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

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  2. Vacation Rentals with Pool
  3.  USA

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3105 Best Vacation Rentals with Pool 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
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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-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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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 - 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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North Ocean City - Montego Bay 3BR Home/ Beach, Pool, Pickleball and Mini Golf
North Ocean City - Montego Bay 3BR Home/ Beach, Pool, Pickleball and Mini Golf
House
Ocean City, MD, 21842, United States
0.5k from Montego Bay center

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

3 Bedrooms10 Guests
10.0

Exceptional

4 reviews

$268
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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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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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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On The Water * Private Dock * Sunset Porch Views
On The Water * Private Dock * Sunset Porch Views
House
Ocean City, MD, 21842, United States
0.5k from Montego Bay center

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

3 Bedrooms6 Guests
9.8

Exceptional

46 reviews

$515
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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Nautical Lane 146 in popular Montego Bay
Nautical Lane 146 in popular Montego Bay
House
Ocean City, MD, 21842, United States
0.5k from Montego Bay center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

4 Bedrooms10 Guests
9.6

Exceptional

11 reviews

$451
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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Lovely Beach House w/ Outdoor Shower - Walk to Beach - Pools, Mini Golf & Tennis
Lovely Beach House w/ Outdoor Shower - Walk to Beach - Pools, Mini Golf & Tennis
House
Ocean City, MD, 21842, United States
0.6k from Montego Bay center

AC, Dryer, Free Parking, Heater, Internet, Laundry, Living Area, No Smoking, Pool

3 Bedrooms12 Guests
New to Booking
$449
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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Luxe Family Home, Sleeps 10, Community Pool
Luxe Family Home, Sleeps 10, Community Pool
House
Ocean City, MD, 21842, United States
0.6k from Montego Bay center

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

3 Bedrooms10 Guests
10.0

Exceptional

18 reviews

$645
Average price / night
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Endless Summer
Endless Summer
House
Montego Bay, Ocean City, Maryland, USA
0.4k from Montego Bay center

Wellness Facilities, Restaurant, View, Spa, Laundry, Child Friendly, Balcony/Terrace

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$400
Average price / night
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Breathtaking Ocean view, few steps to the beach!!!!!
Breathtaking Ocean view, few steps to the beach!!!!!
Condo
Ocean City, MD, 21842, United States
0.7k from Montego Bay center

AC, Balcony, Dryer, Elevator, Extra Bed, Free Parking, Heater, Hot Tub, Internet

1 Bedroom2 Guests
10.0

Exceptional

3 reviews

$330
Average price / night
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Sandyhill Sun
Sandyhill Sun
House
Ocean City, MD, USA
0.4k from Montego Bay center

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

3 Bedrooms6 Guests
6.0

Review score

2 reviews

$247
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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Montego Bay - Ocean 13336
Montego Bay - Ocean 13336
House
Ocean City, MD, USA
0.6k from Montego Bay center

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

4 Bedrooms10 Guests
8.5

Very Good

2 reviews

$743
Average price / night
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Ocean View North OC Oasis - Braemar Towers
Ocean View North OC Oasis - Braemar Towers
Condo
Ocean City, MD, 21842, United States
0.8k from Montego Bay center

AC, Arcade, Balcony, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

2 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$386
Average price / night
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Northside Condo with park view
Northside Condo with park view
Condo
Ocean City, MD, 21842, United States
0.8k from Montego Bay center

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

1 Bedroom7 Guests
10.0

Exceptional

8 reviews

$230
Average price / night
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Beautiful newly renovated ocean block 1 bed 1 bath condo, Wi-Fi and Smart tv's.
Beautiful newly renovated ocean block 1 bed 1 bath condo, Wi-Fi and Smart tv's.
Condo
Ocean City, MD, 21842, United States
0.8k from Montego Bay center

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

1 Bedroom6 Guests
10.0

Exceptional

11 reviews

$165
Average price / night
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Includes Xplorie Activities and Linens. The Waves - Upgraded 2BR oceanblock condo w/covered pool.
Includes Xplorie Activities and Linens. The Waves - Upgraded 2BR oceanblock condo w/covered pool.
Condo
Ocean City, MD, 21842, United States
0.8k from Montego Bay center

AC, Elevator, Microwave, No Smoking, Pool, TV

2 Bedrooms7 Guests
10.0

Exceptional

1 reviews

$330
Average price / night
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Spacious 2 bedroom and 2-bathroom condo located on the ocean block in North Ocean City
Spacious 2 bedroom and 2-bathroom condo located on the ocean block in North Ocean City
Condo
Ocean City, MD, 21842, United States
0.8k from Montego Bay center

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

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$246
Average price / night
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Spacious Oceanside Condo with Pool
Spacious Oceanside Condo with Pool
Condo
Ocean City, MD, 21842, United States
0.8k from Montego Bay center

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

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$472
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 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 Pool on the Map

Frequently Asked Questions

You can explore 3105 verified vacation rentals with a pool in Montego Bay. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Montego Bay vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $112 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Montego Bay offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Montego Bay welcome pets. Currently, 13 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Montego Bay often include additional outdoor features such as Pool, Fireplace/Heating, and Laundry. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Montego Bay offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.