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Middlesex Vacation Rentals

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Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Middlesex vacation rentals

Basic Loft | View from room

Claudeville Condo

Claudeville Condo
3.0 star property
Montego Bay
8.6 out of 10, Excellent, (25 reviews)
"Room was clean and staff was very welcoming with great communication. "
United States
Kenneth
$96 nightly
The price is $111
Jul 9 - Jul 10
Total with taxes and fees
Claudeville Condo
Outdoor pool

Charming Seaview Studio with Private Pool & Complimentary Airport Transfer!

Charming Seaview Studio with Private Pool & Complimentary Airport Transfer!
Hopewell
8.8 out of 10, Excellent, (5 reviews)
"Bonnie was amazing and goes over and beyond to make you feel at home. She is very friendly but gives you your space and privacy I really enjoyed her house with the amazing view and her pool. "
United States
Roberta M.
$135 nightly
The price is $135
Jul 14 - Jul 15
Total with taxes and fees
Charming Seaview Studio with Private Pool & Complimentary Airport Transfer!
Front of property

Unity Villa

Unity Villa
3.0 star property
Montego Bay
8.0 out of 10, Very Good, (1 review)
"I like that the property was quiet. The place was clean. The neighbor I met was really nice. I like that. It was outside of the tourist area."
United States
Fashira
$83 nightly
The price is $93
Jul 10 - Jul 11
Total with taxes and fees
Unity Villa
Outdoor dining

Gorgeous 4-bedroom house with AC in lively Montego Bay

Gorgeous 4-bedroom house with AC in lively Montego Bay
Paradise Acres
10.0 out of 10, Exceptional, (1 review)
"This location was amazing. The view of the harbor and the Gulf waters was off the chart. It was only minutes from the airport and the "Hip Strip" for shopping. Much much better than was advertised. The grounds were maintained immaculate and all the amenities made us feel right at home. Would visit again in a heartbeat. Great fantastic surprise. 5* even 6*"
United States
Michael B.
$137 nightly
The price is $137
Jul 13 - Jul 14
Total with taxes and fees
Gorgeous 4-bedroom house with AC in lively Montego Bay
Exterior

RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL

RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL
4.0 star property
Negril
$97 nightly
The price is $112
Aug 8 - Aug 9
Total with taxes and fees
RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL
Property grounds

The Artist cabin is a mountain cabin overlooking the sea and coastline

The Artist cabin is a mountain cabin overlooking the sea and coastline
Cave
10.0 out of 10, Exceptional, (1 review)
"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
Jul 9 - Jul 10
Total with taxes and fees
The Artist cabin is a mountain cabin overlooking the sea and coastline
House, 2 Bedrooms, Smoking, Balcony | Balcony

Modern Home 10minstobeach, Private Cliff, AC Wifi

Modern Home 10minstobeach, Private Cliff, AC Wifi
2.0 star property
Negril
9.0 out of 10, Wonderful, (2 reviews)
"Great atmosphere and awesome service. Clean and spacious apartment with a modern touch. Definitely looking forward to a future stay"
United States
Shantel
$112 nightly
The price is $130
Jul 12 - Jul 13
Total with taxes and fees
Modern Home 10minstobeach, Private Cliff, AC Wifi
Living area

Hummingbird Room in Guest Home: WiFi, Hot Water AC Montego Bay Live-in Hosts

Hummingbird Room in Guest Home: WiFi, Hot Water AC Montego Bay Live-in Hosts
Mount Salem
10.0 out of 10, Exceptional, (1 review)
"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
Jul 15 - Jul 16
Total with taxes and fees
Hummingbird Room in Guest Home: WiFi, Hot Water AC Montego Bay Live-in Hosts
Restaurant

Sky Beach Rooms

Sky Beach Rooms
5.0 star property
Montego Bay
2.0 out of 10, (1 review)
"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."
United States
chevone
$96 nightly
The price is $107
Jul 9 - Jul 10
Total with taxes and fees
Sky Beach Rooms
View from property

Montego Bay Club Beach Resort

Montego Bay Club Beach Resort
3.5 star property
Hip Strip
4.4 out of 10, (85 reviews)
"The view is amazing just imagine waking to a beautiful blue ocean. Walking distance to the beach and the best restaurants, I recommend this place any day and the price is right.."
United States
Natalie
$146 nightly
The price is $166
Jul 16 - Jul 17
Total with taxes and fees
Montego Bay Club Beach Resort
Premium Cottage, 1 Queen Bed, Pool View | Balcony view

Villas Sur Mer

Villas Sur Mer
4.0 star property
West End
8.8 out of 10, Excellent, (153 reviews)
"We did not use the hot tub put the pool area including the hot tub looked very relaxing. Located in a beautiful garden area "
Canada
Faye
$171 nightly
The price is $189
Jul 26 - Jul 27
Total with taxes and fees
Villas Sur Mer
TV, books, music library, stereo

Betta A Yaad Ocean View Villa, New upgrades

Betta A Yaad Ocean View Villa, New upgrades
West End
9.0 out of 10, Wonderful, (12 reviews)
"Good"
United States
Tomoko
$170 nightly
The price is $175
Aug 1 - Aug 2
Total with taxes and fees
Betta A Yaad Ocean View Villa, New upgrades
Property grounds

Beach House Condos Negril

Beach House Condos Negril
3.5 star property
Negril
9.0 out of 10, Wonderful, (62 reviews)
"Second time staying here.. reasonably priced, low-key idyllic spot"
United States
Elizabeth
$132 nightly
The price is $151
Jul 13 - Jul 14
Total with taxes and fees
Beach House Condos Negril
2 outdoor pools, free cabanas, pool umbrellas

Sunshine Seashore Escape Jamaica

Sunshine Seashore Escape Jamaica
3.5 star property
Lucea
$204 nightly
The price is $236
Jul 25 - Jul 26
Total with taxes and fees
Sunshine Seashore Escape Jamaica
Terrace/patio

Seaside Escape

Seaside Escape
Montego Bay
$134 nightly
The price is $134
Jul 11 - Jul 12
Total with taxes and fees
Seaside Escape
Beach nearby

Hospitality Expert SWF104 - Pool, Beach, Chef

Hospitality Expert SWF104 - Pool, Beach, Chef
Montego Bay
10.0 out of 10, Exceptional, (2 reviews)
"Nice place and breakfast"
Spain
Xavier
$197 nightly
The price is $223
Jul 11 - Jul 12
Total with taxes and fees
Hospitality Expert SWF104 - Pool, Beach, Chef
Exterior

Grassroots Negril

Grassroots Negril
3.0 star property
West End
$78 nightly
The price is $91
Jul 9 - Jul 10
Total with taxes and fees
Grassroots Negril
Beach nearby, beach towels

The Chill Spot - Escape. Relax. Enjoy. Your perfect getaway.

The Chill Spot - Escape. Relax. Enjoy. Your perfect getaway.
Lucea
8.0 out of 10, Very Good, (6 reviews)
"We enjoyed ourselves. And our stay was very pleasant."
United States
Cynthia N.
$201 nightly
The price is $201
Jul 16 - Jul 17
Total with taxes and fees
The Chill Spot - Escape. Relax. Enjoy. Your perfect getaway.
Beach

VIVIENNE'S ROOMS #6

VIVIENNE'S ROOMS #6
Green Island
9.6 out of 10, Exceptional, (7 reviews)
"As Green Island starts to become more popular due to the Princess Hotel this remains the gem in the area. Tucked away, peaceful, serene. "
United States
Ixchel L.
$70 nightly
The price is $70
Jul 9 - Jul 10
Total with taxes and fees
VIVIENNE'S ROOMS #6
Family Townhome, 2 Bedrooms, Kitchen, Ocean View | In-room dining

Stunning Ocean View

Stunning Ocean View
4.0 star property
Negril
10.0 out of 10, Exceptional, (14 reviews)
"Clean and beautiful scenery! Needed assistance after hours and the manager responded quickly to my questions and concerns. Would book again"
United States
Willie
$646 nightly
The price is $726
Jul 30 - Jul 31
Total with taxes and fees
Stunning Ocean View
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

Toby's Resort

Toby's Resort

10/10 Excellent
"I Recommend this location good for the price walking distance to the beach and night life the on-site restaurant it’s convenient close to the airport 10 mins or less the staff is amazing especially the manager my son loved it especially when they called him Sir 😂"
colette 1-night trip
Posted 4 hours ago
Toby's Resort

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 $107 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?

Deluxe appartment at Point village: Visitors like this Middlesex vacation home rental. It has air-conditioning and cable TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave, and kitchenware.

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.