Vacation rentals in Saint Mary

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

Tropical oasis Haven N Ochi Rios

Welcome to our beautiful beachside retreat in Ocho Rios, Jamaica—a harmonious blend of comfort, style, and Caribbean charm. Nestled in the heart of one of Jamaica’s most iconic coastal towns, our residence promises an unforgettable island getaway. Prime Location: Our beach house is enviably situated: Beach:A stone’s throw away from the world-famous James Bond Beach, where the golden sands and turquoise waters invite you for sunbathing, swimming, and relaxation. Minutes away from water rafting

Paradise Retreat - 3 bedrooms, 4 mins from airport

Escape to our tranquil retreat, nestled in the heart of Boscobel, St. Mary. This peaceful haven offers the best of both worlds - a calming atmosphere and unbeatable central location. Take advantage of our prime location, which is 4 mins away from Ian Flemmings International Airport and 15 mins from major towns: Port Maria and Ocho Rios. Experience the thrill of local attractions and hotshots a whisper away, then return to relaxation. Perfect for family get aways, couples and solo travelers...

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.

Almond Tree at Kyah Place

Almond Tree at Kyah Place is located in Guy’s Hill town center. It is a place where you can put a little distance between yourselves and the rest of the world. The lifestyle here is pure Jamaican in rhythm and tempo, “easy.” We offer you a window to local culture and a different way of living. Here you can receive specialized attention or can be left completely alone. We are only steps away from shops, restaurants, supermarkets and transportation. We look forward to hosting you. One Love.

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.

3BR | A/C | 24HR | Ocho Rios 15 min | Beach 10 min

Welcome to ISLAND LUSH, nestled in a gated community in the hills, with 24/7 security. Modern amenities include A/C, ceiling fans, Wi-Fi, hot water, security cameras, 2 water tanks and smart TVs. ISLAND LUSH is close to beaches, water falls, restaurants, spas, local street food, grocery, adventure parks and so much more... We offer a lush space where comfort meets island beauty while being surrounded by the quiet charm of the countryside. It's also just a short drive from Ocho Rios.

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

Oceanfront|Butler|Chef|Housekeeper|WelcomeBar

Villa Hestia is your private oceanfront villa in Boscobel — just 15 min from Ocho Rios and opposite Ian Fleming International Airport. Dive into the pool, swim in a secluded cove or try out the included kayaks & snorkelling equipment. A dedicated butler & housekeeper keep your minibar stocked and cook all in-villa meals. Four ensuite bedrooms, newly renovated interiors, lush outdoors, multiple gazebos and even a giant chess set complete the experience.

Tranquil Times villa

Tranquil Times Villa is located just minutes outside of downtown Ocho Rios. We are located in a private, gated community with 24-hour live security. We are conveniently located within minutes of all major attractions and hotels. Airport Transportation will be arranged. We are fully staffed and cannot wait to help make your vacation one you won't ever forget!!!

BeyondViewVilla/Tropical/ Pool/Starlink/SolarPower

Beyond View Villa offers a 360-degree view of lush mountainsides and stunning sea vistas, allowing guests to wake up to a breathtaking sunrise or unwind with a beautiful sunset hence the name Beyond View Villa. The cool breeze, whistling wind, and fresh, crisp air provide the perfect conditions to rest, relax, and recharge by the pool or on the deck.