
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.

VIBES COVE enjoy your stay while getting pampered
FREE Arrival meal, the first day you arrive to Vibes Cove you’ll receive a complementary arrival meal by our personal chef on the property. Vibes Coves Villa is super Spacious and Private. Enjoy your vacation while getting pampered. This property comes with a personal chef, Butler, and Housekeeper. Enjoy V.I.P services your entire stay. Property staff stays in their helpers quarters ( not attached to your living area of the property ) only those listed on the Airbnb is allowed at the property

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.

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.

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.

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.

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.

Luxury Villa - King Bed /Pool/Near Airport & Beach
Everything Irie@ Les Chateaux Villa - Located within 10 minutes of the airport & beaches - Handicap Access/Backup Generator & Water Tank - Walking distance of Whitter's Village with a supermarket, shops & restaurants - 3 Full Bedrooms w/ en-suite bathrooms - Sleeps up to 8 (1 King, 2 Queens & Sofa bed) - Gated Community with Security - Nestled directly across from the pool & gym - Has Wi-fi internet & over 900 cable channels

The Jewel at Dream 36
What you'll love about The Jewel at Dream 36: Less than 10 minutes drive from MBJ airport is this breathtaking Jewel; a luxurious two storey penthouse suite in a gated community with 24/7 security. Enjoy sea views from every room. Smart TV in every bedroom and living room. Relax in the rooftop infinity edge pool, indoor and outdoor lounge areas. Perfect for families, friends or groups seeking exclusivity and luxury!

Oceanfront 3br Condo Amazing views Beach Pool
A perfect stay for families, business or work from home travelers, couples. This 3 bedroom waterfront condo is superbly located 18 feet from the waterfront in a secured gated complex with 24 hour security. Guests also receive access to a private residence beach just a short stroll across the street. Everything virtually on your doorstep and only 15 minutes from Sangster International Airport.
Popular amenities for Montego Bay rentals with a pool
House rentals with a pool

PleasantView

Free Floating Breakfasts in your private pool

DeJa Vu Villa

Bamboo Villa

Royale Dream Vacation Entire 2 Bedroom Apartment

NEW! Hilltop Escape with Ocean Views

Luxury Montego Bay 2BR Villa | Ocean Views & Pool

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

Serenity HS| Montego Bay 2BR Condo near the Beach

Palmyra Resort - Blue Sky Hideaway

Premium Luxury Oceanfront Apartment

The View.

Modern Luxury Coastal Condo

Celebrity Lifestyle 1 Bedroom Suite @Dream 36

Panoramic Studio with Ocean & Mountain Views

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

Seabreeze at Spring Garden

Luxury Montego Bay Villa | Pool, Gym & Jacuzzi

The Mango Walk Hideaway Bay View/ Very Private

Sea Glass: The Seaside Sanctuary

Montego Bay Townhouse•Pool w/Ocean View|Near Beach

2 BR townhouse, 24 hour security, gym, pool, ocean

Penthouse By The Sea

Turn Plantain Cabin
When is the best time to visit Montego Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $204 SGD | $194 SGD | $204 SGD | $201 SGD | $196 SGD | $201 SGD | $204 SGD | $199 SGD | $190 SGD | $191 SGD | $185 SGD | $200 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 730 holiday rentals in Montego Bay

Nightly prices starting at
Montego Bay holiday rentals start at $38 SGD per night before taxes and fees

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

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

Pet-friendly holiday rentals
Find 60 rentals that welcome pets

Rentals with dedicated workspaces
380 properties have a dedicated workspace

Wifi availability
720 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
Destinations to explore
- Kingston Holiday rentals
- Ocho Rios Holiday rentals
- Trinidad Holiday rentals
- Negril Holiday rentals
- Portmore Holiday rentals
- Mandeville Holiday rentals
- Treasure Beach Holiday rentals
- Old Harbour Holiday rentals
- Holguín Holiday rentals
- Guardalavaca Holiday rentals
- Discovery Bay Holiday rentals
- Port Antonio Holiday rentals
- Rentals with a cinema Montego Bay
- Guest house rentals Montego Bay
- Ski-in/ski-out rentals Montego Bay
- Family-friendly rentals Montego Bay
- Mansion rentals Montego Bay
- Beachfront rentals Montego Bay
- Pet-friendly rentals Montego Bay
- Rentals with a hot tub Montego Bay
- Hotel rooms Montego Bay
- Rentals with lake access Montego Bay
- Private suite rentals Montego Bay
- Waterfront rentals Montego Bay
- Rentals with a fireplace Montego Bay
- Smoking-friendly rentals Montego Bay
- Rentals with a patio Montego Bay
- Townhouse rentals Montego Bay
- House rentals Montego Bay
- Rentals with outdoor seating Montego Bay
- Flat rentals Montego Bay
- Rentals with breakfast Montego Bay
- Luxury rentals Montego Bay
- Rentals with a firepit Montego Bay
- Bed and breakfasts Montego Bay
- Serviced apartment rentals Montego Bay
- Fitness-friendly rentals Montego Bay
- Rentals with a washing machine and dryer Montego Bay
- Rentals with beach access Montego Bay
- Villa rentals Montego Bay
- Apartment rentals Montego Bay
- Rentals with pools Saint James
- Rentals with pools Jamaica




