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

A private community pool is surrounded by palm trees, set against a backdrop of a clear blue sky and distant coastline. The pool's calm water reflects the vibrant surroundings, providing a serene space for relaxation and enjoyment.

Condo in Montego Bay

4.82 out of 5 average rating, 381 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.

Top guest favorite

A serene pool area is visible, featuring lounge chairs arranged beside a clear blue pool. Palm trees and lush greenery frame the space, while a covered gazebo is provided in the background, enhancing the outdoor relaxation experience.

Townhouse in Montego Bay

4.98 out of 5 average rating, 177 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.

Guest favorite

A tranquil pool area is surrounded by lush palm trees, offering a serene environment. The clear blue water reflects the sky, while a modern water feature adds an elegant touch. The nearby building is characterized by multiple windows, blending harmoniously with the tropical setting.

Condo in Reading

4.89 out of 5 average rating, 112 reviews

Luxury Garden 2 BDR, 2 BTH Condo w/ pool

Reading’s Rose is a new apartment located in the heart of Montego Bay. It is a 1 min walk from your nearest Restaurant and a 5 min drive from all major grocery stores, pharmacies, restaurants, shopping centres and medical facilities. A small and peaceful community, it is perfect for couples, families, business travelers and friend groups. This gated complex features a pool on the property and jogging trail. The nearest beach is 5 mins away and the famous Doctor’s Cave beach is 13 mins away.

Superhost

A large outdoor pool is surrounded by lush palm trees and tropical plants. Sun loungers are visible along the pool edge, and a beachfront cabana is seen in the background, enhancing the serene oceanfront setting. The clear water reflects the sky, creating a tranquil atmosphere.

Condo in Montego Bay

4.84 out of 5 average rating, 213 reviews

Fabulous 1 Bedroom Condo with Ocean and Pool View.

This privately owned luxury condo is located on the ocean front property of The Jewel Grande Montego Bay Resort Premises,it is right across from the Rose Hall Great House and 15 minutes away from the Sangsters International Airport. Our condo offers luxury finishes and furnishings , high-end appliances, air-conditioning and everything you may need for a perfect home away from home. There is free wifi throughout the property , 24 hrs gated and electronic security as well as free parking.

Top guest favorite

Condo in Montego Bay

4.95 out of 5 average rating, 140 reviews

1br Lux Oceanfront Apt Pool Beach Gym Pickleball

Discover the ultimate tropical retreat at the Soleil Residences, where luxury meets serenity. This elegant oceanfront one-bedroom condominium features a stunning balcony with 180-degree views of the Bay, inviting you to bask in the beauty of Jamaica's coastline. Highlights - Lge Waterfront Pool & Pool Deck * Private Beach Access * Gym * Tennis/Pickleball* Kids Play Area * Gated Community * Fast Fibre WiFi* Chef on request * Spa Services * Concierge Services * Full Time Driver Upon Request

Guest favorite

A scenic outdoor area is visible, featuring a pool with clear water surrounded by stone tiling. Sun loungers with vibrant cushions are placed beside the pool. A dining set is included, with chairs and a table positioned for enjoying views of the Caribbean Sea and landscape beyond.

Cottage in Montego Bay

4.92 out of 5 average rating, 227 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.

Guest favorite

A clear swimming pool is set within a wooden deck area, surrounded by lounge chairs. The pool is bordered by a white fence, while colorful buildings are seen in the background, partially obscured by lush greenery.

Apartment in Montego Bay

4.94 out of 5 average rating, 127 reviews

2BR Getaway w/Pool, Near Beach in Montego Bay

This gorgeous apartment has been furnished to feel like a true getaway. It’s the ideal retreat for an adventurous & up-scale stay, located in a gated community that is close to the absolute heart of Montego Bay. We believe it’s the ultimate location to experience this part of the island. At only 10 minutes walking distance from Doctor's Cave Beach and the main Hip Strip, you will be very close to all the action. Settle in by zoning out with family or friends and enjoy your getaway.

Superhost

An infinity-edge pool is framed by modern lounge chairs and plush seating. Lush greenery and an expansive lawn create a serene environment, while the Caribbean Sea is visible in the distance under a clear blue sky.

Villa in Montego Bay

4.89 out of 5 average rating, 113 reviews

Hospitality Expert EL1: Private Pool, Beach, Chef

Eden Luxe 1 is set on a beautiful hillside offering panoramic views of the sparkling Caribbean Sea. This 2 BR ultra luxurious villa is part of the Nianna Eden Estate, set in the heart of Spring Farm, an upscale Montego Bay community, right above the Half Moon Golf Club. Luxe 1 sleeps up to 6 guests, a private chef is available for hire and we offer pre-stocking services. All our properties come with complimentary access to Tropical Bliss Beach Club. Add-on services offered.

Superhost

A large pool glistens under clear skies, surrounded by tropical palm trees and manicured gardens. A covered community center is positioned adjacent to the pool, featuring a bar and seating area for relaxation.

Apartment in Montego Bay

4.81 out of 5 average rating, 204 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 Resorts and Spa. Montego Bay Cruise Ship terminal less than 2 miles away.

Top guest favorite

An infinity edge swimming pool glistens under a clear blue sky, offering expansive views of the ocean and distant shoreline. Sun loungers are positioned along the poolside, inviting relaxation and enjoyment of the breathtaking scenery.

Home in St. James Parish

4.99 out of 5 average rating, 111 reviews

Luxury Oceanview 4BR Villa w/ Balcony, Pool & BBQ

Welcome to BayWatch Villa – a 4BR luxury retreat in Montego Bay. Marvel at breathtaking views of the harbor and Caribbean Sea both day and night. Share unforgettable moments with family and friends. Enjoy spacious living spaces, a modern kitchen, and laundry convenience on premises. Stay connected with Wi-Fi throughout, even by the pool. With solar backup, you’ll always have power for the essentials. Note: AC is not available on backup power.

Guest favorite

Apartment in Montego Bay

4.79 out of 5 average rating, 256 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).

Guest favorite

A bright and airy studio space features a spacious bed with patterned pillows, complemented by a cozy seating area adorned with decorative cushions. Natural light filters through a large window, showcasing lush greenery outside. A stylish light fixture adds a modern touch to the ambiance.

Apartment in Montego

4.94 out of 5 average rating, 140 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.