Middlesex County Vacation Rentals from $93: Search Short-Term Rentals

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Our top choices for Middlesex County vacation rentals

Family House, Garden View | Private kitchen | Full-size fridge, microwave, oven, stovetop

Phoenix Park Villas Portmore

Portmore

Kimoya

$277 nightly

Jul 10 - Jul 11

Total with taxes and fees

Opulenz DraxHall

St. Ann's Bay

$4,727 nightly

Aug 8 - Aug 9

Total with taxes and fees

Serenity Oasis Apartment

Spanish Town

$102 nightly

Aug 8 - Aug 9

Total with taxes and fees

Richmond Villa Rental Management

Ocho Rios

Lucien

$554 nightly

Aug 8 - Aug 9

Total with taxes and fees

The Crest - Serenity Oasis Villa

St. Ann's Bay

Laura

$367 nightly

Jul 15 - Jul 16

Total with taxes and fees

Deluxe Double Room, Garden View | Living area

Tuscany Sun Villa at Legacy Townhouse

Thompson Town

$728 nightly

Aug 8 - Aug 9

Total with taxes and fees

Coolshade Villas - Richmond Estate

St. Ann's Bay

Robert

$196 nightly

Jul 9 - Jul 10

Total with taxes and fees

Villa at The Palms

St. Ann's Bay

"This was our first time traveling as a family internationally. I believe the property I booked was different from the property I checked into. The villa we were assigned to was on the Crest lot and not Villa at the Palms. The villa was clean and bright. There was a pool close to the property's entrance along with an open gym. Our overall experience was pleasant and I would probably stay again in the future."

Regina

$245 nightly

Jul 9 - Jul 10

Total with taxes and fees

Luxury Penthouse, Ocean View, Oceanfront | Terrace/patio

Blue-sky penthouse

Tower Isle

Tammy

$370 nightly

Jul 9 - Jul 10

Total with taxes and fees

Cozy Relaxing Home in Old Harbour

Old Harbour

$11,889 nightly

Aug 8 - Aug 9

Total with taxes and fees

Relaxing Stay - Richmond Estate - 15mins Ocho Rios

St. Ann's Bay

Sildarius

$211 nightly

Jul 10 - Jul 11

Total with taxes and fees

Ocho Rios Getaway Villa at The Palms

Ocho Rios

travis jerome

$596 nightly

Jul 15 - Jul 16

Total with taxes and fees

3 Bedroom Cozy House in Drax Hall

Ocho Rios

$316 nightly

Jul 15 - Jul 16

Total with taxes and fees

Spring Palm Estate

Tower Isle

Shagufta

$93 nightly

Jul 9 - Jul 10

Total with taxes and fees

Mountain Top Villa

Mandeville

Anonymous traveler

$84 nightly

Jul 9 - Jul 10

Total with taxes and fees

Coolshade Villa at Richmond

St. Ann's Bay

$294 nightly

Aug 5 - Aug 6

Total with taxes and fees

Blue Berry Hills Villa

Dumbarton

$867 nightly

Jul 9 - Jul 10

Total with taxes and fees

Luxury Oceanfront Villa Fully Staffed

Tower Isle

$1,546 nightly

Aug 8 - Aug 9

Total with taxes and fees

3 Bedroom Beachfront Cozy House

Tower Isle

$678 nightly

Aug 8 - Aug 9

Total with taxes and fees

Family House, 2 Bedrooms, 2 Bathrooms, Beach View | 2 bedrooms, Egyptian cotton sheets, premium bedding, blackout drapes

The Beach Estate Country Club Villa

Hellshire

Anonymous traveler

$412 nightly

Jul 10 - Jul 11

Total with taxes and fees

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Top Middlesex County Hotel Reviews

Bahia Principe Escape Runaway Bay - All Inclusive

8/10 Good

"The staff was extremely helpful and curtious, they try their utmost best to ensure that we are happy and comfortable, we like that."

The Cardiff Hotel & Spa

10/10 Excellent

"This resort serves as a training facility for students in the hospitality industry and what a fantastic job! The staff was amazing, always willing to go the extra mile to ensure you are comfortable. A hearty Jamaican cuisine is served for breakfast. The pastries are fantastic! Not overly sweet and extremely tasty. The pool is clean and well maintained. However, the rooms are a bit dated and there is no entertainment. If you expect a high-end international experience this may not be your best option, but if you’re interested in experiencing an authentic Jamaican interaction, consider visiting. It’s always heartwarming to know that I am able to contribute to the advancement of the Jamaican community and get such a positive experience in return. A win win situation! In general, it was a good experience and I intend to return."

GoldenEye

10/10 Excellent

"A Perfect Oasis in Jamaica—I Did Not Want to Leave! This hotel is a perfect oasis in Jamaica and easily one of the best properties I have ever visited. Exquisite Estate & One-of-a-Kind Service From the absolute moment you arrive, the hospitality is unmatched. The staff have a magical way of making you feel like you are the only people on the property. Between the world-class service, the top-tier amenities, and the breathtaking grounds, this estate is truly one of a kind. Endless Activities & Wildlife You could never get bored here. The resort features two pristine beaches and three gorgeous pools to choose from. For activities, we loved the complimentary snorkeling, paddleboarding, and kayaking right off the shore. A unique highlight was the on-site turtle sanctuary, where we were lucky enough to spot turtles up close—an unforgettable experience. Magnificent Spa & Dining When it's time to unwind, the spa is magnificent and offers a world-class relaxation experience. The culinary side of the resort is just as impressive, with great choices for food and drinks that kept us spoiled for options every single day. If you are looking for an ultra-luxury Jamaican getaway with flawless service and endless activities, look no further. This place is paradise!"

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 $93 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.

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Our top choices for Middlesex County vacation rentals

Phoenix Park Villas Portmore

Opulenz DraxHall

Serenity Oasis Apartment

Richmond Villa Rental Management

The Crest - Serenity Oasis Villa

Tuscany Sun Villa at Legacy Townhouse

Coolshade Villas - Richmond Estate

Villa at The Palms

Blue-sky penthouse

Cozy Relaxing Home in Old Harbour

Relaxing Stay - Richmond Estate - 15mins Ocho Rios

Ocho Rios Getaway Villa at The Palms

3 Bedroom Cozy House in Drax Hall

Spring Palm Estate

Mountain Top Villa

Coolshade Villa at Richmond

Blue Berry Hills Villa

Luxury Oceanfront Villa Fully Staffed

3 Bedroom Beachfront Cozy House

The Beach Estate Country Club Villa

Find vacation rentals that suit your style

Top Middlesex County Hotel Reviews

Bahia Principe Escape Runaway Bay - All Inclusive

Sea Shell Palms

Franklyn D. Resort & Spa

Couples Tower Isle All Inclusive

The Cardiff Hotel & Spa

GoldenEye

Whispering Seas

The Garden Hotel Mandeville

Golf View Hotel

Find out more about Middlesex County

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