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

Middlesex County Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Middlesex County vacation rentals

A modern kitchen with a built-in oven, a refrigerator, and a dining area with a table set for four.

1. 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
$341 nightly
The price is $394
Oct 1 - Oct 2
Total with taxes and fees
Phoenix Park Villas Portmore
A modern living room with a white sofa, a glass coffee table, and a staircase leading to an upper level.

2. Tuscany Sun Villa at Legacy Townhouse

Tuscany Sun Villa at Legacy Townhouse
2.0 star property
Thompson Town
$750 nightly
The price is $864
Oct 1 - Oct 2
Total with taxes and fees
Tuscany Sun Villa at Legacy Townhouse
A balcony with a view of a pool and a building in the background.

3. 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
$117 nightly
The price is $130
Oct 1 - Oct 2
Total with taxes and fees
Caldo Tours
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.

4. Wave Crest Resort Race Course

Wave Crest Resort Race Course
2.5 star property
Oracabessa
$87 nightly
The price is $101
Oct 8 - Oct 9
Total with taxes and fees
Wave Crest Resort Race Course
A large swimming pool with a clear view of the ocean in the background, surrounded by resort-style buildings.

5. 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
$389 nightly
The price is $448
Oct 1 - Oct 2
Total with taxes and fees
The Crest - Serenity Oasis Villa
A modern living room with a leather sofa, a coffee table, and a dining area with a table and chairs.

6. Cozy Relaxing Home in Old Harbour

Cozy Relaxing Home in Old Harbour
2.0 star property
Old Harbour
$11,854 nightly
The price is $13,633
Oct 1 - Oct 2
Total with taxes and fees
Cozy Relaxing Home in Old Harbour
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, (616 reviews)
"Perfect location 👌"
United States
Shawnette
$84 nightly
The price is $97
Oct 25 - Oct 26
Total with taxes and fees
Fisherman's Point Resort
A swimming pool with a gazebo, a clear sky, and a distant view of buildings.

8. Bayfront apartment and villas

Bayfront apartment and villas
Portmore
10.0 out of 10, Exceptional, (6 reviews)
"Good place to stay"
United States
Kimone
$101 nightly
The price is $101
Oct 4 - Oct 5
Total with taxes and fees
Bayfront apartment and villas
Two beach chairs with colorful covers, a cruise ship in the background, and clear blue water.

9. SandCastles Deluxe Beach Resort

SandCastles Deluxe Beach Resort
3.5 star property
Ocho Rios
7.4 out of 10, Good, (136 reviews)
"I like the room it was clean and spacious Staff professional pool was clean I like everything"
United States
Blossom
SandCastles Deluxe Beach Resort
A living room with a sofa, a coffee table, a TV, and a bookshelf.

10. 1BR Comfort 15 mins Ocho Rios

1BR Comfort 15 mins Ocho Rios
2.0 star property
Richmond Estate
$208 nightly
The price is $241
Oct 7 - Oct 8
Total with taxes and fees
1BR Comfort 15 mins Ocho Rios
A kitchen with wooden cabinets, a stainless steel sink, a microwave, and a gas stove.

11. Royal Palm Luxury Villas

Royal Palm Luxury Villas
3.0 star property
Ocho Rios
$641 nightly
The price is $738
Oct 1 - Oct 2
Total with taxes and fees
Royal Palm Luxury Villas
A rectangular swimming pool with a smaller section and a separate hot tub area, surrounded by outdoor seating and potted plants.

12. DraxHall Villa with Private Pool

DraxHall Villa with Private Pool
2.5 star property
Saint Ann's Bay
$473 nightly
The price is $545
Oct 1 - Oct 2
Total with taxes and fees
DraxHall Villa with Private Pool
A modern building with a Starbucks logo on the facade, large windows, and a small tree in front.

13. PLAN YOUR GETAWAY UNDER THE SUN Dazzle Key Suite

PLAN YOUR GETAWAY UNDER THE SUN Dazzle Key Suite
Greenwich Estate
10.0 out of 10, Exceptional, (3 reviews)
"This property was excellent, the host was the best!!, communication with the host was indeed at its best. Cleanliness and comfort was also at its best!!"
United States
Raphaela
$302 nightly
The price is $302
Oct 1 - Oct 2
Total with taxes and fees
PLAN YOUR GETAWAY UNDER THE SUN Dazzle Key Suite
A wooden table with two puzzle boxes, surrounded by wooden chairs, in a covered outdoor area with windows.

14. Comfy 3BR Villa - Paradisiac Beach Club

Comfy 3BR Villa - Paradisiac Beach Club
2.0 star property
St. Ann Parish
$474 nightly
The price is $546
Oct 1 - Oct 2
Total with taxes and fees
Comfy 3BR Villa - Paradisiac Beach Club
A balcony with ornate metal railings and a tiled floor, offering a view of a lush green landscape.

15. Blue Berry Hills Villa

Blue Berry Hills Villa
3.0 star property
Dumbarton
$851 nightly
The price is $980
Oct 31 - Nov 1
Total with taxes and fees
Blue Berry Hills Villa
A poolside area with a white tiled deck, lounge chairs, and a white fence.

16. 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, (71 reviews)
"The host was very friendly and the room was clean and came equipped with air conditioning."
Canada
Shereeka
$85 nightly
The price is $92
Oct 8 - Oct 9
Total with taxes and fees
The Cottage very comfortable, relaxing also secure, 5 minutes walk from beach
A Bay Front Apartments building entrance with glass doors and a sign.

17. 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
$232 nightly
The price is $232
Oct 24 - Oct 25
Total with taxes and fees
Bayfront Budget Friendly 2 Bedrooms and 2 Bathrooms Apt in Gated Community
A living room with two sofas, a coffee table, and a television.

18. 3BR Family Villa at The Crest

3BR Family Villa at The Crest
2.0 star property
St. Ann Parish
$425 nightly
The price is $490
Oct 1 - Oct 2
Total with taxes and fees
3BR Family Villa at The Crest
A covered balcony with white balustrades, a stone floor, and a view of greenery.

19. Sandy Bay Paradise Retreat - 7 Bedrooms

Sandy Bay Paradise Retreat - 7 Bedrooms
3.0 star property
Sandy Bay
$428 nightly
The price is $493
Oct 5 - Oct 6
Total with taxes and fees
Sandy Bay Paradise Retreat - 7 Bedrooms
A beach with boats, a clear sky, and a mountain in the background.

20. Charming 3-bedrooms house in lovely Port Maria with AC, and WiFi and hot water

Charming 3-bedrooms house in lovely Port Maria with AC, and WiFi and hot water
Port Maria
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful place 3 bedroom with nice bathroom in the rooms nice community next to everything... the host was very nice and easy to get along with.... "
United States
Shanna
$354 nightly
The price is $354
Oct 1 - Oct 2
Total with taxes and fees
Charming 3-bedrooms house in lovely Port Maria with AC, and WiFi and hot water
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

Whispering Seas

Whispering Seas

10/10 Excellent
"The property was amazing and the host was exceptional!!"
Wayne 3-night trip
Posted 1 hour ago
Whispering Seas

Find out more about Middlesex County

Everything you need to know about Middlesex County vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middlesex County vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middlesex County vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middlesex County vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middlesex County. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Middlesex County in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $83 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Middlesex County rentals

At Expedia, we put the best Middlesex County vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Middlesex County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middlesex County vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middlesex County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.