Title: Middlesex Vacation Rentals from CA $126: Short-Term Rentals for 2026 | Expedia.ca

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## Check prices for these dates

In two weeks

[Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=553248635975854330&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=553248635975854330&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=553248635975854330&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 5 - Jun 7](https://www.expedia.ca/Hotel-Search?regionId=553248635975854330&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Middlesex vacation rentals

![Exterior](https://images.trvl-media.com/lodging/102000000/101430000/101422600/101422520/ae12f5e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Double Room](https://images.trvl-media.com/lodging/102000000/101430000/101422600/101422520/b6d03a1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Double Room | Bathroom](https://images.trvl-media.com/lodging/102000000/101430000/101422600/101422520/f5b67134.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Double Room](https://images.trvl-media.com/lodging/102000000/101430000/101422600/101422520/5bd32b22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL

[](https://www.expedia.ca/Negril-Hotels-RUNTINGS-HIDEAWAY-STAY-NOMPREL-ROAD-NEGR.h101422520.Hotel-Information)

Negril

CA $138

CA $160 total

includes taxes & fees

Feb 18 - Feb 19

[](https://www.expedia.ca/Negril-Hotels-RUNTINGS-HIDEAWAY-STAY-NOMPREL-ROAD-NEGR.h101422520.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33940000/33936300/33936228/060d80b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/34000000/33940000/33936300/33936228/26a33eb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/34000000/33940000/33936300/33936228/174fc5f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33940000/33936300/33936228/a9dc442c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Free Airport pick-up. private villa with amazing ocean veiw, pool, and maid.

[](https://www.expedia.ca/Montego-Bay-Hotels-Free-Transportation-Private-Villa-With-Amazing-Ocean-Veiw.h33936228.Hotel-Information)

Montego Bay

10/10

Exceptional

(63 reviews)

"Such a nice stay at windfall Villas, Mel was great and always able to get us to anywhere at almost anytime we needed. It was beautiful and peaceful at the property. Would highly recommend to anyone checking out Montego Bay. Think twice begore trying drive here. In my opinion this is one dangerous place to drive unless you’ve driven here before. Mel made this part of our trip completely safe. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jeff B.

CA $392

CA $446 total

includes taxes & fees

Feb 25 - Feb 26

[](https://www.expedia.ca/Montego-Bay-Hotels-Free-Transportation-Private-Villa-With-Amazing-Ocean-Veiw.h33936228.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33560000/33552800/33552783/6d2436f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33560000/33552800/33552783/14ecba43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, towels, soap, toilet paper](https://images.trvl-media.com/lodging/34000000/33560000/33552800/33552783/eda15c45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33560000/33552800/33552783/8141a074.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Firefly cottage with Ocean view

[](https://www.expedia.ca/Bluefields-Hotels-Firefly-Cottage-With-Ocean-View.h33552783.Hotel-Information)

Cave District

10/10

Exceptional

(27 reviews)

"I would recommend this cabin resort to anyone. Geneva was wonderful host, along with her beautiful family"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Rick B.

CA $80

CA $107 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Bluefields-Hotels-Firefly-Cottage-With-Ocean-View.h33552783.Hotel-Information)

![Beach nearby, white sand, beach towels](https://images.trvl-media.com/lodging/39000000/38720000/38719600/38719562/82435d6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/39000000/38720000/38719600/38719562/2bdfd61a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Townhome](https://images.trvl-media.com/lodging/39000000/38720000/38719600/38719562/093f228b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![43-inch Smart TV with cable channels, TV](https://images.trvl-media.com/lodging/39000000/38720000/38719600/38719562/ebaf9b3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Nianna Chatham

[](https://www.expedia.ca/Montego-Bay-Hotels-Nianna-Chatham.h38719562.Hotel-Information)

Hip Strip

CA $205

CA $319 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Montego-Bay-Hotels-Nianna-Chatham.h38719562.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/108000000/107010000/107004800/107004781/a42d3089.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, blackout drapes, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/108000000/107010000/107004800/107004781/2af6588d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/108000000/107010000/107004800/107004781/56e5678a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Electric kettle, toaster](https://images.trvl-media.com/lodging/108000000/107010000/107004800/107004781/d68152e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Unity Villa

[](https://www.expedia.ca/Montego-Bay-Hotels-Unity-Villa.h107004781.Hotel-Information)

Montego Bay

8.0/10

Very good

(1 review)

"I LIKE HOW THEY COMMUNICATED AND ADDRESSED THE PROBLEMS ! Only thing I didn’t like was the no working ac and there wasn’t stuff close to go shop "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Susan

CA $129

CA $177 total

includes taxes & fees

Feb 15 - Feb 16

[](https://www.expedia.ca/Montego-Bay-Hotels-Unity-Villa.h107004781.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/94000000/93680000/93675200/93675113/3b93c256.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Egyptian cotton sheets, premium bedding, pillowtop beds](https://images.trvl-media.com/lodging/94000000/93680000/93675200/93675113/d9ab2cde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Signature Villa, Hot Tub, Ocean View | Private kitchen](https://images.trvl-media.com/lodging/94000000/93680000/93675200/93675113/917f1f5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/94000000/93680000/93675200/93675113/b22eaf06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Wabi-Sabi Villa

[](https://www.expedia.ca/Lucea-Hotels-Wabi-Sabi-Villa.h93675113.Hotel-Information)

Lucea

10/10

Exceptional

(2 reviews)

"This property had amazing staff and the place was beautiful. I absolutely loved them! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Andrea

CA $1,175

CA $1,489 total

includes taxes & fees

Feb 24 - Feb 25

[](https://www.expedia.ca/Lucea-Hotels-Wabi-Sabi-Villa.h93675113.Hotel-Information)

![Beach nearby, beach towels](https://images.trvl-media.com/lodging/84000000/83790000/83782300/83782222/w1240h912x1y0-32b51ce9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/84000000/83790000/83782300/83782222/w1236h865x0y0-a7b7e0ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/84000000/83790000/83782300/83782222/w1240h826x1y0-6cba8d7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83790000/83782300/83782222/w1242h825x0y0-04a562ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy yet elegant Jamaican vacation home with access to pool, beach, gym etc

[](https://www.expedia.ca/Lucea-Hotels-Cozy-Vacation-Home-With-Access-To-Pool.h83782222.Hotel-Information)

Lucea

10/10

Exceptional

(1 review)

"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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Noel B.

CA $149

CA $253 total

includes taxes & fees

Mar 4 - Mar 5

[](https://www.expedia.ca/Lucea-Hotels-Cozy-Vacation-Home-With-Access-To-Pool.h83782222.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/105000000/104070000/104069700/104069655/55424b17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/105000000/104070000/104069700/104069655/28f0293a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/105000000/104070000/104069700/104069655/ed4032b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/105000000/104070000/104069700/104069655/429801b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Home in Oceanpointe, Lucea, Hanover in Jamaica - 2BR 2WR

[](https://www.expedia.ca/Lucea-Hotels-Cozy-Home-In-Oceanpointe.h104069655.Hotel-Information)

Hanover, Parish

CA $191

CA $278 total

includes taxes & fees

Mar 7 - Mar 8

[](https://www.expedia.ca/Lucea-Hotels-Cozy-Home-In-Oceanpointe.h104069655.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/77000000/76890000/76889900/76889831/w906h683x59y0-6f0260c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/77000000/76890000/76889900/76889831/8aee26e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, electric kettle](https://images.trvl-media.com/lodging/77000000/76890000/76889900/76889831/w505h683x260y0-26315f22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi](https://images.trvl-media.com/lodging/77000000/76890000/76889900/76889831/w1024h544x0y70-df20d4e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Tranquil Park

[](https://www.expedia.ca/Orange-Bay-Hotels-Tranquil-Park.h76889831.Hotel-Information)

Orange Bay

CA $84

CA $124 total

includes taxes & fees

Feb 17 - Feb 18

[](https://www.expedia.ca/Orange-Bay-Hotels-Tranquil-Park.h76889831.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/113000000/112550000/112543800/112543733/a9075492.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/113000000/112550000/112543800/112543733/3171ed1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/113000000/112550000/112543800/112543733/62cd2714.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Golf](https://images.trvl-media.com/lodging/113000000/112550000/112543800/112543733/w1280h955x0y0-0e9d9071.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hospitality Expert Seawind - Pool, Beach, Chef

[](https://www.expedia.ca/Montego-Bay-Hotels-Hospitality-Expert-Seawind-Pool.h112543733.Hotel-Information)

Montego Bay

10/10

Exceptional

(1 review)

"Nice place and breakfast"

![Spain](https://a.travel-assets.com/egds/marks/flags/es.svg)

Xavier

CA $199

CA $342 total

includes taxes & fees

Mar 7 - Mar 8

[](https://www.expedia.ca/Montego-Bay-Hotels-Hospitality-Expert-Seawind-Pool.h112543733.Hotel-Information)

![Studio](https://images.trvl-media.com/lodging/91000000/90170000/90161200/90161111/4243fb67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio | Private kitchen](https://images.trvl-media.com/lodging/91000000/90170000/90161200/90161111/56b61b54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hallway](https://images.trvl-media.com/lodging/91000000/90170000/90161200/90161111/ef9d1a4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/91000000/90170000/90161200/90161111/64b69854.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Eleven30 Luxury Apartments 

[](https://www.expedia.ca/Negril-Hotels-Eleven30-Luxury-Apartments.h90161111.Hotel-Information)

Negril

[](https://www.expedia.ca/Negril-Hotels-Eleven30-Luxury-Apartments.h90161111.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/36000000/35220000/35214400/35214363/45b523f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/36000000/35220000/35214400/35214363/3fdacd17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player, table tennis, books](https://images.trvl-media.com/lodging/36000000/35220000/35214400/35214363/170b2fa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/36000000/35220000/35214400/35214363/14123287.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Free Transportation. Private Villa. Amazing Ocean View, Pool, And housekeeper.

[](https://www.expedia.ca/Montego-Bay-Hotels-Free-Transportation-Private-Villa-Amazing-Ocean-View.h35214363.Hotel-Information)

roundhill

9.8/10

Exceptional

(20 reviews)

"This trip was planned for our daughter's 21st birthday, so we wanted to make sure it was memorable for her. Mel communicated and responded quickly to me prior to our trip which made everything so much easier. Mel met us at the airport, took us to the store to grab provisions before heading to the villa. He was friendly and made us feel welcome immediately. Once we arrived at the villa, we were in paradise, the pictures and description were spot on and didn't disappoint. The view was nothing...

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sarah H.

CA $392

CA $446 total

includes taxes & fees

Feb 25 - Feb 26

[](https://www.expedia.ca/Montego-Bay-Hotels-Free-Transportation-Private-Villa-Amazing-Ocean-View.h35214363.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/77000000/76500000/76499700/76499632/0d640e6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/77000000/76500000/76499700/76499632/42913318.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/77000000/76500000/76499700/76499632/be8b904e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, in-room safe, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/77000000/76500000/76499700/76499632/1aac82a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 1 Bedroom Ocean view Apartment, The Lagoons

[](https://www.expedia.ca/Montego-Bay-Hotels-1-Bedroom-Ocean-View-Apartment.h76499632.Hotel-Information)

montego bay

7.6/10

Good

(7 reviews)

"Places is nice view is good"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Thomas G.

CA $221

CA $251 total

includes taxes & fees

Feb 15 - Feb 16

[](https://www.expedia.ca/Montego-Bay-Hotels-1-Bedroom-Ocean-View-Apartment.h76499632.Hotel-Information)

![Comfort House | Private kitchen](https://images.trvl-media.com/lodging/102000000/101540000/101530500/101530499/21ec1b13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/102000000/101540000/101530500/101530499/fe6d3de5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Comfort House | Private kitchen](https://images.trvl-media.com/lodging/102000000/101540000/101530500/101530499/w3991h2657x5y5-8b903661.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Comfort House](https://images.trvl-media.com/lodging/102000000/101540000/101530500/101530499/89a93e0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Casia Villa

[](https://www.expedia.ca/Montego-Bay-Hotels-Casia-Villa.h101530499.Hotel-Information)

Montego Bay

CA $551

CA $703 total

includes taxes & fees

Feb 17 - Feb 18

[](https://www.expedia.ca/Montego-Bay-Hotels-Casia-Villa.h101530499.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/43000000/42330000/42323900/42323804/90-cc931ea9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, video games, DVD player, table tennis](https://images.trvl-media.com/lodging/43000000/42330000/42323900/42323804/w1170h1159x0y0-9d86ae08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi](https://images.trvl-media.com/lodging/43000000/42330000/42323900/42323804/90-94d64df8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/43000000/42330000/42323900/42323804/90-f410b413.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bak A Yaad Timberland Cottage

[](https://www.expedia.ca/Negril-Hotels-Bak-A-Yaad-Timberland-Cottage.h42323804.Hotel-Information)

West End

10/10

Exceptional

(3 reviews)

"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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Bridgette A.

CA $184

CA $229 total

includes taxes & fees

Feb 19 - Feb 20

[](https://www.expedia.ca/Negril-Hotels-Bak-A-Yaad-Timberland-Cottage.h42323804.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/90000000/89940000/89932500/89932410/bf396913.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![50-inch Smart TV with cable channels, TV](https://images.trvl-media.com/lodging/90000000/89940000/89932500/89932410/74157b27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![50-inch Smart TV with cable channels, TV](https://images.trvl-media.com/lodging/90000000/89940000/89932500/89932410/0352c399.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![50-inch Smart TV with cable channels, TV](https://images.trvl-media.com/lodging/90000000/89940000/89932500/89932410/28a1fcbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Shallhome 

[](https://www.expedia.ca/Montego-Bay-Hotels-The-Shallhome.h89932410.Hotel-Information)

Montego Bay

CA $681

CA $784 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Montego-Bay-Hotels-The-Shallhome.h89932410.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/35000000/34670000/34662700/34662641/231e6ed2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/35000000/34670000/34662700/34662641/ebc22154.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/35000000/34670000/34662700/34662641/9f4dfad9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/35000000/34670000/34662700/34662641/b8a21dd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Dragon fly Cottage

[](https://www.expedia.ca/Bluefields-Hotels-Treehouse-Style-Cabin-Overlooking-Caribbean-Ocean.h34662641.Hotel-Information)

Cave

10/10

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](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Kaili

CA $86

CA $113 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Bluefields-Hotels-Treehouse-Style-Cabin-Overlooking-Caribbean-Ocean.h34662641.Hotel-Information)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/107000000/106210000/106209400/106209397/9635d9af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aerial view](https://images.trvl-media.com/lodging/107000000/106210000/106209400/106209397/w1080h1636x0y199-94720b7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Oven, stovetop](https://images.trvl-media.com/lodging/107000000/106210000/106209400/106209397/d95fd5fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/107000000/106210000/106209400/106209397/5fa618b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Bluefields-Hotels-Kimoyas-Cottage.h106209397.Hotel-Information)

Cave

9.0/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

David G.

CA $82

CA $109 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Bluefields-Hotels-Kimoyas-Cottage.h106209397.Hotel-Information)

![House, 2 Bedrooms, Smoking, Balcony | Balcony](https://images.trvl-media.com/lodging/126000000/125300000/125293100/125293043/9118e605.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, 2 Bedrooms, Smoking, Balcony | Interior](https://images.trvl-media.com/lodging/126000000/125300000/125293100/125293043/893c47bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, 2 Bedrooms, Smoking, Balcony | Interior](https://images.trvl-media.com/lodging/126000000/125300000/125293100/125293043/39b7c9b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, 2 Bedrooms, Smoking, Balcony](https://images.trvl-media.com/lodging/126000000/125300000/125293100/125293043/3302d953.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern Home 10minstobeach, Private Cliff, AC Wifi

[](https://www.expedia.ca/Negril-Hotels-Modern-Home-10minstobeach.h125293043.Hotel-Information)

Negril

CA $112

CA $131 total

includes taxes & fees

Feb 15 - Feb 16

[](https://www.expedia.ca/Negril-Hotels-Modern-Home-10minstobeach.h125293043.Hotel-Information)

![Smart TV, books, stereo](https://images.trvl-media.com/lodging/28000000/27450000/27443200/27443137/fef5df26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/28000000/27450000/27443200/27443137/5082150c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books, stereo](https://images.trvl-media.com/lodging/28000000/27450000/27443200/27443137/77411d6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/28000000/27450000/27443200/27443137/e4435175.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Come relax and unwind and enjoy a piece of Paradise in montego Bay Jamaica

[](https://www.expedia.ca/Montego-Bay-Hotels-Come-Relax-And-Unwind-And-Enjoy-A-Piece-Of-Paradise-In-Montego-Bay-Jamaica.h27443137.Hotel-Information)

Paradise Acres

9.4/10

Exceptional

(39 reviews)

"Troy was very helpful & professional! Neighborhood was nice & house was very nice "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Shemeka M.

CA $153

CA $221 total

includes taxes & fees

Mar 10 - Mar 11

[](https://www.expedia.ca/Montego-Bay-Hotels-Come-Relax-And-Unwind-And-Enjoy-A-Piece-Of-Paradise-In-Montego-Bay-Jamaica.h27443137.Hotel-Information)

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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## Find vacation rentals that suit your style

Aparthotels

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Apartments

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Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Middlesex%2C+Hanover%2C+Jamaica&regionId=553248635975854330&latLong=18.416506%2C-78.182808&adults=2&startDate=2026-05-15&d1=2026-05-15&endDate=2026-05-18&d2=2026-05-18&lodging=CABIN)

Villas

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Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Middlesex%2C+Hanover%2C+Jamaica&regionId=553248635975854330&latLong=18.416506%2C-78.182808&adults=2&startDate=2026-05-15&d1=2026-05-15&endDate=2026-05-18&d2=2026-05-18&lodging=COTTAGE)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Middlesex%2C+Hanover%2C+Jamaica&regionId=553248635975854330&latLong=18.416506%2C-78.182808&adults=2&startDate=2026-05-15&d1=2026-05-15&endDate=2026-05-18&d2=2026-05-18&lodging=CONDO)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Middlesex%2C+Hanover%2C+Jamaica&regionId=553248635975854330&latLong=18.416506%2C-78.182808&adults=2&startDate=2026-05-15&d1=2026-05-15&endDate=2026-05-18&d2=2026-05-18&lodging=VACATION_HOME)

Houseboats

[](https://www.expedia.ca/Hotel-Search?destination=Middlesex%2C+Hanover%2C+Jamaica&regionId=553248635975854330&latLong=18.416506%2C-78.182808&adults=2&startDate=2026-05-15&d1=2026-05-15&endDate=2026-05-18&d2=2026-05-18&lodging=HOUSE_BOAT)

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## Top Middlesex Hotel Reviews

![S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel](https://images.trvl-media.com/lodging/32000000/31380000/31370700/31370664/60e88e2a_y.jpg)

### S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel

10/10 Excellent

"Clean rooms, good food, nice place. "

[](https://expedia.ca/Montego-Bay-Hotels-S-Hotel-Jamaica.h31370664.Hotel-Information)

![CocoLaPalm Seaside Resort](https://images.trvl-media.com/lodging/1000000/890000/890000/889919/a21d8ba1_y.jpg)

### CocoLaPalm Seaside Resort

10/10 Excellent

"Clean room, courteous staff, great beach, nice restaurant/bar, a beautiful property and plan to go back next year. "

[](https://expedia.ca/Negril-Hotels-CocoLaPalm-Seaside-Resort.h889919.Hotel-Information)

![The Signature Level At Grand Palladium Lady Hamilton Resort & Spa](https://images.trvl-media.com/lodging/107000000/106250000/106246900/106246829/52810122_y.jpg)

### The Signature Level At Grand Palladium Lady Hamilton Resort & Spa

10/10 Excellent

"Really enjoyed our trip! Service was fantastic, food was very good, and the resort was lovely. Definitely a good time."

[](https://expedia.ca/Lucea-Hotels-The-Signature-Level-At-Grand-Palladium-Lady-Hamilton-Resort-Spa.h106246829.Hotel-Information)

![Princess Senses The Mangrove Resort - Adults Only ](https://images.trvl-media.com/lodging/97000000/96230000/96229200/96229123/9ec5b924_y.jpg)

### Princess Senses The Mangrove Resort - Adults Only 

10/10 Excellent

"Room was spotless, spacious and clean "

[](https://expedia.ca/Green-Island-Hotels-Princess-Senses-The-Mangrove.h96229123.Hotel-Information)

![Hotel Riu Negril - All Inclusive](https://images.trvl-media.com/lodging/2000000/1110000/1103900/1103806/63bdc5bb_y.jpg)

### Hotel Riu Negril - All Inclusive

10/10 Excellent

"Always a great stay"

[](https://expedia.ca/Negril-Hotels-RIU-Negril-All-Inclusive.h1103806.Hotel-Information)

![Country Country](https://images.trvl-media.com/lodging/2000000/1080000/1080000/1079921/2cc02be6_y.jpg)

### Country Country

10/10 Excellent

"Very nice, comfortable clean room and the staff is excellent"

[](https://expedia.ca/Negril-Hotels-Country-Country.h1079921.Hotel-Information)

![Azul Beach Resort Negril, Gourmet All Inclusive by Karisma](https://images.trvl-media.com/lodging/7000000/6580000/6572800/6572748/3328ee79_y.jpg)

### Azul Beach Resort Negril, Gourmet All Inclusive by Karisma

10/10 Excellent

"All was good and the warmth welcome and attention of the staff made it a great and memorable stay "

[](https://expedia.ca/Negril-Hotels-Azul-Beach-Resort-Negril.h6572748.Hotel-Information)

![Toby's Resort](https://images.trvl-media.com/lodging/1000000/930000/922700/922674/a318f317_y.jpg)

### Toby's Resort

10/10 Excellent

"Very. Friendly "

[](https://expedia.ca/Montego-Bay-Hotels-Tobys-Resort.h922674.Hotel-Information)

![Travellers Beach Resort](https://images.trvl-media.com/lodging/2000000/1090000/1089800/1089749/d2eba2ec_y.jpg)

### Travellers Beach Resort

10/10 Excellent

"Yes, the room was spotless and comfy. "

[](https://expedia.ca/Negril-Hotels-Travellers-Beach-Resort.h1089749.Hotel-Information)

## Find out more about Middlesex

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Middlesex. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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## Frequently asked questions

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### What are some of the best vacation rentals that Middlesex has to offer?

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