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

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Middlesex County vacation 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 ￥10,659
￥20,312 total
includes taxes & fees
Oct 13 - Oct 14
DeJee Lodging
A swimming pool with blue lounge chairs and umbrellas, surrounded by houses with sloped roofs.

2. Tropical Tranquility in Jamaica

Tropical Tranquility in Jamaica
Richmond Estate
The price is ￥30,477
￥47,994 total
includes taxes & fees
Oct 8 - Oct 9
Tropical Tranquility in Jamaica
Swimming pool night view

3. 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 ￥13,051
￥22,526 total
includes taxes & fees
Oct 7 - Oct 8
A Suite Home entire pool home
A swimming pool with blue lounge chairs and umbrellas, surrounded by houses with sloped roofs.

4. 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 ￥30,477
￥48,457 total
includes taxes & fees
Oct 7 - Oct 8
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.

5. 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 ￥13,501
￥20,607 total
includes taxes & fees
Oct 19 - Oct 20
Phoenix Rising Superb bungalow with AC in Portmore - 2 bedrooms
A modern building with a Starbucks logo on the facade, large windows, and a small tree in front.

6. 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 ￥24,002
￥54,321 total
includes taxes & fees
Oct 12 - Oct 13
PLAN YOUR GETAWAY UNDER THE SUN Dazzle Key Suite
A bedroom with a bed, dresser, mirror, and curtains.

7. 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 ￥30,737
￥52,088 total
includes taxes & fees
Oct 7 - Oct 8
3 Bedroom Cozy House in Drax Hall
A swimming pool with blue chairs and a covered area, surrounded by a brick walkway.

8. Harbour Oasis Retreat - Charming 2 Bedroom House

Harbour Oasis Retreat - Charming 2 Bedroom House
3.5 star property
Old Harbour
The price is ￥16,746
￥31,423 total
includes taxes & fees
Oct 21 - Oct 22
Harbour Oasis Retreat - Charming 2 Bedroom House
A modern kitchen with a built-in oven, a refrigerator, and a dining area with a table set for four.

9. 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 ￥35,530
￥62,107 total
includes taxes & fees
Oct 7 - Oct 8
Phoenix Park Villas Portmore
A covered outdoor area with a table and chairs, potted plants, and a view of buildings and trees.

10. 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 ￥15,001
￥22,107 total
includes taxes & fees
Oct 8 - Oct 9
one bedroom cozy and quiet neighborhood 10min from ocho rios town
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.
Mckay's Home Away from Home
A beach with a cruise ship in the background, palm trees, and people sunbathing.

12. 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 ￥22,967
￥34,242 total
includes taxes & fees
Oct 11 - Oct 12
Dell’s Exotic Haven 2 bedrooms, 2 baths, pool, gym
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 ￥13,422
￥16,580 total
includes taxes & fees
Oct 7 - Oct 8
Cozy upstairs apartment for two with great views. Book your stay today.
A potted snake plant in a modern indoor setting with a reflective floor and a black shelf unit in the background.

14. 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 ￥13,422
￥27,871 total
includes taxes & fees
Oct 25 - Oct 26
Charming refuge at Colbeck Manor
A coastal view with clear turquoise waters and a grassy foreground.

15. 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 ￥11,839
￥22,889 total
includes taxes & fees
Nov 5 - Nov 6
Ac'ed 2 bedroom Beach House
A kitchen with wooden cabinets, a stainless steel stove, and a tiled backsplash.

16. 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 ￥14,615
￥23,176 total
includes taxes & fees
Oct 7 - Oct 8
Relax and enjoy in this beautiful home in a quiet neighbourhood.
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 ￥3,876
￥8,311 total
includes taxes & fees
Oct 11 - Oct 12
Relax N SunShine Peaceful, Retreat
A bed with a pink bedspread, a blanket, and pillows, a flat-screen TV mounted on the wall, and a window with curtains.

18. 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 ￥21,318
￥30,911 total
includes taxes & fees
Oct 7 - Oct 8
Cozy 2-bedroom house in marvelous Discovery Bay with AC
A beach with thatched-roof huts and palm trees.

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

Book now and u can save 20%OFF JUNE JULY FOR EARLY BIRD SALE IN SUMMER BOOKING
Ocho Rios
10.0 out of 10, Exceptional, (1 review)
"My first impression was wow this place is really nice! It is well kept, spacious and in a quiet neighbourhood, like a hidden gem near everything you would like to explore. After a day it started to feel like home and I didn't want to leave, I had to extend my stay for another day. Just as it's advertised home away it just felt like home!"
Canada
Cecile S.
The price is ￥21,752
￥53,334 total
includes taxes & fees
Oct 7 - Oct 8
Book now and u can save 20%OFF JUNE JULY FOR EARLY BIRD SALE IN SUMMER BOOKING
A swimming pool area with a waterfall feature, a television screen, and a mural of a house.

20. Cute and Cozy Ez Home

Cute and Cozy Ez Home
Bridgeport
9.2 out of 10, Wonderful, (5 reviews)
"Came back at the perfect time of the year, got to try some mangoes and they were absolutely delicious right from treee in the yard. Ms James and her family are amazing hosts! Me and my fiancé look forward to booking again!! Thank you! "
United States
shardae w.
The price is ￥13,417
￥25,256 total
includes taxes & fees
Oct 7 - Oct 8
Cute and Cozy Ez Home
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.
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Top Middlesex County Hotel Reviews

Couples Tower Isle All Inclusive

Couples Tower Isle All Inclusive

8/10 Good
"Na"
Atiah 5-night trip
Posted 5 hours ago
Couples Tower Isle All Inclusive

Find out more about Middlesex County

Middlesex County Vacation Homes information

Number of reviews
44
Accommodation
501 Vacation Homes
Lowest Price
￥8,311
Highest Price
￥62,107