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.

Guest favourite

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.

6–13 Aug

$82 SGD per night
Guest favourite

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.

24–31 Oct

$251 SGD 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!"

25 Apr – 2 May

$185 SGD per night

Popular amenities for Middlesex holiday rentals

Other great holiday rentals in Middlesex

Guest favourite

Home in Lucea

5.0 out of 5 average rating, 36 reviews

Ashore Gem @ Oceanpointe btw Negril & Montego Bay

31 Aug – 7 Sep

$166 SGD per night
Guest favourite

Flat in Sandy Bay

4.94 out of 5 average rating, 70 reviews

Oleander Staycation

20–27 Oct

$92 SGD per night
Superhost

Villa in Cousins Cove

5.0 out of 5 average rating, 34 reviews

Poetreef Villa - Waterfront Cut Stone Luxury

1–8 Nov

$1,028 SGD per night
Guest favourite

Bungalow in Lucea

4.97 out of 5 average rating, 35 reviews

Blue Mahoe Retreat

6–13 Sep

$136 SGD per night
Superhost

Home in Hanover Parish

4.82 out of 5 average rating, 90 reviews

Private & Cozy two bedroom Oceanpointe House

2–9 Jul

$118 SGD per night
Guest favourite

Home in Lucea

4.95 out of 5 average rating, 77 reviews

Paradise Oasis at Oceanpointe

23–30 Apr

$173 SGD per night
Guest favourite

Home in Lucea

4.8 out of 5 average rating, 15 reviews

The Chill Spot Villa

5–12 Mar

$162 SGD per night
Guest favourite

Guest suite in Negril

4.98 out of 5 average rating, 40 reviews

Home Sweet Home @Little Bay Country Club

10–17 Jul

$163 SGD per night
Superhost

Home in Lucea

4.8 out of 5 average rating, 56 reviews

Legends By The Sea private vacation retreat!

26 Aug – 2 Sep

$164 SGD per night
Guest favourite

Home in Hanover Parish

4.91 out of 5 average rating, 43 reviews

Comfort Suite

9–16 Dec

$148 SGD per night
Guest favourite

Cottage in Belmont

4.92 out of 5 average rating, 61 reviews

Papaya Hill "Bird Nest" Treehouse Cottage, Belmont

3–10 Aug

$95 SGD per night
Guest favourite

Home in Lucea

4.95 out of 5 average rating, 78 reviews

I love Lucea Nestled between Montego Bay & Negril

18–25 Mar

$264 SGD per night

Destinations to explore

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