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

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  6.  Hip Strip

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463 Best Vacation Rentals with Pool in Hip Strip (Starting from $85)

Bach Resort Montego Bay
Bach Resort Montego Bay
Apartment
Montego Bay, Jamaica
0.1k from Hip Strip center

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

1 Bedroom2 Guests
5.0

Review score

1 reviews

$100
Average price / night
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Resort Property 3 Minutes From Beach Sleeps up to 3
Resort Property 3 Minutes From Beach Sleeps up to 3
Apartment
Montego Bay, Jamaica
0.1k from Hip Strip center

AC, Balcony, Free Parking, Internet, Kitchen, Outdoor Space, Patio, Pool, TV

1 Bedroom3 Guests
2.0

Review score

1 reviews

$101
Average price / night
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Montego Bay Club-Delux Seaside condo
Montego Bay Club-Delux Seaside condo
Apartment
Montego Bay, Jamaica
0.1k from Hip Strip center

Apartments, Accommodations, Parking, Serviced apartments, Lodgings, Vacation rentals, Beach, Places to stay, Self-catering

1 Bedroom2 Guests
6.8

Good

29 reviews

$110
Average price / night
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Priceless Views – Oceanfront 1-Bedroom Condo Across from Doctor’s Cave Beach
Priceless Views – Oceanfront 1-Bedroom Condo Across from Doctor’s Cave Beach
Condo
Montego Bay, Jamaica
0.2k from Hip Strip center

AC, Crib, Free Parking, Internet, Kitchen, Microwave, No Smoking, Pool, Toys

1 Bedroom4 Guests
New to Booking
$193
Average price / night
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Ocean View Suite
Ocean View Suite
Apartment
Hip Strip, Montego Bay, Saint James, Jamaica
0.1k from Hip Strip center

Pool, Parking, Breakfast, Internet

1 Bedroom3 Guests
New to Booking
$109
Average price / night
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JetsettersEscape307 @ The Montego Bay Club<br>11 Queens Drive, Montego UKG.huu
JetsettersEscape307 @ The Montego Bay Club<br>11 Queens Drive, Montego UKG.huu
Condo
Montego Bay, Jamaica
0.2k from Hip Strip center

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

1 Bedroom4 Guests
9.2

Superb

41 reviews

$115
Average price / night
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Sunny Tides at Montego Bay Club Resort
Sunny Tides at Montego Bay Club Resort
Apartment
Montego Bay, Jamaica
0.2k from Hip Strip center

Apartments, Accommodations, Pools, Parking, Serviced apartments, Lodgings, Places to stay

3 Bedrooms4 Guests
3.0

Review score

3 reviews

$144
Average price / night
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Deja Resort All Inclusive
Deja Resort All Inclusive
Resort
92 Gloucester Avenue, Montego Bay, Jamaica
0.2k from Hip Strip center

AC, Babysitting, Bar, Breakfast Included, Business Services, Extra Bed, Fitness Equipment, Free Parking, Frontdesk 24 Hour

8.0

Good

1671 reviews

$232
Average price / night
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Montego Bay Club Apartments
Montego Bay Club Apartments
Apartment
Montego Bay, Jamaica
0.2k from Hip Strip center

Apartments, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay, Self-catering, Beach rentals

15 Bedrooms15 Guests
7.4

Good

283 reviews

$142
Average price / night
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Beach View Vacation Condo Best Location
Beach View Vacation Condo Best Location
Apartment
Montego Bay, Jamaica
0.2k from Hip Strip center

AC, Balcony, Elevator, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

New to Booking
$170
Average price / night
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Irresistible View-Mobay Club 1408
Irresistible View-Mobay Club 1408
Apartment
Montego Bay, Jamaica
0.2k from Hip Strip center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay, Self-catering

1 Bedroom2 Guests
9.0

Fabulous

79 reviews

$99
Average price / night
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Ocean View Central Location Modern Studio
Ocean View Central Location Modern Studio
Apartment
Montego Bay, Jamaica
0.2k from Hip Strip center

AC, Balcony, Breakfast Included, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

10.0

Exceptional

1 reviews

$170
Average price / night
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Welcome to stunning Ocean Views at Studio 503
Welcome to stunning Ocean Views at Studio 503
Apartment
Hip Strip, Montego Bay, Saint James, Jamaica
0.2k from Hip Strip center

Apartments, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Beach, Places to stay, Self-catering

1 Bedroom2 Guests
6.9

Good

30 reviews

$105
Average price / night
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Modern Sea View Renovated Studio Hip Strip
Modern Sea View Renovated Studio Hip Strip
Apartment
Montego Bay, Jamaica
0.2k from Hip Strip center

AC, Balcony, Breakfast Included, Elevator, Free Parking, Internet, Kitchen, Laundry, Microwave

9.6

Exceptional

4 reviews

$252
Average price / night
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lsstonethrow Apts
lsstonethrow Apts
House
Montego Bay, Jamaica
0.3k from Hip Strip center

B&bs, Cheap, Accommodations, Parking, Guest houses, Homestays, Lodgings, Places to stay

1 Bedroom3 Guests
10.0

Exceptional

1 reviews

$150
Average price / night
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Vacation Modern Garden Lush Studio
Vacation Modern Garden Lush Studio
Apartment
Montego Bay, Jamaica
0.2k from Hip Strip center

AC, Balcony, Elevator, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

New to Booking
$159
Average price / night
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Falcon Oceanview 2br Condo-Airport Transportation Available-24-7Security
Falcon Oceanview 2br Condo-Airport Transportation Available-24-7Security
Apartment
Montego Bay, Jamaica
0.4k from Hip Strip center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Places to stay, Family, Self-catering

2 Bedrooms4 Guests
9.3

Superb

20 reviews

$275
Average price / night
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2 Bedroom 2 Bathroom Modern Ocean View Hip Strip Apartment with Wi-Fi
2 Bedroom 2 Bathroom Modern Ocean View Hip Strip Apartment with Wi-Fi
Apartment
Montego Bay, Jamaica
0.2k from Hip Strip center

AC, Balcony, Breakfast Included, Elevator, Extra Bed, Free Parking, Heater, Internet, Kitchen

2 Bedrooms7 Guests
8.8

Fabulous

3 reviews

$276
Average price / night
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Falcon IslandView - Airport Pickup Available - 24Security
Falcon IslandView - Airport Pickup Available - 24Security
Apartment
Montego Bay, Jamaica
0.4k from Hip Strip center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Places to stay, Family, Self-catering

1 Bedroom2 Guests
9.2

Superb

23 reviews

$190
Average price / night
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Ocean Front Apartment Montego Bay Hip Strip
Ocean Front Apartment Montego Bay Hip Strip
Apartment
Montego Bay, Jamaica
0.2k from Hip Strip center

AC, Balcony, Elevator, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

10.0

Exceptional

3 reviews

$182
Average price / night
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Falcon Sunset 2br- Airport Transport Available -Security-Gated
Falcon Sunset 2br- Airport Transport Available -Security-Gated
Apartment
Jamaica
0.4k from Hip Strip center

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

2 Bedrooms4 Guests
8.5

Very Good

17 reviews

$237
Average price / night
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Ocean View Penthouse on the Hip Strip Montego Bay
Ocean View Penthouse on the Hip Strip Montego Bay
Apartment
Montego Bay, Jamaica
0.2k from Hip Strip center

AC, Balcony, Elevator, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking

1 Bedroom3 Guests
New to Booking
$204
Average price / night
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New Ocean View Modern Studio Hip Strip
New Ocean View Modern Studio Hip Strip
Apartment
Montego Bay, Jamaica
0.2k from Hip Strip center

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

New to Booking
$240
Average price / night
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4-bedroom Luxury Villa in Montego Bay
4-bedroom Luxury Villa in Montego Bay
Villa
Montego Bay, Jamaica
0.3k from Hip Strip center

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

4 Bedrooms10 Guests
New to Booking
$1397
Average price / night
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1 Min from MBJ Airport; Cozy Studio; AC; Wi-Fi
1 Min from MBJ Airport; Cozy Studio; AC; Wi-Fi
Apartment
Montego Bay, Jamaica
0.3k from Hip Strip center

AC, Balcony, Free Parking, Internet, Kitchen, Laundry, No Smoking, Outdoor Space, Pool

1 Bedroom4 Guests
New to Booking
$120
Average price / night
Check Availability
S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel
S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel
Resort
7 Jimmy Cliff Blvd, Montego Bay, Jamaica
0.3k from Hip Strip center

AC, Bar, Business Services, Elevator, Fitness Equipment, Free Parking, Frontdesk 24 Hour, Housekeeping, Internet

9.4

Superb

2076 reviews

$598
Average price / night
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Awesome beach-front vibe maker Right on Montego Bay's Hip Strip. Yours to enjoy
Awesome beach-front vibe maker Right on Montego Bay's Hip Strip. Yours to enjoy
Condo
Montego Bay, Jamaica
0.3k from Hip Strip center

AC, Arcade, Balcony, Breakfast Available, Elevator, Free Parking, Internet, Kitchen, Microwave

1 Bedroom3 Guests
New to Booking
$85
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 Hip Strip.

Where to stay in Hip Strip? Best neighborhoods & areas

Hip Strip Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 463 verified vacation rentals with a pool in Hip Strip. 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 Hip Strip vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $85 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Hip Strip 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 Hip Strip welcome pets. Currently, 5 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 Hip Strip often include additional outdoor features such as Pool, Internet, and View. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Hip Strip 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.