Vacation rentals in Annotto Bay

Buff Bay Farms & Villa - Spacious 4BR Floor

Welcome to Buff Bay Farms & Villa, your peaceful escape tucked between the mountains, the Caribbean Sea, and soft island breezes. This 4-bedroom, 3-bathroom full-floor retreat offers a gentle mix of luxury, comfort, and authentic Jamaican warmth. Wake up to the sunrise, unwind on the patio as the sun sets behind the hills, and enjoy the quiet charm of Portland—one of Jamaica’s most untouched, beautiful parishes. Perfect for family getaways, group trips, reunions, work retreats, and long stays.

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.

Seahorse Cottage

PLEASE NOTE: The property does not accept children under 13. Seahorse Cottage is a modern jungle retreat just five minutes from Frenchman’s Cove. Wake to birds chirping, views of Nonsuch Falls, the Blue Mountains, and the coastline. This two bedroom, one bathroom cottage features a wraparound terrace, strong WiFi, and access to our 25 meter lap pool and outdoor Jungle Gym. Quiet, private, and surrounded by nature, it’s the perfect place to reset and experience the calm side of Port Antonio.

WaFiEartAir Ecoh Village: Earth Cabin

A space for realizing harmonizing with the earth. Here, you'll find pure ,fertile soil, fresh springs and a tranquil river with soothing sounds where there's no city noise, only nature's corenection. Welcoming beings who share our vision of living in harmony with everything there is, whether you’re drawn to art, building with natural materials, or seeking a blissful realm to know self, there’s a space here to vibe, great ones🪶 a space for pure alkaline electric food. nothing dead.

Relaxing 2BR Escape in Buff Bay - AC, Water Heater

Welcome to your home away from home in the heart of Buff Bay, Portland. This bright and spacious 2-bedroom Bliss is perfect for families, couples, or small groups seeking comfort and convenience. Enjoy a fully equipped kitchen, cozy living area, and modern amenities like AC and Wi-Fi. Step outside to a peaceful neighborhood just mins from G&B Jerk Center, Steadman River, and San Shy Beach. Here to relax or explore? Buff Bay Bliss offers the perfect base for ur Portland getaway.

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.

Cottage Blu

Disclaimer: AN SUV OR 4x4 VEHICLE IS RECOMMENDED! AIRPORT PICKUP IS AVAILABLE AT AN ADDITIONAL COST. Cottage Blu is a hidden gem nestled by a serene river, with the aroma of fresh coffee wafting from a nearby farm. It's the perfect retreat to unwind and connect with nature. It is the perfect cozy getaway! Nestled amidst nature, this charming cabin offers rustic charm, modern amenities, and a serene ambiance. Explore nearby hiking trails, and enjoy the tranquility of nature.

Our Escape, Tiny Home in Blue Mountains w/ River

Get cozy and unplug in nature at this off-grid, tiny home at Our Escape's unspoiled twenty acres property. This rustic cabin offers all modern comforts and is nestled in the Portland side of the Blue Mountains. This unique space serves as the perfect retreat from all the modern world noises. Let the countless bird species serenade you, while you hike or swim in our private river. Let the fireflies be the only lights you see at night while you stare at the constellations.

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

Modern Nature's Escape at the Falls

Welcome to your peaceful getaway at Cabin at the falls where nature meets comfort, as the sound of cascading water sets the perfect backdrop for your stay. This cozy, cabin is perched just a hike away from the falls, offering a rare blend of seclusion, comfort, and natural beauty. Whether you are hiking to the base of the falls,or soaking in the sights and sounds of nature, this cabin is your perfect escape into the wilderness without giving up the comforts of home.

Rural trek worth the view farm cottage in Portland

Relax at this unique and tranquil getaway 20 mins drive from the main road (4WD recommended) Nature lovers paradise with exotic fruit farm on property. Amenities including AC, hot water and wifi. Nearby coffee or blue mountain tours, Sommerset falls, numerous beaches and rivers. Guest should expect to see animals, flora and fauna typical of the Jamaican countryside and noises consistent with being on a working farm property