
Holiday 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.

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.

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.

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.

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 😁

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.

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.

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

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.

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

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.

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. Secrets spa is 5 minutes walk from us. The nearest beach is 5 minutes walk (formerly Hard Rock Café beach).
Popular amenities for Montego Bay rentals with a pool
House rentals with a pool

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Apartment rentals with a pool

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Luxury Condo in Montego Bay, Rooftop Pool access

Kotch n Chill, Montego Bay gated complex with pool
When is the best time to visit Montego Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $208 SGD | $197 SGD | $208 SGD | $205 SGD | $200 SGD | $205 SGD | $208 SGD | $203 SGD | $193 SGD | $196 SGD | $195 SGD | $214 SGD |
| 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 holiday rentals with a pool in Montego Bay

Total holiday rentals
Explore 740 holiday rentals in Montego Bay

Nightly prices starting at
Montego Bay holiday rentals start at $39 SGD per night before taxes and fees

Verified guest reviews
Over 23,720 verified reviews to help you choose

Family-friendly holiday rentals
390 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 60 rentals that welcome pets

Rentals with dedicated workspaces
390 properties have a dedicated workspace

Wifi availability
730 of Montego Bay holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Montego Bay rentals

4.7 Average rating
Montego Bay stays receive an average rating of 4.7 out of 5 from guests
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