Holiday rentals with a pool in Montego Bay

Lush palm trees line the well-maintained grounds, leading towards the beach. A winding pathway is bordered by colorful flowers and manicured shrubs, guiding visitors to sandy shores and ocean views. Lounge chairs are positioned by the shore, creating a serene and inviting atmosphere.

4.82 out of 5 average rating, 159 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.

Two lounge chairs are positioned by a private pool, offering views of the coastline and lagoon. The chairs feature bright, colorful fabrics, inviting relaxation under clear blue skies. Lush greenery and vibrant flowers adorn the surrounding area, enhancing the tranquil setting.

4.82 out of 5 average rating, 387 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.

4.98 out of 5 average rating, 186 reviews

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

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.

4.87 out of 5 average rating, 120 reviews

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

Hospitality Expert EL1: Private Pool, Beach, Chef

This property has electricity, water and internet. 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 HOSPITALITYEXPERT 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. Includes complimentary access to Tropical Bliss Beach Club.

4.8 out of 5 average rating, 110 reviews

A bright living area features modern furnishings in neutral tones, accented by a vibrant yellow sofa. Large windows offer views of the ocean, while indoor plants add a touch of greenery. A sleek television sits on a low console, enhancing the open atmosphere.

Flat in Reading

Sunset Serenity - Stunning Ocean View 2 Bedroom

This exquisite 2-bedroom, 2-bathroom apartment with a pool & 24-hour security is ideally situated in Mo Bay. Providing breath taking ocean views close to the city's shopping and attractions. The fully equipped kitchen boasts all modern appliances. Rooms are luxuriously appointed & at your request the King bed in the 2nd bedroom can be converted into 2 twins. The washroom includes a washing machine and dryer. Stay connected with high-speed Wi-Fi throughout the apartment and smart televisions.

An infinity-edge pool stretches into the serene Marina, surrounded by palm trees and sun loungers. Clear blue skies and fluffy white clouds reflect on the water's surface, creating a peaceful ambiance. The picturesque surroundings enhance the sense of relaxation and tranquility.

4.91 out of 5 average rating, 418 reviews

Jus' Beachy A 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.

A bright bedroom is featured, showcasing a spacious bed adorned with soft pillows. Large windows provide panoramic views of the bay, allowing natural light to illuminate the area. A ceiling fan enhances airflow, while modern furnishings add to the inviting atmosphere.

4.94 out of 5 average rating, 145 reviews

Oceanfront 1BR Lux 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

4.92 out of 5 average rating, 229 reviews

A two-story cottage is surrounded by lush greenery, featuring a blue-tiled roof and large balconies. Below, a pool area is highlighted with sun loungers, inviting relaxation. The property is set within a vibrant landscape, showcasing palm trees and well-maintained gardens.

Cottage in Mango Walk

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.

A serene beachfront view showcases palm trees swaying in the breeze, with a pathway leading to the sandy beach. The calm ocean reflects the clear blue sky, while shaded seating areas and a gazebo are visible along the coast.

4.85 out of 5 average rating, 101 reviews

Caribbean Diamond Ocean front 1 Bedrm Condo.

This apartment is a privately owned suite onsite the Jewel Grande Resort property.We are located on the sixth floor of the Silver building directly overlooking the sea. Our condo offers luxury and the feel of paradise. Getting to us is easy from the Sangster's International airport as we are 15 mins drive away. The property is entirely secured with 24hrs gated and electronic security as well as free parking. Accessible to Guests are: Elevator WI-FI AC Hot water Pool Gym Restaurants Bar

A spacious living area features elegant bamboo furniture, including a two-seat sofa and comfortable chairs. Natural light floods in through large windows, highlighting decorative elements like a starburst mirror and potted greenery. A textured rug anchors the space, with a coffee table positioned centrally.

4.92 out of 5 average rating, 130 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.

4.94 out of 5 average rating, 141 reviews

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.

Flat in Montego

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.

A cozy lounge area is showcased, featuring a comfortable blue armchair beside a stylish white coffee table. A Smart TV is mounted on the wall, while decorative elements like plants and lanterns add a touch of charm. Natural light filters through sheer curtains.

4.78 out of 5 average rating, 267 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. Beach access via the former Hardrock Cafe at Secrets Hotel, will remain closed until late Spring 2026.

Popular amenities for Montego Bay rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.61 out of 5 average rating, 70 reviews

A guest is seen from behind, standing on a balcony overlooking the scenic ocean view. The horizon features a blend of soft blues and grays, while gentle waves lap against the shore below. Palm trees frame the view, suggesting a tropical environment.

Home in Mango Walk

Your Little Mobay! 🌟 w/ Pool!

A private swimming pool with crystal-clear water is surrounded by a spacious terrace. Two orange lounge chairs are positioned for relaxation, while the stunning panoramic view of the Caribbean Sea and clear blue sky is visible in the background.

4.85 out of 5 average rating, 176 reviews

PleasantView

A serene bedroom features a spacious bed adorned with premium linens and a neatly folded towel. Large windows are dressed with light curtains, allowing natural light to flow in. A blue accent wall complements the bright decor, while a small desk and plants add to the relaxed ambiance.

4.96 out of 5 average rating, 52 reviews

Fully air-conditioned home w/ pool & garden patio

A spacious living area features large glass doors opening to a private pool, providing views of the vibrant greenery and shimmering waters. Comfortable seating arrangements include a beige couch and colorful accent chairs, complemented by a coffee table. Natural light floods the space, creating an inviting atmosphere.

4.99 out of 5 average rating, 85 reviews

Shimmering Christmas Gift book 4, 5th free

The exterior of Bamboo Villa is presented, featuring dual automated gates that provide access to the spacious front area. A well-maintained garden with plants is included, alongside a paved pathway leading to the home, all under clear blue skies and surrounded by green hills.

4.91 out of 5 average rating, 65 reviews

Bamboo Villa

4.84 out of 5 average rating, 85 reviews

A serene outdoor space is captured with a clear blue swimming pool surrounded by tropical landscaping. Flanking the pool are palm trees and vibrant greenery, while a modern building is visible in the background against a bright blue sky.

Home in Reading

Royale Dream Vacation Entire 2 Bedroom Apartment

4.86 out of 5 average rating, 22 reviews

A modern living space features a large wall-mounted television opposite a comfortable seating arrangement, including a brown leather sofa and armchairs. A round dining table is positioned nearby. Natural light fills the room through expansive windows, highlighting a contemporary art piece on the wall.

Home in Reading

N/H Paradise 2

A spacious living area features an oversize sectional sofa adorned with colorful cushions. Complementary orange armchairs provide additional seating. A large ottoman rests in front of the seating arrangement, with a modest coffee table placed nearby. Soft lighting from a decorative pendant illuminates the room.

4.98 out of 5 average rating, 145 reviews

Villa Ginger: Food paradise/Beach/Pool/keycode

Apartment rentals with a pool

Apartment in St. James Parish

A modern living area is highlighted by a flat-screen television mounted on the wall. Large windows allow natural light to fill the space, which is furnished with a light gray sectional sofa. Soft curtains frame the windows, enhancing the room's inviting appearance.

4.93 out of 5 average rating, 69 reviews

Style & Comfort @Mobay 1 Bd/Roof Top Pool&Jacuzzi

A serene ocean view features a gazebo situated on a rocky outcrop surrounded by clear turquoise waters. Gentle waves lap against the shore, and a sandy beach is visible in the foreground, framed by swaying palm trees.

4.94 out of 5 average rating, 151 reviews

Palmyra Resort - Blue Sky Hideaway

A brightly lit bedroom showcases a spacious bed adorned with a floral-patterned blanket. An armchair and a matching sofa bed provide additional seating. Tall green curtains frame the windows, while a bedside lamp on a nightstand offers soft illumination.

4.75 out of 5 average rating, 97 reviews

Irresistible view (Mobay Club-1408)

An expansive view of the Caribbean Sea is captured from the rooftop patio, highlighting the serene blue water and sandy beach. Lush greenery borders the shoreline, while distant hills provide a picturesque backdrop under an overcast sky.

4.82 out of 5 average rating, 153 reviews

Panoramic Studio with Ocean & Mountain Views

An infinity pool is seen with a tiled edge, complemented by plush white towels stacked beside it. Two glasses of sparkling wine rest on the tiled surface, overlooking a serene ocean view framed by palm trees and vibrant greenery.

4.85 out of 5 average rating, 60 reviews

Kusha Penthouse - Ultimate Luxury Experience

An infinity pool extends towards the bay, surrounded by lounge chairs under a clear blue sky. Tropical greenery lines the pool area, with boats visible in the calm water, enhancing the serene setting.

4.97 out of 5 average rating, 38 reviews

Hidden Gem - 1BR Condo in Upscale Neighborhood

A private balcony showcases stunning turquoise waters, with distant mountains framing a serene view. Potted vibrant pink bougainvillea adds a touch of color. A circular decorative piece is placed on a round table, enhancing the space's minimalist design.

4.96 out of 5 average rating, 46 reviews

Cozy Modern 1BR Oceanfront

A modern studio apartment showcases a spacious bed adorned with neutral linens. A comfortable sofa sits opposite the bed, complemented by decorative pillows. Light filters through sheer white curtains, illuminating the room. Artwork hangs on the walls, enhancing the minimalist decor.

4.86 out of 5 average rating, 37 reviews

HomesByTufenke

Other holiday rentals with a pool

4.93 out of 5 average rating, 43 reviews

An inviting pool area is highlighted, featuring a softly curved pool surrounded by a spacious tiled deck. Several lounge chairs are arranged around the pool, and large windows provide views of the surrounding outdoor spaces and natural light into the villa.

Villa in Montego Bay

Luxury 5 Bedroom Villa with Pool Jacuzzi Gym

4.98 out of 5 average rating, 85 reviews

A well-lit living area features a comfortable brown sofa and a wooden coffee table atop a striped rug. Large windows allow natural light to flow in, with greenery visible outside. A small plant on the table adds a touch of nature to the space.

Cabin in Anchovy

Ripe Plantain Cabin

The spacious bedroom features a large bed with decorative pillows set against a vibrant blue wall. A seating area with a sofa is included, and a desk is positioned next to a window offering views of the outside. Light fills the space through large glass doors.

4.91 out of 5 average rating, 95 reviews

Ocean Caribe Upper Deck: 1BR Apt

A large hotel building is illuminated at night, surrounded by palm trees. The pool area features colorful lighting, with lounge chairs arranged around the edges. Soft reflections of the lights shimmer on the water's surface, creating a serene evening ambiance.

5 out of 5 average rating, 4 reviews

Luxury Condo with Hotel access; WIFI BEACH GYM

4.92 out of 5 average rating, 12 reviews

Townhouse in Mango Walk

2BR Townhouse near Beach & Hip Strip • Pool Access

A spacious living area features a modern blue sectional sofa adorned with colorful cushions. A central white coffee table rests on a floral area rug. The open kitchen and dining space, equipped with sleek appliances, are visible in the background under warm lighting.

4.97 out of 5 average rating, 39 reviews

Dream Sunset Suite

A spacious bedroom is highlighted by large windows that allow natural light to flow in. The room features a king-sized bed with a neutral-toned quilt and decorative pillows. A fan is mounted on the wall, while a pair of bedside lamps and a colorful chest add character to the space.

4.93 out of 5 average rating, 86 reviews

Pollyanna Tropical Retreat Ocean front property.

A dining area presents a dark table set with dishes and a glass. A potted plant with yellow flowers adds a vibrant touch. In the background, a comfortable sofa is adorned with bright cushions, while a modern kitchen with dark cabinetry is visible.