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Holiday houses in Middlesex County

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Middlesex County

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
The exterior of the villa is showcased at night, illuminated by red lighting from the windows. A well-paved driveway leads to the entrance, framed by decorative plants. The two-story structure features a modern design with balcony railings and a welcoming ambiance.
Home in Ocho Rios
4.92 out of 5 average rating, 109 reviews

3BR 2-Story Villa in Ocho Rios with Private Pool

Indulge in pure luxury at our captivating 3-bedroom villa tucked away in a gated community with 24-hour security. This haven is a mere 5-minute drive from the bustling heart of Ocho Rios. Revel in the convenience of proximity to supermarkets, restaurants, nightlife & adventures. Immerse yourself in exhilarating attractions like Dunn's River Falls, Margaritaville, Mystic Mountain & Dolphin Cove. Your Jamaican dream escape begins here – a symphony of comfort, luxury, and unforgettable experiences!

Guest favourite
The exterior of a modern one-bedroom retreat is framed by lush greenery and palm trees. A smooth driveway leads to the entrance, highlighted by minimalist architecture and large windows, inviting guests to enjoy the serene surroundings.
Home in Galina
4.98 out of 5 average rating, 64 reviews

Oasis Getaway in Saint Mary

Escape to OD’s Oasis, a charming one-bedroom retreat in St. Mary! Just 10 minutes from Ian Fleming Airport and close to the iconic Galina Lighthouse, this cozy getaway is perfect for two. Tucked in the Lighthouse community, it features an open-concept kitchen and living area for comfort. Please note the yard and outdoor areas are shared. The road has a few bumps, but the peace, charm, and convenience make it worth it. With Ocho Rios and Port Maria nearby, your dream island escape starts here!

Guest favourite
A charming villa with a spacious covered patio is surrounded by lush greenery. The garden features tropical plants and a seating area with dark-finished furniture. Large windows provide natural light to the interior, while the double-story structure is enhanced by wooden accents and palm trees.
Villa in Ocho Rios
4.93 out of 5 average rating, 75 reviews

Private Seafront Villa near Ochi

Located directly on the ocean and room for 7 -- bring the Fam! Stylish Villa with three bedroom plus sleeper-den with four full bathrooms offers Caribbean charm and modern sensibilities. Full kitchen, super-comfy living area fronts an expansive dining/bar and lounge area with views of the sea that go on forever. Included: Starlink Wifi, a 65" SmartTV and a/c throughout; your private housekeeper/cook is there to take care of your every need. Enjoy a unique, relaxing Jamaican vacation today!

Guest favourite
Home in Ocho Rios
4.91 out of 5 average rating, 56 reviews

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.

Superhost
A spacious outdoor area features a crystal-blue pool with built-in seating and a hot tub. Surrounding the pool, several lounge chairs are positioned under an umbrella, while a well-maintained garden with vibrant flowers offers a natural border.
Villa in Lionel Town
4.86 out of 5 average rating, 93 reviews

Country Villa

Villa de Campaña is a breath taking 3 bedroom,3 bathroom with a exquisite private crystal ocean blue pool and gym. If you adore nature and privacy then this is the place to be . Salt river mineral bath is just 15 mins away and also the wonderful white sand beach seafood restaurant Villa de Campaña is ideally located along the south coast. The property is fitted with a 35ft pool, gym, fish pond and indoor design for comfort. No visitors - only the 6 guests on booking permitted in the villa

Guest favourite
An outdoor dining table is set with plates and cups, accompanied by a centerpiece of fresh fruit. The table overlooks a grassy area leading to the shoreline, providing views of the Caribbean Sea. The calm waters and rock formations are visible in the background.
Condo in Tower Isle
4.9 out of 5 average rating, 102 reviews

Fantastic 2BR Seafront Apt Sea Palms..Ocho Rios

Premium Apt coastal decor done to a high standard. Spacious, airy, lots of light & comfortable. Spectacular sea views . Steps from the Pool and Beach Cove. Fully equipped with linen, towels etc. Kitchen features granite counter tops with all amenities. Sea Palms is 7 minutes east of Ocho Rios. Restaurants, Shopping, Attractions. Self catering or Housekeeper/Cook on request at reasonable costs. Laundry Service included INSTANT BOOKINGS NOT ACCEPTED FOR SAME DAY & NOT ON SAT OR SUN.innong.

Guest favourite
A shaded gazebo offers comfortable seating surrounded by lush greenery. Palm trees and vibrant foliage frame a view of the expansive lawn leading to the beach. The sea glimmers in the distance under a clear blue sky, creating a serene outdoor retreat.
Bungalow in Laughlands District
4.88 out of 5 average rating, 205 reviews

Kling Kling Beach House

Kling Kling is a beach house with a family feel, set within a large lawn running down to an almost fully private beach, a river for freshwater swimming, a reef for snorkelling, a fantastic housekeeper cook and a one of a kind man about the place. Just mins drive to shops or tourist facilities. Nearby scuba facilities, waterfalls, water parks, markets, tennis , golf, riding, the list goes on, both mainstream and off piste local. For more pics follow our Instagram: klingklingbeachhouse.

Guest favourite
A two-story villa showcases a modern Caribbean design, framed by lush greenery and tropical plants. The porch features comfortable seating under shaded beams, and a stone pathway leads to a manicured garden. Large windows invite natural light, enhancing the open and airy feel of the property.
Villa in Ocho Rios
4.93 out of 5 average rating, 117 reviews

Ocean front luxury Villa in Jamaica

Welcome to Tikal, an ocean front luxury villa, exquisitely remodeled in May 2021, with an airy modern Caribbean style. We are adjacent to Chukka Cove Horse & Adventure Farms, noted as Jamaica's premier tourist attraction provider. We are conveniently nestled between Montego Bay and Ocho Rios, only 50 minutes from Montego Bay International Airport. We are within 30 minutes of most major tourist attractions, and the cruise ship port in Ocho Rios.

Superhost
Cottage in Saint Ann's Bay
4.83 out of 5 average rating, 70 reviews

Ecoscape -Private River Eco Cottage Near Ocho Rios

Escape to Ecoscape – Where Nature Restores You You won’t want to leave this one-of-a-kind eco-retreat, tucked away in the lush mountains just 30 minutes from Ocho Rios. At Ecoscape, immerse yourself in nature as it was meant to be - fresh mountain air, flowing spring water, clay beneath your feet, and the soothing sounds of the river all around you. Wake up to the calls of yellow-billed parrots and experience Jamaica in its purest form.

Guest favourite
Home in Plantation Village
4.91 out of 5 average rating, 11 reviews

NEW~ Pool Access 3BR •Gated • Walk to the Beach

Welcome to your island getaway where laid-back coastal living meets modern comfort. This spacious 3-bedroom, 3.5-bath vacation home is perfectly designed for you with a quick stroll to the onsite private beach ✨ Why You’ll Love This Home ✔︎ Private beach access ✔︎ Secure gated community with 24/7 security ✔︎ Pool access ✔︎ Spacious, modern design ✔︎ Seamless self check-in via keypad ✔︎ Free on-site parking ✔︎ Fully air-conditioned

Top Guest favourite
The villa overlooks the ocean, surrounded by lush greenery. A spacious two-story building showcases a red-tiled roof and multiple balconies, while clear blue waters and a rocky coastline are visible in the background. Nearby homes also reflect a tropical environment.
Home in Tower Isle
4.94 out of 5 average rating, 300 reviews

Tranquil Times villa

Tranquil Times Villa is located just minutes outside of downtown Ocho Rios. We are located in a private, gated community with 24-hour live security. We are conveniently located within minutes of all major attractions and hotels. Airport Transportation will be arranged. We are fully staffed and cannot wait to help make your vacation one you won't ever forget!!!

Guest favourite
The exterior of the villa features a contemporary design with large glass windows and a prominent central entrance. Lush greenery is positioned around the property, and potted plants are strategically placed near the entrance. The structure is complemented by a wooden awning and a modern color palette.
Apartment in Rio Nuevo
5 out of 5 average rating, 32 reviews

Villa Topenga Luxury One Bedroom - West Wing

Escape to your own slice of Jamaican luxury at Villa West, a stunning 1-bedroom apartment situated just moments from Sugar Pot Beach, Ocho Rios and Dunn’s River Falls. This impeccably designed haven offers the perfect blend of comfort and sophistication, ideal for a romantic getaway, friend’s trip or a relaxing family vacation.

Popular amenities for Middlesex County holiday rentals