Vacation rentals in Gayle

Jamaica Escape | 2BR | Gated | 15 Min to Ocho Rios

This elegant 2-bedroom retreat is designed for guests who value comfort, privacy, and convenience. Situated in a secure gated community in Boscobel, St. Mary, the property offers a relaxing atmosphere with easy access to Ocho Rios, world-famous attractions, pristine beaches, and authentic Jamaican experiences. Whether you're planning a romantic getaway, family vacation, or extended stay, Hilltop Paradise Retreat provides the perfect setting to relax, recharge, and create unforgettable memories

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!

Braata @ Little Bay (Ocean View Villa)

In Jamaica, Bratta means giving a little bit extra and hoping you’ll come back. And that is exactly what you’ll get at BRAATA@ Little Bay–more space, more comfort, more beauty. You won’t be able to stay away. Great for family reunions & weddings Situated just outside the historical town Port Maria on Jamaica’s north coast, this brand-new villa has a stunning sea view in every room. It has four spacious en-suite bedrooms, each with its own private balcony, and a self-contained studio apartment.

4BR Oceanfront Villa Pool Chef Option Nr Ocho Rios

Wake up to sweeping Caribbean sea views at this private 4-bedroom oceanfront villa, just 15 mins from Ocho Rios. * Perfect for families and groups, it features en-suite bedrooms, a private pool, and inviting outdoor spaces for dining and relaxing. * Enjoy the ideal mix of seclusion and convenience — peaceful and tucked away, yet close to beaches, restaurants, and attractions. * We can arrange a private chef, housekeeping, airport transfers, and grocery pre-stocking so you can arrive and unwind.

Eco Cottage With Private River

Discover your private tropical sanctuary surrounded by lush gardens and hummingbirds. Unplug and unwind in a spacious, bright apartment with a king bed, kitchenette, spring water shower, outdoor bath, hammock, fire pit, and yoga area with hanging seats. Explore nearby waterfalls & beaches for a peaceful nature escape. Nestled in St. Mary’s scenic mountains, just 40 minutes from Ocho Rios or Ian Fleming Airport , this gated retreat offers the perfect blend of rustic comfort, peace and adventure.

Beachfront Villa & Chef | Coral Reef | Ocho Rios

Wake up to Caribbean waves and step onto your private 15x45ft deck, just 15 feet from the ocean. Your private coral reef is a 7-minute swim away snorkel gear, kayak, and paddleboard all included. Inside, every finish is hand-crafted from guango with original Jamaican artwork throughout all available for purchase. Your Chef Choose from our prix-fixe menu or visit the local market and have meals prepared to your exact taste Jamaican jerk to international cuisine, your chef has it covered.

Catch My Drift Villa: Chef services available

Catch My Drift is a gated eco-inspired villa built and uniquely designed to incorporate locally sourced materials. Our units layer modern design with thoughtful touches and sustainability throughout. We offer the privacy and seclusion needed for complete relaxation. Enjoy our splendid view, swimming pool, outdoor kitchen with grill in our spacious backyard. We are only a 20 minute ride from Ocho Rios, home of popular attractions such as Dunns River Falls or a quick trip to the beach.

Zuma Villa|3BR|Rooftop|Gated|Pool|10 min Beach

Welcome to Zuma Villa, your tropical oasis nestled in the heart of Jamaica. Surrounded by lush greenery and just moments from pristine beaches, Zuma Villa offers the perfect blend of comfort, style, and island charm. Whether you're here to relax, explore, or indulge in local culture, our villa is designed for an unforgettable stay. From the rooftop sea views to the infinity pool, you'll feel right at home while experiencing the best of Jamaica. Come as guests, leave as family!

Almond cottages in Tropical and seaside garden

Almond Cottage is a cozy retreat with a bedroom, bathroom, and fully equipped kitchen, opening onto a wonderful, spacious veranda set in a lush tropical garden with glimpses of the sea. Just steps away, our seaside platform is perfect for sunrise, stargazing, yoga, or fishing. In the evenings, enjoy fireflies and the soothing sound of the ocean. You can also fish directly from the property or, when conditions allow, take a refreshing jump from the cliffs into the sea

Purple Passion @ Blessings at Strawberry Fields

Purple Passion is a one-bedroom, dorm style cottage that is furnished with 1 queen bed and 1 bunk bed. Perfect for relaxation with the whole family with less than one minute walk to get to the beach. Our restaurant on property makes a scrumptious warm meal from scratch done to order. Ask about our meal plans. Purple Passion is also one of two dorm style cottages we have on the compound, great choice for traveling on a budget with a group of friends or family!

Eco Cabin in Portland Private Waterfall & Pool

Our Eco Cabin is nestled in the Blue Mountains side of Portland. Our 20 acres are bordered by the crystal-clear waters of a river fed by multiple springs. Just 10min walk away is our private Waterfall, so mesmerizing we named it Beauty-Fall. Reconnect with nature, from the moment you rise, you will feel as if you are among the trees and the birds, our floor-to-ceiling glass windows bring the outdoors in while in complete privacy and comfort.

Hailey’s Hideaway - Hideaway 1

Looking for a quiet, private, cozy stay? We are 5 mins away from the town of Ocho Rios, where you’ll find lovely beaches, restaurants and many attractions such as Dunn’ River Falls, Margarita Ville, Dolphin Cove..and many more. We pride ourselves on delivering a warm and super cozy atmosphere. Cool , airy spaces to relax and stay a while. See you soon at Hailey’s Hideaway. Please note units are located on the top floor of building.