Vacation rentals with a pool in Cherry Gardens, Kingston

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Top-rated rentals with a pool in Cherry Gardens, Kingston

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

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Guest favorite

A sparkling pool is set within a landscaped area, surrounded by a light-colored stone deck. Tall trees and greenery provide a natural backdrop. The fence surrounds the pool area, creating a private and tranquil space, perfect for relaxation.

Apartment in Kingston

4.8 out of 5 average rating, 10 reviews

Spacious 2BR apt in upscale Manor Park, Kingston

Welcome to your tranquil oasis/retreat offering the perfect blend of peace & convenience. Cozy living space, where large windows flood the room w/ natural light and offer serene views of the surroundings, tastefully furnished to ensure your utmost comfort . Start your mornings w/ a refreshing swim in the sparkling pool. Located within walking distance of Manor Park (supermarkets, pharmacies, and a variety of restaurants) , this charming abode puts everything you need right at your fingertips.

Top guest favorite

A private pool area is shown, featuring a rectangular pool surrounded by sleek grey tiles. The space is enclosed by a wooden fence, and greenery is visible beyond, providing a natural backdrop.

Condo in Kingston

5 out of 5 average rating, 18 reviews

Boho Contemporary 1 b/r w/pool- The Shallai

Enjoy a stylish experience at The Shallai (Sha-Lay) . A centrally-located 1 bedroom (living room sofa also converts to a bed) , 1 1/2 bathroom apartment in the coveted community of Barbican (Kingston). This chic space in a 9-unit building exudes comfort and style. It’s perfect for professionals coming for meetings or a couple wanting to enjoy Kingston’s restaurants and hot spots from a convenient location. We are in close proximity to supermarkets, cafes and a wide selection of restaurants.

Guest favorite

The living room features a colorful three-piece suite arranged around a glass coffee table, with a natural sheepskin rug beneath. Large windows are adorned with roman blinds, allowing natural light to fill the space. A ceiling fan enhances the comfort of the area.

Bungalow in Portmore

4.88 out of 5 average rating, 147 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 favorite

A spacious outdoor pool area is visible, featuring a glistening blue pool and a jacuzzi section. Surrounding greenery adds natural elements, while covered areas provide shade. The backdrop showcases distant views of the Blue Mountains and the surrounding neighborhood.

Apartment in Kingston

4.91 out of 5 average rating, 117 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

Superhost

A clear blue pool is framed by neatly landscaped areas and tall trees, offering a peaceful setting. A modern building stands in the background against a bright blue sky, while shaded seating areas are visible nearby.

Condo in Portmore

4.83 out of 5 average rating, 71 reviews

City/Ocean View, 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!

Superhost

A clear swimming pool is positioned on the rooftop, offering stunning views of the surrounding cityscape and the sea beyond. Sunlight reflects off the water's surface, enhancing the serene environment. The glass railing provides unobstructed sightlines of Kingston's skyline and the horizon.

Condo in Kingston

4.9 out of 5 average rating, 150 reviews

Ultimate 1BR Condo with Rooftop Pool

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!

Superhost

An aerial view captures a large outdoor pool bordered by a sun-soaked patio. The inviting pool is complemented by a nearby covered seating area. In the distance, the coastline meets the Caribbean Sea, with rocky shores and green spaces extending along the water.

Apartment in Portmore

4.79 out of 5 average rating, 33 reviews

Apartment With Amazing View

Discover the most unforgettable stay at this luxurious studio apartment with a resort like feel filled with amenities. Enjoy our outdoor pool or a walk on the beach, relax while enjoying the Caribbean most amazing sunsets. From this 10th floor apartment, you will enjoy views of the city, mountains and the Caribbean Sea.