Holiday rentals in Middlesex County

Elite Escape @ Paradisiac (near Ocho Rios)

Escape to paradise in this stylish & fun 3-bedroom, 3.5-bath beachside retreat near Ocho Rios! Perfect for families, this spacious home combines modern design & tropical charm. Enjoy bright, airy interiors, comfortable beds, and an open living space ideal for creating memories. With a view of the Caribbean Sea, you’ll find relaxation and adventure at your doorstep. Whether you’re soaking up the sun, exploring local attractions, or simply unwinding, this family-friendly getaway is yours to enjoy!

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!

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.

Bamboo Breeze Villa 4Bdr PVT Pool Richmond St Ann

Bamboo Breeze is a cozy , comfortably decorated Villa , located in Richmond Cool Shade , St Ann Jamaica. The Villa features its own private Pool and pool deck for added relaxation , and access to Richmond's own private beach . Guests have access to a Gym , Tennis Courts , Pool and Table Tennis , Putting Green , Picnic areas, Walking Trail ,Kids Park and Playground. A fully stocked Supermarket/Drugstore/ Deli is nearby for your added convenience. *( delivery service available ) .

Beachfront Villa & Chef | Coral Reef | Ocho Rios

Wake up to Caribbean waves and step onto your private 15x45ft deck, just 15 feet from the ocean. Your private coral reef is a 7-minute swim away snorkel gear, kayak, and paddleboard all included. Inside, every finish is hand-crafted from guango with original Jamaican artwork throughout all available for purchase. Your Chef Choose from our prix-fixe menu or visit the local market and have meals prepared to your exact taste Jamaican jerk to international cuisine, your chef has it covered.

Cambridge mi casa ur casa w/pool & beach access

We offer newly- renovated comfortable two- floor apts in a friendly safe community overlooking CARDIFF HALL Beach in the Resort Town of Runaway Bay in St. Ann Jamaica ▪️No need to worry about security / safety because there are 24 hour surveillance camera and host lives on property ▪️We offer one 1bdr & 2br ▪️Price starts from 100US for 2 guests and increases by 30US per additional guests ▪️We are about 1hr away from the Sangsters International Airport ✈️ 25 mins from Ocho Rios

Paradise Penthouse w/ Private Chef & Oceanfront

🌞 2026 Winter Discount. Skip the Resort 🌞 Escape to Paradise Penthouse in the heart of Ocho Rios! This 3 story oceanfront gem is nestled in the exclusive, 24 hour gated community of Crystal Cove, offering the ultimate tropical getaway. Relax in style with stunning ocean views, chef prepared breakfast and dinner , access to a driver, and endless comfort. Perfectly located on Main Street, you’re minutes away from local culture and adventure. Your dream Jamaican vacation awaits! ✨

Zuma Villa|3BR|Rooftop|Gated|Pool|10 min Beach

Welcome to Zuma Villa, your tropical oasis nestled in the heart of Jamaica. Surrounded by lush greenery and just moments from pristine beaches, Zuma Villa offers the perfect blend of comfort, style, and island charm. Whether you're here to relax, explore, or indulge in local culture, our villa is designed for an unforgettable stay. From the rooftop sea views to the infinity pool, you'll feel right at home while experiencing the best of Jamaica. Come as guests, leave as family!

Tranquil Oasis Ocho Rios (Starlink/Solar)

Tranquil Oasis at Palm View is the perfect vacation hideaway! With Solar Powered Electricity and Starlink Internet as well as back up water supply and located in the gated complex of Palm View Estate in Drax Hall, this property is just mere minutes away from the resort town of Ocho Rios and is in close proximity to all-inclusive hotels, beaches, restaurants, shopping, entertainment, notable tourist attractions major international airports and Knutsford Express.

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.

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

Central Beachfront Bungalow

This special place is uniquely located in a paradise cove steps away from the city center, where you can find all the best restaurants and bars. Grab a kayak & enjoy the sparkling coastline with the number one snorkeling spot just in the backyard. From nightlife to river excursions we’ve got you covered. Experience what it feels like to be a local in Ochi by staying in this double door, cottage style, ocean view residence.