
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.

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.

Panoramic Studio with Ocean & Mountain Views
Wah Gwan, a.k.a "What's going on? " Come and stay at my newly updated condo!! It is in a great spot, close to all the action and Harmony Beach! It has a great view on the private 3rd floor, it is a good size & can accommodate 4 people with a mini separate bedroom area, blocked off by curtains. I love the full size fridge, the night views, (especially down by the pool area). I love that you can get a beer or a meal anytime. We also have a Mini Mart on the property!! You will enjoy your stay:)

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.

LionHideVilla GD: salt water pool&ocean view roof
The Green Door apartment is a modern space with lots of amenities: A/C, hot water, Wi-Fi, ceiling fans, flat screen smart TV/cable, blue tooth speaker, linens/towels, full kitchen with granite countertops. It has its own patio with seating & is fully grilled with screened windows. The property is fully gated. The lot is well fruited with mango, ackee, june plum, orange, lime, cherry, breadfruit & avocado trees. There is currently construction next door during week day, daytime hours.

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).

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.

HideAway By the Sea - Your HOME away from Home
Welcome to HideAway by the Sea, where you will be able to relax and enjoy the island. This studio apartment offers all the comforts of home with AC, room fan, hot water on demand, a washer, Smart TV, WIFI, comfy Queen bed and a fully equipped cooking space to make meals. This space is great for working professionals, travelers, singles, or a couple. It is very safe with 24-hour security. Smoking is permitted on patios only.

Scotchies Cabin-Cozy Wooden Oasis Escape the City
Have fun ❤️with the whole family and friends at this stylish cabin place. I leave in jamaica 18yrs , we love jamaica , we love travel , we love weather here. loves to meet new people and welcome them in our place as well. We speak English and Korean. I look forward to host all you awesome people! Best Regards, Kevin&Jane
Popular amenities for Montego Bay rentals with a pool
House rentals with a pool

Your Little Mobay! 🌟 w/ Pool!

PleasantView

Fully air-conditioned home w/ pool & garden patio

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Apartment rentals with a pool

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A Jewel at a Luxury All-Inclusive Resort

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Other holiday rentals with a pool

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Luxe 1 Bdrm Apt in Montego Bay!

Boho-Chic Studio Loft with Sea Views Montego Bay
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 € 26 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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