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
Jul 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

Our top choices for Middlesex County vacation rentals

Beach

Coolshade Villas - Richmond Estate

Coolshade Villas - Richmond Estate
2.0 star property
St. Ann's Bay
10.0 out of 10, Exceptional, (2 reviews)
"Convenient location to restaurants, beach and major tourists attractions. Quiet and secure community."
United States
Robert
$196 nightly
The price is $227
Jul 2 - Jul 3
Total with taxes and fees
Coolshade Villas - Richmond Estate
Family House, Garden View | Private kitchen | Full-size fridge, microwave, oven, stovetop

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
$276 nightly
The price is $318
Jul 3 - Jul 4
Total with taxes and fees
Phoenix Park Villas Portmore
Beach nearby, white sand

Ocho Rios Villa at Coolshade

Ocho Rios Villa at Coolshade
3.5 star property
St. Ann's Bay
9.8 out of 10, Exceptional, (10 reviews)
"The host was wonderful and quite responsive. I will definately stay again and highly recomend. "
Canada
Oko
$306 nightly
The price is $328
Jul 2 - Jul 3
Total with taxes and fees
Ocho Rios Villa at Coolshade
Outdoor pool

Mountain Top Villa

Mountain Top Villa
3.5 star property
Mandeville
8.4 out of 10, Very Good, (26 reviews)
"Property was clean plus very quiet ...my overall experience was very good...i would book again"
Canada
Anonymous traveler
$84 nightly
The price is $93
Jul 2 - Jul 3
Total with taxes and fees
Mountain Top Villa
Outdoor pool

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, (67 reviews)
"The room was just as expected and the property manager, Chris, was awesome. The pool was excellent. My son and I had a lovely stay and we really enjoyed the privacy, peace and quiet."
United States
Tina B.
$86 nightly
The price is $92
Jul 22 - Jul 23
Total with taxes and fees
The Cottage very comfortable, relaxing also secure, 5 minutes walk from beach
Exterior

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
$90 nightly
The price is $100
Jul 8 - Jul 9
Total with taxes and fees
Caldo Tours
Outdoor pool

Bayfront apartment and villas

Bayfront apartment and villas
Portmore
10.0 out of 10, Exceptional, (2 reviews)
"Really enjoyed the stay here. Great value and appreciated the communication from the host."
United States
Cranston H.
$99 nightly
The price is $99
Jul 13 - Jul 14
Total with taxes and fees
Bayfront apartment and villas
Outdoor pool

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
$220 nightly
The price is $255
Jul 2 - Jul 3
Total with taxes and fees
Villa at Richmond Estate
Children's activities

Villa at The Palms

Villa at The Palms
3.5 star property
St. Ann's Bay
$245 nightly
The price is $283
Jul 2 - Jul 3
Total with taxes and fees
Villa at The Palms
On the beach

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, (57 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
$125 nightly
The price is $125
Jul 8 - Jul 9
Total with taxes and fees
Light escape mixes luxury with homey - 2 mins from the beach!
Terrace/patio

Serenity Oasis Apartment

Serenity Oasis Apartment
2.0 star property
Spanish Town
$101 nightly
The price is $118
Jul 8 - Jul 9
Total with taxes and fees
Serenity Oasis Apartment
Outdoor pool

Ocho Rios Ocean View Villa at The Palms

Ocho Rios Ocean View Villa at The Palms
4.0 star property
St. Ann's Bay
8.6 out of 10, Excellent, (9 reviews)
"Clean, great customer service. Most importantly we felt safe. Would definitely stay again and again!!"
United States
Clovette
$337 nightly
The price is $362
Jul 2 - Jul 3
Total with taxes and fees
Ocho Rios Ocean View Villa at The Palms
Luxury Villa, 3 Bedrooms, Ensuite, Garden View | Egyptian cotton sheets, premium bedding, in-room safe

Casa Princess Ocho Rios Vacation Villa

Casa Princess Ocho Rios Vacation Villa
3.5 star property
Ocho Rios
9.6 out of 10, Exceptional, (68 reviews)
"Beautiful, safe community and spacious property. Softer pillows would make it excellent"
United States
TRUDY ANN
$277 nightly
The price is $297
Jul 14 - Jul 15
Total with taxes and fees
Casa Princess Ocho Rios Vacation Villa
Family House | Free WiFi

3 Bedroom Cozy House in Drax Hall

3 Bedroom Cozy House in Drax Hall
3.5 star property
Ocho Rios
$320 nightly
The price is $369
Jul 2 - Jul 3
Total with taxes and fees
3 Bedroom Cozy House in Drax Hall
Outdoor pool, pool umbrellas, sun loungers

Ocho Rios Villa at Coolshade IV

Ocho Rios Villa at Coolshade IV
3.5 star property
St. Ann's Bay
9.4 out of 10, Exceptional, (10 reviews)
"I loved everything about it. Beautiful place"
United States
Anonymous traveler
$330 nightly
The price is $353
Jul 19 - Jul 20
Total with taxes and fees
Ocho Rios Villa at Coolshade IV
Outdoor pool

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
$200 nightly
The price is $200
Jul 7 - Jul 8
Total with taxes and fees
2Bedrooms 2Bathroom - Swimming pool - Gated community - Drier - Free Wifi
Interior

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, (7 reviews)
"Room was spotless, very caring host."
United Kingdom
Sophia
$83 nightly
The price is $83
Jul 23 - Jul 24
Total with taxes and fees
Charming 2-bedroom house in Portmore with WiFi, AC
2 outdoor pools

The Country Club Villa I

The Country Club Villa I
3.5 star property
Kingston
9.0 out of 10, Wonderful, (10 reviews)
"The management team was awesome, the AC didn’t work in the main room on the first night but Ms Vicki made sure that I didn’t go a second night without it."
United States
Anonymous traveler
$230 nightly
The price is $245
Jul 3 - Jul 4
Total with taxes and fees
The Country Club Villa I
Front of property

DeJee Lodging

DeJee Lodging
3.5 star property
Ocho Rios
8.0 out of 10, Very Good, (2 reviews)
"Kids enjoyed the pool but could have been cleaner and have some seating around the pool. Small local shops around for food items. House had everything needed for the stay and very fast response from property manager when had any questions "
Canada
Erica
$199 nightly
The price is $223
Jul 3 - Jul 4
Total with taxes and fees
DeJee Lodging
Terrace/patio

Tapioca Village Retreat

Tapioca Village Retreat
3.0 star property
Castleton
6.0 out of 10, (2 reviews)
"There is so much nature and friendliness! "
United States
Günter
$78 nightly
The price is $91
Jul 2 - Jul 3
Total with taxes and fees
Tapioca Village Retreat
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

The Cardiff Hotel & Spa

The Cardiff Hotel & Spa

8/10 Good
"Everything was good"
Kertis 2-night trip
Posted 1 hour ago
The Cardiff Hotel & Spa

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 $76 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.