Holiday rentals with a pool in Reading

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Top-rated rentals with a pool in Reading

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

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Superhost
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.
Apartment in Montego Bay
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.

Guest favourite
Flat in Montego Bay
4.81 out of 5 average rating, 210 reviews

Seawind On The Bay Studio

Seawind On The Bay is a safe gated community. A semi-private beach is across the street a short distance beside Secrets Hotel. The property has a pool and shared bar and grill with a covered community centre or cabana. A spectacular view of Montego Bay Harbor with cruise ships in the back yard view. 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.

Superhost
An aerial view of the swimming pool area showcases a clear water pool surrounded by sun loungers. A palm tree adds a tropical touch, while modern buildings line the background, creating a relaxed atmosphere in the community.
Apartment in Montego Bay
4.83 out of 5 average rating, 225 reviews

1 Bedroom Miramar Condo

1 bedroom 900 square feet spacious condo in a secure gated community across from the natural beach. Close to public transport. About 10-15 minutes drive from downtown Montego Bay and 20-25 mins drive from the airport. Great amenities including 24 hour security, pool, laundry, fully equipped kitchen. Elevate Lounge - 3 mins drive, Fairview Shopping Center (Uncorked, Mystic Thai, Tutti Frutti, HILO, Progressive Foods Fairview, Fontana Pharmacy, Palace Multiplex movie theater etc.) - 10 mins drive.

Guest favourite
A spacious bedroom features a plush bed dressed in white bedding, complemented by colorful wall art above. Mirrored side tables are positioned on either side of the bed. Natural light enters through sheer curtains, enhancing the modern atmosphere.
Apartment in St. James Parish
4.9 out of 5 average rating, 137 reviews

Luxury In Paradise: Pool, Jacuzzi, Gated, 3rd Flr

Whether you’re in Jamaica for work or vacation, this condo will check all your boxes. Located in Ironshore, one of Montego Bay’s most prominent communities, sits Dream 36. A luxury condominium complex that’s close to entertainment, beaches, restaurants, and airport (12 mins). This one bedroom condo is extremely spacious at 900 sq ft. It boasts modern furnishings with a warm feel. You can truly relax with amazing amenities such as gated 24/7 security, lounge, pool, and rooftop views. Book now 😁

Top guest favourite
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, 185 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.

Superhost
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
4.81 out of 5 average rating, 109 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.

Guest favourite
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.
Apartment in Reading
4.9 out of 5 average rating, 116 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.

Top guest favourite
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.
Apartment in Montego Bay
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

Superhost
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.
Flat in Montego Bay
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.

Guest favourite
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, 118 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 favourite
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
4.94 out of 5 average rating, 141 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.

Superhost
A well-furnished sleeping area features a spacious bed adorned with a white quilt and accent pillows in hues of blue. Two dark wooden nightstands with lamps are positioned on either side. Colorful artwork hangs above the headboard against a vibrant teal accent wall.
Flat in Montego Bay
4.93 out of 5 average rating, 110 reviews

Anna's Joye Seawind - Montego Bay

This well appointed, air-conditioned studio is located in the Seawind On The Bay complex in the upscale Montego Freeport area with full access to the beach at The Hard Rock Cafe. The complex is surrounded by two major hotels, Secrets Resorts and Sunscape Resorts and is next door to the Montego Bay Yacht Club. It is about 15 mins from the Sangster Int'l Airport with easy access to restaurants, supermarket and entertainment.

Popular amenities for Reading rentals with a pool

When is the best time to visit Reading?

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Avg. price$219 SGD$219 SGD$227 SGD$216 SGD$219 SGD$214 SGD$229 SGD$229 SGD$206 SGD$217 SGD$221 SGD$231 SGD
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Quick stats about holiday rentals with a pool in Reading

  • Total holiday rentals

    Explore 60 holiday rentals in Reading

  • Nightly prices starting at

    Reading holiday rentals start at $65 SGD per night before taxes and fees

  • Verified guest reviews

    Over 2,890 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space & child-friendly amenities

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    60 of Reading holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Reading rentals

  • 4.8 Average rating

    Reading stays are highly rated by guests – averaging 4.8 out of 5!

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