Holiday rentals with a pool in Portmore

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Portmore

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

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Guest favourite

Condo in Kingston

5 out of 5 average rating, 11 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 favourite

Bungalow in Portmore

4.88 out of 5 average rating, 146 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, 10 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.

Superhost

Condo in Kingston

4.72 out of 5 average rating, 53 reviews

The Sunset Villa - 2BD APT w/ Pool & Lovely Views

The whole group will enjoy easy access to everything from this centrally located place. This newly built modern apartment features an open concept layout, two spacious bedrooms with en suite bathrooms and AC units, tasteful furnishings and décor, and a swimming pool to enjoy. In addition, this APT boasts designated underground parking, free WIFI, Cable TV, wheelchair access (elevator), and 24HR security. Restaurants, a supermarket and shops are within walking distance or a short drive.

Guest favourite

Home in Caymanas Country Club Phase I

4.86 out of 5 average rating, 14 reviews

Irie Luxury Home, Caymanas w/pool

Forget your worries at Irie Luxury, a spacious and serene home centrally minutes away from major tourist and business points (Airport 30, New Kingston 20, Dunn’s River Falls 45, restaurants 10-15, Hellshire 10, Portmore 10. It is perfect whether vacationing or travelling for business. Nestled in a gated community with 24 hours security you can safely sit outside, explore the pool, gazebos, football field, basketball and tennis courts, etc. A comfortable stay is guaranteed!

Guest favourite

Condo in Kingston

4.9 out of 5 average rating, 146 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.