Content Holiday Rentals

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Our top choices for Content holiday rentals

Unity Villa

Unity Villa
3.0 star property
Montego Bay
8.0 out of 10, Very good, (1)
"I like that the property was quiet. The place was clean. The neighbor I met was really nice. I like that. It was outside of the tourist area."
United States
Fashira
The price is AU$139
includes taxes & fees
8 Jan - 9 Jan 2026
Unity Villa

Unity Villa

Unity Villa
3.0 star property
Montego Bay
8.0 out of 10, Very good, (1)
"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
Susan
Unity Villa

Villa Serene Jewel of Black River 4 bedroom 5bathrooms

Villa Serene Jewel of Black River 4 bedroom 5bathrooms
Black River
9.6 out of 10, Exceptional, (11)
"The pictures do not give this Villa justice, it is beautiful! We had an amazing time there! We were looking for rest and relaxation and that is exactly what we got!! Shamoir the cook was incredible! Sheryl was quick to respond to any questions we had! We will definitely go back!"
United States
diana s.
Villa Serene Jewel of Black River 4 bedroom 5bathrooms

Turquoise Sea Villa

Turquoise Sea Villa
3.5 star property
Montego Bay
The price is AU$3,878
includes taxes & fees
16 Jan - 17 Jan 2026
Turquoise Sea Villa

Sativa cottages

Sativa cottages
2.0 star property
Little London
Sativa cottages

Sky Beach Rooms

Sky Beach Rooms
5.0 star property
Montego Bay
2.0 out of 10, (1)
"The room was very clean, however the rooms are located in a very local shopping mall with lots of loitering outside, very noisy, no windows so felt claustrophobic. The outside was dirty , crowded and noisy I did not feel safe enough to stay there so I left."
United States
chevone
The price is AU$180
includes taxes & fees
17 Dec - 18 Dec
Sky Beach Rooms

Clarridge Hall Guesthouse

Clarridge Hall Guesthouse
3.0 star property
Montego Bay
7.4 out of 10, Good, (3)
"Up in the mountains. Hard to get to but once there, its a hidden gem. Very cozy and quiet. Rooms are beautiful. Feels loke home. The pool is beautiful and the view is lovely. "
United States
Tamar
Clarridge Hall Guesthouse

Luxury Fully Staffed 5 Bedroom Ocean View Villa with Infinity Pool

Luxury Fully Staffed 5 Bedroom Ocean View Villa with Infinity Pool
Montego Bay
10.0 out of 10, Exceptional, (74)
"We were a group of 12 with 8 adults and 4 children between 12 and 6 years old. The kids had an amazing time in the pool. The food was amazing and the staff felt like family. We would go back in a heartbeat!"
United States
Misgana T.
Luxury Fully Staffed 5 Bedroom Ocean View Villa with Infinity Pool

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

Free Airport pick-up. private villa with amazing ocean veiw, pool, and maid.
Montego Bay
10.0 out of 10, Exceptional, (63)
"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
Jeff B.
The price is AU$497
includes taxes & fees
18 Dec - 19 Dec
Free Airport pick-up. private villa with amazing ocean veiw, pool, and maid.

Cannabis friendly B&B at Hayley's Paradise.

Cannabis friendly B&B at Hayley's Paradise.
Little Bay
Cannabis friendly B&B at Hayley's Paradise.

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

Free Transportation. Private Villa. Amazing Ocean View, Pool, And housekeeper.
roundhill
9.8 out of 10, Exceptional, (19)
"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
Sarah H.
The price is AU$497
includes taxes & fees
17 Dec - 18 Dec
Free Transportation. Private Villa. Amazing Ocean View, Pool, And housekeeper.

Lovely 2-bedroom Townhouse

Lovely 2-bedroom Townhouse
Savanna la Mar
10.0 out of 10, Exceptional, (2)
"Enjoyed the stay."
United States
Henry
Lovely 2-bedroom Townhouse

Cozy Escape Negril

Cozy Escape Negril
Negril
10.0 out of 10, Exceptional, (2)
"I loved it here... it had everything we needed and I would stay here again!!"
United States
Christina H.
Cozy Escape Negril

Silent Waters Villa

Silent Waters Villa
5.0 star property
Montego Bay
8.0 out of 10, Very good, (1)
"The only concern I had was failure to follow the allergy list for meals."
United States
April
Silent Waters Villa

Blue Seas Two Unity Hall

Blue Seas Two Unity Hall
3.0 star property
Montego Bay
Blue Seas Two Unity Hall

Allamanda Villa- Tryall Resort Membership- van/driver- nanny

Allamanda Villa- Tryall Resort Membership- van/driver- nanny
Montego Bay,
10.0 out of 10, Exceptional, (47)
"Allamanda is a truly special place. We are repeat guests and love it more each time. The staff is amazing and we were so well cared for. Tryall Club was beautiful, both the beach, pool and grill, and an easy drive from the villa. We will be back! "
United States
Kristen I.
Allamanda Villa- Tryall Resort Membership- van/driver- nanny

Great panoramic views. Beach and shopping close by.

Great panoramic views. Beach and shopping close by.
Montego Bay
10.0 out of 10, Exceptional, (1)
"It was a beautiful home and convenient to the airport. The host was also very responsive and understanding . I appreciate her hospitality and kindness. I would def recommend this place and would stay again."
United States
Shannon S.
The price is AU$168
includes taxes & fees
20 Dec - 21 Dec
Great panoramic views. Beach and shopping close by.

Award-winning villa with private beachfront and pool

Award-winning villa with private beachfront and pool
Culloden White House
10.0 out of 10, Exceptional, (1)
"Just what the family needed. This will be an annual experience. "
United States
Andrew R.
Award-winning villa with private beachfront and pool

10BR Luxury Villa w/ Private Beach , Fully Staffed w/ Chef - STSHA

10BR Luxury Villa w/ Private Beach , Fully Staffed w/ Chef - STSHA
Sandy Ground
10.0 out of 10, Exceptional, (1)
"Perfect for our team of 18! Everyone enjoyed the food, the staff, the ambience. It was great to have our own privacy to bond as a team. Everything was immaculate! Minor problems- The internet connectivity was slow or didn't work, and the power tripped out 1-2 times per day, however, speedily restored by our butler."
United States
Anna L.
10BR Luxury Villa w/ Private Beach , Fully Staffed w/ Chef - STSHA

Deano's Cottages

Deano's Cottages
3.0 star property
Black River
6.8 out of 10, (5)
"Very quiet, felt very safe "
United States
Derrick
Deano's Cottages
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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Top Content Hotel Reviews

Find out more about Content

Everything you need to know about Content 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 Content 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 Content holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Content holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Content. 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Content 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 Content holiday rentals we have selected for you start as low as AU$139 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Content rentals

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

Frequently asked questions

Can I find holiday rentals in Content?

Yes, there are holiday rentals close to the most popular sights in Content, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Content has to offer?

Cannabis friendly B&B at Hayley's Paradise.: This holiday home rental outside of Content offers a balcony, a selection of games and air conditioning to help you feel perfectly comfortable in your new surroundings.

How many holiday rentals are there in Content?

With 61 Expedia holiday rentals, you're guaranteed to find just the right place for your Content stay.

What can I see and do in Content?

While you're exploring the area, Bluefields Beach and YS Falls are a couple of picturesque spots to get outside and enjoy nature. In the wider area, you’ll find Bubbling Spring Mineral Bath and Bluefields Bay.

What are holiday rentals like in Content?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Content. Holiday rentals feature amenities such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from shared hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a popular option for family trips.