Villa holiday rentals in St. Mary Parish

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.

Escape to Paradise @ Breezy Castle St.Mary Jamaica

Escape to paradise at Breezy Castle, a nature lover's hideaway in the cool hills of St.Mary, overlooking the lush Blue Mountains and turquoise Caribbean Sea. Wake up to the refreshing mountain air and a cup of freshly brewed Jamaican coffee. The chirps of birds and warm Jamaican sunshine is to die for. Pamper yourself, retreat into this beautiful, serene villa and savour delicious Jamaican cooking. Cost for the villa = List price × number of guest/s AN UNFORGETTABLE EXPERIENCE AWAITS YOU!

Oceanside Villa Oracabessa Access to Ocean & Pool

VIVA LA MAR, a luxurious Oceanside Villa in exclusive Golden Cove gated community, just 20 minutes from Ocho Rios. Enjoy daily housekeeping and enhance your stay with a private Chef and Butler for a truly indulgent experience. Savor authentic Caribbean cuisine prepared just for you. One of only four resort villas, offering unparalleled luxury, tranquility, and breathtaking ocean views, with easy access to the new Ocho Rios Airport and direct Miami flights. Ask about adding a private Chef.

Catch My Drift Villa

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.

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.

Villa Retreat (Retreat, St. Mary, Jamaica)

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 mountains and ocean. 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 mins drive to (Ocho Rios, St. Ann), 10 mins drive to Tower Isle, 10 mins drive to 3 beaches and Rio Neuvo.

Staffed Villa with Spectacular North Shore Views

Located about 40 mins east of Ocho Rios, escape the hustle and bustle of crowded resorts and enjoy your new home away from home in Jamaica! Cabarita Lookout comfortably sleeps three families or three couples with extra air mattress available. Whether you are looking for an active family vacation loaded with activities for you and your kids or just a quiet private getaway with friends, Cabarita Lookout promises memories you'll treasure forever.

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.

Ocean front villa, Full Staff, Snorkeling on Reef

Our 4-bedroom villa has 180* of fantastic views of the Caribbean Sea. Steps down to the sea, where you can relax and sun or snorkel in the reef. Off the jetty, the sea is usually 2-3 ft high, great for swimming. A beach is 3 minutes' walk or you can snorkel to the beach. Each bedroom has A/C and ensuite bathroom. The villa is fully staffed with cook, housekeeper and caretaker.