Villa holiday rentals in Saint Mary

Olive Branch Villa Oracabessa *Luxury*

Just minutes from the beach and nestled in the exotic hills of Oracabessa, Olive Branch Villa sits on beautifully landscaped grounds with a panoramic view of the Caribbean Sea. This 10,900 square foot villa boasts 4 well appointed bedrooms each with a sea view. The villa features a swimming pool with a large deck overlooking the Oracabessa Bay with a fine dining experience and first class service to leave you with a smile. If it is your first visit we are confident that it won't be your last.

Tranquility Bay Oceanfront Retreat

Leave the stressors of home behind and revitalize yourself and your loved ones in the mystical retreat at Tranquility Bay. This oceanfront home is a little less than 2 hours from Montego Bay Airport and is centralized with dozens of tourist hot spots, including the famous Dunn's River Falls and Margaritaville in Ocho Rios. The location of the property has the convenience of grocery markets, banking, western union, gas stations, shopping, churches, gyms, restaurants, a local beach and much more.

Villa Retreat (Retreat, St. Mary, Jamaica)

Ocean View: Villa Retreat (at Tranquility Glades, Retreat, St. Mary) is a (fully furnished 3 bedroom / 2 bathroom) vacation villa/home. This hilltop residential neighborhood gives a view of both ocean and mountains. This villa is kissed by the wind which blows throughout the house. This entire house is ALL YOURS (when booked). Close to shopping, dining, famous attractions. It's 20 - 30 mins drive to (Ocho Rios, St. Ann), 10 mins drive to Tower Isle, 10 mins drive to 3 beaches and Rio Neuvo.

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.

Grande Haven Villa

Grande Haven Villa - Ultimate Relaxation * Located 5 minutes from Ian Fleming International Airport * This Mediterranean style villa is nestled behind a palm tree lined driveway in the hills of Gibraltar, overlooking the infamous James Bond Beach. The villa has 4 bedrooms each with private bathrooms, outdoor pool, wraparound veranda, 3 private balconies and shady palm trees for napping or reading a good book. Grande Haven Villa has everything needed for ultimate relaxation.

2BR Villa I Ocho Rios 15 min I Beach 10 min I 24HR

This air‑conditioned 2BR is just 15 mins from Ocho Rios and 10 mins from beautiful beaches. Bring your groceries to the fully equipped kitchen — make breakfast, or a relaxed dinner after a day of sun. Sip your morning coffee on the front patio as the sunrise warms the day, or settle on the cozy back patio to watch the sky glow with our tropical sunset colours. The community is peaceful and friendly—perfect for safe morning or evening walks and exchanging a warm “hello”.

Clare's Manor | Ocho Rios | Mini Golf Course

Enjoy a bright, private 2-bedroom home in a quiet, gated community just 10 mins from Ocho Rios town centre. The home features spacious king-size beds, modern bathrooms, and an open-plan living and dining area with a fully equipped kitchen. Enjoy a private mini-golf area and a peaceful backyard lounge with a waterfall fountain. Laundry is included, and most of the home is solar powered. Ideal for families or couples seeking comfort and easy access to the North Coast.

3BR | 24HR SOLAR | Ocho Rios 15 min | Beach 10 min

THE RUBY is a serene ECO SMART VILLA nestled in a gated community in the hills, 15 minutes from Ocho Rios and ideal for families & remote workers. THE RUBY features 24/7 security, solar, A/C, ceiling fans, Wi-Fi, 2 water tanks, fenced/gated yard, security cameras, workstation with monitors, 4 smart TVs, water filtration, patio with lit pergola, BBQ, basketball arcade & board games (Cards/Jenga/Chess/Checkers/Dominoes/Ludo). Extras: crib, baby bath and highchair.

A View To A Kill - Your Private Tree House Villa

Kick back and relax in this beautifully renovated stylish home. Set at the top of a hill, this idyllic home offers an expansive view of the ocean, and Jamaica’s Blue Mountains. Newly renovated, A View To a Kill has 3 bedrooms, all with full en suite bathrooms. A gorgeous modern kitchen, large pool and entertaining deck, and a full outdoor bathroom. Stay with us, relax, and get away from busy life. Great for families and friends!

Beachfront Villa in Strawberry Fields St Mary

The Lookout is a chic seafront villa tucked way in a secluded part of Jamaica, that gazes out over the Caribbean Sea. Boasting its own private beach, it offers a serene escape where the only sounds are the rhythm of the waves and the local birds. Designed for effortless relaxation, The Lookout comes fully equipped for your convenience. Amenities include a pool, BBQ area, a charming rustic beach bar and fire pit.

Breezy Castle villa with Sea & Blue Mountain views

A secluded mountain villa with ocean views, a private pool, a fireplace, and a swing in the heart of tourist Jamaica. Just 10 minutes from Dunn’s River Falls, Ocho Rios Harbor, Dolphin’s Cave, and Mystic Mountain. Enjoy panoramic ocean views from a lush bird sanctuary. The sea breeze, birdsong, and tranquility surrounded by a tropical garden. Complete seclusion and relaxation. We look forward to welcoming you!