Middlesex County Vacation Rentals from NT$2,634: Search Short-Term Rentals

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Our top choices for Middlesex County vacation rentals

A beach with clear water, a sandy shore, and buildings in the background.

1. Fisherman's Point Resort

Ocho Rios

Shawnette

NT$3,094 total

includes taxes & fees

Oct 7 - Oct 8

A resort with a large pool, lush greenery, and a view of the ocean.

2. Sky Castles

Ocho Rios

Rose

NT$5,037 total

includes taxes & fees

Oct 21 - Oct 22

A living room with a sofa, a coffee table, and a TV mounted on the wall. There is a kitchen area in the background with a window and a bar stool.

3. Wave Crest Resort Race Course

Oracabessa

NT$3,896 total

includes taxes & fees

Nov 4 - Nov 5

A balcony with a view of a pool and a building in the background.

4. Caldo Tours

Ewarton

Stephen

NT$4,121 total

includes taxes & fees

Oct 18 - Oct 19

A modern kitchen with a built-in oven, a refrigerator, and a dining area with a table set for four.

5. Phoenix Park Villas Portmore

Portmore

Kimoya

NT$12,497 total

includes taxes & fees

Nov 4 - Nov 5

A pool area with a gazebo, lounge chairs, and a view of the surrounding landscape.

6. Mountain Top Villa

Mandeville

Robert

NT$2,969 total

includes taxes & fees

Oct 7 - Oct 8

A person overlooking a coastal area with a cruise ship, lush greenery, and a swimming pool.

7. Spring Palm Estate

Tower Isle

Shagufta

NT$2,634 total

includes taxes & fees

Oct 8 - Oct 9

A resort with multiple swimming pools, lounge chairs, and umbrellas.

8. North Star Villa

Mammee Bay Estates

PATRICIA

A large swimming pool with a clear view of the ocean in the background, surrounded by resort-style buildings.

9. The Crest - Serenity Oasis Villa

St. Ann's Bay

Laura

NT$14,239 total

includes taxes & fees

Oct 7 - Oct 8

A gated entrance with a central building and two smaller structures on either side.

10. DeJee Lodging

Ocho Rios

Winston

NT$4,087 total

includes taxes & fees

Oct 13 - Oct 14

A resort with a large swimming pool, covered areas, and palm trees.

11. Villa at Richmond Estate

St. Ann's Bay

"This was an absolutely terrible experience, never in my entire life I have been treated like this after spending my money I highly recommend that this person be barred from using this platform for their shady business I was insulted by security guards telling me they are doing me a favor to sort out this woman’s incompetence we weren’t even given a code to enter the house we had to go back to security. The house was musty the sofa was grimy and smelly , not even a bottle of water was in the...

Devon

NT$8,730 total

includes taxes & fees

Oct 7 - Oct 8

A spacious living area with a high ceiling, a ceiling fan, a sofa set, a dining table with chairs, and a TV mounted on the wall.

12. DraxHall Villa

Saint Ann's Bay

Brian

NT$10,676 total

includes taxes & fees

Oct 15 - Oct 16

A lush, green outdoor area with dense foliage and a variety of trees, including palm trees.

13. Xpress Vacations Lifestyle

Ocho Rios

NT$4,909 total

includes taxes & fees

Nov 6 - Nov 7

A bedroom with a bed, dresser, mirror, and curtains.

14. 3 Bedroom Cozy House in Drax Hall

Ocho Rios

"Last minute while at airport I received an email to say that the place reserved was no longer available. After being on the phone for over an hour I was offered another place which was smaller. I had no choice but to take it or me and my kids would have been on the street. Upon entering the place, it was immediately noticed that it was not clean, no light bulbs, 1 tv in one of the bedrooms. Front door did not close properly. Cushions ripped up. I got the impression that the place was on the...

Samantha

NT$10,481 total

includes taxes & fees

Oct 7 - Oct 8

A swimming pool with clear blue water, surrounded by a white fence and palm trees.

15. 1 Bed Villa - Sleeps 2 - Garden - Parking - Wifi

Ocho Rios

Kristin

NT$3,579 total

includes taxes & fees

Oct 7 - Oct 8

16. Coke's Guest House

Mandeville

NT$3,156 total

includes taxes & fees

Oct 17 - Oct 18

17. Cozy 1bed Apartment in Priory Walk to the Beach

St. Ann's Bay

NT$3,692 total

includes taxes & fees

Oct 7 - Oct 8

A living room with a sofa, a coffee table, a TV, and a bookshelf.

18. 1BR Comfort 15 mins Ocho Rios

Richmond Estate

NT$7,664 total

includes taxes & fees

Oct 7 - Oct 8

A modern living room with a white sofa, a glass coffee table, and a staircase leading to an upper level.

19. Tuscany Sun Villa at Legacy Townhouse

Thompson Town

NT$27,437 total

includes taxes & fees

Nov 5 - Nov 6

A two-story house with a yellow exterior and brown roof.

20. Ocho Rios at Coolshade Richmond

St. Ann's Bay

"Lack of communication was terrible Reached at the property, was double booked for multiples family. The host was not answering her phone and was difficult to reach due to lack of wifi access No hot upon reaching, was not mention to guest about turning on hot water system No change of linen No access to masterbed room bathroom for bathing due to broken pipe/facet in bath tub Leakage of water from toilet broken Only was thing,that was excited was the mango tree."

Michelle f

NT$9,123 total

includes taxes & fees

Nov 4 - Nov 5

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Top Middlesex County Hotel Reviews

Couples Tower Isle All Inclusive

10/10 Excellent

"My husband and I had a fantastic time. Couples went above and beyond to make our trip special."

The Cardiff Hotel & Spa

10/10 Excellent

"From the minute of check in staff was very welcoming and accommodating! Room was already cool upon arrival and to my surprise a fridge with beverages! Room was very comfortable with a nice view! Breakfast was not just toast and fruit ~ full menu! Dinner was also very delicious with great prices! Pool was clean and private beach was close! Extended our stay!"

Tiamo Beach Resort and Spa

10/10 Excellent

"TOP TIER Birthday Experience! From the time I booked through Expedia until the moment I departed, my experience at Tiamo Beach Resort was TOP TIER! I spent two nights celebrating my birthday, and I truly felt special in every way. Check in was seamless, I was greeted with a delicious mocktail, and the staff went above and beyond to decorate my room with beautiful Happy Birthday touches. My room was spotless and comfortable, with hot water and a luxurious tub on the balcony overlooking the water. Waking up to that view every morning was everything. The entire resort was extremely clean, the beach was peaceful and relaxing, and the food was absolutely delicious. Breakfast was included with both traditional and Jamaican style options available, and every meal was so flavorful. A very special shoutout to Malik at the front desk, Chef Birch, and Romi, the General Manager. What an incredible team! Your hospitality, kindness, and attention to detail made my birthday celebration unforgettable. Chef Birch prepared amazing meals, Malik made check in effortless, and Romi ensured every part of my stay was exceptional. They even arranged my transportation to Kingston Airport, making my departure completely stress free. Tiamo gave me the perfect reset, relaxation, and self care experience I truly needed. If you're celebrating a birthday, milestone, or any special occasion, Tiamo Beach Resort is the place to be. I can't wait to come back. Thank you Team Tiamo!"

Find out more about Middlesex County

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Check prices for these dates

Our top choices for Middlesex County vacation rentals

1. Fisherman's Point Resort

2. Sky Castles

3. Wave Crest Resort Race Course

4. Caldo Tours

5. Phoenix Park Villas Portmore

6. Mountain Top Villa

7. Spring Palm Estate

8. North Star Villa

9. The Crest - Serenity Oasis Villa

10. DeJee Lodging

11. Villa at Richmond Estate

12. DraxHall Villa

13. Xpress Vacations Lifestyle

14. 3 Bedroom Cozy House in Drax Hall

15. 1 Bed Villa - Sleeps 2 - Garden - Parking - Wifi

16. Coke's Guest House

17. Cozy 1bed Apartment in Priory Walk to the Beach

18. 1BR Comfort 15 mins Ocho Rios

19. Tuscany Sun Villa at Legacy Townhouse

20. Ocho Rios at Coolshade Richmond

Find vacation rentals that suit your style

Top Middlesex County Hotel Reviews

Couples Tower Isle All Inclusive

The Cardiff Hotel & Spa

Villa Sonate

Whispering Seas

JamGolia Place

Tiamo Beach Resort and Spa

Little Savoy Guest House

Jewel Paradise Cove Adult Beach Resort & Spa – All Inclusive

Find out more about Middlesex County

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