A beach with palm trees, a thatched-roof hut, and the ocean.

Middlesex County Vacation Rentals

Dates

November 2026

December 2026

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Our top choices for Middlesex County vacation rentals

A hotel with multiple floors, a swimming pool, and palm trees.

1. Fisherman's Point Resort

Ocho Rios

Shawnette

₩146,616 total

includes taxes & fees

Dec 1 - Dec 2

A balcony with a white umbrella, a wicker chair, and a view of the ocean.

2. Adorable 1Bed Cottage Walk to the Beach

St. Ann's Bay

Marisa

₩141,577 total

includes taxes & fees

Nov 24 - Nov 25

A two-story building with a swimming pool in the foreground.

3. Wave Crest Resort Race Course

Oracabessa

Beverly

₩213,326 total

includes taxes & fees

Nov 10 - Nov 11

A gated entrance with a central building and two smaller structures on either side.

4. DeJee Lodging

Ocho Rios

Winston

₩175,610 total

includes taxes & fees

Nov 18 - Nov 19

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

5. Mountain Top Villa

Mandeville

Robert

₩127,585 total

includes taxes & fees

Nov 10 - Nov 11

A building with a balcony and a staircase.

6. Lovely 1-bed Cottage in St Catherine

Ewarton

DESMOND

₩39,614 total

includes taxes & fees

Nov 21 - Nov 22

A resort with multiple swimming pools, lounge chairs, and umbrellas.

7. North Star Villa

Mammee Bay Estates

PATRICIA

₩172,572 total

includes taxes & fees

Nov 25 - Nov 26

A resort with a large pool, lush greenery, and a view of the ocean.

8. Sky Castles

Ocho Rios

Rose

₩198,104 total

includes taxes & fees

Nov 10 - Nov 11

A hotel room with two beds, a small table, a bathroom with a sink, and a window with curtains.

9. Adorable 1bed Cottage Too Walk to the Beach

St. Ann's Bay

₩139,410 total

includes taxes & fees

Nov 10 - Nov 11

A swimming pool with a slide, a building with a balcony, and a sign that reads "Restaurant".

10. Sandcastles Ocho Rios

Ocho Rios

Gregory

₩150,183 total

includes taxes & fees

Dec 6 - Dec 7

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

11. Caldo Tours

Ewarton

Stephen

₩177,078 total

includes taxes & fees

Nov 10 - Nov 11

A kitchen with a central island, bar stools, wooden cabinets, a window with a view, and a microwave.

12. Coke's Guest House

Mandeville

₩135,607 total

includes taxes & fees

Nov 10 - Nov 11

A kitchen counter with a wooden phone, a bag of chips, a potted plant, and a roll of paper towels.

13. SOL Euphoria Ocho Rios walk to the beach

Ocho Rios

₩374,021 total

includes taxes & fees

Nov 15 - Nov 16

View all properties

Find vacation rentals that suit your style

Top Middlesex County Hotel Reviews

A swimming pool with a white deck, surrounded by lush greenery and a white fence.

Millsborough B&B

Jack's Hill

10/10 Excellent

Boris

A modern building with a pool, large windows, and trees.

The Garden Hotel Mandeville

Mandeville

10/10 Excellent

Lovett

A white building with a blue door, black railings, and potted plants.

Sky's Villa Resort

Buff Bay

10/10 Excellent

Tannecia

A tropical resort with a clear turquoise pool, a wooden deck with lounge chairs, and a stone wall.

GoldenEye

Oracabessa

10/10 Excellent

My wife and I just had the most incredible 4 night stay at GoldenEye for our anniversary. We stayed in one of the Lagoon Cottages which was very roomy and comfortable. We loved being directly on the lagoon where we could swim, kayak or just sit and watch the turtles go by. We enjoyed the beaches and pools on the property as well. All of the staff (front desk, restaurants, grounds, water sports, spa, etc.) were wonderful. And, every meal we had at Bizot Bar and Bamboo Bar was delicious and...

Nicholas

A balcony with a green railing overlooking a garden with red-roofed buildings and lush greenery.

Villa Sonate

Runaway Bay

10/10 Excellent

Swift DB2

A swimming pool with yellow railings and palm trees in the background.

Kingsbird by the sea Inn

Discovery Bay

10/10 Excellent

Kingsbird is an excellent place to stay. Once you get there, you are welcomed as if you were family,and treated as such throughout you stay; Natalie, KIngsley and Natalia were wonderful Hosts. They greet you with beautiful smiles every time they see you,always ensuring that you are OK and in need of nothing. They are knowledgeable locally, so anything you need done, they can "hook you up"; will stay with them next time I visit Jamaica. Thanks for the hospitality! Robert

Robert

A modern kitchen with a built-in oven, a refrigerator, and a dining area with a table set for four.

Phoenix Park Villas Portmore

Portmore

10/10 Excellent

Steven

A modern two-story building with a paved courtyard and a car parked in front.

Sago Palm Hotel

Ocho Rios

10/10 Excellent

I had the absolute pleasure of staying at this beautiful boutique hotel in Jamaica, and I can confidently say it exceeded all expectations. From the moment I arrived, the staff made me feel incredibly welcomed every single person I interacted with was warm, friendly, and genuinely helpful. Their hospitality truly made the experience feel like a home away from home. The food was another highlight of my stay every meal was fresh, flavorful, and clearly made with love. Knowing that the hotel...

Anonymous traveler

A yellow building with multiple balconies, large windows, and a paved entrance area with plants.

A taste of Jamaica Lavern place

Ocho Rios

10/10 Excellent

Melissa

A coastal view with a tree-lined walkway leading to a beach area with a thatched-roof structure.

Hibiscus Lodge

Ocho Rios

10/10 Excellent

Hibiscus was a beautiful hotel in a beautiful location. The view of the ocean is incredible. It's a 5 minute walk to the little beach though. It's on a cliff side with a beautiful garden and walkways that go down to the water. It has the feel of a Caribbean hotel, which is what I prefer over a big gated resort. Restaurants and shopping are a very short walk. Every part of the hotel is placed perfectly to view the ocean (rooms, bar, restaurants.)

Anonymous traveler

A clear swimming pool with blue tiles, surrounded by palm trees and a white wall.

Sea Shell Palms

Tower Isle

10/10 Excellent

Anonymous traveler

A dining table with a plate of food, a glass of orange juice, and a flower vase by a poolside.

The Cardiff Hotel & Spa

Runaway Bay

10/10 Excellent

I took my 22 month old daughter with me on this trip and it was excellent. The staff were great, friendly and very professional. The food was excellent! My room was the best, I had a great view of the ocean from my patio! The trees were next to the patio so that breeze felt so good. Every morning my daughter got up and head straight to the patio. The house keeper, Lisa took excellent care of us! Loved it! Definitely going back with my son. Thank You Cardiff staff for a great time!

Sandy

A modern living room with a large sofa, a coffee table, and a TV. There is a balcony with a view of the sea.

Moon Palace Jamaica – All Inclusive

Ocho Rios

10/10 Excellent

Yesenia Merced

Mountain Top Villa

Mandeville

10/10 Excellent

Janet

Adorable 1Bed Cottage Walk to the Beach

St. Ann's Bay

10/10 Excellent

Marisa

Find out more about Middlesex County

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Look no further and take a look at our great range of rental properties in Middlesex County!

Middlesex County Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Middlesex County vacation rentals

1. Fisherman's Point Resort

2. Adorable 1Bed Cottage Walk to the Beach

3. Wave Crest Resort Race Course

4. DeJee Lodging

5. Mountain Top Villa

6. Lovely 1-bed Cottage in St Catherine

7. North Star Villa

8. Sky Castles

9. Adorable 1bed Cottage Too Walk to the Beach

10. Sandcastles Ocho Rios

11. Caldo Tours

12. Coke's Guest House

13. SOL Euphoria Ocho Rios walk to the beach

Find vacation rentals that suit your style

Top Middlesex County Hotel Reviews

Millsborough B&B

10/10 Excellent

Find out more about Middlesex County