Vacation rentals with a pool in Reading

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, 436 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.

FamilyLocationBreakfast

4.98 out of 5 average rating, 213 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.

ValueFamilyNearby

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.

4.82 out of 5 average rating, 144 reviews

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.

LocationFamilyWalkability

4.88 out of 5 average rating, 136 reviews

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

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.

LocationFamilyCheck-in

A panoramic view of lush greenery leading to a serene body of water under a partly cloudy sky. The landscape features a mix of trees and distant hills, creating a calming natural scene that encapsulates the beauty of the surroundings.

4.89 out of 5 average rating, 110 reviews

Spacious Ocean View 2 BR Condo

Ocean view condo centrally-located provides a peaceful environment for a weekend getaway. The open concept allows you to enjoy the ocean view from the kitchen, dining and living room. With balcony doors that completely open to the spacious balcony for the perfect indoor outdoor feel. The spacious master bedroom with an ocean view has an on-suite bathroom. A second bedroom with garden and mountain view. Our outdoor amenities include a jogging trail through the lush garden and a swimming pool

LocationValueKitchen

A modern living area is presented with sleek furnishings and a large TV mounted on the wall. A gray sofa invites relaxation, complemented by a white coffee table and decorative plants. Natural light fills the space, highlighting the stylish decor and contemporary design elements.

4.87 out of 5 average rating, 121 reviews

Affluence - Lux 1Bd MoBay Apt(Central+RooftopPool)

Name - AFFLUENCE This stunning luxury 1-bedroom apartment is designed for comfort and elegance, located 15 minutes from Sangster International Airport (Montego Bay Airport), with easy access to top restaurants, shopping, and entertainment. The complex features a total of 5 units, offering adequate privacy for our guests. Located only 7 minutes from Fairview shopping Centre and 10 minutes from Downtown Montego Bay and the popular Hipstrip. The beach is also 10 minutes away from your stay.

LocationValueGetting around

4.94 out of 5 average rating, 158 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

FamilyValueComfort

4.97 out of 5 average rating, 103 reviews

A spacious bedroom is depicted, featuring a large bed with crisp white linens and decorative pillows. Nightstands with table lamps are positioned on either side. Soft blue walls complement the room, while curtains frame a window, and a small table and chair are visible in the corner.

Apartment in Montego Bay

Vivid Getaway Condo/Pool/Gym/Gated/Modern

Dream up your ideal stay and there you will find Vivid Getaway. Nestled in the secure gated Ocean Springs Apartments, Reading, Montego Bay is this peaceful 1 bed 2 bath ground floor unit with all the comforts to suit your vacation and business needs. Well situated, just minutes away from Chukka Tours, Fairview Mall with shopping, restaurants and entertainment, Elevate Lounge and Pineapple Beach, 11km from Sangster International Airport. Free high speed WiFi, Gym, Pool, 24 hour security.

LocationValueRiver

4.98 out of 5 average rating, 135 reviews

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

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.

LocationValueQuiet

Guest suite in Montego Bay

A bright outdoor area features an aboveground pool with clear blue water, surrounded by a wooden deck. Expansive views of the sea and Montego Bay are visible in the background, under a clear blue sky with a few scattered clouds.

View 99 Spring Gardens; 3 bed rms & amazing views

A spacious 3‑bedroom apartment with ensuite bathrooms, full kitchen, living/dining areas, private patio, above‑ground pool, gym, and stunning views of the sea and Montego Bay’s lush hills. Located in a secure gated community close to beaches, shopping, and the town centre. Please note: The upper level of the home is still undergoing post‑hurricane repairs, but your private lower‑flat apartment is fully finished, quiet, and self‑contained.

LocationFamilyComfort

4.86 out of 5 average rating, 112 reviews

4.83 out of 5 average rating, 115 reviews

A tranquil infinity edge pool is surrounded by palm trees, offering a view of the sea in the background. Comfortable lounge chairs, adorned with vibrant towels, are positioned beside the water, inviting relaxation under clear blue skies.

Townhouse in Montego Bay

Montego Bay Luxury 3BR Villa | Ocean Views & Pool

Luxury Montego Bay 3BR Villa with Ocean Views & Pool Welcome to your elevated Caribbean escape. This luxury 3-bedroom villa in Montego Bay offers stunning ocean views, a resort-style pool, and a beautifully designed space ideal for families, couples, or small groups seeking comfort and privacy in a secure setting. All within a secure, 24 hour gated community just 15 minutes from Sangster International Airport.

FamilyValuePool

A sparkling outdoor pool is framed by sun loungers and palm trees under a clear blue sky. A covered pavilion with a white roof is situated nearby, providing shaded seating options. The pool area is surrounded by stone decking and lush greenery.

4.9 out of 5 average rating, 29 reviews

Gated 2BR | Pool + Gym | Wi-Fi | Washer/ Dryer

Escape to a spacious and modern 2BR retreat in one of Montego Bay’s most secure gated communities. Perfect for longer stays and business travel, this quiet home offers a fully equipped kitchen, washer and dryer, two private patios, and access to a pool, gym, and tennis court. Just minutes from Fairview, it’s ideal for guests seeking comfort, privacy, and convenience away from the busy tourist areas.

FamilyLocationIndoor spaces

House rentals with a 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.

4.84 out of 5 average rating, 183 reviews

PleasantView

LocationFamilyIndoor spaces

A tranquil swimming pool offers crystal-clear water, framed by lush tropical plants. The serene ocean view stretches beyond, showcasing gentle waves and distant hills under a partly cloudy sky. Lounge chairs are positioned nearby, inviting relaxation by the water's edge.

4.92 out of 5 average rating, 74 reviews

"Smallah" 4-br seaside villa own pool, resort area

LocationFamilyIndoor spaces

4.88 out of 5 average rating, 17 reviews

A spacious living area is highlighted by a dark sectional sofa facing a large television. Natural light filters in through sliding glass doors, leading to an outdoor view of greenery. Additional plants are placed beside the television unit, creating a calm and inviting atmosphere.

Home in Reading

Selah Vista- 3BR Home+ 24 hr security, Montego Bay

LocationIndoor spacesView

4.83 out of 5 average rating, 54 reviews

A serene view is captured from a pool area, showcasing lush tropical plants and a glimpse of the ocean in the distance during sunset. The sky is adorned with soft hues, reflecting on the water's surface, creating a calming atmosphere.

Home in Reading

Whiterock Pink Bougainvillea Villa

ValueFamilyHospitality

4.91 out of 5 average rating, 76 reviews

Bamboo Villa

ValueLocationIndoor spaces

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.

4.98 out of 5 average rating, 98 reviews

Enjoy Floating Breakfasts in your private pool

ValueFamilyOutdoor spaces

4.88 out of 5 average rating, 25 reviews

5BD Gated, Pool, incl Full Staff & Private Driver

FamilyValueAccuracy

An aerial view captures the modern architecture of the Miramar complex, featuring a central infinity pool surrounded by lush landscaping. Tropical plants and decorative elements enhance the inviting atmosphere, while ocean views are visible in the background, reflecting the tranquil surroundings of the gated community.

4.9 out of 5 average rating, 62 reviews

Tropical Retreat Villas Miramar

FamilyLocationHospitality

Condo rentals with a pool

A well-appointed kitchen is shown, featuring gray cabinetry and stainless steel appliances. A gas stove and microwave are included, with a white countertop displaying a vase of flowers and fresh limes. Subtle lighting enhances the clean and organized space.

4.86 out of 5 average rating, 106 reviews

A Yah Suh Nice 2 bed rooms Mango Walk country club

ValueLocationHospitality

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, 446 reviews

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

LocationValueCheck-in

4.86 out of 5 average rating, 115 reviews

Condo

Luxury Condo in Montego Bay, Gated, 24/7 Security

FamilyValueGetting around

The living area features a modern design with a spacious gray sofa adorned with decorative pillows. A round marble table sits at the center, and a dining table with six chairs is visible in the background. The kitchen, equipped with stainless steel appliances, is integrated into the open space.

4.85 out of 5 average rating, 99 reviews

Celebrity Lifestyle 1 Bedroom Suite @Dream 36

ValueLocationCleanliness

4.81 out of 5 average rating, 167 reviews

Panoramic Studio with Ocean & Mountain Views

ValueFamilyQuiet

A spacious living area is illuminated by natural light through large sheer curtains. A light beige sofa is accompanied by a blue patterned chair and a wooden coffee table, creating a relaxed seating arrangement. Decorative elements include a vase of flowers on the side table.

4.96 out of 5 average rating, 156 reviews

Idle Time On The Bay Relaxing beautiful serene

FamilyLocationKitchen

4.86 out of 5 average rating, 14 reviews

Condo in Reading

Sandy Cove Spacious Condo

FamilyLocationQuiet

4.93 out of 5 average rating, 58 reviews

A comfortable bedroom features a spacious bed covered with a light gray blanket. A dark blue armchair is positioned nearby for seating. A piece of artwork hangs above the bed. Natural light enters through a window, complementing the soft blue walls.

Condo in Reading

Upscale 3BR Apartment, Montego Bay, Sea Views

FamilyValueWalkability

Other vacation rentals with a pool

4.88 out of 5 average rating, 16 reviews

Sky Suite - 2BR/2Bth Apartment

LocationFamilyAccuracy

A serene view of the Caribbean Sea is presented, featuring a sailboat gliding across the water. The sky is bright blue with scattered clouds, and the horizon showcases varying shades of blue and green in the water.

4.92 out of 5 average rating, 53 reviews

Irie Paradise Apartment in Montego Bay

FamilyValueAccuracy

4.88 out of 5 average rating, 25 reviews

A bright living area features a modern television mounted above a sleek white console. A glass coffee table stands on a textured rug, while a grey couch adorned with yellow cushions invites relaxation. Natural light floods through the window, complemented by patterned curtains.

Townhouse in Montego Bay

Shallhome Masterful Luxe City Ocean Views

FamilyLocationBathroom

A bright studio apartment features a spacious bed with soft linens, complemented by decorative cushions. A modern kitchenette is visible, with table settings arranged on a white countertop. Natural light fills the room, highlighting the neutral color palette and artwork decorating the walls.

4.83 out of 5 average rating, 58 reviews

LUXE Studio | w/Pool Near Beach | WIFI

FamilyLocationAmenities

5.0 out of 5 average rating, 14 reviews

Casa G Stylish Montego Bay Escape with pool & gym

LocationQuietAccuracy

5.0 out of 5 average rating, 4 reviews

Pure Bliss Oasis

LocationNearbyHospitality

4.96 out of 5 average rating, 23 reviews

Villa in Montego Bay

Seabreeze at Spring Garden

LocationFamilyBathroom

A spacious living room is presented, featuring modern furnishings in blue and gold tones. A glass coffee table sits atop an area rug, surrounded by comfortable seating. Colorful wall art enhances the decor, while large windows allow natural light to fill the room.