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

Middlesex County Vacation Rentals

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Our top choices for Middlesex County vacation rentals

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 CA $163
CA $181 total
includes taxes & fees
Aug 10 - Aug 11
Caldo Tours

2. 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
9.6 out of 10, Exceptional, (68 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 $131 total
includes taxes & fees
Sep 8 - Sep 9
The Cottage very comfortable, relaxing also secure, 5 minutes walk from beach

3. Mountain Top Villa

Mountain Top Villa
3.5 star property
Mandeville
8.4 out of 10, Very good, (27 reviews)
"This hidden gem was more than I expected and I was super surprised and feel blessed because I had the place all to myself the entire stay and I really enjoyed the pool. The house was gorgeous, clean, beds were comfortable and everything was in working condition. The check in process was seamless. I am definitely looking forward to staying here again."
United States
Deon
The price is CA $82
CA $130 total
includes taxes & fees
Aug 10 - Aug 11
Mountain Top Villa

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 CA $65
CA $146 total
includes taxes & fees
Sep 2 - Sep 3
Adorable 1Bed Cottage Walk to the Beach

5. 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 $93
CA $178 total
includes taxes & fees
Sep 8 - Sep 9
DeJee Lodging

6. 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, (58 reviews)
"Travel from Nashville Tennessee for a 5 day stay, from start to finish the communication was on point. Anything missed was address within a reasonable timeframe.. If you’re thinking about getting the place, just go ahead and get it. we definitely will be staying here again in the future. There’s not much to say other than come.. come and enjoy a secluded stay. Thank you Everton ✊ respect"
United States
Denise
The price is CA $113
CA $177 total
includes taxes & fees
Aug 10 - Aug 11
Light escape mixes luxury with homey - 2 mins from the beach!

7. Ac'ed 2 bedroom Beach House

Ac'ed 2 bedroom Beach House
Hellshire
9.4 out of 10, Exceptional, (16 reviews)
"Felt like home."
United States
Ashlie G.
The price is CA $105
CA $202 total
includes taxes & fees
Aug 10 - Aug 11
Ac'ed 2 bedroom Beach House

8. Serenity Oasis Apartment

Serenity Oasis Apartment
2.0 star property
Spanish Town
The price is CA $92
CA $170 total
includes taxes & fees
Aug 10 - Aug 11
Serenity Oasis Apartment

9. 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 $289
CA $523 total
includes taxes & fees
Aug 10 - Aug 11
Phoenix Park Villas Portmore

10. Bayfront Budget Friendly 2 Bedrooms and 2 Bathrooms Apt in Gated Community

Bayfront Budget Friendly 2 Bedrooms and 2 Bathrooms Apt in Gated Community
Portmore
9.4 out of 10, Exceptional, (9 reviews)
"My stay was perfect!"
United States
ANDRENE
The price is CA $106
CA $304 total
includes taxes & fees
Aug 19 - Aug 20
Bayfront Budget Friendly 2 Bedrooms and 2 Bathrooms Apt in Gated Community

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

Relaxing Stay - Richmond Estate - 15mins Ocho Rios
2.0 star property
St. Ann's Bay
8.4 out of 10, Very good, (5 reviews)
"Nice"
United States
Sildarius
The price is CA $123
CA $290 total
includes taxes & fees
Aug 14 - Aug 15
Relaxing Stay - Richmond Estate - 15mins Ocho Rios

12. Villa at The Palms

Villa at The Palms
3.5 star property
St. Ann's Bay
8.0 out of 10, Very good, (1 review)
"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 CA $216
CA $445 total
includes taxes & fees
Aug 11 - Aug 12
Villa at The Palms

13. Immaculate 2-bed Apartment in Spanish Town

Immaculate 2-bed Apartment in Spanish Town
3.0 star property
Spanish Town
The price is CA $95
CA $110 total
includes taxes & fees
Aug 10 - Aug 11
Immaculate 2-bed Apartment in Spanish Town

14. 2Bedrooms 2Bathroom - Swimming pool - Gated community - Drier - Free Wifi

2Bedrooms 2Bathroom - Swimming pool - Gated community - Drier - Free Wifi
Ocho Rios
9.6 out of 10, Exceptional, (29 reviews)
"Overall a perfect stay for 2 people or couples "
United States
Devon
The price is CA $174
CA $293 total
includes taxes & fees
Aug 17 - Aug 18
2Bedrooms 2Bathroom - Swimming pool - Gated community - Drier - Free Wifi

15. Bayfront apartment and villas

Bayfront apartment and villas
Portmore
10.0 out of 10, Exceptional, (5 reviews)
"Good place to stay"
United States
Kimone
The price is CA $85
CA $141 total
includes taxes & fees
Aug 11 - Aug 12
Bayfront apartment and villas

16. 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
Aug 24 - Aug 25
Charming 2-bedroom house in Portmore with WiFi, AC

17. 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 CA $319
CA $515 total
includes taxes & fees
Aug 13 - Aug 14
3 Bedroom Cozy House in Drax Hall

18. Cozy 1-bedroom apartment in charming Mandeville with WiFi, AC

Cozy 1-bedroom apartment in charming Mandeville with WiFi, AC
Mandeville
10.0 out of 10, Exceptional, (1 review)
"Everything was what I expected❤️ will definitely come bk "
United States
Latifa
The price is CA $105
CA $181 total
includes taxes & fees
Aug 23 - Aug 24
Cozy 1-bedroom apartment in charming Mandeville with WiFi, AC

19. 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
8.8 out of 10, Excellent, (59 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
Aug 17 - Aug 18
Spacious contemporary, relaxing apartment only 5 minutes walk to fabulous 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.
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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.