Holiday rentals in Middlesex

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Top-rated holiday rentals in Middlesex

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

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Guest favourite

Guest suite in Tryall Gardens, Montego Bay

4.91 out of 5 average rating, 195 reviews

✿Sunflower Escape✿ ❤️✔Car✔Parking✔beach✔AC✔WiFi

Located 20 minutes outside of Montego Bay en route to Negril, Sunflower Escape with all the basic modern amenities and the privacy of your space, you can truly have a pleasant escape to relaxation. 5mins walk to the beach and local seafood spot, Chukka Adventures and Dolphin Cove are just minutes away. Walk to nearby town Sandy Bay or drive to Hopewell. Enjoy dining on your private patio or chill at a spot in the yard. We also offer airport transfers and a nice car for rent at affordable rates.

Guest favourite

Home in Lucea

4.94 out of 5 average rating, 33 reviews

Kelly’s Ocean Paradise

Unwind in this gorgeous modern yet rustic decorated coastal home in a quiet gated community. Fully equipped to be your home away from home. The home boasts 3 beautiful bedrooms and 2 bathrooms. Plenty of space to keep up with your daily routine. The kitchen features stainless steel appliances. Enjoy your meals around our dining table or take it to the backyard lounge area. Enjoy a view of the sea and the mountains just looking from the veranda. End the day with a movie in our comfy living room.

Superhost

Home in Hanover Parish

4.83 out of 5 average rating, 30 reviews

Seaside Gem Oceanfront Hideaway btwn MoBay/Negril

Experience an authentic Jamaican sanctuary in the rustic coastal community of Lances Bay. Seaside Gem offers breathtaking sunsets & a private beach for easy access to kayaking or snorkeling. This tranquil escape is perfect for relaxation, special work projects, or day trips including Negril's 7-Mile beach & vibrant music scene. Situated just 10 minutes from Lucea and a direct drive from Montego Bay or to Negril, it's a peaceful haven. As the locals say. "Every likkle ting Irie by the Sea, Mon!"

Guest favourite

Home in Lucea

5.0 out of 5 average rating, 31 reviews

Ocean Escape| Beach, Pools, Gym, Courts, Clubhouse

Relax with the whole family at this peaceful place to stay. Conveniently situated on the north coast. Enjoy this two bedroom and two bathroom home. The home is about 40 to 45 minutes from the Sangsters international airport and is 30 minutes from the resort towns of Montego Bay and Negril. In the community there is a pool, clubhouse, tennis court, multipurpose court, football field, running track, gym and nearby beaches. Looking to chill inside, we have tons of stuff for you to do and watch.

Guest favourite

Cabin in Westmoreland Parish

4.93 out of 5 average rating, 309 reviews

Little Bird Cottage @ High Cove

Little Bird is located on High Cove property, nestled on a pristine swimming cove on the famous West End. There are 2 other cottages on the property that can be rented separately, or jointly with Little Bird for groups of up to 14. A stone's throw away from the world-renowned Rick's Cafe, amazing African drummers on Saturday nights, restaurants/watering holes, and has incredible sunsets. 10mins drive to Negril's vibrant Seven Mile Beach. You can also unplug for a secluded or romantic getaway.

Guest favourite

Home in Lucea

5.0 out of 5 average rating, 66 reviews

Ultimate SeaClusion-POOL/GYM/Solar/Table Tennis.

Book NOW!!! Ultimate SeaClusion: Stylish 2bedroom/ 2 bathroom home, Free Parking, Fast Wifi, Community Pool, Gym, Tennis Court, Basket Ball Court, 24hr Security, Gated Community, 30-35 mins drive from Montego Bay airport. We strive to give our guest an experience versus just a place to stay. The home has everything you need for a relaxing vacation. A true spirit of " A home away from home". The view from the Club House/Backyard is breath-taking with a sea view and wonderful sea breeze.

Guest favourite

Villa in Lucea

4.82 out of 5 average rating, 50 reviews

Natalia’s Sweet Oasis

Natalia’s Sweet Oasis in the gated community of Oceanpointe is ideally located 30km between Jamaica’s 2 most popular tourist destinations: Montego Bay the tourist capital and Negril the capital of casual, famous for its seven miles of white sandy beach and pristine waters. Take a quick 1 minute drive to Dolphin Cove OR a 5 minutes drive to Chukka Adventure Park for a day of fun activities. This gem is an ideal space for family vacations, business trips, group travel or a getaway by yourself.

Guest favourite

Cottage in Cousins Cove

4.89 out of 5 average rating, 128 reviews

Ocean Cabin Private Sea Access Plunge Pool WIFI

2020 Travelers Choice Award Winner ❤️ COVID-19 Protocol Compliant Approved Listing. Charming rustic wooden cabin situated on the coral rocks just steps from the crystal clear Caribbean waters edge. Located in pristine Cousins Cove, a beautiful quiet fishing village away from the tourist traps. You can spend your days snorkeling, swimming, fishing, lazing in a hammock, chillin out in the "Cool Pool", sipping a rum (or two) playing dominoes yet all within 15 minutes of Negril's 7 mile beach.

Guest favourite

Home in Lucea

5.0 out of 5 average rating, 13 reviews

Pick fast while it lasts\Sun-Kissed\2BD\Sleep 4

Welcome to our charming two-bedroom, two-bathroom home in an exclusive oceanfront gated community. Situated between the world-renowned seven-mile beaches of Negril and the bustling cruise ship destination of Montego Bay, our home offers a haven of tranquility with 24-hour security. Just minutes away from the historic town of Lucea, where part of the famous movie Cool Runnings and one of James Bond's movies were filmed, let this cozy home serve as the perfect setting for your vacation.

Superhost

Home in Oceanpointe, Lucea

4.91 out of 5 average rating, 22 reviews

Best Vacation Ever/Private Pool/Local Beach

The cottage at Oceanpointe is exquisite, stylish, relaxing and designed as the ultimate getaway. Highlights: Private chef available to book, full kitchen and BBQ grill, heated pool, king size beds, WiFi and cable, AC in every room, 2 twin size daybeds on back patio, day/night pass to Grand Palladium, walk to beach for a quick swim, gated, 2 community pools, event space, tennis and basketball courts, close to Montego Bay and Negril, gorgeous garden and amazing decor.

Guest favourite

Flat in Lucea

4.95 out of 5 average rating, 19 reviews

Blu Vista - Nature's Place to Relax

Large upper studio with panoramic sea and mountain views, set in 3 acres of landscaped grounds with a outdoor activities suitable for adults and children. Fruits and vegetables in season are made available to guests. Ask about our optional meal and car and driver transportation packages which can be tailored to your requirements. A shuttle is available between Blu Vista , the town of Lucea and nearby Bulls Bay beach. Further excursions can be arranged on request.

Guest favourite

Villa in Lucea

4.94 out of 5 average rating, 16 reviews

Lavish Luxury Living 2Bedroom Villa in Lucea

Hamilton Is A Serene Family Friendly Villa With Lots Of Room For Fun. A Brand New Vacation Home Situated In A Secure 24/7 Gated Community With All The Amenities For An Enjoyable Time Away, Clubhouse, Swimming Pool, Tennis Court, Gym, Football Field And More. The Spacious Open Living/Diner Area Is Nicely Decorated With Contemporary & Antique Style Décor To Compliment A Sophisticated Finish. It Comes With Everything You Need To Have A Home Away From Home Experience.