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

4.84 out of 5 average rating, 332 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.

Guest favorite

Condo in Montego Bay

5 out of 5 average rating, 17 reviews

Coastal Gem: Pool, Waterfront, Gym, Gated, 3rd Flr

Come enjoy coastal living in one of the most sought-after communities in Montego Bay—the affluent resort area of Freeport is situated on a beautiful peninsula. Enjoy the quintessential coastal decor inside, relax on the balcony next to the palms, and lounge by the infinity pool while observing the passing yachts. Along the shore lined with beautiful coconut trees, feel the trade wind caress your body and set your mind at ease. Just a short walk away, enjoy dinner and drinks at the Yacht Club.

Superhost

Condo in Montego Bay

4.75 out of 5 average rating, 40 reviews

Dream fantasy One Bedroom Suite with Pool Access.

Get away to comfort and style and be surrounded by elegance and panoramic views. Come and enjoy our Dream fantasy one bedroom suite at Dream 36, Ironshore, Montego Bay. Our home offers all you need for comfort and more. Accessible to our guests are : *Rooftop pool with amazing view *Rooftop Jaccuzzi *Fitness centre *Jogging trail *Secure parking *24hrs security *WIFI *AC *Hot water *Cable We are 10 mins away from the Sangster's international airport and 5 mins away from the Sandals and Riu.

Guest favorite

Home in Montego Bay

4.98 out of 5 average rating, 130 reviews

Villa Ginger: Food paradise/Beach/Pool/keycode

Private Retreat for close friends and family in the safety of a pristine garden-like gated community. New and dazzlingly beautiful, the oversize sectional will be your favorite place to lounge. Linger on the patio for breakfast, go across the street for snorkeling, tour the nearby beaches and waterfalls, or make your birthday celebration extra special with a spectacular private dinner. Savor the candlelight reflecting from wine glasses as you toast your amazing good luck.

Superhost

Home in Montego Bay

4.84 out of 5 average rating, 187 reviews

Bayview, City and Ocean View with rooftop pool

One of a kind spacious open studio, with patio offering stunning view of Montego Bay City and the fabulous beaches. Features a Queen-Size bed, Sofa sleeper, 42" TV with Netflix and wifi connection. Secured building Centrally located close to all Beaches, Restaurant, Clubs and Shopping. Less than 10 min away from Airport, Margaritaville, and the Island famous Doctor's Cave beach. Gated Community, with a mini-mart store Located in the back parking lot. Privately owned.

Guest favorite

Villa in Montego Bay

4.99 out of 5 average rating, 69 reviews

Luxury Villa - King Bed /Pool/Near Airport & Beach

Everything Irie@ Les Chateaux Villa - located in coveted Iron Shore Community! - Located within 10 minutes of the airport, beaches, and the Hip Strip nightlife - Walking distance of Whitter's Village with a supermarket, shops & restaurants - 3 Full Bedrooms w/ en-suite bathrooms - Sleeps up to 8 (1 King, 2 Queens & Sofa bed) - Gated Community with Security - Nestled directly across from the pool & gym - Has Wi-fi internet & over 900 cable channels

Superhost

Rental unit in Montego Bay

4.87 out of 5 average rating, 224 reviews

OceanView 2bedrooms,rooftop pool,AirCon throughout

PLEASE READ LISTING DESCRIPTION BEFORE BOOKING! Wake up and pull away your curtains to a breathtaking view of the Caribbean Sea whilst you relax and unwind in your spacious and modern home away from home. The apartment is palatial, cool and central to all major locations. The property is 5mins by car from the airport and 20mins walk or 5mins by car to the Hip Strip. Enjoy the roof top pool overlooking the ocean and watch as the planes land at the airport.

Superhost

Rental unit in Montego Bay

5 out of 5 average rating, 3 reviews

Very Beautiful House

The Westport complex provides an unparalleled level of safety, with a robust security system including an array of security cameras, 24/7 manned security posts, perimeter alarm systems, and armed response teams on call. Residents and guests can enjoy a wide range of amenities, including a fully-equipped gym, a unique kid-friendly pool with an overwater gazebo, a barbecue grill overlooking the tranquil marina, and boardwalks for romantic evening strolls.

Superhost

Townhouse in Montego Bay

4.82 out of 5 average rating, 110 reviews

SeeSea Waterfront Villa

SeeSea Waterfront Villa is an unique, recently renovated, beachfront townhouse located in Montego Bay's most prestigious gated community Lagoons. This exquisite villa offers it's own sandy beach overseeing Montego Bay. Spacious patio coupled with tropical garden creates private relaxing atmosphere. Large public swimming pool is right outside of the house. In addition, guests have access to kids playground, 3 more pools, tennis courts, 24 hour security.

Guest favorite

Home in Montego Bay

4.98 out of 5 average rating, 63 reviews

Shimmering Waters Floating Breakfasts "Included"

“SHIMMERING WATERS” BIG VIEWS Chef Option is also available. "PERFECTLY LOCATED"! "PRIVATE HOUSE & PRIVATE POOL" with powerful WIFI 160Mbs, in the exclusive guard-gated waterfront community, "The Lagoons" 10-minute drive to the Montego Bay "Sangster International Airport" (MBJ). The guardhouse secures 24/7. The Master Bedroom Suite has own balcony, a King Bed, walk-in closet, and additional lounging area. Each of the 3 bedrooms has own bathroom!

Guest favorite

Villa in Montego Bay

4.84 out of 5 average rating, 58 reviews

Villa w/heated Jacuzzi, pool, gated community

Spectacular villa in gated community with heated jacuzzi, private pool, deck and outdoor living areas with spectacular views of Montego Bay and Caribbean Sea. The villa comes standard with housekeeping services but can be offered fully staffed with chef for a fee. Only 10 minutes away from the Hip Strip and Doctor's Cave beach with easy access to restaurants and shopping. The villa is a perfect hideaway for a family vacation or couples holiday.

Superhost

Rental unit in Montego Bay

4.81 out of 5 average rating, 139 reviews

Brise De Mer, Montego Bay

A spacious 2 bedroom apartment, located in a gated apartment complex in Freeport, Montego Bay. It is on the second floor with a view of the garden, the two pools on the property and the sea. About 15 minutes from the airport. The Freeport residents private beach is in walking distance and several other beaches, restaurants and supermarkets are nearby.