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

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Check prices for these dates

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

Our top choices for Middlesex County holiday rentals

A beach with clear water, a sandy shore, and buildings in the background.

1. Fisherman's Point Resort

Fisherman's Point Resort
3.0 star property
Ocho Rios
6.0 out of 10, (622 reviews)
"Perfect location 👌"
United States
Shawnette
The price is ฿2,496
฿3,610 total
includes taxes & fees
10 Oct - 11 Oct
Fisherman's Point Resort
A resort with a large pool, lush greenery, and a view of the ocean.

2. Sky Castles

Sky Castles
2.5 star property
Ocho Rios
5.4 out of 10, (33 reviews)
"Was an ok experience "
United States
Rose
The price is ฿3,231
฿4,431 total
includes taxes & fees
9 Oct - 10 Oct
Sky Castles
A living room with a sofa, a coffee table, and a TV mounted on the wall. There is a kitchen area in the background with a window and a bar stool.

3. Wave Crest Resort Race Course

Wave Crest Resort Race Course
2.5 star property
Oracabessa
The price is ฿3,558
฿4,125 total
includes taxes & fees
13 Oct - 14 Oct
Wave Crest Resort Race Course
A balcony with a view of a pool and a building in the background.

4. Caldo Tours

Caldo Tours
2.5 star property
Ewarton
10.0 out of 10, Exceptional, (3 reviews)
"Very inviting and the owner's are wonderful people that keeps you comfortable and satisfied "
United States
Stephen
The price is ฿3,933
฿4,360 total
includes taxes & fees
9 Oct - 10 Oct
Caldo Tours
A television on a wooden TV stand with a remote control on it.

5. 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 ฿9,084
฿14,972 total
includes taxes & fees
9 Oct - 10 Oct
Phoenix Park Villas Portmore
A pool area with a gazebo, lounge chairs, and a view of the surrounding landscape.

6. Mountain Top Villa

Mountain Top Villa
3.5 star property
Mandeville
8.4 out of 10, Very good, (27 reviews)
"Hotal it self was beautiful , lay out great , room was a bit small but manageable. Overall a great stay I would highly recommend"
United Kingdom
Robert
The price is ฿1,973
฿3,144 total
includes taxes & fees
9 Oct - 10 Oct
Mountain Top Villa
A person overlooking a coastal area with a cruise ship, lush greenery, and a swimming pool.

7. Spring Palm Estate

Spring Palm Estate
3.0 star property
Tower Isle
6.2 out of 10, (11 reviews)
"I would stay here again"
Canada
Shagufta
The price is ฿2,185
฿3,379 total
includes taxes & fees
10 Oct - 11 Oct
Spring Palm Estate
A resort with multiple swimming pools, lounge chairs, and umbrellas.

8. North Star Villa

North Star Villa
3.5 star property
Mammee Bay Estates
7.0 out of 10, Good, (7 reviews)
"We enjoyed our time at North Star Villa. The place was well kept, and Miss Norma was great."
United States
PATRICIA
The price is ฿3,644
฿4,042 total
includes taxes & fees
11 Oct - 12 Oct
North Star Villa
A large swimming pool with a clear view of the ocean in the background, surrounded by resort-style buildings.

9. The Crest - Serenity Oasis Villa

The Crest - Serenity Oasis Villa
2.0 star property
St. Ann's Bay
8.0 out of 10, Very good, (1 review)
"Location is beautiful and very secure and safe. The house and pool were lovely as well. "
United States
Laura
The price is ฿10,009
฿15,078 total
includes taxes & fees
15 Oct - 16 Oct
The Crest - Serenity Oasis Villa
A gated entrance with a central building and two smaller structures on either side.

10. 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 ฿2,269
฿4,324 total
includes taxes & fees
13 Oct - 14 Oct
DeJee Lodging
A resort with a large swimming pool, covered areas, and palm trees.

11. Villa at Richmond Estate

Villa at Richmond Estate
4.5 star property
St. Ann's Bay
5.0 out of 10, (2 reviews)
"This was an absolutely terrible experience, never in my entire life I have been treated like this after spending my money I highly recommend that this person be barred from using this platform for their shady business I was insulted by security guards telling me they are doing me a favor to sort out this woman’s incompetence we weren’t even given a code to enter the house we had to go back to security. The house was musty the sofa was grimy and smelly , not even a bottle of water was in the...
United States
Devon
The price is ฿4,034
฿9,211 total
includes taxes & fees
11 Oct - 12 Oct
Villa at Richmond Estate
A spacious living area with a high ceiling, a ceiling fan, a sofa set, a dining table with chairs, and a TV mounted on the wall.

12. DraxHall Villa

DraxHall Villa
2.0 star property
Saint Ann's Bay
2.0 out of 10, (1 review)
"I was not able to experience this property. The were no house address to go to or number to dial to connect with the host of this property. The was NO experience to review, or SHARE. This must be a PRANK or BAD dream"
United States
Brian
The price is ฿6,729
฿11,305 total
includes taxes & fees
9 Oct - 10 Oct
DraxHall Villa
A lush, green outdoor area with dense foliage and a variety of trees, including palm trees.

13. Xpress Vacations Lifestyle

Xpress Vacations Lifestyle
4.0 star property
Ocho Rios
The price is ฿3,028
฿5,198 total
includes taxes & fees
9 Oct - 10 Oct
Xpress Vacations Lifestyle
A bedroom with a bed, dresser, mirror, and curtains.

14. 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 ฿6,544
฿11,089 total
includes taxes & fees
13 Oct - 14 Oct
3 Bedroom Cozy House in Drax Hall
A swimming pool with clear blue water, surrounded by a white fence and palm trees.

15. 1 Bed Villa - Sleeps 2 - Garden - Parking - Wifi

1 Bed Villa - Sleeps 2 - Garden - Parking - Wifi
3.5 star property
Ocho Rios
7.4 out of 10, Good, (3 reviews)
"I like Skycastles and Columbus Heights and stayed many times in this past. Its views are exceptional. This particular place was cheap. It had a futon for a sofa and plastic chairs for dinning and old seating outside. There were loads of locked spaces and it seamed cramped."
United States
Kristin
The price is ฿3,265
฿3,789 total
includes taxes & fees
11 Oct - 12 Oct
1 Bed Villa - Sleeps 2 - Garden - Parking - Wifi
A table with two bottles and several dice, set against a window with a view of greenery.

16. Coke's Guest House

Coke's Guest House
2.0 star property
Mandeville
The price is ฿2,877
฿3,342 total
includes taxes & fees
9 Oct - 10 Oct
Coke's Guest House
Room

17. Cozy 1bed Apartment in Priory Walk to the Beach

Cozy 1bed Apartment in Priory Walk to the Beach
2.0 star property
St. Ann's Bay
The price is ฿2,410
฿4,174 total
includes taxes & fees
11 Oct - 12 Oct
Cozy 1bed Apartment in Priory Walk to the Beach
A living room with a sofa, a coffee table, a TV, and a bookshelf.

18. 1BR Comfort 15 mins Ocho Rios

1BR Comfort 15 mins Ocho Rios
2.0 star property
Richmond Estate
The price is ฿3,936
฿8,094 total
includes taxes & fees
12 Oct - 13 Oct
1BR Comfort 15 mins Ocho Rios
A modern living room with a white sofa, a glass coffee table, and a staircase leading to an upper level.

19. Tuscany Sun Villa at Legacy Townhouse

Tuscany Sun Villa at Legacy Townhouse
2.0 star property
Thompson Town
The price is ฿25,234
฿29,052 total
includes taxes & fees
7 Nov - 8 Nov
Tuscany Sun Villa at Legacy Townhouse
A two-story house with a yellow exterior and brown roof.

20. Ocho Rios at Coolshade Richmond

Ocho Rios at Coolshade Richmond
3.5 star property
St. Ann's Bay
2.0 out of 10, (1 review)
"Lack of communication was terrible Reached at the property, was double booked for multiples family. The host was not answering her phone and was difficult to reach due to lack of wifi access No hot upon reaching, was not mention to guest about turning on hot water system No change of linen No access to masterbed room bathroom for bathing due to broken pipe/facet in bath tub Leakage of water from toilet broken Only was thing,that was excited was the mango tree."
United States
Michelle f
The price is ฿5,047
฿10,531 total
includes taxes & fees
12 Oct - 13 Oct
Ocho Rios at Coolshade Richmond
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
"100% am going again loved this resort!"
Michael 6-night trip
Posted 1 hour ago
Couples Tower Isle All Inclusive

Find out more about Middlesex County

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