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Our top choices for Caledonia holiday rentals

Serenitys Hideaway Montego Bay

Serenitys Hideaway Montego Bay
3.5 star property
Montego Bay
10.0 out of 10, Exceptional, (1 review)
"Camille and the rest of the team were amazing! They definitely made it an unforgettable experience! Thank you so much"
United States
Adrian Ruiz
The price is £98
includes taxes & fees
20 May - 21 May
Serenitys Hideaway Montego Bay

Hummingbird Room in Guest Home: WiFi, Hot Water AC Montego Bay Live-in Hosts

Hummingbird Room in Guest Home: WiFi, Hot Water AC Montego Bay Live-in Hosts
Mount Salem
10.0 out of 10, Exceptional, (1 review)
"I stayed at Topaz Dream Guesthouse in Montego Bay during Sumfest 2025, and it was such a beautiful and unforgettable experience. The space is cozy, artistic, and full of character, but what truly makes it special is Cherri, the host.Cherri is warm, wise, and simply amazing. She carries the spirit of Jamaica in her heart and has the most incredible stories of life, love, triumph, and resilience. Connecting with her was the true highlight of my trip—our conversations left me feeling inspired and...
United States
English C.
The price is £63
includes taxes & fees
26 May - 27 May
Hummingbird Room in Guest Home: WiFi, Hot Water AC Montego Bay Live-in Hosts

The Artist cabin is a mountain cabin overlooking the sea and coastline

The Artist cabin is a mountain cabin overlooking the sea and coastline
Cave
10.0 out of 10, Exceptional, (1 review)
"We had an amazing stay in the mountains of Jamaica! The food was excellent, and we loved watching the sunset every evening. Terry was wonderful company — he even picked us up in Negril to bring us to the beautiful cabins in the woods. A truly magnificent stay!"
United States
Ana G.
The price is £55
includes taxes & fees
26 May - 27 May
The Artist cabin is a mountain cabin overlooking the sea and coastline

Kimoya's cottage is a mountain cottage overlooking the sea and coastline

Kimoya's cottage is a mountain cottage overlooking the sea and coastline
Cave
9.0 out of 10, Wonderful, (2 reviews)
"Absolutely gorgeous property and views, bird sounds, fantastic food prepared by the friendly hosts. Simple living with wi-fi if needed."
United States
David G.
The price is £63
includes taxes & fees
26 May - 27 May
Kimoya's cottage is a mountain cottage overlooking the sea and coastline

Hospitality Expert SWF104 - Pool, Beach, Chef

Hospitality Expert SWF104 - Pool, Beach, Chef
Montego Bay
10.0 out of 10, Exceptional, (2 reviews)
"Nice place and breakfast"
Spain
Xavier
The price is £171
includes taxes & fees
20 May - 21 May
Hospitality Expert SWF104 - Pool, Beach, Chef

Hospitality Expert CP

Hospitality Expert CP
2.5 star property
Hip Strip
The price is £213
includes taxes & fees
6 Jun - 7 Jun
Hospitality Expert CP

Cozy house in charming Montego Bay with AC, WiFi and all other amenities.

Cozy house in charming Montego Bay with AC, WiFi and all other amenities.
Montego Bay
The price is £103
includes taxes & fees
22 May - 23 May
Cozy house in charming Montego Bay with AC, WiFi and all other amenities.

Impeccable Spacious 3 Bedroom Home Near Beach!

Impeccable Spacious 3 Bedroom Home Near Beach!
Montego Bay
9.0 out of 10, Wonderful, (7 reviews)
"Our stay at this property was pleasant, relaxing and quiet. Host was very responsive and checked in during our stay to make sure all was well. There is a local grocery store and restaurant within walking distance which was a plus. Will definitely stay again!"
United States
Bridgette E.
The price is £122
includes taxes & fees
11 Jun - 12 Jun
Impeccable Spacious 3 Bedroom Home Near Beach!

Unity Villa

Unity Villa
3.0 star property
Montego Bay
8.0 out of 10, Very good, (1 review)
"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
The price is £97
includes taxes & fees
20 May - 21 May
Unity Villa

Quiet relaxing mountainous get away!

Quiet relaxing mountainous get away!
Montego Bay
9.2 out of 10, Wonderful, (5 reviews)
"The location was gorgeous, not far from the city. Easy/beautiful walk to cabs. Host was great and the bed/sheets felt great!!"
United States
Kintoria W.
The price is £77
includes taxes & fees
26 May - 27 May
Quiet relaxing mountainous get away!

Claudeville Condo

Claudeville Condo
3.0 star property
Montego Bay
8.6 out of 10, Excellent, (24 reviews)
"Room was clean and staff was very welcoming with great communication. "
United States
Kenneth
The price is £83
includes taxes & fees
25 May - 26 May
Claudeville Condo

Firefly cottage with Ocean view

Firefly cottage with Ocean view
Cave District
10.0 out of 10, Exceptional, (27 reviews)
"I would recommend this cabin resort to anyone. Geneva was wonderful host, along with her beautiful family"
United States
Rick B.
The price is £62
includes taxes & fees
1 Jun - 2 Jun
Firefly cottage with Ocean view

Luxury ocean view villa

Luxury ocean view villa
Westmoreland
7.6 out of 10, Good, (4 reviews)
"Chef Donna if we could take her home with us we would! Anything that you need Marvette, Marca or Sheldon will get for you! We will definitely be back with a group again! I promise you , you won’t be disappointed!"
United States
Danete G.
The price is £152
includes taxes & fees
26 May - 27 May
Luxury ocean view villa

marshan villa located in the relaxed quite upscale prestigiuos neighrbourhood

marshan villa located in the relaxed quite upscale prestigiuos neighrbourhood
montego bay
The price is £71
includes taxes & fees
26 May - 27 May
marshan villa located in the relaxed quite upscale prestigiuos neighrbourhood

Charming 1-bedroom apartment in gorgeous Montego Bay with AC, WiFi

Charming 1-bedroom apartment in gorgeous Montego Bay with AC, WiFi
Montego Bay
The price is £125
includes taxes & fees
23 May - 24 May
Charming 1-bedroom apartment in gorgeous Montego Bay with AC, WiFi

The Chill Spot - Escape. Relax. Enjoy. Your perfect getaway.

The Chill Spot - Escape. Relax. Enjoy. Your perfect getaway.
Lucea
8.0 out of 10, Very good, (4 reviews)
"We enjoyed ourselves. And our stay was very pleasant."
United States
Cynthia N.
The price is £131
includes taxes & fees
22 May - 23 May
The Chill Spot - Escape. Relax. Enjoy. Your perfect getaway.

Dragon fly Cottage

Dragon fly Cottage
Cave
10.0 out of 10, Exceptional, (7 reviews)
"We had a lot of fun relaxing here. Geneva made excellent breakfast and suppers and we spent the majority of our time relaxing on the deck/hammock reading and hiking around the property and the town of Kentucky. If you want an escape from the tourism scene, this is a nice place to go! "
Canada
Kaili
The price is £65
includes taxes & fees
31 May - 1 Jun
Dragon fly Cottage

Casia Villa

Casia Villa
3.0 star property
Montego Bay
The price is £385
includes taxes & fees
26 May - 27 May
Casia Villa

YanceyLargo Estate - Newly Built Modern 1 Bedroom Suite 1 Villa by RedAwning

YanceyLargo Estate - Newly Built Modern 1 Bedroom Suite 1 Villa by RedAwning
3.0 star property
Montego Bay
10.0 out of 10, Exceptional, (1 review)
The price is £200
includes taxes & fees
18 Jun - 19 Jun
YanceyLargo Estate - Newly Built Modern 1 Bedroom Suite 1 Villa by RedAwning

The Shallhome

The Shallhome
3.0 star property
Montego Bay
The price is £415
includes taxes & fees
20 May - 21 May
The Shallhome
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 Caledonia Hotel Reviews

Find out more about Caledonia

Everything you need to know about Caledonia 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 Caledonia holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 Caledonia holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Caledonia holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Caledonia. 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 Caledonia 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 Caledonia holiday rentals we have selected for you start as low as £79 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Caledonia rentals

At Expedia, we put the best Caledonia 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 Caledonia 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 Caledonia 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 Caledonia. 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 Caledonia?

Yes, there are holiday rentals close to the most popular sights in Caledonia, 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 Caledonia has to offer?

5 bed villa, gated community, private pool, fully staffed, private chauffeur: This holiday home rental outside of Caledonia is located next to a golf course, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What’s there to see and do in Caledonia?

While exploring the area, visit family-friendly sights like Rocklands Bird Sanctuary, or get outside and enjoy nature at Bluefields Beach. YS Falls and Tryall Golf Club are a couple of places you'll find in the wider area.

What’s a holiday rental in Caledonia like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Caledonia. Holiday rentals feature amenities like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about cleanliness, a holiday rental can offer a sense of security away from public hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a family trip or a small group gathering.