Vacation rentals with a pool in Montego Bay

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Montego Bay

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Superhost

Condo in Montego Bay

4.85 out of 5 average rating, 308 reviews

Modern apartment with a pool & amazing views!

Modern, 1BR, ground level apartment with all the modern amenities you will need for a perfect stay. Start your day having coffee on the patio gazing at the awe-inspiring coastline and turquoise lagoon. The property is part of a secure, gated development with a private community pool for guests to laze away while perfecting their tan, or hide in the shade sipping on a cold drink. You're close enough to the airport, shopping malls and nightlife - but nestled on the outskirts for quiet relaxation.

Nov 3 – 10

G$17,942 GYD per night

Superhost

Condo in Montego Bay

4.8 out of 5 average rating, 125 reviews

Sabal at One Palmyra your own personal retreat

Located on the Jewel Grande Spa & resort with all amenities on the 3rd floor of the owner building. Options for all-inclusive food and beverage offered by the hotel at check-in. IT IS NOT MANDATORY. All inclusive is $180 per person per day. Must book for entire stay or only for last day. Infants are free. Children 5-7 $75 per person. Day Pass (11:00am-5:00pm includes (Lunch) and Night pass (6:00pm to 11:00pm) and includes Room Service for $125 per person per day. Ask at time of Check-in.

Jan 11 – 18

G$71,833 GYD per night

Guest favorite

Townhouse in Montego Bay

4.98 out of 5 average rating, 124 reviews

2BR Townhouse with staff, gym, pool & beach access

Escape@20 is a lovely townhome that guarantees a truly relaxing and memorable experience. A friendly housekeeper/cook is included at NO EXTRA COST!! You just need to purchase the groceries. The townhome has an open floor plan with living and dining room opening out to a covered patio and a backyard. Guests can enjoy breathtaking views of the neighboring yacht docking area, swimming pool, gazebo/bbq grill space, gym, playground for kids, 24 hour security and complimentary beach access nearby.

Nov 26 – Dec 3

G$64,384 GYD per night

Guest favorite

Cottage in Montego Bay

4.94 out of 5 average rating, 171 reviews

Glory @ Montego Bay

Welcome to “Glory”. The cottage is situated on the grounds of our home “Victory“. We invite you to experience our concept of “Jamaican Home Living”. Glory overlooks the Sangster International Airport and the Caribbean Sea and is 5 mins from world-famous Doctors Cave Beach. We are also conveniently 5 minutes drive from the airport. We own the SeaGull @ Little Bay Country Club in Negril, and are Airbnb SuperHosts; we know how to take care of our guests. Join us for a special experience.

Sep 27 – Oct 4

G$55,603 GYD per night

Guest favorite

Condo in Montego Bay

4.92 out of 5 average rating, 367 reviews

Jus' Beachy! Luxury Apt in a B/front Gated Cmnty.

This new beach theme apartment is located in 22 Freeport – A gated community in Freeport Montego Bay. 22 Freeport is a beach front complex on a Marina that features 24 hour security, a gym, infinity edge pool and playground; whilst the unit on the ground floor opens onto a cozy back yard space that flows into an open green space. Be sure to check out my other units in this community on my profile if your dates are not available or if you would like to book them all for your large group.

Mar 1 – 8

G$46,774 GYD per night

Superhost

Apartment in Montego Bay

4.82 out of 5 average rating, 129 reviews

2 BD 2 Bth apt(Resort area Close to beach)

This secure private gated gem is located within the most vibrant city on the Island.It is nestled in one of the safest neighborhoods in the country and is just a 15 minute drive from the airport . There are two private pools on property as well as a 5 minute walk to a private beach . Also within walking distance are restaurants, grocery shopping , medical facilities and pretty much anything else you may need throughout your stay. Great for individuals couples or business travelers .

Jul 6 – 13

G$32,361 GYD per night

Superhost

Condo in Montego Bay

4.82 out of 5 average rating, 107 reviews

'Moscow' in MoBay, Artsy Apt in Beach Resort Area

This eclectic, Big City themed apartment will tantalize your senses and take you far away from your comfort zone. Creatively integrating images from cities around the world, prepare to be transported across seas and time zones. This 1 bedroom apartment is called “Moscow” and it is located in 22 Freeport, Montego Bay, on the most sought after upscale Freeport peninsula. This gated complex features beach front views, exercise classes, 24-hour security, infinity pool and playground.

Nov 9 – 16

G$30,741 GYD per night

Guest favorite

Villa in Montego Bay

4.95 out of 5 average rating, 188 reviews

Villa Maria Montego Bay, Beach front with Pool

Villa Maria: A True Jamaican Experience (one of few Beach front villas in Mobay Fully staff Fully A/C Chef service available Up to 2 free airport pick-up and drop-off from MBJ. Property : We are located in a seaside fishing village. Even though not needed, we are monitored by security and outside video 24-hour OPTIONAL FEE The following fee is paid in addition to and after the reservation is paid for $180 / per day for pool heater. This is only if you want the pool heated.

Feb 2 – 9

G$170,500 GYD per night

Superhost

Apartment in Montego Bay

4.79 out of 5 average rating, 150 reviews

Seawind On The Bay Freeport Montego Bay

Seawind On The Bay is a safe gated community. The property has a pool and shared bar and grill with a covered community centre. The beach is a short distance away beside Secrets Hotel. A spectacular view of Montego Bay Harbor with cruise ships awaits you. Montego Bay Yacht Club is next door with great food and bar. Also, within walking distance is Secrets Wild Orchid, Breathless, and Sunscape Montego Bay Resorts and Spa. Montego Bay Cruise Ship terminal less than 2 miles away.

Nov 7 – 14

G$22,362 GYD per night

Guest favorite

Villa in Montego Bay

4.93 out of 5 average rating, 148 reviews

VIBES COVE enjoy your stay while getting pampered

FREE Arrival meal , the first day you arrive to vibes cove you’ll receive a complementary arrival meal by our personal chef on the property. Vibes coves villa is super Spacious and private enjoy your vacation by getting pampered. This property comes with a personal chef , Butler, and housekeeper. Enjoy V.I.P services your entire stay. Property staff stays in their helpers quarters ( not apart of the property ) only those listed on the Airbnb is allowed at the property.

Nov 9 – 16

G$136,071 GYD per night

Superhost

Apartment in Montego Bay

4.78 out of 5 average rating, 193 reviews

Seawind on the Bay Studio

A 300 square feet studio in the safest, prestigious residential neighborhood of Montego Bay. Steps away from a few restaurants. About 15 minutes drive from famous Hip Strip. 5 min drive to Fairview Plaza with multiple grocery stores, restaurants, movie theater, 24 hour pharmacy etc. Free parking and swimming pool and 24 hour security. Secrets spa is 5 minutes walk from us. The nearest beach is 5 minutes walk (formerly Hard Rock Café beach). That beach has entrance fee.

Dec 16 – 23

G$23,955 GYD per night

Guest favorite

Apartment in Montego Freeport

4.94 out of 5 average rating, 105 reviews

SERENITY ON THE BAY

Serenity On The Bay is located on the exclusive Freeport Peninsula, nestled between The Secrets and Sunscape Resorts. This is a safe community. The Montego Bay Yacht Club offers fine dining and an excellent bar, property borders the club. Along the Peninsula, there is a jogging trail, for your early morning or sunset run. At Serenity On The Bay one can take opportunity to visit the attractions/adventures as well as relaxation at every turn.

Mar 18 – 25

G$23,818 GYD per night