Vacation rentals in Middlesex
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Top-rated vacation rentals in Middlesex
Guests agree: these stays are highly rated for location, cleanliness, and more.
Guest suite in Tryall Gardens, Montego Bay
4.92 out of 5 average rating, 193 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.
Aug 6 – 13
Home in Lucea
4.94 out of 5 average rating, 32 reviewsKelly’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.
Oct 24 – 31
Home in Hanover Parish
4.81 out of 5 average rating, 27 reviewsSeaside Gem Hideaway Oceanfront 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!"
Apr 25 – May 2
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Middlesex vacation rentals
Other great vacation rentals in Middlesex
Home in Lucea
5.0 out of 5 average rating, 36 reviewsAshore Gem @ Oceanpointe btw Negril & Montego Bay
Aug 31 – Sep 7
Apartment in Sandy Bay
4.94 out of 5 average rating, 70 reviewsOleander Staycation
Oct 20 – 27
Villa in Cousins Cove
5.0 out of 5 average rating, 34 reviewsPoetreef Villa - Waterfront Cut Stone Luxury
Nov 1 – 8
Bungalow in Lucea
4.97 out of 5 average rating, 35 reviewsBlue Mahoe Retreat
Sep 6 – 13
Home in Hanover Parish
4.82 out of 5 average rating, 90 reviewsPrivate & Cozy two bedroom Oceanpointe House
Jul 2 – 9
Home in Lucea
4.95 out of 5 average rating, 77 reviewsParadise Oasis at Oceanpointe
Apr 23 – 30
Home in Lucea
4.81 out of 5 average rating, 16 reviewsThe Chill Spot Villa
Mar 5 – 12
Guest suite in Negril
4.98 out of 5 average rating, 40 reviewsHome Sweet Home @Little Bay Country Club
Jul 10 – 17
Home in Lucea
4.8 out of 5 average rating, 56 reviewsLegends By The Sea private vacation retreat!
Aug 26 – Sep 2
Home in Hanover Parish
4.91 out of 5 average rating, 44 reviewsComfort Suite
Dec 9 – 16
Cottage in Belmont
4.92 out of 5 average rating, 61 reviewsPapaya Hill "Bird Nest" Treehouse Cottage, Belmont
Aug 3 – 10
Home in Lucea
4.95 out of 5 average rating, 78 reviewsI love Lucea Nestled between Montego Bay & Negril
Mar 18 – 25
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