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
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Middlesex County holiday rentals

A balcony with a view of a pool and a building in the background.

1. 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$165
includes taxes & fees
5 Sept - 6 Sept
Caldo Tours
A modern kitchen with a built-in oven, a refrigerator, and a dining area with a table set for four.

2. 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$478
includes taxes & fees
30 Aug - 31 Aug
Phoenix Park Villas Portmore

3. Adorable 1bed Cottage Too Walk to the Beach

Adorable 1bed Cottage Too Walk to the Beach
2.0 star property
St. Ann's Bay
The price is S$137
includes taxes & fees
11 Sept - 12 Sept
Adorable 1bed Cottage Too Walk to the Beach
A balcony with a white umbrella, a wicker chair, and a view of the ocean.

4. Adorable 1Bed Cottage Walk to the Beach

Adorable 1Bed Cottage Walk to the Beach
2.0 star property
St. Ann's Bay
8.0 out of 10, Very good, (4 reviews)
"A proper home from home just a wonderful place to stay "
United Kingdom
Peppa
The price is S$152
includes taxes & fees
23 Sept - 24 Sept
Adorable 1Bed Cottage Walk to the Beach

5. 1BR Comfort 15 mins Ocho Rios

1BR Comfort 15 mins Ocho Rios
2.0 star property
Richmond Estate
The price is S$344
includes taxes & fees
31 Aug - 1 Sept
1BR Comfort 15 mins Ocho Rios
A gated entrance with a central building and two smaller structures on either side.

6. 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$235
includes taxes & fees
1 Sept - 2 Sept
DeJee Lodging
A beach with clear water, a sandy shore, and buildings in the background.

7. Fisherman's Point Resort

Fisherman's Point Resort
3.0 star property
Ocho Rios
6.0 out of 10, (601 reviews)
"Staff was friendly,helpful and accommodating the beach view was beautiful as well"
United States
Desmond
The price is S$129
includes taxes & fees
2 Sept - 3 Sept
Fisherman's Point Resort
A bedroom with a bed, dresser, mirror, and curtains.

8. 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$436
includes taxes & fees
30 Aug - 31 Aug
3 Bedroom Cozy House in Drax Hall
A lush, green outdoor area with dense foliage and a variety of trees, including palm trees.

9. Xpress Vacations Lifestyle

Xpress Vacations Lifestyle
4.0 star property
Ocho Rios
The price is S$196
includes taxes & fees
14 Sept - 15 Sept
Xpress Vacations Lifestyle
A pool table, ceiling fans, and a pool area with seating.

10. 2BR The Crest - 15 mins Ocho Rios

2BR The Crest - 15 mins Ocho Rios
2.5 star property
St. Ann's Bay
The price is S$370
includes taxes & fees
7 Sept - 8 Sept
2BR The Crest - 15 mins Ocho Rios
A person standing in a swimming pool with clear blue water, surrounded by palm trees and greenery.

11. Villa at The Palms

Villa at The Palms
3.5 star property
St. Ann's Bay
6.0 out of 10, (3 reviews)
"The villa was very family oriented . The pool area very clean and enjoyable. Surrounding very quiet and clean, location very nice."
United States
Michelle
The price is S$380
includes taxes & fees
31 Aug - 1 Sept
Villa at The Palms
A pool area with a gazebo, lounge chairs, and a view of the surrounding landscape.

12. 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$119
includes taxes & fees
30 Aug - 31 Aug
Mountain Top Villa

13. 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$142
includes taxes & fees
15 Sept - 16 Sept
Cozy 1bed Apartment in Priory Walk to the Beach
A large swimming pool with a clear view of the ocean in the background, surrounded by resort-style buildings.

14. 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$570
includes taxes & fees
30 Aug - 31 Aug
The Crest - Serenity Oasis Villa
A swimming pool with blue chairs and a covered area, surrounded by a brick walkway.

15. Harbour Oasis Retreat - Charming 2 Bedroom House

Harbour Oasis Retreat - Charming 2 Bedroom House
3.5 star property
Old Harbour
The price is S$260
includes taxes & fees
2 Sept - 3 Sept
Harbour Oasis Retreat - Charming 2 Bedroom House
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.

16. DraxHall Villa

DraxHall Villa
2.0 star property
Saint Ann's Bay
The price is S$427
includes taxes & fees
5 Sept - 6 Sept
DraxHall Villa
A covered outdoor area with a table and chairs, a sink, and a view of a green-roofed building in the background.

17. Serenity Oasis Apartment

Serenity Oasis Apartment
2.0 star property
Spanish Town
The price is S$158
includes taxes & fees
30 Aug - 31 Aug
Serenity Oasis Apartment
A modern living room with a leather sofa, a coffee table, and a dining area with a table and chairs.

18. Cozy Relaxing Home in Old Harbour

Cozy Relaxing Home in Old Harbour
2.0 star property
Old Harbour
The price is S$17,348
includes taxes & fees
30 Aug - 31 Aug
Cozy Relaxing Home in Old Harbour
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 S$1,098
includes taxes & fees
30 Aug - 31 Aug
Tuscany Sun Villa at Legacy Townhouse
A rectangular swimming pool with a smaller section and a separate hot tub area, surrounded by outdoor seating and potted plants.

20. DraxHall Villa with Private Pool

DraxHall Villa with Private Pool
2.5 star property
Saint Ann's Bay
The price is S$693
includes taxes & fees
11 Sept - 12 Sept
DraxHall Villa with Private Pool
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

Mandeview Hotel

Mandeview Hotel

8/10 Good
"The place is dated but comfortable. The staff is very helpful and kind. Mandeville is usually cool so no AC in room; may want to reconsider this."
Norman 1-night trip
Posted 1 day ago
Mandeview Hotel