Middlesex Vacation Rentals

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Our top choices for Middlesex vacation rentals

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.
The price is ¥8,015
¥12,824 total
includes taxes & fees
Jun 27 - Jun 28
Hummingbird Room in Guest Home: WiFi, Hot Water AC Montego Bay Live-in Hosts

Firefly cottage with Ocean view

Firefly cottage with Ocean view
Cave District
10.0 out of 10, Exceptional, (27 reviews)
"I would recommend this cabin resort to anyone. Geneva was wonderful host, along with her beautiful family"
United States
Rick B.
The price is ¥9,401
¥12,607 total
includes taxes & fees
Jun 10 - Jun 11
Firefly cottage with Ocean view

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.
The price is ¥8,015
¥11,221 total
includes taxes & fees
Jun 10 - Jun 11
The Artist cabin is a mountain cabin overlooking the sea and coastline

Grassroots Negril

Grassroots Negril
3.0 star property
West End
The price is ¥10,419
¥14,546 total
includes taxes & fees
Jun 8 - Jun 9
Grassroots Negril

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
The price is ¥15,655
¥17,381 total
includes taxes & fees
Jun 9 - Jun 10
Sky Beach Rooms

Kimoya's cottage is a mountain cottage overlooking the sea and coastline

Kimoya's cottage is a mountain cottage overlooking the sea and coastline
Cave
9.0 out of 10, Wonderful, (2 reviews)
"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.
The price is ¥9,617
¥12,823 total
includes taxes & fees
Jun 8 - Jun 9
Kimoya's cottage is a mountain cottage overlooking the sea and coastline

Claudeville Condo

Claudeville Condo
3.0 star property
Montego Bay
8.6 out of 10, Excellent, (24 reviews)
"Room was clean and staff was very welcoming with great communication. "
United States
Kenneth
The price is ¥15,328
¥17,787 total
includes taxes & fees
Jun 15 - Jun 16
Claudeville Condo

Wonderful 1-bedroom apartment with AC in vibrant Montego Bay

Wonderful 1-bedroom apartment with AC in vibrant Montego Bay
Coral Gardens
The price is ¥8,656
¥21,479 total
includes taxes & fees
Jun 8 - Jun 9
Wonderful 1-bedroom apartment with AC in vibrant Montego Bay

Muris Light Sanctuary

Muris Light Sanctuary
Savanalamar
10.0 out of 10, Exceptional, (1 review)
"Host was attentive and super nice to deal with. Great stay. No air conditioning but was pleaaant regardless. "
Canada
Leeann D.
The price is ¥5,610
¥21,318 total
includes taxes & fees
Jun 8 - Jun 9
Muris Light Sanctuary

Dragon fly Cottage

Dragon fly Cottage
Cave
10.0 out of 10, Exceptional, (7 reviews)
"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
The price is ¥10,130
¥13,336 total
includes taxes & fees
Jun 8 - Jun 9
Dragon fly Cottage

Charming & Comfortable 1-Bedroom Suite in Montego Bay

Charming & Comfortable 1-Bedroom Suite in Montego Bay
Montego Bay
8.4 out of 10, Very Good, (13 reviews)
"Enjoyed my stay here. It met all my needs, will always stay here when i am in Montego Bay. "
United Kingdom
Lynfus
The price is ¥9,457
¥12,663 total
includes taxes & fees
Jun 10 - Jun 11
Charming & Comfortable 1-Bedroom Suite in Montego Bay

Charming Seaview Studio with Private Pool & Complimentary Airport Transfer!

Charming Seaview Studio with Private Pool & Complimentary Airport Transfer!
Hopewell
10.0 out of 10, Exceptional, (4 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.
The price is ¥14,426
¥21,639 total
includes taxes & fees
Jun 12 - Jun 13
Charming Seaview Studio with Private Pool & Complimentary Airport Transfer!

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
The price is ¥10,419
¥14,827 total
includes taxes & fees
Jun 21 - Jun 22
Unity Villa

Hip Strip Beach Apartment walkable to clubs, beaches and restaurants

Hip Strip Beach Apartment walkable to clubs, beaches and restaurants
Hip Strip
8.6 out of 10, Excellent, (7 reviews)
"Such a great place great location!!"
United States
Matthew K.
The price is ¥10,820
¥14,026 total
includes taxes & fees
Jun 8 - Jun 9
Hip Strip Beach Apartment walkable to clubs, beaches and restaurants

Apartment 5 @ Top Bay Apartments

Apartment 5 @ Top Bay Apartments
Montego Bay
The price is ¥12,903
¥21,719 total
includes taxes & fees
Jun 10 - Jun 11
Apartment 5 @ Top Bay Apartments

King Bd with Kitchen, AC, Hot Water, Stove & Large Standing Fridge

King Bd with Kitchen, AC, Hot Water, Stove & Large Standing Fridge
Mango Walk
The price is ¥7,566
¥12,822 total
includes taxes & fees
Jun 11 - Jun 12
King Bd with Kitchen, AC, Hot Water, Stove & Large Standing Fridge

Quiet relaxing mountainous get away!

Quiet relaxing mountainous get away!
Montego Bay
9.2 out of 10, Wonderful, (5 reviews)
"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.
The price is ¥11,220
¥16,029 total
includes taxes & fees
Jun 14 - Jun 15
Quiet relaxing mountainous get away!

Montego Bay Club Beach Resort

Montego Bay Club Beach Resort
3.5 star property
Hip Strip
4.4 out of 10, (82 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
The price is ¥19,764
¥27,056 total
includes taxes & fees
Jun 9 - Jun 10
Montego Bay Club Beach Resort

RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL

RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL
4.0 star property
Negril
The price is ¥15,743
¥18,265 total
includes taxes & fees
Jun 8 - Jun 9
RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL

Villa Giovanni Paris - Beautiful Secured Complex! Fully Gated!

Villa Giovanni Paris - Beautiful Secured Complex! Fully Gated!
Savanna la Mar
The price is ¥14,426
¥22,441 total
includes taxes & fees
Jun 8 - Jun 9
Villa Giovanni Paris - Beautiful Secured Complex! Fully Gated!
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

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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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.