Title: Middlesex County Vacation Rentals from $29: Search Short-Term Rentals | Expedia.com

[Middlesex County Travel Guide](https://expedia.com/Middlesex-County.dx553248635975177226)[Hotels in Middlesex County](https://expedia.com/Middlesex-County-Hotels.d553248635975177226.Travel-Guide-Hotels)[Flights to Middlesex County](https://expedia.com/Cheap-Flights-To-Middlesex-County.d553248635975177226.Travel-Guide-Flights)[Car Rentals in Middlesex County](https://expedia.com/Car-Rentals-In-Middlesex-County.d553248635975177226.Car-Rental-Guide)[Middlesex County Vacation Packages](https://expedia.com/Middlesex-County.d553248635975177226.Destination-Travel-Guides)

![](https://images.trvl-media.com/place/553248635209673480/780a0162-974c-427e-b049-593f2e948510.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Mike Gauthier

![](https://images.trvl-media.com/place/553248635209673480/780a0162-974c-427e-b049-593f2e948510.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=553248635975177226&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=553248635975177226&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 26 - Jun 28](https://www.expedia.com/Hotel-Search?regionId=553248635975177226&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 24 - Jul 26](https://www.expedia.com/Hotel-Search?regionId=553248635975177226&startDate=2026-07-24&endDate=2026-07-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Middlesex County vacation rentals

![Beach](https://images.trvl-media.com/lodging/122000000/121300000/121290700/121290640/15397253.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![10 outdoor pools](https://images.trvl-media.com/lodging/122000000/121300000/121290700/121290640/f02cd54e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/122000000/121300000/121290700/121290640/e1679965.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining room](https://images.trvl-media.com/lodging/122000000/121300000/121290700/121290640/40d1a0aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Coolshade Villas - Richmond Estate

[](https://www.expedia.com/St-Anns-Bay-Hotels-Coolshade-Villas-Richmond-Estate.h121290640.Hotel-Information)

St. Ann's Bay

$211 nightly

$244 total

Apr 2 - Apr 3

Total with taxes and fees

[](https://www.expedia.com/St-Anns-Bay-Hotels-Coolshade-Villas-Richmond-Estate.h121290640.Hotel-Information)

![Family House, Garden View | Private kitchen | Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109990000/109981200/109981158/138c4d2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family House, Garden View | Living area](https://images.trvl-media.com/lodging/110000000/109990000/109981200/109981158/caef3e00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family House, Garden View | Private kitchen | Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109990000/109981200/109981158/6ed00de2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family House, Garden View | Living area](https://images.trvl-media.com/lodging/110000000/109990000/109981200/109981158/cfe793d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Phoenix Park Villas Portmore

[](https://www.expedia.com/Portmore-Hotels-Phoenix-Park-Villas-Portmore.h109981158.Hotel-Information)

Portmore

9.8/10

Exceptional

(6 reviews)

"I will definitely recommend that you stay here is so peaceful security are strictly on point with everything and the comfort of the home is great will be staying back for sure ."

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

Kimoya

$260 nightly

$300 total

Apr 2 - Apr 3

Total with taxes and fees

[](https://www.expedia.com/Portmore-Hotels-Phoenix-Park-Villas-Portmore.h109981158.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/107000000/106080000/106074600/106074531/a95c9d31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, Kitchen, Courtyard View | Private kitchen](https://images.trvl-media.com/lodging/107000000/106080000/106074600/106074531/7925ab33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/107000000/106080000/106074600/106074531/911349cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, Kitchen, Courtyard View | 2 bedrooms, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/107000000/106080000/106074600/106074531/efdcc75d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Serenity Oasis Apartment 

[](https://www.expedia.com/Spanish-Town-Hotels-Serenity-Oasis-Apartment.h106074531.Hotel-Information)

Spanish Town

$112 nightly

$130 total

Apr 9 - Apr 10

Total with taxes and fees

[](https://www.expedia.com/Spanish-Town-Hotels-Serenity-Oasis-Apartment.h106074531.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/50000000/49030000/49028600/49028580/16b8fd6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Apartment | Individually furnished, blackout drapes, soundproofing](https://images.trvl-media.com/lodging/50000000/49030000/49028600/49028580/babb097e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Apartment | Living area | Flat-screen TV, books](https://images.trvl-media.com/lodging/50000000/49030000/49028600/49028580/16006680.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Apartment, 2 Queen Beds, Pool View | Individually furnished, blackout drapes, soundproofing](https://images.trvl-media.com/lodging/50000000/49030000/49028600/49028580/72c55ac0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Caldo Tours

[](https://www.expedia.com/Ewarton-Hotels-Caldo-Tours.h49028580.Hotel-Information)

Ewarton

10/10

Exceptional

(3 reviews)

"Very inviting and the owner's are wonderful people that keeps you comfortable and satisfied "

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

Stephen

$90 nightly

$100 total

Apr 2 - Apr 3

Total with taxes and fees

[](https://www.expedia.com/Ewarton-Hotels-Caldo-Tours.h49028580.Hotel-Information)

![Comfort Villa, Garden View | Garden view](https://images.trvl-media.com/lodging/126000000/125400000/125390600/125390591/w1195h783x5y0-6d09bbee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free WiFi](https://images.trvl-media.com/lodging/126000000/125400000/125390600/125390591/51d5ead6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Comfort Villa, Garden View | Private kitchen | Electric kettle, toaster](https://images.trvl-media.com/lodging/126000000/125400000/125390600/125390591/w1200h801x0y1-ae94e597.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/126000000/125400000/125390600/125390591/58805be6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa at Richmond Estate

[](https://www.expedia.com/St-Anns-Bay-Hotels-Villa-At-Richmond-Estate.h125390591.Hotel-Information)

St. Ann's Bay

$247 nightly

$285 total

Apr 2 - Apr 3

Total with taxes and fees

[](https://www.expedia.com/St-Anns-Bay-Hotels-Villa-At-Richmond-Estate.h125390591.Hotel-Information)

![2 outdoor pools](https://images.trvl-media.com/lodging/20000000/19110000/19105500/19105425/d4bcfe9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, 2 Bedrooms, Pool Access, Garden View | Living room | 50-inch flat-screen TV with cable channels, TV, DVD player](https://images.trvl-media.com/lodging/20000000/19110000/19105500/19105425/aa5a177a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, 2 Bedrooms, Pool Access, Garden View | In-room dining](https://images.trvl-media.com/lodging/20000000/19110000/19105500/19105425/15ff1fcd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Villa, 3 Bedrooms, Accessible, Hill View | View from room](https://images.trvl-media.com/lodging/20000000/19110000/19105500/19105425/e1aaba74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Country Club Villa I

[](https://www.expedia.com/Kingston-Hotels-The-Country-Club-Villa-I.h19105425.Hotel-Information)

Kingston

9.0/10

Wonderful

(10 reviews)

"The management team was awesome, the AC didn’t work in the main room on the first night but Ms Vicki made sure that I didn’t go a second night without it."

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

Anonymous traveler

$227 nightly

$241 total

Apr 4 - Apr 5

Total with taxes and fees

[](https://www.expedia.com/Kingston-Hotels-The-Country-Club-Villa-I.h19105425.Hotel-Information)

![Family House, 2 Bedrooms, Accessible, Garden View | 2 bedrooms, Egyptian cotton sheets, premium bedding, in-room safe](https://images.trvl-media.com/lodging/14000000/13090000/13081000/13080939/1c5629b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Signature Villa, 2 Bedrooms, Accessible, Garden View | 2 bedrooms, Egyptian cotton sheets, premium bedding, in-room safe](https://images.trvl-media.com/lodging/14000000/13090000/13081000/13080939/5d2e02f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![50-inch flat-screen TV with cable channels, TV, DVD player](https://images.trvl-media.com/lodging/14000000/13090000/13081000/13080939/0fb66e83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/14000000/13090000/13081000/13080939/34ed618c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Casa Victoria Golf Retreat

[](https://www.expedia.com/Kingston-Hotels-Casa-Victoria-Golf-Retreat.h13080939.Hotel-Information)

Kingston

9.8/10

Exceptional

(72 reviews)

"Our stay was very comfortable and relaxing,we didn't stay in but it had all the nesscessary things that we were looking for. I would recommend it to anyone who are travelling with their family to stay there.lovely place,!!"

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

Desmond

$202 nightly

$221 total

Apr 10 - Apr 11

Total with taxes and fees

[](https://www.expedia.com/Kingston-Hotels-Casa-Victoria-Golf-Retreat.h13080939.Hotel-Information)

![House, 2 Bedrooms | Private kitchen | Cookware/dishes/utensils](https://images.trvl-media.com/lodging/101000000/100320000/100313700/100313694/fb27508f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/101000000/100320000/100313700/100313694/e93ab8ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/101000000/100320000/100313700/100313694/79ecd9ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/101000000/100320000/100313700/100313694/5481ccdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Soleil Palm View Villa

[](https://www.expedia.com/St-Anns-Bay-Hotels-Palm-View-Villa.h100313694.Hotel-Information)

St. Ann's Bay

$196 nightly

$226 total

Apr 2 - Apr 3

Total with taxes and fees

[](https://www.expedia.com/St-Anns-Bay-Hotels-Palm-View-Villa.h100313694.Hotel-Information)

![Family Studio, Mountain View | Iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/127000000/126720000/126718500/126718426/a632d3a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Studio, Mountain View | Interior](https://images.trvl-media.com/lodging/127000000/126720000/126718500/126718426/f74ace48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/127000000/126720000/126718500/126718426/35ee7175.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Studio, Mountain View | Property grounds](https://images.trvl-media.com/lodging/127000000/126720000/126718500/126718426/74111966.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Thebreeze22

[](https://www.expedia.com/Tollgate-Clarendon-Park-Hotels-Thebreeze22.h126718426.Hotel-Information)

Tollgate Clarendon Park

$128 nightly

$148 total

Apr 2 - Apr 3

Total with taxes and fees

[](https://www.expedia.com/Tollgate-Clarendon-Park-Hotels-Thebreeze22.h126718426.Hotel-Information)

![Deluxe Room, Courtyard View | Hypo-allergenic bedding, blackout drapes, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/115000000/114540000/114534600/114534523/9c2f3b75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/115000000/114540000/114534600/114534523/2847795d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Studio Suite, Mountain View | Living area | Printers](https://images.trvl-media.com/lodging/115000000/114540000/114534600/114534523/af1809c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/115000000/114540000/114534600/114534523/d1cb3aaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Thebreeze2022

[](https://www.expedia.com/May-Pen-Hotels-Thebreeze2022.h114534523.Hotel-Information)

May Pen

8.0/10

Very Good

(1 review)

"Room was clean and facilitated very well. The host was very pleasant, helpful and entertaining. Efforts to make our stay a good experience was good and greatly appreciated. The biggest issue we had was finding the location of the building and its direction. For a quiet and enjoyable stay, we would strongly recommend the Breeze2022\. "

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

Richard

$51 nightly

$60 total

Apr 5 - Apr 6

Total with taxes and fees

[](https://www.expedia.com/May-Pen-Hotels-Thebreeze2022.h114534523.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/17000000/16780000/16777900/16777889/1cc0d3ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Villa, 3 Bedrooms, 2 Bathrooms, Mountain View | Terrace/patio](https://images.trvl-media.com/lodging/17000000/16780000/16777900/16777889/0879e2ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/17000000/16780000/16777900/16777889/7fa3b774.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private beach nearby, white sand](https://images.trvl-media.com/lodging/17000000/16780000/16777900/16777889/6a671ef6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ocho Rios Getaway Villa at The Palms

[](https://www.expedia.com/Ocho-Rios-Hotels-Ocho-Rios-Getaway-Villa-At-The-Palms.h16777889.Hotel-Information)

Ocho Rios

9.4/10

Exceptional

(8 reviews)

"This is an ideal family oriented gateway. The pool was awesome, the rooms were clean and spacious and the many planted trees and flowers brought ambience to the outdoors. Kevin and Lorraine were very accomodating as well. We experienced few minor issues with the bathroom plumbing and AC units but our overall stay was terrific. We will definitively be back again."

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

Afiya

$338 nightly

$370 total

Apr 6 - Apr 7

Total with taxes and fees

[](https://www.expedia.com/Ocho-Rios-Hotels-Ocho-Rios-Getaway-Villa-At-The-Palms.h16777889.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/101000000/100970000/100965600/100965598/2afaecf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House | 3 bedrooms, blackout drapes, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/101000000/100970000/100965600/100965598/bdc4f030.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property entrance](https://images.trvl-media.com/lodging/101000000/100970000/100965600/100965598/2c0a19bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Porch](https://images.trvl-media.com/lodging/101000000/100970000/100965600/100965598/539b1efc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Soleil Sea Renity

[](https://www.expedia.com/St-Anns-Bay-Hotels-Sea-Renity.h100965598.Hotel-Information)

St. Ann's Bay

10/10

Exceptional

(1 review)

"House was clean and comfy. Lots of tvs but was not able to watch them. I didn’t like the idea that a 3 bedroom was booked, but had to pay for each per beside the rental…. Hidden costs"

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

Jo-Ann

$300 nightly

$346 total

Apr 9 - Apr 10

Total with taxes and fees

[](https://www.expedia.com/St-Anns-Bay-Hotels-Sea-Renity.h100965598.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/15000000/14730000/14728000/14727991/w800h497x0y1-57347c64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/15000000/14730000/14728000/14727991/3923da70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/15000000/14730000/14728000/14727991/cae695a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/15000000/14730000/14728000/14727991/4aa4ff21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ocho Rios Ocean View Villa at The Palms

[](https://www.expedia.com/Montego-Bay-Hotels-Ocho-Rios-Ocean-View-Villa-At-The-Palms.h14727991.Hotel-Information)

St. Ann's Bay

8.6/10

Excellent

(9 reviews)

"Clean, great customer service. Most importantly we felt safe. Would definitely stay again and again!!"

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

Clovette

$334 nightly

$356 total

Apr 2 - Apr 3

Total with taxes and fees

[](https://www.expedia.com/Montego-Bay-Hotels-Ocho-Rios-Ocean-View-Villa-At-The-Palms.h14727991.Hotel-Information)

![Luxury Villa, 3 Bedrooms, Ensuite, Garden View | Egyptian cotton sheets, premium bedding, in-room safe](https://images.trvl-media.com/lodging/24000000/23590000/23588000/23587948/9fbf4a74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Villa, 2 Bedrooms, 2 Bathrooms, Courtyard View | Living area | 50-inch flat-screen TV with cable channels, TV, DVD player](https://images.trvl-media.com/lodging/24000000/23590000/23588000/23587948/cd9aff03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Courtyard](https://images.trvl-media.com/lodging/24000000/23590000/23588000/23587948/f709f427.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Villa, 3 Bedrooms, Ensuite, Garden View | Egyptian cotton sheets, premium bedding, in-room safe](https://images.trvl-media.com/lodging/24000000/23590000/23588000/23587948/f86023a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Casa Princess Ocho Rios Vacation Villa

[](https://www.expedia.com/Montego-Bay-Hotels-Casa-Princess-Ocho-Rios-Vacation-Villa.h23587948.Hotel-Information)

Ocho Rios

9.6/10

Exceptional

(68 reviews)

"Beautiful, safe community and spacious property. Softer pillows would make it excellent"

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

TRUDY ANN

$282 nightly

$299 total

Apr 2 - Apr 3

Total with taxes and fees

[](https://www.expedia.com/Montego-Bay-Hotels-Casa-Princess-Ocho-Rios-Vacation-Villa.h23587948.Hotel-Information)

![6 outdoor pools](https://images.trvl-media.com/lodging/125000000/124220000/124211100/124211069/7d1d7f74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/125000000/124220000/124211100/124211069/c22b0c40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Classic House, 3 Bedrooms | Extra beds](https://images.trvl-media.com/lodging/125000000/124220000/124211100/124211069/4e55f8ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining room](https://images.trvl-media.com/lodging/125000000/124220000/124211100/124211069/40957ab7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Crest - Serenity Oasis Villa

[](https://www.expedia.com/St-Anns-Bay-Hotels-The-Crest-Serenity-Oasis-Villa.h124211069.Hotel-Information)

St. Ann's Bay

8.0/10

Very Good

(1 review)

"Location is beautiful and very secure and safe. The house and pool were lovely as well. "

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

Laura

$415 nightly

$479 total

Apr 2 - Apr 3

Total with taxes and fees

[](https://www.expedia.com/St-Anns-Bay-Hotels-The-Crest-Serenity-Oasis-Villa.h124211069.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/17000000/16790000/16781100/16781092/4ec0c03b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private beach nearby, white sand, free beach cabanas](https://images.trvl-media.com/lodging/17000000/16790000/16781100/16781092/3f188f25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/17000000/16790000/16781100/16781092/71e60eb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/17000000/16790000/16781100/16781092/4149a795.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Oceanic View Apartment at Fern Court

[](https://www.expedia.com/Montego-Bay-Hotels-Oceanic-View-Apartment-At-Fern-Court.h16781092.Hotel-Information)

St. Ann's Bay

9.8/10

Exceptional

(11 reviews)

"Staying at fern court really gave me the island feel. With the garden view and lush colors of the island, it was a lot different from back home. The community is gated which is really nice. The apartment was super comfortable and I really liked the fact that I had a full kitchen. I would definitely stay here again!"

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

Kathy

$281 nightly

$298 total

Apr 2 - Apr 3

Total with taxes and fees

[](https://www.expedia.com/Montego-Bay-Hotels-Oceanic-View-Apartment-At-Fern-Court.h16781092.Hotel-Information)

![10 outdoor pools](https://images.trvl-media.com/lodging/122000000/121290000/121286200/121286187/05bf179f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/122000000/121290000/121286200/121286187/ac3c5921.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining room](https://images.trvl-media.com/lodging/122000000/121290000/121286200/121286187/aaae377b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/122000000/121290000/121286200/121286187/9fc0b322.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Relaxing Stay - Richmond Estate - 15mins Ocho Rios

[](https://www.expedia.com/St-Anns-Bay-Hotels-Relaxing-Apartment-With-Ocean-View.h121286187.Hotel-Information)

St. Ann's Bay

8.0/10

Very Good

(1 review)

"La habitación no es mala esta todo muy descuidado y no funcionan varias cosas "

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

Eucario

$222 nightly

$256 total

Apr 9 - Apr 10

Total with taxes and fees

[](https://www.expedia.com/St-Anns-Bay-Hotels-Relaxing-Apartment-With-Ocean-View.h121286187.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/114000000/113840000/113839400/113839373/f1a998fd.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/114000000/113840000/113839400/113839373/073f3237.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113840000/113839400/113839373/af7f5371.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/114000000/113840000/113839400/113839373/7bbe0b5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 2-bedroom house in Portmore with WiFi, AC

[](https://www.expedia.com/Kingston-Hotels-Charming-2-Bedroom-House-In-Portmore-With-WiFi.h113839373.Hotel-Information)

Portmore

10/10

Exceptional

(7 reviews)

"Room was spotless, very caring host."

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

Sophia

$110 nightly

$110 total

Apr 2 - Apr 3

Total with taxes and fees

[](https://www.expedia.com/Kingston-Hotels-Charming-2-Bedroom-House-In-Portmore-With-WiFi.h113839373.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/22000000/21660000/21651200/21651134/3e6cc2be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/22000000/21660000/21651200/21651134/c4e428ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/22000000/21660000/21651200/21651134/b99f6ff4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player, books, stereo](https://images.trvl-media.com/lodging/22000000/21660000/21651200/21651134/185b9502.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ac'ed 2 bedroom Beach House

[](https://www.expedia.com/Hellshire-Hotels-Aced-2-Bedroom-Beach-House.h21651134.Hotel-Information)

Hellshire

9.2/10

Wonderful

(15 reviews)

"Felt like home."

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

Ashlie G.

$133 nightly

$133 total

Apr 2 - Apr 3

Total with taxes and fees

[](https://www.expedia.com/Hellshire-Hotels-Aced-2-Bedroom-Beach-House.h21651134.Hotel-Information)

![Comfort House | Living area | Flat-screen TV](https://images.trvl-media.com/lodging/100000000/99970000/99964600/99964519/b722aeb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Comfort House | 2 bedrooms, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/100000000/99970000/99964600/99964519/18068f1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Comfort House | 2 bedrooms, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/100000000/99970000/99964600/99964519/460289c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![BBQ/picnic area](https://images.trvl-media.com/lodging/100000000/99970000/99964600/99964519/9e7d6172.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stafford Oasis

[](https://www.expedia.com/Discovery-Bay-Hotels-Stafford-Oasis.h99964519.Hotel-Information)

Ocho Rios

$476 nightly

$539 total

Apr 2 - Apr 3

Total with taxes and fees

[](https://www.expedia.com/Discovery-Bay-Hotels-Stafford-Oasis.h99964519.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

Villas

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Cabins

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Private vacation homes

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Condos

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Aparthotels

[](https://www.expedia.com/Hotel-Search?destination=Middlesex+County%2C+Jamaica&regionId=553248635975177226&latLong=18.128002%2C-77.205589&adults=2&startDate=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&lodging=APART_HOTEL)

Apartments

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Cottages

[](https://www.expedia.com/Hotel-Search?destination=Middlesex+County%2C+Jamaica&regionId=553248635975177226&latLong=18.128002%2C-77.205589&adults=2&startDate=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&lodging=COTTAGE)

Chalets

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Residences

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## Top Middlesex County Hotel Reviews

![Franklyn D. Resort & Spa](https://images.trvl-media.com/lodging/1000000/700000/690700/690644/8762ebfb_y.jpg)

### Franklyn D. Resort & Spa

10/10 Excellent

"The airport shuttle was straightforward and the driver was welcoming. "

[](https://expedia.com/Runaway-Bay-Hotels-Franklyn-D-Resort-Spa-All-Inclusive.h690644.Hotel-Information)

![Couples Tower Isle All Inclusive](https://images.trvl-media.com/lodging/1000000/530000/522100/522057/17fe4790_y.jpg)

### Couples Tower Isle All Inclusive

10/10 Excellent

"The most all inclusive resort we have visited. The watersports and some excursions are included which makes this resort stand out. The services and food are very good. The dinning food was exceptional. The only negatives would be the internet coverage. It was spotty at best. Also, I requested minibar service three times and never received. "

[](https://expedia.com/Montego-Bay-Hotels-Couples-Tower-Isle-All-Inclusive.h522057.Hotel-Information)

![Sea Shell Palms](https://images.trvl-media.com/lodging/58000000/57970000/57966500/57966414/65831c01_y.jpg)

### Sea Shell Palms

4/10 Poor

"The best aspect of this stay was the breakfast because the delivery was punctual, and the portions were suffice. I was not provided with wifi upon entry nor were the instructions placed in the room - had to use data throughout. And lastly, I did not get any housecleaning services. I was told that they offer that service every other day, but my room remained the same way I left it every morning on my way out; I only got towel changed once and I had to request it. "

[](https://expedia.com/Montego-Bay-Hotels-SEA-SHELL-PALMS.h57966414.Hotel-Information)

![Whispering Seas](https://images.trvl-media.com/lodging/10000000/9370000/9362800/9362711/38317c41_y.jpg)

### Whispering Seas

10/10 Excellent

"We thoroughly enjoyed our stay at whispering seas. The place is absolutely beautiful. The view is amazing. Nice air conditioning and fans. Very very cold refrigerator. We had a bit of a hiccup but Melanie was so wonderful and patient and handling the issue. We will be back soon!"

[](https://expedia.com/Montego-Bay-Hotels-Whispering-Seas.h9362711.Hotel-Information)

![Golf View Hotel](https://images.trvl-media.com/lodging/5000000/4670000/4663600/4663541/7d679efd_y.jpg)

### Golf View Hotel

10/10 Excellent

"Cold water in the bathroom faucet wasn’t to nice hot water in the shower close to EVERYTHING!!! The staff was amazing lareasha Jessica I forgot the others names lol if your looking for a quiet stay golf view is the place they have a lounge a lil gift shop a pool but it was to cold to enjoy that part would definitely recommend loved it will be back soon thank you golf view ❤️❤️"

[](https://expedia.com/Mandeville-Hotels-Golf-View-Hotel.h4663541.Hotel-Information)

![The Cardiff Hotel & Spa](https://images.trvl-media.com/lodging/1000000/30000/26700/26635/1b9db82f_y.jpg)

### The Cardiff Hotel & Spa

4/10 Poor

"This hotel was the worst experience. I got food poisoning from the breakfast parti. The room was located right out side of the main road so it was LOUD! The censor in the bathroom kept going out. If you could afford to, stay somewhere else. "

[](https://expedia.com/Montego-Bay-Hotels-The-Cardiff-Hotel-Spa.h26635.Hotel-Information)

![Mandeview Hotel](https://images.trvl-media.com/lodging/11000000/10240000/10238600/10238599/8f4fac6d_y.jpg)

### Mandeview Hotel

4/10 Poor

"Some rooms have no A/C, so be aware. But you may not need it since night temps are cool. My wall outlet was fried where the microwave sat, so microwave. There is steep ramp down to lower housing with a real chance of slipping when wet. I requested a walk strip for that. Come for the view but tamp down other expectations. "

[](https://expedia.com/Mandeville-Hotels-Mandeview-Hotel.h10238599.Hotel-Information)

![Villa Sonate](https://images.trvl-media.com/lodging/5000000/4050000/4046100/4046044/0c71a462_y.jpg)

### Villa Sonate

8/10 Good

"My husband said all the staff were very friendly and polite. The food was "

[](https://expedia.com/Montego-Bay-Hotels-Villa-Sonate.h4046044.Hotel-Information)

![Little Savoy Guest House](https://images.trvl-media.com/lodging/92000000/91330000/91328400/91328381/fbdb002a_y.jpg)

### Little Savoy Guest House

10/10 Excellent

"Lovely jamacian owned ran business The back garden is lovely the pool lovely and the breakfast and staff were wonderful and helpful "

[](https://expedia.com/Runaway-Bay-Hotels-Little-Savoy-Guest-House.h91328381.Hotel-Information)

## Find out more about Middlesex County

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

**Middlesex County vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Middlesex County. 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 County 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 $29 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 County rentals**

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

## Explore a world of travel with Expedia

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- [Vacation Homes in Middlesex County ](https://expedia.com/Middlesex-County-Private-Vacation-Homes.d553248635975177226-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Apartments in Middlesex County ](https://expedia.com/Middlesex-County-Apartments.d553248635975177226-aaApartments.Travel-Guide-Accommodation)
- [Villas in Middlesex County ](https://expedia.com/Middlesex-County-Villas.d553248635975177226-aaVillas.Travel-Guide-Accommodation)
- [Condo Rentals in Middlesex County ](https://expedia.com/Middlesex-County-Condos.d553248635975177226-aaCondos.Travel-Guide-Accommodation)
- [Aparthotels in Middlesex County ](https://expedia.com/Middlesex-County-Apart-Hotels.d553248635975177226-aaApartHotels.Travel-Guide-Accommodation)
- [B&B in Middlesex County ](https://expedia.com/Middlesex-County-Bed-And-Breakfast.d553248635975177226-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Cottages in Middlesex County ](https://expedia.com/Middlesex-County-Cottages.d553248635975177226-aaCottages.Travel-Guide-Accommodation)
- [Guest Houses in Middlesex County ](https://expedia.com/Middlesex-County-Guest-Houses.d553248635975177226-aaGuestHouses.Travel-Guide-Accommodation)
- [Resorts in Middlesex County ](https://expedia.com/Middlesex-County-Resorts.d553248635975177226-aaResorts.Travel-Guide-Accommodation)
- [Residences in Middlesex County ](https://expedia.com/Middlesex-County-Residences.d553248635975177226-aaResidences.Travel-Guide-Accommodation)
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### Expedia's Latest Trends

Hotels

- [Hotels in Montego Bay](https://expedia.com/Montego-Bay-Hotels.d180106.Travel-Guide-Hotels)
- [All-inclusive Resorts in North Coast](https://expedia.com/North-Coast-Hotels-All-Inclusive-Hotel.0-0-d6235803-tAllinclusiveHotel.Travel-Guide-Filter-Hotels)
- [Family Hotels in North Coast](https://expedia.com/North-Coast-Hotels-Family-Hotel.0-0-d6235803-tFamilyHotel.Travel-Guide-Filter-Hotels)
- [Hotels in Ocho Rios](https://expedia.com/Ocho-Rios-Hotels.d553248635209673480.Travel-Guide-Hotels)
- [All-inclusive Resorts in Negril](https://expedia.com/Negril-Hotels-All-Inclusive-Hotel.0-0-d2543-tAllinclusiveHotel.Travel-Guide-Filter-Hotels)
- [All-inclusive Resorts in Ocho Rios](https://expedia.com/Ocho-Rios-Hotels-All-Inclusive-Hotel.0-0-d553248635209673480-tAllinclusiveHotel.Travel-Guide-Filter-Hotels)
- [All-inclusive Resorts in Montego Bay](https://expedia.com/Montego-Bay-Hotels-All-Inclusive-Hotel.0-0-d180106-tAllinclusiveHotel.Travel-Guide-Filter-Hotels)
- [Adults Only Resorts & Hotels in Montego Bay](https://expedia.com/Montego-Bay-Hotels-Adults-Only-Resorts.0-0-d180106-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels)
- [All-inclusive Resorts in Kingston](https://expedia.com/Kingston-Hotels-All-Inclusive-Hotel.0-0-d180034-tAllinclusiveHotel.Travel-Guide-Filter-Hotels)
- [Palladium Hotels in Cornwall County](https://expedia.com/Cornwall-County-Hotels-Palladium.0-0-d553248635975177276--bPalladium.Travel-Guide-Filter-Hotels)
- [Hotels in Kingston](https://expedia.com/Kingston-Hotels.d180034.Travel-Guide-Hotels)
- [Hotels in North Coast](https://expedia.com/North-Coast-Hotels.d6235803.Travel-Guide-Hotels)
- [Hotels in Negril](https://expedia.com/Negril-Hotels.d2543.Travel-Guide-Hotels)
- [Adults Only Resorts & Hotels in Negril](https://expedia.com/Negril-Hotels-Adults-Only-Resorts.0-0-d2543-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels)

Flights

- [Flights to Kingston](https://expedia.com/Cheap-Flights-To-Kingston.d180034.Travel-Guide-Flights)
- [Flights to Surrey County](https://expedia.com/Cheap-Flights-To-Surrey-County.d553248635975177212.Travel-Guide-Flights)
- [Flights to Montego Bay](https://expedia.com/Cheap-Flights-To-Montego-Bay.d180106.Travel-Guide-Flights)
- [Flights to Ocho Rios](https://expedia.com/Cheap-Flights-To-Ocho-Rios.d553248635209673480.Travel-Guide-Flights)

Cars

- [Car rentals in Montego Bay](https://expedia.com/Car-Rentals-In-Montego-Bay.d180106.Car-Rental-Guide)
- [Car rentals in Kingston](https://expedia.com/Car-Rentals-In-Kingston.d180034.Car-Rental-Guide)

Activities

- [Things to do in Ocho Rios](https://expedia.com/Things-To-Do-In-Ocho-Rios.d553248635209673480.Travel-Guide-Activities)
- [Things to do in Kingston](https://expedia.com/Things-To-Do-In-Kingston.d180034.Travel-Guide-Activities)
- [Things to do in Montego Bay](https://expedia.com/Things-To-Do-In-Montego-Bay.d180106.Travel-Guide-Activities)
- [Things to do in Mandeville](https://expedia.com/Things-To-Do-In-Mandeville.d8845.Travel-Guide-Activities)

Packages

- [Montego Bay All Inclusive Vacation Packages](https://expedia.com/lp/theme-vacations/all-inclusive-vacations/180106/Montego-Bay)
- [Montego Bay Vacation](https://expedia.com/Montego-Bay.d180106.Destination-Travel-Guides)
- [Ocho Rios Vacation](https://expedia.com/Ocho-Rios.d553248635209673480.Destination-Travel-Guides)

General

- [Visit Surrey County](https://expedia.com/Surrey-County.dx553248635975177212)
- [Visit Montego Bay](https://expedia.com/Montego-Bay.dx180106)
- [Visit North Coast](https://expedia.com/North-Coast.dx6235803)

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