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 favorite

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

ﺩ.ﺇ223 per night
Guest favorite

Home in Lucea

4.94 out of 5 average rating, 32 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.

Oct 24 – 31

ﺩ.ﺇ685 per night
Superhost

Home in Hanover Parish

4.81 out of 5 average rating, 27 reviews

Seaside 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

ﺩ.ﺇ504 per night

Popular amenities for Middlesex vacation rentals

Other great vacation rentals in Middlesex

Guest favorite

Home in Lucea

5.0 out of 5 average rating, 36 reviews

Ashore Gem @ Oceanpointe btw Negril & Montego Bay

Aug 31 – Sep 7

ﺩ.ﺇ452 per night
Guest favorite

Apartment in Sandy Bay

4.94 out of 5 average rating, 70 reviews

Oleander Staycation

Oct 20 – 27

ﺩ.ﺇ251 per night
Superhost

Villa in Cousins Cove

5.0 out of 5 average rating, 34 reviews

Poetreef Villa - Waterfront Cut Stone Luxury

Nov 1 – 8

ﺩ.ﺇ2,802 per night
Guest favorite

Bungalow in Lucea

4.97 out of 5 average rating, 35 reviews

Blue Mahoe Retreat

Sep 6 – 13

ﺩ.ﺇ372 per night
Superhost

Home in Hanover Parish

4.82 out of 5 average rating, 90 reviews

Private & Cozy two bedroom Oceanpointe House

Jul 2 – 9

ﺩ.ﺇ323 per night
Guest favorite

Home in Lucea

4.95 out of 5 average rating, 77 reviews

Paradise Oasis at Oceanpointe

Apr 23 – 30

ﺩ.ﺇ472 per night
Guest favorite

Home in Lucea

4.81 out of 5 average rating, 16 reviews

The Chill Spot Villa

Mar 5 – 12

ﺩ.ﺇ445 per night
Guest favorite

Guest suite in Negril

4.98 out of 5 average rating, 40 reviews

Home Sweet Home @Little Bay Country Club

Jul 10 – 17

ﺩ.ﺇ442 per night
Superhost

Home in Lucea

4.8 out of 5 average rating, 56 reviews

Legends By The Sea private vacation retreat!

Aug 26 – Sep 2

ﺩ.ﺇ449 per night
Guest favorite

Home in Hanover Parish

4.91 out of 5 average rating, 44 reviews

Comfort Suite

Dec 9 – 16

ﺩ.ﺇ404 per night
Guest favorite

Cottage in Belmont

4.92 out of 5 average rating, 61 reviews

Papaya Hill "Bird Nest" Treehouse Cottage, Belmont

Aug 3 – 10

ﺩ.ﺇ260 per night
Guest favorite

Home in Lucea

4.95 out of 5 average rating, 78 reviews

I love Lucea Nestled between Montego Bay & Negril

Mar 18 – 25

ﺩ.ﺇ730 per night

Destinations to explore

  1. Airbnb
  2. Jamaica
  3. Hanover Parish
  4. Middlesex