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

Holiday Homes in Middlesex County

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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

DeJee Lodging
3.5 star property
Ocho Rios
9.0 out of 10, Wonderful, (4 reviews)
"The facility is safe clean attractive and the rooms have everything you needed for ur comfort experience was wonderful 100/100👍"
United States
Winston
The price is €114
includes taxes & fees
25 Oct - 26 Oct
DeJee Lodging
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

Charming 4-bedroom bungalow with WiFi, AC in lovely St. Ann Parish close to Ochi
St. Ann Parish
The price is €271
includes taxes & fees
17 Nov - 18 Nov
Charming 4-bedroom bungalow with WiFi, AC in lovely St. Ann Parish close to Ochi
A compact living space with a sofa, dining table, chairs, a TV, a microwave, a refrigerator, and a potted plant.

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

Phoenix Rising Superb bungalow with AC in Portmore - 2 bedrooms
Caribbean Estates
10.0 out of 10, Exceptional, (3 reviews)
"We had a good stay. The place was clean and everything accurate. Host was reachable anytime I called .10/10 would recommend"
United States
Shanique
The price is €120
includes taxes & fees
21 Oct - 22 Oct
Phoenix Rising Superb bungalow with AC in Portmore - 2 bedrooms
Swimming pool night view

4. A Suite Home entire pool home

A Suite Home entire pool home
Ocho Rios
7.2 out of 10, Good, (15 reviews)
"Nice view, close to attractions and stores and entertainment."
United States
Donovan
The price is €131
includes taxes & fees
18 Oct - 19 Oct
A Suite Home entire pool home
A swimming pool with blue lounge chairs and umbrellas, surrounded by houses with sloped roofs.

5. Tropical Tranquility in Jamaica

Tropical Tranquility in Jamaica
Richmond Estate
The price is €278
includes taxes & fees
19 Oct - 20 Oct
Tropical Tranquility in Jamaica
A bedroom with a bed, dresser, mirror, and curtains.

6. 3 Bedroom Cozy House in Drax Hall

3 Bedroom Cozy House in Drax Hall
3.5 star property
Ocho Rios
4.0 out of 10, (1 review)
"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...
United States
Samantha
The price is €235
includes taxes & fees
21 Oct - 22 Oct
3 Bedroom Cozy House in Drax Hall
A modern kitchen with a built-in oven, a refrigerator, and a dining area with a table set for four.

7. Phoenix Park Villas Portmore

Phoenix Park Villas Portmore
4.0 star property
Portmore
9.8 out of 10, Exceptional, (6 reviews)
"I will definitely recommend that you stay here is so peaceful security are strictly on point with everything and the comfort of the home is great will be staying back for sure ."
United States
Kimoya
The price is €305
includes taxes & fees
19 Oct - 20 Oct
Phoenix Park Villas Portmore
A kitchen with wooden cabinets, a stainless steel stove, and a tiled backsplash.

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

Relax and enjoy in this beautiful home in a quiet neighbourhood.
Mineral Hieghts
The price is €136
includes taxes & fees
20 Oct - 21 Oct
Relax and enjoy in this beautiful home in a quiet neighbourhood.
A swimming pool with blue chairs and a covered area, surrounded by a brick walkway.

9. Harbour Oasis Retreat - Charming 2 Bedroom House

Harbour Oasis Retreat - Charming 2 Bedroom House
3.5 star property
Old Harbour
The price is €182
includes taxes & fees
19 Oct - 20 Oct
Harbour Oasis Retreat - Charming 2 Bedroom House
A modern building with a Starbucks logo on the facade, large windows, and a small tree in front.

10. PLAN YOUR GETAWAY UNDER THE SUN Dazzle Key Suite

PLAN YOUR GETAWAY UNDER THE SUN Dazzle Key Suite
Greenwich Estate
10.0 out of 10, Exceptional, (3 reviews)
"This property was excellent, the host was the best!!, communication with the host was indeed at its best. Cleanliness and comfort was also at its best!!"
United States
Raphaela
The price is €303
includes taxes & fees
20 Oct - 21 Oct
PLAN YOUR GETAWAY UNDER THE SUN Dazzle Key Suite
A black SUV parked on a grassy area with trees and a building in the background.

11. Mckay's Home Away from Home

Mckay's Home Away from Home
Hatfield
8.4 out of 10, Very good, (7 reviews)
"My stay at Mckay’s was amazing any issues we had it was resolved. The host was very helpful and considerate. Next time I go back I hope they have availability because I would definitely book them again. The place was in a very nice and quiet area not far from the town. "
United States
Juana M.
The price is €126
includes taxes & fees
31 Oct - 1 Nov
Mckay's Home Away from Home
A covered outdoor area with a table and chairs, potted plants, and a view of buildings and trees.

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

one bedroom cozy and quiet neighborhood 10min from ocho rios town
St. Mary Parish
10.0 out of 10, Exceptional, (1 review)
The price is €129
includes taxes & fees
19 Oct - 20 Oct
one bedroom cozy and quiet neighborhood 10min from ocho rios town
A multi-story building with a red-tiled roof, multiple balconies, and a car parked in front.

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

Cozy upstairs apartment for two with great views. Book your stay today.
Williamsfield
10.0 out of 10, Exceptional, (1 review)
"Our stay was excellent. The Hosts are very gracious and kind. The property is very clean and welcoming. We are very appreciative of all the complementary teas coffees, and other beverages left there for us to sample.We will be booking a return, hopefully sometime over the summer"
United States
Janea G.
The price is €98
includes taxes & fees
18 Oct - 19 Oct
Cozy upstairs apartment for two with great views. Book your stay today.
A beach with a cruise ship in the background, palm trees, and people sunbathing.

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

Dell’s Exotic Haven 2 bedrooms, 2 baths, pool, gym
Saint Ann's Bay
10.0 out of 10, Exceptional, (1 review)
"We enjoyed the home! Absolutely beautiful inside and outside. The property is so safe close to the security gate to always walk. You will love everything in the home! So modern just like your own house. Make sure you take advantage of renting this gold mine!! The host always checked in on us to make sure we were okay.. Amazing Communication! Definitely a 10 stay….. "
United States
Danielle
The price is €202
includes taxes & fees
18 Oct - 19 Oct
Dell’s Exotic Haven 2 bedrooms, 2 baths, pool, gym
A bed with a pink bedspread, a blanket, and pillows, a flat-screen TV mounted on the wall, and a window with curtains.

15. Cozy 2-bedroom house in marvelous Discovery Bay with AC

Cozy 2-bedroom house in marvelous Discovery Bay with AC
Discovery Bay
The price is €178
includes taxes & fees
18 Oct - 19 Oct
Cozy 2-bedroom house in marvelous Discovery Bay with AC
A bathroom with a white toilet, a sink with a mirror, a wooden cabinet, and a blue wall.

16. Ac'ed 2 bedroom Beach House

Ac'ed 2 bedroom Beach House
Hellshire
9.4 out of 10, Exceptional, (16 reviews)
"Great location, great host, great stay!"
United States
Chevaughn G.
The price is €133
includes taxes & fees
21 Oct - 22 Oct
Ac'ed 2 bedroom Beach House
A colorful building with a sign that reads "Relax N Sunshine."

17. Relax N SunShine Peaceful, Retreat

Relax N SunShine Peaceful, Retreat
May Pen
4.8 out of 10, (3 reviews)
"I enjoyed my brief stay with my son we were received warmly. The vibes were awesome. Nice garden area also."
United States
Mikisa
The price is €51
includes taxes & fees
18 Oct - 19 Oct
Relax N SunShine Peaceful, Retreat
A potted snake plant in a modern indoor setting with a reflective floor and a black shelf unit in the background.

18. Charming refuge at Colbeck Manor

Charming refuge at Colbeck Manor
Old Harbour
10.0 out of 10, Exceptional, (2 reviews)
"Host Duwayne was excellent, very attentive, house was clean and comfy. Would stay again "
United States
chin
The price is €157
includes taxes & fees
26 Oct - 27 Oct
Charming refuge at Colbeck Manor
A two-story house with a red-tiled roof, a gated entrance, and a balcony on the second floor.

19. Home in St. Catherine section 2

Home in St. Catherine section 2
Spanish Town
9.0 out of 10, Wonderful, (2 reviews)
"Have no complaints, my stay was a great stay "
United States
Icashea M.
The price is €116
includes taxes & fees
18 Oct - 19 Oct
Home in St. Catherine section 2
A beachside café with outdoor seating, a palm tree, and a view of the ocean.

20. Beachfront Bed & breakfast - 2 mins walk to river

Beachfront Bed & breakfast - 2 mins walk to river
st ann
The price is €142
includes taxes & fees
17 Nov - 18 Nov
Beachfront Bed & breakfast - 2 mins walk to river
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middlesex County Hotel Reviews

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

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

10/10 Excellent
"Really enjoyed my stay, will be back in 2027."
Rumiel 2-night trip
Posted 3 hours ago
Bahia Principe Escape Runaway Bay - Hyatt Inclusive Collection - Adults Only - All Inclusive

Find out more about Middlesex County

Middlesex County Holiday Homes information

Number of reviews
40
Accommodation
536 Holiday Homes
Lowest Price
€51
Highest Price
€305