Villa holiday rentals in Saint Mary

*Luxury Rental* The Palms at Galina

Let us take the work out of planning your next trip to Jamaica! We offer an all inclusive option! > 8 bedrooms > 7.5bathrooms >>Property accommodates up to 16 guest >> Housekeeping & personal daily Chef are included in the rental price >> We can arrange round-trip airport transportation and/or a full-time driver >>Tour guide services if needed >> Need more room? Book our sister property: The Palms at Wentworth for an additional 4 bedrooms and up to 8 more guest (inquire for more details)

Family · Value · Wi-Fi

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.

Location · Value · Laundry

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.

Location · Value · Access

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.

Value · Location · Outdoor spaces

Villa Blue Jade - 2BDRM |Solar, AC| Near Ocho Rios

✨ Retreat to a serene 2 bedroom home in a secure gated community featuring reliable solar power, fast satellite internet, comfortable beds, fresh linens and cold air conditioning. Located between Boscobel and Ocho Rios, Villa Blue Jade is just 7 mins drive to the Ian Fleming Airport and several beaches. Relax knowing there’s water reserve and 24/7 security. End your evenings stargazing under the backyard pergola and enjoying the cool mountain breeze. Independently owned and operated.

Location · Cleanliness · Quiet

3BR+DEN Ocho Rios 15 min SOLAR Beach 10 min 24hSec

SUNLIGHT RETREAT is your luxurious family friendly home away from home in a gated community in the hills with 24/7 security. It's close to Ocho Rios, local beaches and designed with modern amenities such as SOLAR, A/C, ceiling fans, Wi-Fi, water tank, hot water, security cameras and smart TVs. It's close to restaurants, adventure parks, water falls, sightseeing, street food and lots of other activities. It's also a quiet, peaceful, relaxing retreat; you choose how to spend the time.

Family · Location · Walkability

3BR SOLAR Ocho Rios 15 min Beach 10 min 24hrSec AC

THE RUBY is a serene ECO SMART VILLA in a gated community in the hills, 15 minutes to Ocho Rios and ideal for families/remote workers. It features 24/7 Security, SOLAR, A/C, Fans, Wi-Fi, 2 Water Tanks, Fenced/Gated Yard, Security Cameras, 4 Smart TV, Water Filtration, Patio with Lit Pergola, Basketball, Cards, Jenga, Chess, Checkers, Ludo, Dominoes, BBQ, Baby Crib & Bath, Highchair and Workstation with Dual Monitors. THE RUBY VILLA is our home away from home... Enjoy your stay!

Family · Location · Check-in

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 Ocho Rios, beaches, water falls, restaurants, spas, local street food, grocery, adventure parks and so much more... NEW: 7-seater van for rent! We offer a lush space where comfort meets island beauty while being surrounded by the quiet charm of the countryside.

Family · Location · Condition

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.

Value · Family · Barbecue

3BR+Den | Beach 10 min |Ocho Rios 15 min |24HR Sec

Welcome to HILLTOP RETREAT — a serene design-forward villa, in a gated community in the hills, with 24/7 security. Modern amenities include A/C, ceiling fans, Wi-Fi, hot water, custom cabinetry, premium toiletries, security cameras, workstation with ergonomic chair and smart TVs. It's also just a short drive from Ocho Rios. Bright, light-filled spaces invite you to slow down and settle in. Gather in the open living area or unwind in the enclosed patio surrounded by greenery.

Value · Location · Nearby

Clare’s Manor | Mini Golf w/ Outdoor TV Lounge

September Savings at Clare's Manor!!!! Add a little fun to your Ocho Rios stay! This two-bedroom villa features a private mini golf area at the front and a covered outdoor lounge with a TV and waterfall fountain at the back. Inside, you’ll have two air-conditioned bedrooms with king beds, two bathrooms, a full kitchen and open-concept living space. Guests also have access to the shared community pool, all within a gated community approximately 10 minutes from Ocho Rios.

Family · Value · Comfort

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.

Family · Location · Outdoor spaces