Middlesex Vacation Rentals

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Check prices for these dates

Tonight
Jun 28 - Jun 29
Tomorrow
Jun 29 - Jun 30
Next weekend
Jul 4 - Jul 6
In two weeks
Jul 11 - Jul 13

Vacation Rentals in Middlesex

Sand and Blue Seas
Outdoor dining

Sand and Blue Seas

3.0 star property
8.2 out of 10, Very Good, (123)
"Beautiful clean property the chef cooks very good.. pool needs some paint .. otherwise this place is amazingly beautiful and on the beach just don’t expect anything fancy.. it’s simple and easy .. definitely a vibe I’ll be back!"
Sand and Blue Seas
Montego Bay Club Apartments
Beach towels

Montego Bay Club Apartments

4.0 star property
7.4 out of 10, Good, (32)
"The exact location was a little tricky but Karl was a phone call away to assist. The building was safe and close to everything, but it’s in need of repairs and updating. The apartment itself met our expectations for the price paid. Loved the balcony to watch sunsets and the hip strip. My family loved the fact that the beach was across the street and dining out was walkable. I would definitely book this place again, only about 10mins to the airport. "
Montego Bay Club Apartments
Dalley's Cozy Apartments
Balcony view

Dalley's Cozy Apartments

3.0 star property
7.4 out of 10, Good, (3)
"It was a great place, right spot clean big place i have everything i need to have a good time i do recommend this place"
Dalley's Cozy Apartments
Villas Sur Mer
Premium Cottage, 1 Queen Bed, Pool View | Balcony view

Villas Sur Mer

4.0 star property
8.8 out of 10, Excellent, (147)
"Amazing as always!!! "
The price is ₩236,838
₩261,875 total
includes taxes & fees
Jul 6 - Jul 7
Villas Sur Mer
Montego Bay Club Beach Resort
View from property

Montego Bay Club Beach Resort

3.5 star property
3.8 out of 10, (31)
"Room was not ready to after 4pm. Property is poorly maintained. Later check out was not granted. No amenities at all. "
Montego Bay Club Beach Resort
Idle Awhile Villas
Luxury Villa, 5 Bedrooms | Outdoor pool | 4 outdoor pools

Idle Awhile Villas

4.0 star property
10.0 out of 10, Exceptional, (14)
"The property was beautiful and the service was phenomenal. We had an amazing chef Raquel and butler Ryan. They accommodated our every need and Ryan had a lot of great recommendations for restaurants and activities. Would love to come back!!"
Idle Awhile Villas
Monimo Ridge Suites
Property grounds

Monimo Ridge Suites

3.0 star property
8.4 out of 10, Very Good, (16)
"Was a clean and safe space to spend a night before my flight back home. Very close to Montego Bay airport."
Monimo Ridge Suites
Stunning Ocean View
Family Townhome, 2 Bedrooms, Kitchen, Ocean View | In-room dining

Stunning Ocean View

4.0 star property
10.0 out of 10, Exceptional, (10)
"The view and ambience was pure bliss!"
The price is ₩622,649
₩914,763 total
includes taxes & fees
Jul 10 - Jul 11
Stunning Ocean View
Beach House Condos Negril
Terrace/patio

Beach House Condos Negril

3.5 star property
9.0 out of 10, Wonderful, (54)
"Pro: separate AC in all rooms. Fully equipped kitchen. Clean. Approachable and helpful staff. Con: no toiletries. Tiny private beach with only four dry grass beach umbrellas. "
The price is ₩162,403
₩204,357 total
includes taxes & fees
Jun 29 - Jun 30
Beach House Condos Negril
Sunny-shore Hideaway
House, 3 Bedrooms, Smoking, Patio | Pool | Outdoor pool

Sunny-shore Hideaway

2.0 star property
Sunny-shore Hideaway
Sky Beach Rooms
Restaurant

Sky Beach Rooms

5.0 star property
2.0 out of 10, (1)
"The room was very clean, however the rooms are located in a very local shopping mall with lots of loitering outside, very noisy, no windows so felt claustrophobic. The outside was dirty , crowded and noisy I did not feel safe enough to stay there so I left."
The price is ₩146,995
₩163,056 total
includes taxes & fees
Jul 11 - Jul 12
Sky Beach Rooms
Turquoise Sea Villa
Front of property

Turquoise Sea Villa

3.5 star property
The price is ₩117,364
₩272,437 total
includes taxes & fees
Jun 29 - Jun 30
Turquoise Sea Villa
Idle Awhile Cliffs
Outdoor pool, pool umbrellas, sun loungers

Idle Awhile Cliffs

3.5 star property
9.0 out of 10, Wonderful, (119)
"We adored this “rustic” property with its early morning birdsong, simple clean (very clean!) rooms and lovely pool overlooking the ocean. Delicious breakfast poolside or on our terrace. Courteous and kind staff. Highly recommend!"
Idle Awhile Cliffs
YanceyLargo- 4BR Villa Jacuzzi & Mountain Views by RedAwning
Villa, 4 Bedrooms | 4 bedrooms, laptop workspace, iron/ironing board, free WiFi

YanceyLargo- 4BR Villa Jacuzzi & Mountain Views by RedAwning

3.5 star property
The price is ₩196,253
₩470,959 total
includes taxes & fees
Jul 27 - Jul 28
YanceyLargo- 4BR Villa Jacuzzi & Mountain Views by RedAwning
Luxury villa in Montego Bay Jamaica
Basic Apartment | Terrace/patio

Luxury villa in Montego Bay Jamaica

3.0 star property
Luxury villa in Montego Bay Jamaica
Unity Villa
Electric kettle, toaster

Unity Villa

3.0 star property
Unity Villa
King Suite at Oceanview Resort in Jamaica - Enjoy 7 Miles Of White Sand Beach! 1 Bedroom Villa by RedAwning
Studio | View from property

King Suite at Oceanview Resort in Jamaica - Enjoy 7 Miles Of White Sand Beach! 1 Bedroom Villa by RedAwning

3.0 star property
King Suite at Oceanview Resort in Jamaica - Enjoy 7 Miles Of White Sand Beach! 1 Bedroom Villa by RedAwning
Silent Waters Villa
2 outdoor pools, an infinity pool, sun loungers

Silent Waters Villa

5.0 star property
8.0 out of 10, Very Good, (1)
"The only concern I had was failure to follow the allergy list for meals."
Silent Waters Villa
Beachcliff Villa Negril
Comfort Villa, Private Bathroom, Sea View (Llantrissant Beachcliff) | Private kitchen | Full-size fridge, highchair, cookware/dishes/utensils

Beachcliff Villa Negril

4.0 star property
10.0 out of 10, Exceptional, (1)
"I was beyond impressed with this property. Being in the hospitality and retail industry, I set my bar pretty high. These folks beyond exceeded my expectations and gave us the best imaginable experience ever!! The food prepared by Lovie and Ruth was beyond any of the local cuisine I have ever had (3rd time to Jamaica). They prepared amazing local cuisine (I am a Chef as well), purveyed all the goods at local places, etc. The rooms and bedding were more than comfortable and the antique colonial...
Beachcliff Villa Negril
Sativa cottages
Comfort Cottage | 1 bedroom, free WiFi, bed sheets

Sativa cottages

2.0 star property
Sativa cottages
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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Frequently asked questions

Can I find vacation rentals in Middlesex?

Yes, we have vacation rentals near popular local attractions in Middlesex, or you can choose a more remote option if you want a relaxing place to stay.

What are some of the best vacation rentals that Middlesex has to offer?

Stunning Ocean View: Visitors like this Middlesex vacation home rental. It is located by the ocean and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop, and a microwave. Kick off your shoes and enjoy yourself with a terrace and a private yard.

What can I see and do in Middlesex?

Explore the area and family-friendly sights such as Kool Runnings Water Park, or get out into nature at a spot like Seven Mile Beach. Half Moon Beach and Tryall Golf Club are a couple of places you'll find in the larger area.

What are vacation rentals like in Middlesex?

Vacation rentals are private accommodations you can book for a few days or a quick weekend in Middlesex. Vacation rentals offer extras such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a vacation rental can offer a sense of security away from public hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for family trips or small group gatherings.