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

Middlesex County Holiday Rentals

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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 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 S$159
includes taxes & fees
14 Oct - 15 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)
The price is S$169
includes taxes & fees
14 Oct - 15 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 S$157
includes taxes & fees
14 Oct - 15 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 S$166
includes taxes & fees
14 Oct - 15 Oct
Caldo Tours
A resort with multiple swimming pools, lounge chairs, and umbrellas.

5. 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 S$154
includes taxes & fees
14 Oct - 15 Oct
North Star Villa
A modern kitchen with a built-in oven, a refrigerator, and a dining area with a table set for four.

6. 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 S$570
includes taxes & fees
17 Oct - 18 Oct
Phoenix Park Villas Portmore
A pool area with a gazebo, lounge chairs, and a view of the surrounding landscape.

7. 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 S$120
includes taxes & fees
14 Oct - 15 Oct
Mountain Top Villa
A person overlooking a coastal area with a cruise ship, lush greenery, and a swimming pool.

8. 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 S$106
includes taxes & fees
14 Oct - 15 Oct
Spring Palm Estate
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 S$600
includes taxes & fees
14 Oct - 15 Oct
The Crest - Serenity Oasis Villa
A resort with a large swimming pool, covered areas, and palm trees.

10. Villa at Richmond Estate

Villa at Richmond Estate
4.5 star property
St. Ann's Bay
5.0 out of 10, (2 reviews)
The price is S$365
includes taxes & fees
14 Oct - 15 Oct
Villa at Richmond Estate
A gated entrance with a central building and two smaller structures on either side.

11. 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 S$165
includes taxes & fees
25 Oct - 26 Oct
DeJee Lodging
A lush, green outdoor area with dense foliage and a variety of trees, including palm trees.

12. Xpress Vacations Lifestyle

Xpress Vacations Lifestyle
4.0 star property
Ocho Rios
The price is S$186
includes taxes & fees
14 Oct - 15 Oct
Xpress Vacations Lifestyle
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.

13. 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 S$430
includes taxes & fees
14 Oct - 15 Oct
DraxHall Villa
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 S$439
includes taxes & fees
20 Oct - 21 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 S$138
includes taxes & fees
15 Oct - 16 Oct
1 Bed Villa - Sleeps 2 - Garden - Parking - Wifi
A modern living room with a white sofa, a glass coffee table, and a staircase leading to an upper level.

16. Tuscany Sun Villa at Legacy Townhouse

Tuscany Sun Villa at Legacy Townhouse
2.0 star property
Thompson Town
The price is S$1,106
includes taxes & fees
15 Oct - 16 Oct
Tuscany Sun Villa at Legacy Townhouse
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 S$159
includes taxes & fees
14 Oct - 15 Oct
Cozy 1bed Apartment in Priory Walk to the Beach
A table with two bottles and several dice, set against a window with a view of greenery.

18. Coke's Guest House

Coke's Guest House
2.0 star property
Mandeville
The price is S$120
includes taxes & fees
21 Oct - 22 Oct
Coke's Guest House
A swimming pool with a palm tree, lounge chairs, and a clear blue sky.

19. Relaxing Stay - Richmond Estate - 15mins Ocho Rios

Relaxing Stay - Richmond Estate - 15mins Ocho Rios
2.0 star property
St. Ann's Bay
6.6 out of 10, (7 reviews)
"Modern settings, however a few things needed repairs or upgrade!"
United States
erron
The price is S$266
includes taxes & fees
14 Oct - 15 Oct
Relaxing Stay - Richmond Estate - 15mins Ocho Rios
A living room with a sofa, a coffee table, a TV, and a bookshelf.

20. 1BR Comfort 15 mins Ocho Rios

1BR Comfort 15 mins Ocho Rios
2.0 star property
Richmond Estate
The price is S$308
includes taxes & fees
28 Oct - 29 Oct
1BR Comfort 15 mins Ocho Rios
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

JamGolia Place

JamGolia Place

10/10 Excellent
"⭐⭐⭐⭐⭐ Wonderful stay at JamGolia Place! The property is clean, peaceful, comfortable, and offers a safe and secure environment. Breakfast was delicious and always served on time. The entire staff was friendly, welcoming, and attentive. Excellent hospitality! Highly recommended, and we would definitely return!"
Elías 3-night trip
Posted 9 hours ago
JamGolia Place