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

Middlesex County Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Middlesex County vacation rentals

1. The Cottage very comfortable, relaxing also secure, 5 minutes walk from beach

The Cottage very comfortable, relaxing also secure, 5 minutes walk from beach
Ocho Rios
9.4 out of 10, Exceptional, (70 reviews)
"The host was very friendly and the room was clean and came equipped with air conditioning."
Canada
Shereeka
The price is CA $91
CA $130 total
includes taxes & fees
Sep 24 - Sep 25
The Cottage very comfortable, relaxing also secure, 5 minutes walk from beach

2. 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 CA $164
CA $182 total
includes taxes & fees
Oct 23 - Oct 24
Caldo Tours

3. 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 CA $243
CA $470 total
includes taxes & fees
Sep 24 - Sep 25
Phoenix Park Villas Portmore

4. Bayfront apartment and villas

Bayfront apartment and villas
Portmore
10.0 out of 10, Exceptional, (5 reviews)
The price is CA $86
CA $142 total
includes taxes & fees
Sep 27 - Sep 28
Bayfront apartment and villas

5. Wave Crest Resort Race Course

Wave Crest Resort Race Course
2.5 star property
Oracabessa
The price is CA $80
CA $94 total
includes taxes & fees
Oct 23 - Oct 24
Wave Crest Resort Race Course

6. 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 CA $72
CA $155 total
includes taxes & fees
Sep 28 - Sep 29
Adorable 1Bed Cottage Walk to the Beach

7. Fisherman's Point Resort

Fisherman's Point Resort
3.0 star property
Ocho Rios
6.0 out of 10, (614 reviews)
"Staff was friendly,helpful and accommodating the beach view was beautiful as well"
United States
Desmond
The price is CA $111
CA $145 total
includes taxes & fees
Sep 25 - Sep 26
Fisherman's Point Resort

8. 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 CA $83
CA $154 total
includes taxes & fees
Sep 24 - Sep 25
Cozy 1bed Apartment in Priory Walk to the Beach

9. Xpress Vacations Lifestyle

Xpress Vacations Lifestyle
4.0 star property
Ocho Rios
The price is CA $127
CA $217 total
includes taxes & fees
Sep 24 - Sep 25
Xpress Vacations Lifestyle

10. Light escape mixes luxury with homey - 2 mins from the beach!

Light escape mixes luxury with homey - 2 mins from the beach!
Ocho Rios
9.6 out of 10, Exceptional, (60 reviews)
"Good property and as advertised, it was very close to the beach, and all the main amenities are within walking distance. I didn't like having to pay (10 USD) to go to the beach, but that is outside the landlord's control. I'm including that comment so people know. The living room didn't have any AC, and I wish I had known this before going. The ceiling fan worked OK, and the heat wasn't overwhelming, but AC would have been ideal. In all, I would stay here again if I ever come to Jamaica."
United States
Dane
The price is CA $117
CA $182 total
includes taxes & fees
Sep 25 - Sep 26
Light escape mixes luxury with homey - 2 mins from the beach!

11. 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 CA $83
CA $131 total
includes taxes & fees
Sep 24 - Sep 25
Mountain Top Villa

12. Spacious contemporary, relaxing apartment only 5 minutes walk to fabulous beach

Spacious contemporary, relaxing apartment only 5 minutes walk to fabulous beach
Mammee Bay Estates
9.0 out of 10, Wonderful, (62 reviews)
"This property was unique close to the beach very clean host was very good love this place"
United States
Rose
The price is CA $109
CA $150 total
includes taxes & fees
Sep 24 - Sep 25
Spacious contemporary, relaxing apartment only 5 minutes walk to fabulous beach

13. 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 CA $95
CA $181 total
includes taxes & fees
Oct 1 - Oct 2
DeJee Lodging

14. SandCastles Deluxe Beach Resort

SandCastles Deluxe Beach Resort
3.5 star property
Ocho Rios
7.4 out of 10, Good, (135 reviews)
"I like the room it was clean and spacious Staff professional pool was clean I like everything"
United States
Blossom
The price is CA $139
CA $156 total
includes taxes & fees
Sep 25 - Sep 26
SandCastles Deluxe Beach Resort

15. 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 CA $100
CA $128 total
includes taxes & fees
Sep 24 - Sep 25
Charming 2-bedroom house in Portmore with WiFi, AC

16. Harbour Oasis Retreat - Charming 2 Bedroom House

Harbour Oasis Retreat - Charming 2 Bedroom House
3.5 star property
Old Harbour
The price is CA $152
CA $284 total
includes taxes & fees
Oct 22 - Oct 23
Harbour Oasis Retreat - Charming 2 Bedroom House

17. 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 CA $105
CA $203 total
includes taxes & fees
Oct 22 - Oct 23
Ac'ed 2 bedroom Beach House

18. 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 CA $152
CA $169 total
includes taxes & fees
Oct 11 - Oct 12
North Star Villa

19. 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 CA $164
CA $380 total
includes taxes & fees
Oct 4 - Oct 5
Villa at Richmond Estate

20. 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 CA $84
CA $156 total
includes taxes & fees
Oct 8 - Oct 9
Adorable 1bed Cottage Too Walk to the Beach
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Middlesex County Hotel Reviews

Find out more about Middlesex County

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Middlesex County. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.