Middlesex County Holiday Rentals from NZ$146: Search Short-Term Rentals

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Our top choices for Middlesex County holiday rentals

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

1. Phoenix Park Villas Portmore

Portmore

Kimoya

includes taxes & fees

28 Sept - 29 Sept

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

2. Tuscany Sun Villa at Legacy Townhouse

Thompson Town

includes taxes & fees

28 Sept - 29 Sept

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

3. Caldo Tours

Ewarton

Stephen

includes taxes & fees

28 Sept - 29 Sept

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.

4. Wave Crest Resort Race Course

Oracabessa

includes taxes & fees

28 Oct - 29 Oct

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

5. The Crest - Serenity Oasis Villa

St. Ann's Bay

Laura

includes taxes & fees

28 Sept - 29 Sept

A modern living room with a leather sofa, a coffee table, and a dining area with a table and chairs.

6. Cozy Relaxing Home in Old Harbour

Old Harbour

includes taxes & fees

28 Sept - 29 Sept

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

7. Fisherman's Point Resort

Ocho Rios

Shawnette

includes taxes & fees

29 Sept - 30 Sept

A swimming pool with a gazebo, a clear sky, and a distant view of buildings.

8. Bayfront apartment and villas

Portmore

Kimone

includes taxes & fees

28 Sept - 29 Sept

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Top Middlesex County Hotel Reviews

Couples Tower Isle All Inclusive

10/10 Excellent

"The staff were very friendly. The food was amazing! Pools were clean. Property was kept up. Will return in the future!"

The Garden Hotel Mandeville

10/10 Excellent

"To find this property in the heart of Mandeville was a joy. As the gate open and I was greeted by the security staff the place felt and looked safe. The reception staff were knowledgable and polite which made the information easy to understand. We slept well on our stay but I must mention the breakfast 🇯🇲🇯🇲🇯🇲 authentic mouth watering Jamaican food served with a smile. If you want something else you just simply ask. There were great parking facilities and there was also a buggy to show you around. It was a blessing finding this hotel and we will be returning with the rest of our family. Well done to the owners of this property and your staff has done you proud."

The Cardiff Hotel & Spa

8/10 Good

"The room was nice and breakfast was good. Didn’t use most of the amenities, but I did go to the beach every day I was there. There is supposed to be a shuttle, however it was mostly unavailable. I walked to and from the beach most of my stay which was about 20 mins each way. On one occasion I called for pick up about a hour ahead of time and asked if the driver could pick me up. I was told “I hope so.” The private beach itself is just “okay.” If you’re looking to do any beach activities, this isn’t the hotel for you as they don’t offer any. The bar isn’t really stocked and there’s no bar tender but they do have beer. Overall, I liked the hotel and the unavailability of the beach shuttle was my only complaint."

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

Everything you need to know about Middlesex County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middlesex County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middlesex County holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middlesex County holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middlesex County holiday rentals we have selected for you start as low as NZ$146 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Middlesex County rentals

At Expedia, we put the best Middlesex County holiday 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 holiday.

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.

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Check prices for these dates

Our top choices for Middlesex County holiday rentals

1. Phoenix Park Villas Portmore

2. Tuscany Sun Villa at Legacy Townhouse

3. Caldo Tours

4. Wave Crest Resort Race Course

5. The Crest - Serenity Oasis Villa

6. Cozy Relaxing Home in Old Harbour

7. Fisherman's Point Resort

8. Bayfront apartment and villas

9. SandCastles Deluxe Beach Resort

10. 1BR Comfort 15 mins Ocho Rios

11. Royal Palm Luxury Villas

12. DraxHall Villa with Private Pool

13. PLAN YOUR GETAWAY UNDER THE SUN Dazzle Key Suite

14. Comfy 3BR Villa - Paradisiac Beach Club

15. Blue Berry Hills Villa

16. The Cottage very comfortable, relaxing also secure, 5 minutes walk from beach

17. Bayfront Budget Friendly 2 Bedrooms and 2 Bathrooms Apt in Gated Community

18. 3BR Family Villa at The Crest

19. Sandy Bay Paradise Retreat - 7 Bedrooms

20. Charming 3-bedrooms house in lovely Port Maria with AC, and WiFi and hot water

Find holiday rentals that suit your style

Top Middlesex County Hotel Reviews

Couples Tower Isle All Inclusive

The Garden Hotel Mandeville

GoldenEye

Villa Sonate

Sea Shell Palms

The Cardiff Hotel & Spa

Whispering Seas

Tiamo Beach Resort and Spa

Mandeview Hotel

Find out more about Middlesex County

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