Middlesex County Vacation Rentals from ￥14,838: Search Short-Term Rentals

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Our top choices for Middlesex County vacation rentals

A modern living room with a white sofa, a glass coffee table, and a staircase leading to an upper level.

1. Tuscany Sun Villa at Legacy Townhouse

Thompson Town

￥137,106 total

includes taxes & fees

Sep 4 - Sep 5

A person overlooking a coastal area with a cruise ship, lush greenery, and a swimming pool.

2. Spring Palm Estate

Tower Isle

Shagufta

￥15,958 total

includes taxes & fees

Sep 5 - Sep 6

A spacious living area with a high ceiling, a ceiling fan, a sofa set, a dining table with chairs, and a TV mounted on the wall.

3. DraxHall Villa

Saint Ann's Bay

￥53,352 total

includes taxes & fees

Sep 4 - Sep 5

A beach with clear water, a sandy shore, and buildings in the background.

4. Fisherman's Point Resort

Ocho Rios

Desmond

￥15,956 total

includes taxes & fees

Sep 7 - Sep 8

A rooftop pool area with multiple seating areas, a hot tub, and a view of palm trees and greenery.

5. Opulenz DraxHall

St. Ann's Bay

￥889,041 total

includes taxes & fees

Sep 4 - Sep 5

A pool area with a gazebo, lounge chairs, and a view of the surrounding landscape.

6. Mountain Top Villa

Mandeville

Robert

￥14,838 total

includes taxes & fees

Sep 21 - Sep 22

A balcony with a view of a pool and a building in the background.

7. Caldo Tours

Ewarton

Stephen

￥20,594 total

includes taxes & fees

Sep 4 - Sep 5

A hotel room with two beds, a window with curtains, a wall-mounted air conditioner, and a decorative wall piece.

8. Adorable 1bed Cottage Too Walk to the Beach

St. Ann's Bay

￥17,844 total

includes taxes & fees

Sep 4 - Sep 5

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Top Middlesex County Hotel Reviews

The Cardiff Hotel & Spa

10/10 Excellent

"I loved everything about the room except the fact i was unable to use the tub that was in my room. I suggest you tell customers that even tho the tub will be in the room they wouldn't be able to have it filled, but they can choose to keep it or take a standing shower instead. Overall the property and it's staff was truly amazing. This was my second visit and i will be back."

Whispering Seas

10/10 Excellent

"Our stay at Whispering Seas was lovely. It did start out a little rocky, but Melanie, Melanie, Melanie!! The communication with Melanie was top-tier, and she addressed our issue immediately. I am planning on returning with my entire family next year and hope Melanie will have space to accommodate us all. Two suggestions I have are: having 2 blow dryers available to those who frequent the pool/beach, and a full-length mirror. I have to add that the location is perfect, as it is right outside of Ocho Rios, less than 10 minutes from the hustle and bustle. I am already missing the views and hearing the waves crashing along the shore. Thanks, Melanie for an awesome week away."

Villa Sonate

10/10 Excellent

"The room and bathroom were clean and spacious. The staff were courteous and helpful. The Jamaican breakfast was delicious. The air conditioning along with the fan worked well. Good running water in the shower. The grounds were well kept. I have absolutely no complaints. When I saw the hotel rating I was curious as to how this older hotel has such an excellent rating (9/1 0). There was nothing here that could be considered modern except for their brilliant idea to use solar panels as covering for the car park. What makes this hotel a winner, I believe, is the quiet, laid back, relaxing atmosphere (old charm) away from the crowds associated with large all-inclusive resorts."

Find out more about Middlesex County

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Check prices for these dates

Our top choices for Middlesex County vacation rentals

1. Tuscany Sun Villa at Legacy Townhouse

2. Spring Palm Estate

3. DraxHall Villa

4. Fisherman's Point Resort

5. Opulenz DraxHall

6. Mountain Top Villa

7. Caldo Tours

8. Adorable 1bed Cottage Too Walk to the Beach

9. Spacious contemporary, relaxing apartment only 5 minutes walk to fabulous beach

10. Adorable 1Bed Cottage Walk to the Beach

11. Phoenix Park Villas Portmore

12. Cozy Relaxing Home in Old Harbour

13. Ac'ed 2 bedroom Beach House

14. DeJee Lodging

15. Bayfront apartment and villas

16. The Cottage very comfortable, relaxing also secure, 5 minutes walk from beach

17. 2Bedrooms 2Bathroom - Swimming pool - Gated community - Drier - Free Wifi

18. Cozy 1bed Apartment in Priory Walk to the Beach

19. Immaculate 2-bed Apartment in Spanish Town

20. Comfy 3BR Villa - Paradisiac Beach Club

Find vacation rentals that suit your style

Top Middlesex County Hotel Reviews

The Cardiff Hotel & Spa

Bahia Principe Escape Runaway Bay - Hyatt Inclusive Collection - Adults Only - All Inclusive

Golf View Hotel

Whispering Seas

Villa Sonate

Mandeview Hotel

The Garden Hotel Mandeville

Tamarind Tree Hotel

Tiamo Beach Resort and Spa

Find out more about Middlesex County

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