Middlesex Vacation Rentals from AED 183: Search Short-Term Rentals

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Our top choices for Middlesex vacation rentals

An outdoor dining area with a view of the sea, featuring a thatched-roof structure and wicker furniture.

1. Sky Beach Rooms

Montego Bay

Clayton

AED 388 total

includes taxes & fees

15 Nov - 16 Nov

A cliffside property with a swimming pool, outdoor seating, and a staircase leading to the water.

2. Villas Sur Mer

West End

Nadine

AED 713 total

includes taxes & fees

15 Nov - 16 Nov

A modern outdoor pool area with lounge chairs, a hot tub, and a fireplace.

3. Wabi-Sabi Villa

Lucea

Andrea

AED 3,652 total

includes taxes & fees

15 Nov - 16 Nov

A row of colorful houses with a white staircase leading up to a porch.

4. Stunning Ocean View

Negril

Willie

AED 2,700 total

includes taxes & fees

15 Nov - 16 Nov

A beach with thatched umbrellas, a white building, and pink flowers.

5. Beach House Condos Negril

Negril

Patrick

AED 876 total

includes taxes & fees

15 Nov - 16 Nov

A two-story yellow building with balconies, a gated entrance, and a small garden area.

6. Unity Villa

Montego Bay

Susan

AED 476 total

includes taxes & fees

15 Nov - 16 Nov

A coastal swimming area with boats and people.

7. Sunshine Seashore Escape Jamaica

Lucea

AED 878 total

includes taxes & fees

15 Nov - 16 Nov

A two-story building with a balcony on the upper floor, featuring decorative railings and barred windows.

8. Unity Villa

Montego Bay

Fashira

AED 340 total

includes taxes & fees

15 Nov - 16 Nov

A swimming pool with a hot tub, surrounded by palm trees and a white building.

9. Turquoise Sea Villa

Montego Bay

AED 1,008 total

includes taxes & fees

15 Nov - 16 Nov

A staircase with stone steps and metal railings, leading upwards.

10. RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL

Negril

AED 380 total

includes taxes & fees

15 Dec - 16 Dec

A coastal resort with multiple blue buildings, a sandy beach, and a clear view of the ocean.

11. Deluxe appartment at Point village

West End

Schanna

AED 476 total

includes taxes & fees

16 Nov - 17 Nov

A large house with a swimming pool, surrounded by lush greenery and palm trees.

12. La Costa Villa

Montego Bay

AED 3,067 total

includes taxes & fees

15 Nov - 16 Nov

A hanging chair on a balcony with a white railing and a view of trees.

13. Modern Home 10minstobeach, Private Cliff, AC Wifi

Negril

Shantel

AED 487 total

includes taxes & fees

24 Nov - 25 Nov

A room with two wicker chairs and a small table, a door, and a window with blinds.

14. Grassroots Negril

West End

AED 333 total

includes taxes & fees

16 Nov - 17 Nov

A beach view from a balcony with a clear ocean, a pier, and a few umbrellas on the sand.

15. Montego Bay Club Beach Resort

Hip Strip

Gerald

AED 649 total

includes taxes & fees

15 Nov - 16 Nov

A beach with clear turquoise water, a sandy shore, and a view of the ocean.

16. Montego Bay Club Apartments

Hip Strip

Samrawit

AED 779 total

includes taxes & fees

15 Nov - 16 Nov

A spacious kitchen with wooden cabinets, a refrigerator, and a dining area with a table and chairs.

17. Claudeville Condo

Montego Bay

Sabrina

AED 374 total

includes taxes & fees

16 Nov - 17 Nov

A beach with lounge chairs and a clear view of the ocean.

18. Seawind F104

Montego Bay

"Let me start with the property was very nice including the apartment we stayed in. Very modern and tastefully decorated. Location of this property was perfect as we were visiting family and it was close by. To pay for the cleaning fee prior to check in was a little challenging; when traveling with a cell phone you are unable to pay using the link they provide. We were able to pay cash onsite which helped. I would like to focus on the false advertising of guest laundry, there is no guest laundry...

Rachel

AED 924 total

includes taxes & fees

20 Nov - 21 Nov

A balcony with a view of the ocean and a tropical landscape.

19. The Shallhome

Montego Bay

AED 2,116 total

includes taxes & fees

15 Nov - 16 Nov

A bedroom with a bed, a desk, two chairs, a wardrobe, and a bathroom with a mirror and sink.

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

Montego Bay

AED 713 total

includes taxes & fees

15 Nov - 16 Nov

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Find vacation rentals that suit your style

Top Middlesex Hotel Reviews

A swimming pool with lounge chairs and thatched umbrellas, surrounded by trees and a white fence.

Blue Paloma Bed & Breakfast

Lucea

10/10 Excellent

BRIATNEY

A beach with rows of blue and white striped lounge chairs and a signboard.

CocoLaPalm Seaside Resort

Negril

10/10 Excellent

Debra

Princess Senses The Mangrove Resort - Luxury Adults Only - All Inclusive

Green Island

10/10 Excellent

We were the first guest ever to arrive at the resort on the adult side and they treated us like celebrities. I really enjoyed the food the food was bomb and yes I am black. I loved the buffet when I went home I missed the buffet that’s the best part and everything is all inclusive. The resort itself is beautiful very modern and clean and our room was spacious enough for 2 people. The customer service was the best I ever had they really strived to make our birthdays special. We had a little...

Ameina Kumye

A resort with a large central pool, multiple levels of cabanas, and a beach area.

The Signature Level At Grand Palladium Lady Hamilton Resort & Spa

Lucea

10/10 Excellent

Steven

A rooftop infinity pool with a clear view of the ocean and a distant shoreline.

Princess Grand Jamaica Resort - All Inclusive

Green Island

10/10 Excellent

Chanze

A resort with a central pool, multiple lounge areas, and a beach.

Grand Palladium Jamaica Resort & Spa All Inclusive

Lucea

10/10 Excellent

I go to Jamaica almost every year and stay at different resorts. I find this resort to be great for the price. They even accommodated me to a room on the ground level because I have trouble with stairs. All the staff were pleasant and always asked if they could help you in anyway. The food was good and I know some reviews state differently. You have to realize people come from all over the world and trying to please everyone would be impossible. I know tipping is not mandatory but they work so...

Rita Melita

A beachside area with blue-roofed structures, a parasail in the distance, and a clear view of the ocean.

Negril Tree House Resort

Negril

10/10 Excellent

This was our first time in Jamaica. Friends told us about the Negril Treehouse and we absolutely loved it. The rooms were clean, with great tv's (not that you need one but Ohio State championship was that week and we got to watch in room or in the lobby on a big screen). The restaurant and beach bar were very good (just don't expect service like in states, they are on Jamaican time, slow or slower) but staff and bartenders were all very pleasant. We booked next year on the third day in.

T.K.

Grand Palladium Lady Hamilton Resort & Spa All Inclusive

Lucea

10/10 Excellent

Robert Romeo

An aerial view of a pool with a unique design, surrounded by rocky terrain and ocean waves.

The Westender Inn

West End

10/10 Excellent

Me & My Lady came in mid March & it was absolutely beautiful, as soon as we arrived we were greeted & taking care of. Rooms clean, nice pools, beautiful scenery. The staff here was amazing. Mr Parchment was very nice & helped tremendously. The area around is nice, kinda separated from the town a little bit, but if you coordinate with the staff members they will surely take care of you in transportation. Definitely a beautiful place & I will be returning soon.

Triston

A poolside area with lounge chairs and a view of a beach and ocean.

Round Hill Hotel And Villas

Montego Bay

10/10 Excellent

Took a week-long trip with my girlfriend in late July 2015 and stayed in the oceanfront room. Grounds/staff: The grounds are extremely well-kept and every single member of the staff is incredibly polite and friendly. The ambiance is highly relaxing and extremely quiet; not what my girlfriend and I were expecting in Jamaica, but isn't necessarily a bad thing. The mosquitoes became a bit bothersome, but the hotel made every effort to prevent this by 'fogging' the lower area of the resort twice...

Joe

A couple relaxing in a private infinity pool with a view of the ocean, a table with fruit and drinks, and lounge chairs.

Grand Lido Negril Au-Naturel, An Autograph Collection All-Inclusive Resort - Adults Only

Negril

10/10 Excellent

Stacy

A nighttime pool area with a clear reflection, surrounded by lush greenery and warm lighting.

Rayon Hotel

Negril

10/10 Excellent

Michael

An aerial view of a coastal resort with a clear blue sea, rocky formations, and a wooden pier leading to a beach with sun loungers.

Tensing Pen Hotel

West End

10/10 Excellent

Tensing Pen is the perfect escape. This tiny resort with the cottages scattered across the property provides a perfect taste of Jamaica. The location on the cliffs is gorgeous and starting each morning with a swim from the cliffs is ideal. The staff is friendly and helpful. The restaurant is quite delicious for those days that you want to relax and not wander afield. However there are several other resorts with amazing restaurants and little local bars and eateries near by that you can...

Melissa

A beachside restaurant with outdoor seating, a pool, and a view of the ocean.

Rondel Village

Negril

10/10 Excellent

I have been to Rondell Village several times, each visit here has been good for me, the staff is very courteous and polite. The rooms are spacious, and this time I had a nice big patio which was great in morning to have my coffee. The property grounds are safe with security around the clock. Security is always alert when coming and going especially when crossing to other side and graciously ask how is everything. Thanks for another great stay. Stayed July 2016

Deborah

Negril Palms

Negril

10/10 Excellent

This was our second time at this hotel. While two years ago, we had a wonderul time too - we did notice that the Staff especially tried to connect and make our stay good. We had no issues last time, but read some people saying service wasn't good. Hello, it's jamaica, It's cooked fresh and what is the rush? Great restaurant too. We actually spent many meals at the hotel. We normally go to our favorite places up the beach-but the food at the Hotel was so good and a better price than our other...

Jennifer

Stunning Ocean View

Negril

10/10 Excellent

The two story town house is located on the cliff facing the ocean, with spectacular view. I can’t say enough how beautiful this property is. In the end we decided to spend more time in the house to enjoy the view and surroundings, reading and having dinner, watching sunset. The property itself is well equipped, clean and modern. The master bed room has beautiful view of the ocean -almost like painting with every morning waking up to embrace the sun and blue ocean. The property manager Mr. Brown...

A treehouse with a rustic design, surrounded by dense foliage and illuminated by string lights.

Bak A Yaad

West End

10/10 Excellent

I had stayed here @Bak A Yaad once before recently beginning my Jamaican adventure for several days and loved everything about it! So I decided to come back for sure when I extended my stay in Negril. From the fantastic location and secluded Jamaican jungle style of the resort itself, a laid-back relaxing pool deck area & refreshing pool to the convenience of having a full kitchen access, BBQ & a community clubhouse with wide screen smart TV, ping-pong table & plush couches to interact &...

Ricky Lee

Frequently Asked Questions

Can I find vacation rentals in Middlesex?

Yes, we have vacation rentals near popular local attractions in Middlesex, or you can choose a more remote option if you want a relaxing place to stay.

What are some of the best vacation rentals that Middlesex has to offer?

5 bed villa, gated community, private pool, fully staffed, private chauffeur: Visitors like this Middlesex vacation home rental. It is located next to a golf course and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What can I see and do in Middlesex?

Explore the area and family-friendly sights such as Hope Botanical Garden and Zoo, or get out into nature at a spot like Seven Mile Beach. Half Moon Beach and Bloody Bay Beach are a couple of places you'll find in the larger area.

What are vacation rentals like in Middlesex?

Vacation rentals are private accommodations you can book for a few days or a quick weekend in Middlesex. Vacation rentals offer extras such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a vacation rental can offer a sense of security away from public hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for family trips or small group gatherings.

Middlesex Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Middlesex vacation rentals

1. Sky Beach Rooms

2. Villas Sur Mer

3. Wabi-Sabi Villa

4. Stunning Ocean View

5. Beach House Condos Negril

6. Unity Villa

7. Sunshine Seashore Escape Jamaica

8. Unity Villa

9. Turquoise Sea Villa

10. RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL

11. Deluxe appartment at Point village

12. La Costa Villa

13. Modern Home 10minstobeach, Private Cliff, AC Wifi

14. Grassroots Negril

15. Montego Bay Club Beach Resort

16. Montego Bay Club Apartments

17. Claudeville Condo

18. Seawind F104

19. The Shallhome

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

Find vacation rentals that suit your style

Top Middlesex Hotel Reviews

Blue Paloma Bed & Breakfast

10/10 Excellent

Frequently Asked Questions

Can I find vacation rentals in Middlesex?

What are some of the best vacation rentals that Middlesex has to offer?

What can I see and do in Middlesex?

What are vacation rentals like in Middlesex?