Middlesex Vacation Rentals

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Our top choices for Middlesex vacation rentals

Villa in West End

Idle Awhile Cliffs
3.5 star property
9.0 out of 10, Wonderful, (119)
"Friendly staff, excellent customer service. Enjoyed the ambience and accommodations. Clean and pleasant."
United States
Nayana
Idle Awhile Cliffs
10.0 out of 10, Exceptional, (1)
"We fully enjoyed our stay. On arrival we had a few issues mainly because we arrived early and had some missed communication with Nadia. She promptly helped us resolve a few minor issues and the rest of our stay was literally a breeze, as in wonderful sea breezes! The accommodations were just as described, it felt safe and comfortable."
United States
Noel B.
$173 nightly
The price is $173
Jan 3 - Jan 4, 2026
Total with taxes and fees
Cozy yet elegant Jamaican vacation home with access to pool, beach, gym etc
9.0 out of 10, Wonderful, (11)
"Lovely place"
United States
Thad A.
$216 nightly
The price is $246
Jan 2 - Jan 3, 2026
Total with taxes and fees
Hospitality Expert CP: Private Pool/Beach/Chef
4.0 star property
$94 nightly
The price is $110
Dec 31 - Jan 1, 2026
Total with taxes and fees
RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL

Vacation Home in Cave District

Firefly cottage with Ocean view
10.0 out of 10, Exceptional, (27)
"I would recommend this cabin resort to anyone. Geneva was wonderful host, along with her beautiful family"
United States
Rick B.
$79 nightly
The price is $79
Dec 31 - Jan 1, 2026
Total with taxes and fees
Firefly cottage with Ocean view
8.0 out of 10, Very Good, (4)
"We enjoyed ourselves. And our stay was very pleasant."
United States
Cynthia N.
$174 nightly
The price is $174
Jan 23 - Jan 24, 2026
Total with taxes and fees
The Chill Spot - Escape. Relax. Enjoy. Your perfect getaway.

Apartment in Montego Bay

Claudeville Condo
3.0 star property
8.6 out of 10, Excellent, (22)
"Staff was very friendly and welcoming. "
United Kingdom
Sophia
$96 nightly
The price is $111
Jan 3 - Jan 4, 2026
Total with taxes and fees
Claudeville Condo
10.0 out of 10, Exceptional, (1)
$148 nightly
The price is $171
Jan 3 - Jan 4, 2026
Total with taxes and fees
YanceyLargo Estate - Newly Built Modern 1 Bedroom Suite 1 Villa by RedAwning
10.0 out of 10, Exceptional, (1)
"It was a beautiful home and convenient to the airport. The host was also very responsive and understanding . I appreciate her hospitality and kindness. I would def recommend this place and would stay again."
United States
Shannon S.
$110 nightly
The price is $110
Dec 31 - Jan 1, 2026
Total with taxes and fees
Great panoramic views. Beach and shopping close by.
10.0 out of 10, Exceptional, (1)
"We had an amazing stay in the mountains of Jamaica! The food was excellent, and we loved watching the sunset every evening. Terry was wonderful company — he even picked us up in Negril to bring us to the beautiful cabins in the woods. A truly magnificent stay!"
United States
Ana G.
$70 nightly
The price is $70
Dec 31 - Jan 1, 2026
Total with taxes and fees
The Artist cabin is a mountain cabin overlooking the sea and coastline
9.0 out of 10, Wonderful, (2)
"Absolutely gorgeous property and views, bird sounds, fantastic food prepared by the friendly hosts. Simple living with wi-fi if needed."
United States
David G.
$80 nightly
The price is $80
Dec 31 - Jan 1, 2026
Total with taxes and fees
Kimoya's cottage is a mountain cottage overlooking the sea and coastline
9.8 out of 10, Exceptional, (19)
"Everything was wonderful!! This was our second time staying there and we will definitely stay there whenever we visit Montego Bay!!!"
United States
Alicia W.
$160 nightly
The price is $160
Jan 10 - Jan 11, 2026
Total with taxes and fees
PINES VACATION RENTALS- EXCELLENT LOCATION, MINUTES FROM EVERYTHING.
10.0 out of 10, Exceptional, (3)
"My family and I stayed for 2 days and it was unforgettable! The place was clean and tidy! Jordan (host) offered great recommendations for restaurants nearby- many within walking distance. Rick’s cafe across the street with amazing views! We had a great time and can’t wait to be back "
United States
Bridgette A.
$160 nightly
The price is $174
Jan 4 - Jan 5, 2026
Total with taxes and fees
Bak A Yaad Timberland Cottage
10.0 out of 10, Exceptional, (1)
"My stay at Sunset Arms was amazing. The apartment was just the right amount of space that our family needed. It was clean, well lit and with modern decor. We enjoyed our time there immensely. Ana, our host, was super kind and helpful!"
United States
Nathalee
$183 nightly
The price is $183
Jan 3 - Jan 4, 2026
Total with taxes and fees
Sunset Arms 3: 2brm/2wsr, Airport-Beach-Hipstrip
9.4 out of 10, Exceptional, (39)
"Troy was very helpful & professional! Neighborhood was nice & house was very nice "
United States
Shemeka M.
$178 nightly
The price is $178
Jan 19 - Jan 20, 2026
Total with taxes and fees
Come relax and unwind and enjoy a piece of Paradise in montego Bay Jamaica
10.0 out of 10, Exceptional, (3)
"We stayed here for 10 days and absolutely loved it. The bedroom is so perfect and our host (Bonnie) let us use the kitchen and whatever we needed anytime. The porch is lovely with a gorgeous ocean view. This was the perfect spot for our vacation!!! "
United States
Roger Y.
$135 nightly
The price is $135
Jan 11 - Jan 12, 2026
Total with taxes and fees
Charming Seaview Studio with Private Pool & Complimentary Airport Transfer!

Vacation Home in Cave

Dragon fly Cottage
10.0 out of 10, Exceptional, (7)
"We had a lot of fun relaxing here. Geneva made excellent breakfast and suppers and we spent the majority of our time relaxing on the deck/hammock reading and hiking around the property and the town of Kentucky. If you want an escape from the tourism scene, this is a nice place to go! "
Canada
Kaili
$83 nightly
The price is $83
Dec 31 - Jan 1, 2026
Total with taxes and fees
Dragon fly Cottage
10.0 out of 10, Exceptional, (1)
"I stayed at Topaz Dream Guesthouse in Montego Bay during Sumfest 2025, and it was such a beautiful and unforgettable experience. The space is cozy, artistic, and full of character, but what truly makes it special is Cherri, the host.Cherri is warm, wise, and simply amazing. She carries the spirit of Jamaica in her heart and has the most incredible stories of life, love, triumph, and resilience. Connecting with her was the true highlight of my trip—our conversations left me feeling inspired and...
United States
English C.
$80 nightly
The price is $80
Jan 6 - Jan 7, 2026
Total with taxes and fees
Hummingbird Room in Guest Home: WiFi, Hot Water AC Montego Bay Live-in Hosts
10.0 out of 10, Exceptional, (7)
"Jean was an awesome host."
Canada
Tammy
$142 nightly
The price is $154
Jan 3 - Jan 4, 2026
Total with taxes and fees
Negril Beach Condo - Jamaica - Hotel Room, no kitchen, Unit 3
9.2 out of 10, Wonderful, (5)
"The location was gorgeous, not far from the city. Easy/beautiful walk to cabs. Host was great and the bed/sheets felt great!!"
United States
Kintoria W.
$83 nightly
The price is $83
Dec 31 - Jan 1, 2026
Total with taxes and fees
Quiet relaxing mountainous get away!
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 Hotel Reviews

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 $93 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?

RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL: You might want to consider this vacation home rental near Middlesex, which has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, an oven, and a microwave.

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 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.