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

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Check prices for these dates

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

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 ￥10,667
￥20,326 total
includes taxes & fees
Oct 25 - Oct 26
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 ￥30,498
￥48,490 total
includes taxes & fees
Oct 18 - Oct 19
Charming 4-bedroom bungalow with WiFi, AC in lovely St. Ann Parish close to Ochi
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 ￥13,060
￥22,541 total
includes taxes & fees
Oct 18 - Oct 19
A Suite Home entire pool home
A compact living space with a sofa, dining table, chairs, a TV, a microwave, a refrigerator, and a potted plant.

4. 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 ￥13,511
￥20,622 total
includes taxes & fees
Oct 19 - Oct 20
Phoenix Rising Superb bungalow with AC in Portmore - 2 bedrooms
A bedroom with a bed, dresser, mirror, and curtains.

5. 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 ￥21,723
￥41,742 total
includes taxes & fees
Oct 28 - Oct 29
3 Bedroom Cozy House in Drax Hall
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 ￥19,515
￥52,541 total
includes taxes & fees
Oct 20 - Oct 21
PLAN YOUR GETAWAY UNDER THE SUN Dazzle Key Suite
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
9.2 out of 10, Wonderful, (7 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 ￥28,458
￥54,077 total
includes taxes & fees
Oct 30 - Oct 31
Phoenix Park Villas Portmore
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 ￥17,064
￥31,892 total
includes taxes & fees
Oct 19 - Oct 20
Harbour Oasis Retreat - Charming 2 Bedroom House
A covered outdoor area with a table and chairs, potted plants, and a view of buildings and trees.

9. 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 ￥15,012
￥22,123 total
includes taxes & fees
Oct 19 - Oct 20
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.

10. 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 ￥13,432
￥16,592 total
includes taxes & fees
Oct 19 - Oct 20
Cozy upstairs apartment for two with great views. Book your stay today.
A bed with a pink bedspread, a blanket, and pillows, a flat-screen TV mounted on the wall, and a window with curtains.

11. 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 ￥21,333
￥30,933 total
includes taxes & fees
Oct 18 - Oct 19
Cozy 2-bedroom house in marvelous Discovery Bay with AC
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 ￥23,164
￥34,746 total
includes taxes & fees
Nov 16 - Nov 17
Dell’s Exotic Haven 2 bedrooms, 2 baths, pool, gym
A black SUV parked on a grassy area with trees and a building in the background.

13. 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 ￥11,061
￥21,648 total
includes taxes & fees
Oct 31 - Nov 1
Mckay's Home Away from Home
A coastal view with clear turquoise waters and a grassy foreground.

14. 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 ￥11,852
￥22,913 total
includes taxes & fees
Oct 19 - Oct 20
Ac'ed 2 bedroom Beach House
A two-story house with a red-tiled roof, a gated entrance, and a balcony on the second floor.

15. 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 ￥13,368
￥19,829 total
includes taxes & fees
Oct 18 - Oct 19
Home in St. Catherine section 2
A colorful building with a sign that reads "Relax N Sunshine."

16. 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 ￥3,899
￥8,249 total
includes taxes & fees
Oct 18 - Oct 19
Relax N SunShine Peaceful, Retreat
A living room with a sofa, a glass coffee table, and red patterned curtains.

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

Charming 2-bedroom house in Portmore with WiFi, AC
Portmore
10.0 out of 10, Exceptional, (8 reviews)
"Room was spotless, very caring host."
United Kingdom
Sophia
The price is ￥11,175
￥14,304 total
includes taxes & fees
Oct 19 - Oct 20
Charming 2-bedroom house in Portmore with WiFi, AC
A beach with thatched-roof huts and palm trees.

18. 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 ￥19,515
￥52,541 total
includes taxes & fees
Oct 19 - Oct 20
Book now and u can save 20%OFF JUNE JULY FOR EARLY BIRD SALE IN SUMMER BOOKING
A potted snake plant in a modern indoor setting with a reflective floor and a black shelf unit in the background.

19. 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 ￥12,800
￥26,924 total
includes taxes & fees
Oct 27 - Oct 28
Charming refuge at Colbeck Manor
A bedroom with a bed, a dresser, a television, and a wall decoration.

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

The White Room Charming 1-bedroom & Bathroom Off Old Harbour road with WiFi
Spanish Town
The price is ￥10,271
￥19,436 total
includes taxes & fees
Oct 18 - Oct 19
The White Room Charming 1-bedroom & Bathroom Off Old Harbour road with WiFi
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

10/10 Excellent
"The courteous and professional staff ensured you were comfortable and well taken care of."
Trevor 5-night trip
Posted 6 hours ago
Couples Tower Isle All Inclusive

Find out more about Middlesex County

Middlesex County Vacation Homes information

Number of reviews
49
Accommodation
501 Vacation Homes
Lowest Price
￥8,249
Highest Price
￥54,077