Vacation rentals with a pool in Old Harbour

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Old Harbour

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

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Top guest favorite

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.

Superhost

Home in Hellshire

5 out of 5 average rating, 3 reviews

Luxurious 6 Bed Villa w/own Private Plunge Pool

Your whole group will be comfortable in this spacious, tastefully furnished and unique villa. Chill at the private plunge pool or stroll to the pristine waters of healthshire for sand, sun and sea. Gather as a family or a as a group to make memories in this hidden paradise. Equipped with fast free WiFi, smart TVs, large kitchens, many seating areas and a gym, you will have everything you need for a weekend, family reunion, and small events. Don't hesitate to book early for the best prices.

Guest favorite

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.

Superhost

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

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

Home in Spanish Town

4.82 out of 5 average rating, 11 reviews

Cheerful cottage w/private pool | gated community

Relax with the whole family at this peaceful place to stay. Everything you need to feel right at home is here! Relax indoors and curl up with a good book or Netflix and chill. Love the outdoors? No problem! The gazebo is a great place to recline, unwind and enjoy the pool.

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What guests are saying

Spacious 2BR apt in upscale Manor Park, Kingston

4.8 out of 5 average rating, 10 reviews1 month ago

I had a fantastic stay at Kristin’s Airbnb! The location was perfect.. just a short drive to supermarkets, a variety of dining options, a bakery, and the famous Devon House Ice Cream Parlor. Check-in was seamless and hassle-free, which set the tone for a great experience. The apartment itself was spacious, very comfortable, and well thought-out. I especially appreciated the labels on the drawers and light fixture….it made everything so much easier to navigate, from finding cutlery and cookware to figuring out which switch controlled the lights or fans. The water pressure was excellent, and there was always hot water…no complaints there at all. The couch was super cozy, perfect for relaxing after a day out, and the TV with easy Netflix access was a nice bonus. Would definitely stay here again and highly recommend it to anyone visiting the area!

Apartment in Kingston

What guests are saying

Luxury Condo with view @ Paddington

4.95 out of 5 average rating, 39 reviews1 month ago

I had an incredible stay at 48 Paddington in Kingston, Jamaica! From the moment I arrived, I was impressed by the cleanliness, comfort, and overall ambiance of the space. The location is perfect—safe, quiet, and conveniently close to everything I needed. The home itself was beautifully maintained, with modern amenities that made my stay super comfortable. The bed was cozy, the WiFi was fast, and the air conditioning was a lifesaver in the Jamaican heat! The host was exceptionally welcoming and responsive, ensuring I had everything I needed for a smooth and enjoyable stay. I would absolutely recommend this Airbnb to anyone visiting Kingston, whether for business or leisure. I’ll definitely be booking again on my next trip!

Condo in Kingston

What guests are saying

Cloud Vista Luxury 1BR Ocean Front Apt W. Pool

5 out of 5 average rating, 9 reviews3 months ago

Wonderful place!!! Looked just like the photos. Location, location, location very walkable to restaurants, the park overlooking the beach ⛱️ it was in the center of everything. There was a parking garage which was great because we had a rental car. The hosts were very communicative and responded timely. Only thing is we weren't able to gain access to the laundry closet because it was accidentally locked and no one was able to come out and unlock it. Other than that great stay! Will be back and book again!

Apartment in Kingston

What guests are saying

Luxe Oasis: Private, Gated, Chef-Ready, Pool, A/Cs

4.93 out of 5 average rating, 14 reviews3 weeks ago

Donya is indeed a super host. Her home is as pictured…I think it's even better in person! Am glad that I booked her beautiful home. We thoroughly enjoyed our stay as her place is super clean and organized, and everything is provided that you’d need for a perfect stay. The neighborhood is very peaceful and close to restaurants and other places of business, a quick drive, and you are on the highway. Don't hesitate to book this gem, you will love it Thanks, Donya for hosting us!

Home in Old Harbour