Middlesex Vacation Rentals from NT$2,797: Search Short-Term Rentals

Q: 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.

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Vacation Rentals in Middlesex

"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"

"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!"

"Great location "

Premium Cottage, 1 Queen Bed, Pool View | Balcony view

"Amazing as always!!! "

NT$5,579 total

includes taxes & fees

Jul 7 - Jul 8

"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. "

NT$4,354 total

includes taxes & fees

Jul 7 - Jul 8

"The view is out of this world and the is kept clean. "

Luxury Villa, 5 Bedrooms | Outdoor pool | 4 outdoor pools

"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!!"

"Was a clean and safe space to spend a night before my flight back home. Very close to Montego Bay airport."

Family Townhome, 2 Bedrooms, Kitchen, Ocean View | In-room dining

"The view and ambience was pure bliss!"

NT$19,378 total

includes taxes & fees

Jul 5 - Jul 6

House, 3 Bedrooms, Smoking, Patio | Pool | Outdoor pool

"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!"

"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."

NT$3,454 total

includes taxes & fees

Jul 5 - Jul 6

NT$6,129 total

includes taxes & fees

Jul 5 - Jul 6

NT$9,977 total

includes taxes & fees

Aug 4 - Aug 5

"Clean and family oriented. Owner were very accommodating. I wouldn’t mind staying there again."

2 outdoor pools, an infinity pool, sun loungers

"The only concern I had was failure to follow the allergy list for meals."

"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...

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Find out more about Middlesex

Search for holiday rentals in Middlesex on Expedia! You can easily find your home rentals, villas, holiday apartments in Middlesex using one of the methods below:

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Recent reviews of Middlesex properties

Princess Grand Jamaica Resort - All Inclusive

5/5 Excellent

"This property was great. The family side was great for kids. They had a kids club and water park. The buffet was the best dining option I would say. Didn’t try any other besides Jamrock which was good. The days we were there it was not to many guest but I couldn’t imagine if it was full. Lots of rooms but limited beach space. I feel the adult side had more options especially with dining. We had a swim out suite which was awesome because we could swim at anytime. Would definitely go back but probably without the kids. It’s also like an hour away from MBJ airport if you fly in to there."

A verified traveler stayed at Princess Grand Jamaica Resort - All Inclusive

Posted 1 day ago

Princess Senses The Mangrove Resort - Adults Only

5/5 Excellent

"Not only were our butlers amazingly professional and kind but so were the other staffers we encountered. Only thing that wqa a bummer, my husbands drink of choice is Hennessey. They were out until the last day but he was accommodated. Understandably so that its imported there. "

A verified traveler stayed at Princess Senses The Mangrove Resort - Adults Only

Posted 2 days ago

5/5 Excellent

"What an amazing trip! We’re so glad we chose Couples Swept Away and will definitely be back. This was our first all-inclusive, and we were nervous about the food—but it far exceeded expectations. Lots of variety, great quality, and the morning breakfast delivery was a lovely touch. The grounds are stunning, and we loved walking the property. The groundskeepers were friendly and happy to share info about the plants. The beach is beautiful—yes, you’ll need to get up early for a palapa, but there are still shaded options later in the day. We’re not big bar people, but drinks were always served with a smile. If you love piña coladas, consider ordering coconut rum with pineapple juice instead—the pre-mix wasn’t our favorite. The gym is excellent, and the lap pool is a great way to cool off. The only drawbacks were no coed sauna and a less-than-clean hot tub. Our room was fantastic—comfortable bed, deep sleep every night, and excellent housekeeping. Most staff were friendly and helpful (a few weren’t, but that happens everywhere). Overall, we had a wonderful vacation and often said aloud how happy we were with our choice. If you come with a good attitude and open mind, you’ll have an amazing time at CSA."

A verified traveler stayed at Couples Swept Away All Inclusive

Posted 3 days ago

Grand Palladium Lady Hamilton Resort & Spa All Inclusive

5/5 Excellent

"The staff was absolutely incredible, booking the signature level was well worth it solely for the access to the exclusive beach and pool with two of the best bartenders we have ever met (Ornella and Mario)! We were so well taken care of here that we are already planning on coming back!"

A verified traveler stayed at Grand Palladium Lady Hamilton Resort & Spa All Inclusive

Posted 3 days ago

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.

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Middlesex Vacation Rentals

Check prices for these dates

Vacation Rentals in Middlesex

Dalley's Cozy Apartments

Sand and Blue Seas

Montego Bay Club Apartments

Villas Sur Mer

Beach House Condos Negril

Montego Bay Club Beach Resort

Idle Awhile Villas

Monimo Ridge Suites

Stunning Ocean View

Sunny-shore Hideaway

Idle Awhile Cliffs

Sky Beach Rooms

Turquoise Sea Villa

Luxury villa in Montego Bay Jamaica

YanceyLargo- 4BR Villa Jacuzzi & Mountain Views by RedAwning

Unity Villa

Seascape Apartment

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

Silent Waters Villa

Beachcliff Villa Negril

Find out more about Middlesex

Recent reviews of Middlesex properties

Princess Grand Jamaica Resort - All Inclusive

Princess Senses The Mangrove Resort - Adults Only

CocoLaPalm Seaside Resort

Toby's Resort

Couples Swept Away All Inclusive

Secrets St. James Montego Bay - Luxury - Adults Only - All Inclusive

Grand Palladium Lady Hamilton Resort & Spa All Inclusive

SeaGarden Beach Resort - All Inclusive

Secrets Wild Orchid Montego Bay - Luxury - Adults Only - All Inclusive

Frequently asked questions