Search Holiday Rentals in Middlesex

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
28 Jul - 29 Jul
Tomorrow
29 Jul - 30 Jul
This weekend
1 Aug - 3 Aug
Next weekend
8 Aug - 10 Aug

Top Holiday Rentals in Middlesex

Dalley's Cozy Apartments
Enjoy a refreshing drink on the balcony with a city view.

Dalley's Cozy Apartments

3.0 star property
8.4 out of 10, Very good, (6)
"Nice spot. Check in could have been better but everything else was good. "
Dalley's Cozy Apartments
Sand and Blue Seas
Enjoy meals in a casual outdoor setting with tables and stools, a mounted TV, and a simple design.

Sand and Blue Seas

3.0 star property
8.2 out of 10, Very good, (124)
"Beautiful clean property the chef cooks very good.. pool needs some paint .. otherwise this place is amazingly beautiful and on the beach just don’t expect anything fancy.. it’s simple and easy .. definitely a vibe I’ll be back!"
Sand and Blue Seas
Villas Sur Mer
Relax by the serene pool surrounded by lush tropical plants and trees.

Villas Sur Mer

4.0 star property
8.8 out of 10, Excellent, (148)
"Amazing as always!!! "
The price is 4.574.500 ₫
5.058.090 ₫ total
includes taxes & fees
29 Jul - 30 Jul
Villas Sur Mer
Montego Bay Club Apartments
Guests can enjoy stunning ocean views from the beachfront location.

Montego Bay Club Apartments

4.0 star property
7.4 out of 10, Good, (34)
"Great location "
Montego Bay Club Apartments
Beach House Condos Negril
Dine with a view of the ocean from this beachfront dining area, featuring tables and chairs under a thatched roof.

Beach House Condos Negril

3.5 star property
9.0 out of 10, Wonderful, (55)
"Pro: separate AC in all rooms. Fully equipped kitchen. Clean. Approachable and helpful staff. Con: no toiletries. Tiny private beach with only four dry grass beach umbrellas. "
The price is 3.136.800 ₫
3.947.140 ₫ total
includes taxes & fees
10 Aug - 11 Aug
Beach House Condos Negril
Montego Bay Club Beach Resort
Enjoy stunning ocean views from your balcony overlooking the beach and palm trees.

Montego Bay Club Beach Resort

3.5 star property
4.4 out of 10, (35)
"The view is out of this world and the is kept clean. "
Montego Bay Club Beach Resort
Unity Villa
Enjoy cooking in this well-equipped kitchen with a gas stove, microwave, and dishwasher.

Unity Villa

3.0 star property
8.0 out of 10, Very good, (1)
"I LIKE HOW THEY COMMUNICATED AND ADDRESSED THE PROBLEMS ! Only thing I didn’t like was the no working ac and there wasn’t stuff close to go shop "
Unity Villa
Idle Awhile Villas
Relax by the serene pool surrounded by lush tropical vegetation and a well-maintained garden.

Idle Awhile Villas

4.0 star property
10.0 out of 10, Exceptional, (14)
"The property was beautiful and the service was phenomenal. We had an amazing chef Raquel and butler Ryan. They accommodated our every need and Ryan had a lot of great recommendations for restaurants and activities. Would love to come back!!"
Idle Awhile Villas
Idle Awhile Cliffs
Relax by the pool surrounded by lounge chairs and umbrellas, with stunning ocean views.

Idle Awhile Cliffs

3.5 star property
9.0 out of 10, Wonderful, (119)
"We adored this “rustic” property with its early morning birdsong, simple clean (very clean!) rooms and lovely pool overlooking the ocean. Delicious breakfast poolside or on our terrace. Courteous and kind staff. Highly recommend!"
Idle Awhile Cliffs
Monimo Ridge Suites
Escape to a serene tropical oasis with lush greenery and a natural pathway.

Monimo Ridge Suites

3.0 star property
8.6 out of 10, Excellent, (18)
"Was a clean and safe space to spend a night before my flight back home. Very close to Montego Bay airport."
Monimo Ridge Suites
Sky Beach Rooms
Guests can dine al fresco with a view of the sea from this outdoor dining area.

Sky Beach Rooms

5.0 star property
2.0 out of 10, (1)
"The room was very clean, however the rooms are located in a very local shopping mall with lots of loitering outside, very noisy, no windows so felt claustrophobic. The outside was dirty , crowded and noisy I did not feel safe enough to stay there so I left."
The price is 2.823.120 ₫
3.131.572 ₫ total
includes taxes & fees
29 Jul - 30 Jul
Sky Beach Rooms
Stunning Ocean View
Enjoy a room with a sliding glass door leading to an outdoor area with a beach view.

Stunning Ocean View

4.0 star property
10.0 out of 10, Exceptional, (11)
"The view and ambience was pure bliss!"
The price is 11.958.266 ₫
17.568.446 ₫ total
includes taxes & fees
10 Aug - 11 Aug
Stunning Ocean View
Unity Villa
Stunning two-story building with curved facade and balconies featuring intricate lattice designs.

Unity Villa

3.0 star property
8.0 out of 10, Very good, (1)
"I like that the property was quiet. The place was clean. The neighbor I met was really nice. I like that. It was outside of the tourist area."
The price is 1.699.100 ₫
2.417.950 ₫ total
includes taxes & fees
8 Aug - 9 Aug
Unity Villa
Turquoise Sea Villa
Relax by the serene pool surrounded by lush greenery and enjoy breathtaking views of the marina.

Turquoise Sea Villa

3.5 star property
The price is 2.535.632 ₫
5.556.117 ₫ total
includes taxes & fees
31 Jul - 1 Aug
Turquoise Sea Villa
YanceyLargo Estate - Newly Built Modern 1 Bedroom Suite 1 Villa by RedAwning
Villa, 1 Bedroom | 1 bedroom, iron/ironing board, free WiFi

YanceyLargo Estate - Newly Built Modern 1 Bedroom Suite 1 Villa by RedAwning

3.0 star property
The price is 2.088.847 ₫
4.255.617 ₫ total
includes taxes & fees
29 Jul - 30 Jul
YanceyLargo Estate - Newly Built Modern 1 Bedroom Suite 1 Villa by RedAwning
Seascape Apartment
Guests can stroll along the pathway surrounded by lush tropical plants in this serene outdoor area.

Seascape Apartment

2.5 star property
7.4 out of 10, Good, (8)
"Clean and family oriented. Owner were very accommodating. I wouldn’t mind staying there again."
Seascape Apartment
Solet's Paradise Negril
Enjoy leisure activities on this medium-sized boat with a canopy.

Solet's Paradise Negril

2.5 star property
9.8 out of 10, Exceptional, (9)
"Great little gem in Negril.If you are looking for a nice relaxing place away from the hustle and bustle, this is the place. Rooms are beautiful and the staff was awesome. would absolutely stay again. Dave"
Solet's Paradise Negril
Sunny-shore Hideaway
House, 3 Bedrooms, Smoking, Patio | Pool | Outdoor pool

Sunny-shore Hideaway

2.0 star property
The price is 3.341.083 ₫
5.915.184 ₫ total
includes taxes & fees
17 Aug - 18 Aug
Sunny-shore Hideaway
Negril Beachside
Enjoy the city view from this balcony with a tiled floor and balustrade, offering a glimpse of the street below.

Negril Beachside

2.0 star property
Negril Beachside
Nianna Chatham
Enjoy a serene beach experience with clear turquoise waters and a sandy shore.

Nianna Chatham

2.5 star property
The price is 6.561.140 ₫
9.139.851 ₫ total
includes taxes & fees
11 Aug - 12 Aug
Nianna Chatham
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middlesex Hotel Reviews

Hotel Riu Palace Tropical Bay - All Inclusive

Hotel Riu Palace Tropical Bay - All Inclusive

10/10 Excellent
"I found this hotel very beautiful. I had such a wonderful experience. The only factor that affected was the hospitality. I felt that staff sometimes did not want to be bothered with questions or requests. However, this did not apply to the bartenders and pool/beach servers. I do wish they had an elevator, especially when you or the 3rd floor, but that wasn’t anything we couldn’t handle. The food, beach, pool, entertainment, and room were amazing. Will definitely be back!"
Alice Nicole Diaz 4-night trip
Posted 7 hours ago
Hotel Riu Palace Tropical Bay - All Inclusive

Frequently asked questions

Can I find holiday rentals in Middlesex?

Yes, there are holiday rentals close to the most popular sights in Middlesex, or you can select a more secluded option if you're looking for a relaxing stay.

What can I see and do in Middlesex?

Explore the area and family-friendly sights such as Kool Runnings Water Park, or get out into nature at a spot like Seven Mile Beach. Half Moon Beach and Tryall Golf Club are a couple of places you'll find in the wider area.

What are holiday rentals like in Middlesex?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Middlesex. Holiday rentals feature extras such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from public hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for small groups.