Vacation rentals in Middlesex County

Beachfront Villa · Private Chef · Ocho Rios

Eden Sands is a beachfront sanctuary in Ocho Rios, handcrafted from local guango and cedar. Wake up to waves, step onto your private deck surrender to Jamaica completely. Your world-class chef is included — bold Jamaican soul food and international cuisine served on the deck or beach. À la carte or market-fresh, your choice. Swim seven minutes to a stunning coral reef. Snorkel gear, paddleboard and kayak all included. Two bedrooms, sleeps 4. Air conditioning and housekeeping included throughout.

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.

Ecoscape - Private Spring & River Retreat

Escape to Ecoscape, a secluded eco-retreat by a spring, river & lush Jamaican countryside. Wake to birdsong & the lively calls of Jamaica’s yellow-billed parrots, enjoy coffee by the spring, unwind on your deck or dip in the river. Designed for 2, this boho cottage offers a king bed, full kitchen & fast Wi-Fi, just 25–30 minutes from Ocho Rios. Perfect for couples, creatives & nature lovers ready to slow down, reconnect and discover Jamaica’s quieter side. Follow the water. Find your calm.

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.

Elegant 2BR, Pool, Gym & Games Room - Book Now

Make lasting memories with your loved ones at this family-friendly 2-bedroom retreat! The home is fully furnished with modern comforts and features a vibrant games room for endless fun, plus access to a pool and gym for all ages to enjoy. With plenty of room for everyone, the home combines relaxation, entertainment, and convenience. Located just minutes from town, you’ll have quick access to restaurants, shops, and local attractions, making it easy to plan family outings.

OCEAN-VIEW Minimalistic Central “Studio”APT

Welcome to our Studio Apartment! Perfectly nestled near MargaritaVille and 8 Rivers Town Center on Main Street Ocho Rios, Jamaica. The interior is tastefully decorated, it has a comfortable seating area. Stay connected with WiFi, ensuring you're always in touch . With a well-equipped kitchen with appliances and ample counter space. We look forward to welcoming you to our delightful Airbnb studio apartment, where comfort and convenience are our top priorities.

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

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The Luxe Paradise

Modern 2-bedroom Retreat in Clarendon! Just 3 minutes away from Millennium Mall, popular restaurants, supermarket, gas station, Highway 2000, close to Murrays Fish & Jerk Hut, and much more! Enjoy a fully equipped apartment with a private terrace, A/C, fully kitchen, Wifi & Smart TV. Book now and enjoy Clarendon with comfort, convenience, and a touch of luxury!

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!!!

Fully AC 2BR | Secure, Centrally Located Kingston

Enjoy a modern, quiet 2-bedroom home centrally located in Kingston, perfect for business travelers, couples, or small groups looking for comfort, security, and convenience. ✔ Fully air-conditioned (all rooms) ✔ Fast WiFi ✔ Gated property with 24hr security cameras ✔ Self check-in with secure access code ✔ Minutes from Half Way Tree, shopping & business hubs.

Sea Vista Escape | Pool | Hot Tub | Gated | For 12

Welcome to Sea Vista Escape. A luxury villa in the Greater Ocho Rios. Perfect for families, friends, reunions, birthdays, anniversaries, bachelor/bachelorette trips, and special events. • Ocean views • Hot tub • Game room • Fast Wi-Fi • Gated community • Private chef & catering available • Airport transfers & celebration packages