Middlesex Vacation Rentals from $97: Search Short-Term Rentals

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Our top choices for Middlesex vacation rentals

An outdoor dining area with a view of the sea, featuring a thatched-roof structure and wicker furniture.

1. Sky Beach Rooms

Montego Bay

Clayton

$87 nightly

Sep 30 - Oct 1

Total with taxes and fees

A spacious kitchen with wooden cabinets, a refrigerator, and a dining area with a table and chairs.

2. Claudeville Condo

Montego Bay

Sabrina

$96 nightly

Oct 1 - Oct 2

Total with taxes and fees

A beach with thatched umbrellas, a white building, and pink flowers.

3. Beach House Condos Negril

Negril

Elizabeth

$132 nightly

Oct 23 - Oct 24

Total with taxes and fees

A person standing on a beach with arms raised, facing a calm sea and a small island in the distance.

4. Deluxe appartment at Point village

West End

Nikki

$112 nightly

Oct 1 - Oct 2

Total with taxes and fees

A beach with clear turquoise water, a sandy shore, and a view of the ocean.

5. Montego Bay Club Apartments

Hip Strip

Heather

$148 nightly

Oct 13 - Oct 14

Total with taxes and fees

A coastal swimming area with boats and people.

6. Sunshine Seashore Escape Jamaica

Lucea

$207 nightly

Oct 13 - Oct 14

Total with taxes and fees

A two-story building with a balcony on the upper floor, featuring decorative railings and barred windows.

7. Unity Villa

Montego Bay

Fashira

$83 nightly

Sep 30 - Oct 1

Total with taxes and fees

A beach view from a balcony with a clear ocean, a pier, and a few umbrellas on the sand.

8. Montego Bay Club Beach Resort

Hip Strip

Kimanie

$147 nightly

Sep 30 - Oct 1

Total with taxes and fees

A hanging chair on a balcony with a white railing and a view of trees.

9. Modern Home 10minstobeach, Private Cliff, AC Wifi

Negril

Shantel

$115 nightly

Oct 7 - Oct 8

Total with taxes and fees

A swimming pool with a hot tub, surrounded by palm trees and a white building.

10. Turquoise Sea Villa

Montego Bay

$236 nightly

Sep 30 - Oct 1

Total with taxes and fees

A beach with clear turquoise water, a sandy shore, and lounge chairs.

11. Seawind E202

Montego Bay

$205 nightly

Oct 5 - Oct 6

Total with taxes and fees

A bedroom with a bed, a ceiling fan, an air conditioner, and a view of the outdoors.

12. Eleven30 Luxury Apartments

Negril

$123 nightly

Sep 30 - Oct 1

Total with taxes and fees

A thatched-roof hut with a concrete pathway leading to it, surrounded by greenery and a low wall.

13. Unity Villa

Montego Bay

Susan

$112 nightly

Sep 30 - Oct 1

Total with taxes and fees

A dining area with a wooden table and chairs, a fruit bowl, and a view of the ocean through large glass doors.

14. Stunning Ocean View

Negril

Willie

$654 nightly

Sep 30 - Oct 1

Total with taxes and fees

A beach with clear turquoise water and sandy shore.

15. Hospitality Expert CP

Hip Strip

$207 nightly

Sep 30 - Oct 1

Total with taxes and fees

16. Grassroots Negril

West End

$78 nightly

Sep 30 - Oct 1

Total with taxes and fees

A dining area with a round table set for four, surrounded by chairs. There is a sofa and a chair in the background, and a window with curtains.

17. Casia Villa

Montego Bay

Michael

$448 nightly

Sep 30 - Oct 1

Total with taxes and fees

A large house with a swimming pool, surrounded by lush greenery and palm trees.

18. La Costa Villa

Montego Bay

$725 nightly

Sep 30 - Oct 1

Total with taxes and fees

19. Sunny-shore Hideaway

Lucea

$244 nightly

Oct 30 - Oct 31

Total with taxes and fees

A lush garden with a swimming pool, surrounded by dense foliage and tropical plants.

20. Villas Sur Mer

West End

Faye

$177 nightly

Oct 3 - Oct 4

Total with taxes and fees

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Top Middlesex Hotel Reviews

Samsara Cliff Resort

10/10 Excellent

"Staying at Samsara was a delightful experience! I came for my fiancés birthday weekend, I had an amazing time."

Princess Grand Jamaica Resort - All Inclusive

10/10 Excellent

"We had a wonderful stay at Princess Grand Jamaica. The property is beautiful, modern and well maintained, with an impressive range of amenities that made it easy to enjoy the resort without needing to leave. We especially appreciated the pools, beach access, variety of restaurants and bars, entertainment options, spacious rooms, and the additional perks and personalized service that came with the Platinum experience. There was always something to do, while still having plenty of space to simply relax and enjoy the property. What really elevated our stay, however, was the staff. Garth, the Platinum Manager, was exceptional: attentive, professional and genuinely committed to ensuring we had a great experience. Tajay, Melissa and Shanna-Lee at Reception were warm, accommodating and consistently helpful, while Christopher and Ewan, the bellmen, made our arrivals, departures and movements around the resort effortless. The combination of the resort’s amenities and the hospitality of these team members made our stay especially memorable. We felt genuinely welcomed and well taken care of throughout our visit. Princess Grand delivered a beautiful resort experience, but the people truly made it special. We would absolutely return."

SeaGarden Beach Resort - All Inclusive

10/10 Excellent

"We had such a wonderful stay at Sea Garden Resort! The entire staff was incredibly friendly, accommodating, and so kind to us and our baby. Our room was clean, comfortable, and well-maintained. Now for the food, whoever is in that kitchen is doing an amazing job. Every single meal, breakfast, lunch, and dinner, was delicious and beautifully prepared. While we didn't drink much from the bar, the few drinks my husband and I tried were good. We loved our time here!"

Find out more about Middlesex

Everything you need to know about Middlesex 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 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middlesex vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middlesex. 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 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 $97 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 rentals

At Expedia, we put the best Middlesex 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 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 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. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

5 bed villa, gated community, private pool, fully staffed, private chauffeur: Visitors like this Middlesex vacation home rental. It is located next to a golf course and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What can I see and do in Middlesex?

Explore the area and family-friendly sights such as Hope Botanical Garden and Zoo, or get out into nature at a spot like Seven Mile Beach. Half Moon Beach and Bloody Bay Beach 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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Check prices for these dates

Our top choices for Middlesex vacation rentals

1. Sky Beach Rooms

2. Claudeville Condo

3. Beach House Condos Negril

4. Deluxe appartment at Point village

5. Montego Bay Club Apartments

6. Sunshine Seashore Escape Jamaica

7. Unity Villa

8. Montego Bay Club Beach Resort

9. Modern Home 10minstobeach, Private Cliff, AC Wifi

10. Turquoise Sea Villa

11. Seawind E202

12. Eleven30 Luxury Apartments

13. Unity Villa

14. Stunning Ocean View

15. Hospitality Expert CP

16. Grassroots Negril

17. Casia Villa

18. La Costa Villa

19. Sunny-shore Hideaway

20. Villas Sur Mer

Find vacation rentals that suit your style

Top Middlesex Hotel Reviews

Samsara Cliff Resort

Hotel 39 Jamaica

Grand Palladium Jamaica Resort & Spa All Inclusive

Princess Grand Jamaica Resort - All Inclusive

Hotel Riu Palace Tropical Bay - All Inclusive

Royalton Negril, An Autograph Collection All-Inclusive Resort

Hotel Grand A View

SeaGarden Beach Resort - All Inclusive

Grand Palladium Lady Hamilton Resort & Spa All Inclusive

Find out more about Middlesex

Frequently asked questions

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