reviews

$218
Average price / night
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Outrigger 210
Outrigger 210
Apartment
Ocean City, MD, USA
1.2k from Montego Bay center

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

1 Bedroom4 Guests
New to Booking
$302
Average price / night
Check Availability
140th St Beach Condo w/2 Pools & Free Wifi...1.5 blocks from the Sand/Surf
140th St Beach Condo w/2 Pools & Free Wifi...1.5 blocks from the Sand/Surf
Condo
Ocean City, MD, 21842, United States
1.1k from Montego Bay center

AC, Balcony, Dryer, Elevator, Free Parking, Heater, Internet, Kitchen, Laundry

1 Bedroom4 Guests
10.0

Exceptional

79 reviews

$241
Average price / night
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Sunsets, Peace & Quiet, Next to Northside Park, Over 60 5 Star Reviews!
Sunsets, Peace & Quiet, Next to Northside Park, Over 60 5 Star Reviews!
Condo
Ocean City, MD, 21842, United States
1.1k from Montego Bay center

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

2 Bedrooms4 Guests
10.0

Exceptional

60 reviews

$262
Average price / night
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Moos Casa Sea Casa, beach side, private balcony, outdoor pool
Moos Casa Sea Casa, beach side, private balcony, outdoor pool
Condo
Ocean City, MD, 21842, United States
1.1k from Montego Bay center

AC, Balcony, Dryer, Elevator, Free Parking, Heater, Internet, Kitchen, Laundry

1 Bedroom6 Guests
9.6

Exceptional

37 reviews

$244
Average price / night
Check Availability
Great for Families-Spacious 3 Bedroom Condo with pool in North Ocean City, Md.
Great for Families-Spacious 3 Bedroom Condo with pool in North Ocean City, Md.
Condo
Ocean City, MD, 21842, United States
1.2k from Montego Bay center

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

3 Bedrooms7 Guests
9.8

Exceptional

28 reviews

$198
Average price / night
Check Availability
Royal Hawaiian 401 - 2 bedroom ocean side with indoor and outdoor pool
Royal Hawaiian 401 - 2 bedroom ocean side with indoor and outdoor pool
Condo
Ocean City, MD, 21842, United States
1.3k from Montego Bay center

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

2 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$320
Average price / night
Check Availability
BEAUTIFUL & CLEAN! Waterfront condo with epic sunsets and a POOL!
BEAUTIFUL & CLEAN! Waterfront condo with epic sunsets and a POOL!
Condo
Ocean City, MD, 21842, United States
1.3k from Montego Bay center

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

2 Bedrooms8 Guests
9.8

Exceptional

131 reviews

$230
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 Private 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 Private Pool on the Map

Frequently Asked Questions

You can explore 624 verified vacation rentals with a private pool in Montego Bay. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Montego Bay vary depending on the property size, location, and travel season. Rates typically start from around $89 per night, with higher prices for larger homes, prime locations, or peak travel periods.

Yes, properties listed with private pools are intended for the exclusive use of guests staying at that home. You can review listing photos and descriptions to better understand the layout and level of privacy offered.

Yes, some vacation rentals with private pools in Montego Bay also welcome pets. Currently, 5 listings allow pets, although policies may vary. It’s a good idea to review any rules related to pets and outdoor areas before booking.

Private pool properties are often in high demand, especially during holidays and warmer months, so booking 90 to 120 days in advance is recommended. During quieter periods, you may still find availability closer to your travel dates.

Vacation rentals with private pools in Montego Bay often include additional features such as Pool, Private Pool, and Fireplace/Heating. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Montego Bay include safety features such as pool fences, covers, or screened enclosures. It’s recommended to check the property details to confirm whether a specific rental meets your safety preferences.