Holiday rentals with a pool in Jamaica

3BR 2-Story Villa in Ocho Rios with Private Pool

Indulge in pure luxury at our captivating 3-bedroom villa tucked away in a gated community with 24-hour security. This haven is a mere 5-minute drive from the bustling heart of Ocho Rios. Revel in the convenience of proximity to supermarkets, restaurants, nightlife & adventures. Immerse yourself in exhilarating attractions like Dunn's River Falls, Margaritaville, Mystic Mountain & Dolphin Cove. Your Jamaican dream escape begins here – a symphony of comfort, luxury, and unforgettable experiences!

2BR Townhouse with staff, gym, pool & beach access

Escape@20 is a lovely townhome that guarantees a truly relaxing and memorable experience. A friendly housekeeper/cook is included at NO EXTRA COST!! You just need to purchase the groceries. The townhome has an open floor plan with living and dining room opening out to a covered patio and a backyard. Guests can enjoy breathtaking views of the neighboring yacht docking area, swimming pool, gazebo/bbq grill space, gym, playground for kids, 24 hour security and complimentary beach access nearby.

"Smallah" 4-br seaside villa own pool, resort area

Welcome to Smallah Villa, our spacious and elegantly designed 4-bedroom, 4.5-bathroom oceanfront townhouse in the Freeport Area of Montego Bay! This stunning property is the perfect getaway for families or groups of friends looking for a relaxing retreat in Caribbean Paradise. It comfortably accommodates up to 10 guests. With private infinity pool and a pier for private boat pickup. Premium Services ($ - Additional Fee) • Grocery Shopping & Delivery Service ($) • Cook & Clean ($) • Driver ($)

Mother Nature

*Mother Nature ist ein freistehendes rundes Steinhaus mit begrünter Dachterrasse. Das Haus verfügt über ein Kingsize-Bett, einem eigenem Badezimmer, Holz- und Steinterrasse, sowie großem Garten. *Außerdem steht eine überdachte Außenküche zur Verfügung mit allen Utensilien die du benötigst. Kochen mit Blick auf die Berge. *Und wieder einen anderen Blick hast du vom überdachten Gasebo. Inmitten Mutter Natur kannst du die Seele baumeln lassen und Vögel, Sterne und Wolken beobachten. *Feel free

Oceanfront Panoramic Views 3br Beach Pool Gym

Your Caribbean dream escape awaits in our spacious oceanfront 3br/3.5ba condo with private corner balcony and sweeping ocean views. Lounge by the pool, stay fit in the gym/pickleball court or unwind at the sandy beach. Highlights- Large Waterfront Pool & Pool Deck * Private Beach Access * Gym * Tennis/Pickleball * Kids Play Area * Fast WiFi* Gated Waterfront Community * Chef on request * Spa Services * Concierge Services * Driver Upon Request* Add our listing to your favorites by clicking❤️

Private | Beach | Pool | Luxury | Culinary Escape

Villa Blanca, our airy white-on-white modern beach villa, is part of the ONLY Villas Collection — a curated blend of boutique-hotel service and private barefoot luxury above a secluded sandy beach. Designed primarily as an adults-oriented escape focused on peaceful, elevated, culinary-driven experiences. Enjoy complete privacy in your villa, plunge pool, and outdoor living spaces with private chef and villa hostess services. Guests 18+ preferred. Younger children only with prior approval.

Seafront Modern Loft w/ Pool - Negril’s West End

Experience the best of Negril from this stylish loft studio perched on the area’s famous cliffs. With sweeping ocean views, modern design, and resort-style amenities, this seafront escape is perfect for couples, friends, or small families seeking both relaxation and adventure. Good to Know: The property is part of a newly developed condo-hotel, with certain areas still under construction. Guests may notice light construction during their stay, but all private areas of the loft are ready.

Starfish Cottage

IMPORTANT NOTE: This property does not accept children under 13. Experience tranquility and beauty at our cottage, perfectly positioned for stunning views of the Blue Mountain peak, the Port Antonio coastline, and a nearby waterfall. Delight in the frequent visits from hummingbirds to our feeders, adding a touch of nature’s charm to your stay. Conveniently located, you'll find yourself at the heart of all the attractions that the area has to offer.

Ocean front luxury Villa in Jamaica

Welcome to Tikal, an ocean front luxury villa, exquisitely remodeled in May 2021, with an airy modern Caribbean style. We are adjacent to Chukka Cove Horse & Adventure Farms, noted as Jamaica's premier tourist attraction provider. We are conveniently nestled between Montego Bay and Ocho Rios, only 50 minutes from Montego Bay International Airport. We are within 30 minutes of most major tourist attractions, and the cruise ship port in Ocho Rios.

Hospitality Expert EL1: Private Pool, Beach, Chef

Eden Luxe 1 is set on a beautiful hillside offering panoramic views of the sparkling Caribbean Sea. This 2 BR ultra luxurious villa is part of the HOSPITALITYEXPERT Eden Estate, set in the heart of Spring Farm, an upscale Montego Bay community, right above the Half Moon Golf Club. Luxe 1 sleeps up to 6 guests, a private chef is available for hire and we offer pre-stocking services. Includes complimentary access to Tropical Bliss Beach Club.

Luxury Oceanview 4BR Villa w/ Balcony, Pool & BBQ

Welcome to BayWatch Villa – a 4BR luxury retreat in Montego Bay. Marvel at breathtaking views of the harbor and Caribbean Sea both day and night. Share unforgettable moments with family and friends. Enjoy spacious living spaces, a modern kitchen, and laundry convenience on premises. Stay connected with Wi-Fi throughout, even by the pool. With solar backup, you’ll always have power for the essentials. Note: AC is not available on backup power.

Summer special Sanguine Suite Treasure Beach

Unwind in this serene and stylish seaside retreat, thoughtfully designed for relaxation and comfort. Enjoy your own private plunge pool, fully equipped kitchen, and expansive rooftop deck with refreshing sea breezes and tranquil surroundings. Spacious, bright, and beautifully airy, this coastal escape offers an atmosphere that truly must be experienced in person. Traveling with family or friends? Reach out to us for our 3-bedroom option