
Vacation rentals with a pool in Reading
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Reading
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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.

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.

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.

Serenity HS| Montego Bay 2BR Condo near the Beach
This modern abode in Montego Bay stands out with its unique Jamaican flair. Nestled in the Ocean Springs gated community, this gem offers a serene oasis. Close proximity to the Caribbean Sea, world class beaches & surrounded by lush vegetation. The blend of contemporary design with a touch of local charm makes it a sort after property for guests who appreciate modern amenities + Jamaican authenticity. Central location – For relaxation or to explore the lively Montego Bay -the perfect balance!

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.

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.

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.

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.

Idle Time On The Bay Relaxing beautiful serene
IDLE TIME ON THE BAY - Welcome to your vacation home at Seawind On The Bay and enjoy our warm and friendly Jamaican hospitality. The apartment is located in a secured gated community on the Freeport Peninsula in a lush garden setting. The drive from Sangster International Airport is approximately 15 minutes. This is a gated property and you are sure to meet new acquaintances. Seawind hosts a number of Airbnb guests and long lasting friendships are always guaranteed..peaceful and relaxing

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.

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.

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.
Popular amenities for Reading rentals with a pool
House rentals with a pool

PleasantView

Whiterock Montego Bay O Villa

Free Floating Breakfasts in your private pool

DeJa Vu Villa

Bamboo Villa

Royale Dream Vacation Entire 2 Bedroom Apartment

Luxury town house W/airport pick up & beach access

Sophisticated Spacious Home: Pool, Gym& Near Beach
Condo rentals with a pool

Seawind one bedroom

Palmyra Resort - Blue Sky Hideaway

Ocean Spring Sandy

Premium Luxury Oceanfront Apartment

The View.

BettyBeach Retreat

Panoramic Studio with Ocean & Mountain Views

Kusha Penthouse - Ultimate Luxury Experience
Other vacation rentals with a pool

Seabreeze at Spring Garden

Spacious Ocean View 2 BR Condo

The Oasis - 1 Bedroom with Pool

Shallhome Masterful Luxury 5 Bedroom Home

Ariel Luxury 3 BR Suite. Modern and spacious. MBJ

Sea Glass: The Seaside Sanctuary

Ripe Plantain Cabin

3BR Tranquil Townhome w/ Beach Access, Pool & Gym.
When is the best time to visit Reading?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$35,362 GYD | G$35,362 GYD | G$36,618 GYD | G$34,735 GYD | G$35,362 GYD | G$34,525 GYD | G$36,827 GYD | G$36,827 GYD | G$33,270 GYD | G$35,362 GYD | G$36,199 GYD | G$39,129 GYD |
| Avg. temp | 26°C | 26°C | 27°C | 27°C | 28°C | 29°C | 29°C | 29°C | 29°C | 28°C | 28°C | 27°C |
Quick stats about vacation rentals with a pool in Reading

Total vacation rentals
Explore 60 vacation rentals in Reading

Nightly prices starting at
Reading vacation rentals start at G$10,462 GYD per night before taxes and fees

Verified guest reviews
Over 2,910 verified reviews to help you choose

Family-friendly vacation rentals
40 properties offer extra space & kid-friendly amenities

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
60 of Reading vacation rentals include wi-fi 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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