
Vacation 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.

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.

Paradise by the Sea
Fully furnished studio apartment, located directly on a white sand beach at Sea Castles Condo along Montego Bay’s elegant corridor. Located on the North Coast highway the complex is 10 minutes from MBJ Airport, 15 minutes from the town center, with access to everywhere on the island. The complex has 24 hours security, swimming pool, beach, bar & local restaurant with a relaxed atmosphere catering to both working professionals & vacationers wanting to enjoy themselves after a long day.

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.

Comfortable 1bedroom, 1 bath, rooftop pool
Listing description PLEASE READ LISTING DESCRIPTION BEFORE BOOKING! Wake up and pull away your curtains to a breathtaking view of the Caribbean Sea whilst you relax and unwind in your spacious and modern home away from home. The apartment is palatial, cool and central to all major locations. The property is 5mins by car from the airport and 20mins walk or 5mins by car to the Hip Strip. Enjoy the roof top pool overlooking the ocean and watch as the planes land at the airport.

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.
Popular amenities for Montego Bay rentals with a pool
House rentals with a pool

PleasantView

Montego Bay air conditioned home with private pool

Free Floating Breakfasts in your private pool

Bamboo Villa

Royale Dream Vacation Entire 2 Bedroom Apartment

Luxury Montego Bay 2BR Villa | Ocean Views & Pool

Villa Ginger: Food paradise/Beach/Pool/keycode

"Smallah" 4-br seaside villa own pool, resort area
Condo rentals with a pool

Palmyra Resort - Blue Sky Hideaway

Irresistible view (Mobay Club-1408)

Luxury Garden 2 BDR, 2 BTH Condo w/ pool

Luxury 2 Bedroom w/ Beach Access

Hidden Gem - 1BR Condo in Upscale Neighborhood

Boho-Chic Studio Loft with Sea Views Montego Bay

Cozy Modern 1BR Oceanfront

HomesByTufenke
Other vacation rentals with a pool

Style & Comfort @Mobay 1 Bd/Roof Top Pool&Jacuzzi

Spacious Ocean View 2 BR Condo

⭐️ Cozy Condo ❤️ Free Beach ❤️ Seawind On The Bay

Two Bedroom Suite-Beach Restaurants Shop Nightlife

2BR Townhouse near Beach & Hip Strip • Pool Access

Modern Sunset Condo | 10 mins from MBJ airport.

Sunshine Suite 2 -Air C King Suite & kitchenette

Luxe 1 Bdrm Apt in Montego Bay!
When is the best time to visit Montego Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$33,499 GYD | G$31,824 GYD | G$33,499 GYD | G$33,080 GYD | G$32,243 GYD | G$33,080 GYD | G$33,499 GYD | G$32,661 GYD | G$31,196 GYD | G$31,614 GYD | G$31,405 GYD | G$34,546 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 Montego Bay

Total vacation rentals
Explore 740 vacation rentals in Montego Bay

Nightly prices starting at
Montego Bay vacation rentals start at G$6,281 GYD per night before taxes and fees

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

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

Pet-friendly vacation rentals
Find 60 rentals that welcome pets

Rentals with dedicated workspaces
390 properties have a dedicated workspace

Wi-Fi availability
730 of Montego Bay vacation rentals include wi-fi 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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