Holiday rentals with a pool in Kingston

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Kingston

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite

Bungalow in Portmore

4.88 out of 5 average rating, 141 reviews

Luxury 2 bedroom beach villa in gated community

53 Bay Front is a stunningly furnished 2 bed 2 bath villa beside Forum beach. The secure gated community features 24/7/365 manned entrance gates & is centrally located in Port Henderson, Portmore. The villa has high-speed wireless internet, cable and Smart TVs. Air-conditioning in both bedrooms, a fully-equipped kitchen, spacious living room, breakfast bar, open plan dining area and a utility room with washer & dryer. You will also enjoy the outside areas: back patio, front garden & lawn.

Guest favourite

Home in Kingston

5 out of 5 average rating, 6 reviews

Private Upscale Bedrooms w Pool

This stylish home is perfect for single persons, family/group trips. Secluded and tranquil with attractive amenities. Private pool, dining and living rooms, study/work area, cable TV, Wi-fi, Netflix, well-equipped kitchen, washer/dryer, king size beds, air conditioned bedrooms, patio with koi fish pond, waterfall, outdoor terrace, generator, water tanks. Shopping areas and gym within 7 minutes driving radius. Starbucks, Wendy’s, Pharmacy (Fontana). Housekeeper/cook available upon request.

Guest favourite

Rental unit in Kingston

4.9 out of 5 average rating, 107 reviews

CityFive Kgn 1 or 2 BDRMS Blue Mtn & City Views

***IMPORTANT*** READ ALL SECTIONS This contemporary listing is located right off the Liguanea Plain and affords you a view of the beautiful Blue Mountain. It offers you the absolute peacefulness of a residential neighborhood with quick access to the city. For the business traveller, wi-fi connection, a comfortable work area and easy accessibility to the CBD. For families, cozy living area. For the vacationer, 10 mins to Bob Marley Museum, Devon House or 35 mins to Port Royal

Guest favourite

Apartment in Portmore

4.86 out of 5 average rating, 37 reviews

City/Ocean views, Pool, Beach:Resort like Vacation

Step into your dream getaway! This luxurious apartment blends coastal charm with city vibes, offering killer views of both skyline, beach and mountains. Splash in the pool, hit the beach, or chill in the lobby—whatever floats your boat! Elevator? Check. Meeting room? Got it. Plus, an epic mix of city buzz and mountain zen. Ready for an unforgettable escape? Let's do this!

Guest favourite

Apartment in Kingston

4.88 out of 5 average rating, 127 reviews

Ultimate 1BR Condo with Rooftop Pool (GC V102)

Explore the sophistication of this stylish condo located on the second floor, positioned within one of Kingston's most prestigious short-term lodging choices. Immerse yourself in the mesmerizing rooftop entertainment, perfectly paired with the exceptional care provided by our devoted team. We're eagerly awaiting the chance to host you!

Guest favourite

Home in Portmore

4.89 out of 5 average rating, 74 reviews

Hidden Gem by Shekinah Homes 2Bd 1Bath, Pool

Ideally located in a 24Hr secure, gated community, close to dining, shopping, and nightlife. Enjoy our private pool, free Netflix, WiFi, and air conditioning. Great to treat your family/friends to some backyard fun using our backyard grill. Catering services are offered at an additional cost.