Middlesex County Vacation Homes

A waterfall cascading into a turquoise pool surrounded by lush greenery.

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Our top choices for Middlesex County holiday homes

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

1. DeJee Lodging

Ocho Rios

Winston

HK$1,008 total

includes taxes & fees

27 Oct - 28 Oct

A swimming pool with blue lounge chairs and umbrellas, surrounded by houses with sloped roofs.

2. Charming 4-bedroom bungalow with WiFi, AC in lovely St. Ann Parish close to Ochi

St. Ann Parish

HK$2,405 total

includes taxes & fees

25 Oct - 26 Oct

3. PLAN YOUR GETAWAY UNDER THE SUN Dazzle Key Suite

Greenwich Estate

Raphaela

HK$2,606 total

includes taxes & fees

25 Oct - 26 Oct

A swimming pool with blue chairs and a covered area, surrounded by a brick walkway.

4. Harbour Oasis Retreat - Charming 2 Bedroom House

Old Harbour

HK$1,608 total

includes taxes & fees

25 Oct - 26 Oct

5. A Suite Home entire pool home

Ocho Rios

Donovan

HK$1,118 total

includes taxes & fees

27 Oct - 28 Oct

A bedroom with a bed, dresser, mirror, and curtains.

6. 3 Bedroom Cozy House in Drax Hall

Ocho Rios

"Last minute while at airport I received an email to say that the place reserved was no longer available. After being on the phone for over an hour I was offered another place which was smaller. I had no choice but to take it or me and my kids would have been on the street. Upon entering the place, it was immediately noticed that it was not clean, no light bulbs, 1 tv in one of the bedrooms. Front door did not close properly. Cushions ripped up. I got the impression that the place was on the...

Samantha

HK$2,895 total

includes taxes & fees

27 Oct - 28 Oct

A covered outdoor area with a table and chairs, potted plants, and a view of buildings and trees.

7. one bedroom cozy and quiet neighborhood 10min from ocho rios town

St. Mary Parish

HK$1,097 total

includes taxes & fees

25 Oct - 26 Oct

A kitchen with a wooden island, two bar stools, a refrigerator, and a microwave.

8. Relax and enjoy in this beautiful home in a quiet neighbourhood.

Mineral Hieghts

HK$1,164 total

includes taxes & fees

28 Oct - 29 Oct

A beach with a cruise ship in the background, palm trees, and people sunbathing.

9. Dell’s Exotic Haven 2 bedrooms, 2 baths, pool, gym

Saint Ann's Bay

Danielle

HK$1,731 total

includes taxes & fees

27 Oct - 28 Oct

A multi-story building with a red-tiled roof, multiple balconies, and a car parked in front.

10. Cozy upstairs apartment for two with great views. Book your stay today.

Williamsfield

Janea G.

HK$823 total

includes taxes & fees

29 Oct - 30 Oct

A compact living space with a sofa, dining table, chairs, a TV, a microwave, a refrigerator, and a potted plant.

11. Phoenix Rising Superb bungalow with AC in Portmore - 2 bedrooms

Caribbean Estates

Charmaine G.

HK$1,023 total

includes taxes & fees

3 Nov - 4 Nov

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

12. Phoenix Park Villas Portmore

Portmore

Kimoya

HK$3,502 total

includes taxes & fees

3 Nov - 4 Nov

A coastal view with a wooden fence, a gazebo, and a palm tree.

13. Boscobel Hilltop Home 2 Bedrooms & Ocean Views

Salt Gut

HK$1,176 total

includes taxes & fees

28 Oct - 29 Oct

A beach with thatched-roof huts and palm trees.

14. Book now and u can save 20%OFF JUNE JULY FOR EARLY BIRD SALE IN SUMMER BOOKING

Ocho Rios

Cecile S.

HK$2,606 total

includes taxes & fees

25 Oct - 26 Oct

A modern bedroom with a large bed, a ceiling fan, and a view of the outdoors through the window.

15. Ochi Modern Boho Villa - Seaside Escape

Bonham Springs

Vanessa W.

HK$2,682 total

includes taxes & fees

25 Oct - 26 Oct

A bedroom with a bed, a dresser, a television, and a wall decoration.

16. The White Room Charming 1-bedroom & Bathroom Off Old Harbour road with WiFi

Spanish Town

HK$914 total

includes taxes & fees

25 Oct - 26 Oct

A living room with a sofa, a glass coffee table, and red patterned curtains.

17. Charming 2-bedroom house in Portmore with WiFi, AC

Portmore

Sophia

HK$716 total

includes taxes & fees

25 Oct - 26 Oct

A swimming pool area with a waterfall feature, a television screen, and a mural of a house.

18. Cute and Cozy Ez Home

Bridgeport

shardae w.

HK$1,254 total

includes taxes & fees

4 Nov - 5 Nov

A building with a sign that reads "Lahaina Vie Estate" and a landscaped area with tropical plants.

19. Palmview Estate Townhouse

ocho rios

HK$2,202 total

includes taxes & fees

25 Oct - 26 Oct

A black SUV parked on a grassy area with trees and a building in the background.

20. Mckay's Home Away from Home

Hatfield

Juana M.

HK$1,074 total

includes taxes & fees

31 Oct - 1 Nov

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Top Middlesex County Hotel Reviews

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

10/10 Excellent

"Everything was fun"

GoldenEye

8/10 Good

"The concept is amazing – you feel so close to nature. My bungalow was nestled in the natural landscape, emerging just enough to catch a view of the ocean. The staff were very accommodating, and Romane (Night Shift Supervisor) and Richard (Maintenance Supervisor) went above and beyond to make sure I was comfortable and safe. Thank you, Team GoldenEye, for your guest-centred approach. It made my stay on your property truly amazing!"

Tiamo Beach Resort and Spa

10/10 Excellent

"TOP TIER Birthday Experience! From the time I booked through Expedia until the moment I departed, my experience at Tiamo Beach Resort was TOP TIER! I spent two nights celebrating my birthday, and I truly felt special in every way. Check in was seamless, I was greeted with a delicious mocktail, and the staff went above and beyond to decorate my room with beautiful Happy Birthday touches. My room was spotless and comfortable, with hot water and a luxurious tub on the balcony overlooking the water. Waking up to that view every morning was everything. The entire resort was extremely clean, the beach was peaceful and relaxing, and the food was absolutely delicious. Breakfast was included with both traditional and Jamaican style options available, and every meal was so flavorful. A very special shoutout to Malik at the front desk, Chef Birch, and Romi, the General Manager. What an incredible team! Your hospitality, kindness, and attention to detail made my birthday celebration unforgettable. Chef Birch prepared amazing meals, Malik made check in effortless, and Romi ensured every part of my stay was exceptional. They even arranged my transportation to Kingston Airport, making my departure completely stress free. Tiamo gave me the perfect reset, relaxation, and self care experience I truly needed. If you're celebrating a birthday, milestone, or any special occasion, Tiamo Beach Resort is the place to be. I can't wait to come back. Thank you Team Tiamo!"

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