Vacation rentals with a pool in Saint Catherine

Chillax Island Stay

Welcome to our upgraded retreat! Unwind in our spacious backyard, featuring a large pool and a cedarwood gazebo with soft lighting—perfect for relaxation. Our property offers unparalleled privacy with a high wall and intimate layout for your peace of mind. Important Note: All amenities are exactly as shown in the photos and described here. The property does not include a garden or landscaped yard. Refunds will not be provided for amenities or features not listed or pictured in the description.

3D's Comfort Villa w/ Pool

Enjoy this peaceful and comfortable villa with a large pool and lots of amenities in the centrally-located gated community of Phoenix Park Village. Perfect for a refreshing vacation or staycation. The property is less than 10 mins from Hellshire Beach, KFC, Starbucks, theatre & more, 45 mins from Ocho Rios, Dunns River Falls and Norman Manley Airport. Take advantage of our fully stocked mini bar (3 night min stay required) and our beautifully landscaped outdoor space with lots of room for fun.

The Vistas Caymanas

Escape to tranquility in this tastefully decorated single family home (4 persons limit). Nestled amidst rolling hills and serene landscape, this idyllic retreat offers a haven of peace and comfort. Surrounded by nature's beauty, this gated community boasts a beautiful communal space with facilities such as a pool, jogging/ walking track, football field, basketball court, tennis court and multiple gazebos for relaxation. Just minutes away, there is an inviting golf/ country club and a polo club.

Exquisite Manor

Kick back and relax in this calm, stylish and ultramodern space. This luxurious property is located in Old Harbour's most prestigious gated community. This unique and family friendly space boats a myriad of modern amenities that gives the perfect home away from home. It is 45 minutes from Kingston and 5 minutes away from Old Harbour's finest restaurants, entertainment hubs and shopping malls. This relaxing, safe and entertaining environment is close to many well renowned Jamaican attractions.

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.

The Caymanas Villa

My place is a modern country side home that is close to golf resorts, polo clubs, beaches, the city center, with mountain side views. My place is good for couples, solo adventurers, business travelers, and families. This is a secure facility that is centrally located in Jamaica with within 1km from both north-south and east-west high way 2hrs drive to Montego bay and 20 min to Kingston. This facility has recreational spaces, such as jogging trail, swing pool, basket ball and tennis court.

Sandhill's Private Pool and Gym, Luxxe 2 Bed Villa

Escape to your private oasis! Enjoy a private plunge pool, a large gym, private backyard; entire ground floor, and easy access to Hellshire’s beautiful beaches. Our fully air-conditioned villa features high-speed WiFi, smart TVs, and all the comforts of a modern home—perfect for families or groups. Stock up on groceries or savor fresh seafood from Hellshire’s famous food stalls. Relax, unwind, and create unforgettable memories in this cozy retreat. Save now and book later.

Elegant 2BR, Pool, Gym & Fully Loaded Games Room

Make lasting memories with your loved ones at this family-friendly 2-bedroom retreat! The home is fully furnished with modern comforts and features a vibrant games room for endless fun, plus access to a pool and gym for all ages to enjoy. With plenty of room for everyone, the home combines relaxation, entertainment, and convenience. Located just minutes from town, you’ll have quick access to restaurants, shops, and local attractions, making it easy to plan family outings.

Chillax Manor Your Private Oasis for Relaxation

Get this entire space with Pool access! Nestled in a gated community, Chillax Manor is perfect for your next getaway. The Manor offers you a luxury hotel feel. It is the getaway that your family will enjoy while being centrally located place to everything. You deserve to chill in this impeccable two-bedroom, one-bathroom peaceful spot with a pergola. Chillax Manor is also equipped with the necessary toiletries and a few complimentary beverages/snacks.