Guesthouse vacation rentals in Saint Mary

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Top-rated guesthouse rentals in Saint Mary

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The exterior of the property is showcased, featuring a spacious stone-paved area surrounded by well-maintained gardens. Lush greenery and tropical plants enhance the inviting atmosphere, while the white balcony railings add a touch of elegance. Bright blue skies create a cheerful backdrop.

Guesthouse in Boscobel

Serenity Guest House near Ocho Rios

Newly Refurbished 2BR Apartment with Pool – Near Ocho Rios Enjoy a relaxing stay in this modern 2-bedroom apartment, just 15 minutes from Ocho Rios. Recently refurbished, it features a stylish living space, a fully equipped kitchen, and pool access for the perfect tropical retreat. Close to stunning beaches, restaurants, and top attractions like Dunn’s River Falls, Mystic Mountain & many more, this is the ideal spot for your Jamaican getaway. Book now for comfort, convenience, and island vibes!

Guest favorite

A stunning coastal view features a vibrant array of turquoise waters, with lush greenery outlining the shoreline. An island is prominently situated in the distance, framed by gentle waves and a diverse landscape, creating a serene and inviting atmosphere.

Guesthouse in Tower Isle

4.77 out of 5 average rating, 31 reviews

Rio Nuevo View Guest House - For Work or Family

The Rio Nuevo View Guest House is a modern elegant sea-view property with accommodations for 6 guests located 15 minutes east of Ocho Rios. The property provides modern amenities with all the privacy our guests require. The grounds are secured with an electronic gate and closed-circuit cameras monitoring the outside property. Enjoy a 100 Mbps TP-Link mesh Wi-Fi network for seamless connections. Air-conditioned bedrooms, living room, and dining room. Ideal for busy workers and large families.

A comfortable seating area is shown, featuring a light-colored sofa with accent pillows and a matching armchair. A glass coffee table is centered on a woven rug, with decorative bowls positioned on top. Soft lighting from lamps enhances the inviting atmosphere.

Guesthouse in Glengoffe

5 out of 5 average rating, 4 reviews

Mama T's Guest House

Recently renovated with the latest modern amenities, this 50 year old home is nestled in the cool mountains of Glengoffe, St. Catherine. An oasis for relaxing, disconnecting and being one with nature. You can choose to sleep in or just lay in bed listening to parrots chatting in the surrounding trees. Arise to a spectacular sunrise and step outside to the east patio where you can pick breakfast from the trees (bananas, coconuts, mangoes) curl up in a hammock to read a book or walk the trail.

A shared pool area is surrounded by lush palm trees, with a thatched cabana offering shaded seating. The clear blue water of the circular pool reflects the bright sky, while the picturesque ocean can be seen in the background.

Guesthouse in Salt Gut

Ocean Front 4 Bedroom Villa with Housekeeper

Welcome to Villa Laura in Oracabessa, Jamaica - a beachfront paradise just 15 minutes from Ocho Rios. This fully equipped villa features a spacious veranda with stunning Caribbean Sea views, perfect for tropical relaxation. Enjoy direct beach access and snorkeling at the coral reef 100 feet offshore. The 4 bedroom villa includes a full kitchen, free WiFi, internet TV, and access to a shared pool with a thatched cabana. Villa Laura offers both tranquility and proximity to local attractions.

Guest favorite

Lounge chairs with blue cushions are arranged around a clear swimming pool, surrounded by potted plants and flowering bushes. A dining area can be seen in the background, with white furniture set against a serene garden landscape.

Guesthouse in Boscobel

4.87 out of 5 average rating, 84 reviews

Endless Summer

Endless Summer is a beautiful, quiet seafront property, located immediately across from Ian Fleming International Airport. We are located 15 minutes east of Ocho Rios, so we are close to several major attractions, beaches, family-friendly activities and dining. You’ll love my place because of the ambiance, and the location. Public or private transportation is readily available. Endless Summer is ideal for individuals seeking a quiet, place to relax, definitely not for the party crowd.

Guest favorite

A two-story residence is framed by lush greenery and well-maintained gardens. The exterior features large bay windows, adorned with decorative ironwork. A welcoming balcony extends from the second floor, while a pathway leads to the entrance, enhancing the inviting atmosphere of the property.

Guesthouse in Port Maria

4.88 out of 5 average rating, 77 reviews

Cheerful two bedrooms with large backyard space

Forget all your worries in this spacious green and serene space. Five (5) minutes from the beach for total relaxation. Grab your juicy Jamaican patties in Town and then don't forget your jerk chicken and jerk pork right in the back yard. Swing in comfort and enjoy cool breeze on your phones or reading a book under the overflow of Jamaican fruit trees. Cut your favourite rose in the lush garden. 15 minutes from the Ian Flemmings Int'l Airport and 35 mins from the famous Dunns River Falls.

Superhost

A serene beach scene captures gently lapping waves against a sandy shore, framed by lush palm trees. The calm water reflects the clear blue sky, creating a tranquil coastal atmosphere. A stone wall marks the edge of the beach, blending with the natural landscape.

Guesthouse in Boscobel

4.92 out of 5 average rating, 13 reviews

Cozy Island Bliss

Escape to tranquility just 20 minutes from Ocho Rios! Nestled in a safe residential area, our cozy 2-family style guest house offers comfort and relaxation. With 2 bedrooms, a full kitchen, and a small patio, it’s perfect for unwinding. Discover nearby attractions like Dunn’s River Falls and Dolphin Cove, both a short drive away. Whether you’re seeking adventure or serenity, our guest house is your gateway to the true essence of Jamaica. Book your stay to experience island living!

Guesthouse in Robins Bay

New place to stay

Moonlight Magic Seaside Studio

Moonlight Magic (suite upstairs) boasts a whirlpool bath encased in natural chalk stone with a bay window opening right to the sea! The Queen size bamboo bed looks right out onto your own private beach. Includes a nicely designed kitchenette, so you have the option of cooking for yourself or getting meals from our restaurant. Moonlight Magic is just one of the accommodations on our 18 acre eco-friendly resort called Strawberry Fields Together!

Superhost

A light-filled studio features twin beds with soft, blue bedding, arranged alongside a wooden side table and a lamp. Natural light flows through the window, illuminating the high ceiling with exposed beams. A cozy area rug adds warmth to the floor.

Guesthouse in Oracabessa

New place to stay

Quiet Cottage in Oracabessa

Oracabessa Escape! Peaceful garden studio in Oracabessa, 5 mins from a private beach (key on request). Shared pool on property with main house and 1 other cottage. Twin beds convert to king. Separate kitchen with 2-burner stove. Close to GoldenEye (day passes available) and Ian Fleming airport with daily Miami flights. Meal plans and housekeeping available on request. Lush, simple, and serene. Ideal for couples, creatives, and nature lovers.

The inviting swimming pool features a zebra-striped float in vibrant blue water. White lounge chairs surround the pool area, complemented by an umbrella providing shade. Lush greenery in the background enhances the serene atmosphere.

Guesthouse in St. Mary Parish

4.7 out of 5 average rating, 10 reviews

876 Oasis -King Bed - Sunset View-Unheated Jacuzzi

Escape to 876 Oasis, just 12 mins from Ocho Rios. This spacious retreat in a safe place offers a stunning ocean view, onsite pool & pool table, full kitchen, and a 1 bedroom with a king bed and AC. With a huge veranda that has a swinging chair, you can enjoy peace and comfort. We offer self-check-in, friendly service, and optional taxi, food delivery and much more. The perfect escape. Clean, serene & close to attractions your oasis awaits!

A functional kitchen corner is seen, featuring a stove, sink, and countertop with utensils. The door stands open, providing a view of the lush garden outside. Natural light enters through the doorway, illuminating the tiled floor and the colorful patterned curtains.

Guesthouse in Tower Isle

4.67 out of 5 average rating, 9 reviews

Shanty Shack

This shanty shack is a converted garage. Perfect for the budget conscious back packer who does not want to stay in a tent and have your own private bathroom and shower. Wake up to our lush garden and pick your banana or avocado for breakfast. Depending on the season, we have many fruited trees available for your picking. Sunbath on our deck and take dip in the pool. We are close to all Ocho Rios attractions as we are 10 minutes away.

A paved pathway winds through a lush garden, bordered by tall palm and evergreen trees under a clear blue sky. The white building can be seen in the distance, providing a hint of the retreat's spacious surroundings.

Guesthouse in Ocho Rios

3BR/2.5BA*Ocho*Rios*Stay w/Chef*Ready*Nearby*Beach

✨ Escape to the tranquil hills of Upton and indulge in this stunning 3-bedroom, 2.5-bathroom retreat that offers breathtaking mountain views and comfort. Perfect for families and friends, this newly refurbished home has everything you need—from private chef options to nearby beaches like Sunset Beach and Frankfort Bay. Only 10 minutes from Ocho Rios, your dream vacation starts here! 🏝️