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Caledonia Holiday Rentals

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Our top choices for Caledonia holiday rentals

1. 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 NZ$117
includes taxes & fees
27 Aug - 28 Aug
The Artist cabin is a mountain cabin overlooking the sea and coastline

2. 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 NZ$132
includes taxes & fees
30 Aug - 31 Aug
Firefly cottage with Ocean view

3. 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 NZ$139
includes taxes & fees
27 Aug - 28 Aug
Dragon fly Cottage

4. 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 NZ$134
includes taxes & fees
27 Aug - 28 Aug
Kimoya's cottage is a mountain cottage overlooking the sea and coastline

5. Muris Light Sanctuary

Muris Light Sanctuary
Savanalamar
10.0 out of 10, Exceptional, (1 review)
"Host was attentive and super nice to deal with. Great stay. No air conditioning but was pleaaant regardless. "
Canada
Leeann D.
The price is NZ$222
includes taxes & fees
27 Aug - 28 Aug
Muris Light Sanctuary

6. Sky Beach Rooms

Sky Beach Rooms
5.0 star property
Montego Bay
8.0 out of 10, Very good, (4 reviews)
"I recommend them and will book agin"
United States
Ainsley
The price is NZ$181
includes taxes & fees
27 Aug - 28 Aug
Sky Beach Rooms

7. Beautiful 2-bedroom house with AC in peaceful Savanna la mar

Beautiful 2-bedroom house with AC in peaceful Savanna la mar
Savanna la mar
10.0 out of 10, Exceptional, (1 review)
"From the moment I arrived, the property felt very secure, which immediately gave me peace of mind. The space itself was warm, cozy, and inviting it really felt like a home away from home rather than just a place to sleep.The amenities were exactly as advertised and on point. Everything I needed for a comfortable stay was readily available, and the overall setup made it easy to settle in and relax.One of the standout parts of the stay was the communication with the host, Latoya She was excellent,...
United States
Chris R.
The price is NZ$375
includes taxes & fees
29 Aug - 30 Aug
Beautiful 2-bedroom house with AC in peaceful Savanna la mar

8. Villa Giovanni Paris - Beautiful Secured Complex! Fully Gated!

Villa Giovanni Paris - Beautiful Secured Complex! Fully Gated!
Savanna la Mar
The price is NZ$234
includes taxes & fees
27 Aug - 28 Aug
Villa Giovanni Paris - Beautiful Secured Complex! Fully Gated!

9. Charming Seaview Studio with Private Pool & Complimentary Airport Transfer!

Charming Seaview Studio with Private Pool & Complimentary Airport Transfer!
Hopewell
8.8 out of 10, Excellent, (6 reviews)
"Bonnie was amazing and goes over and beyond to make you feel at home. She is very friendly but gives you your space and privacy I really enjoyed her house with the amazing view and her pool. "
United States
Roberta M.
The price is NZ$259
includes taxes & fees
27 Aug - 28 Aug
Charming Seaview Studio with Private Pool & Complimentary Airport Transfer!

10. Turquoise Sea Villa

Turquoise Sea Villa
3.5 star property
Montego Bay
The price is NZ$318
includes taxes & fees
27 Aug - 28 Aug
Turquoise Sea Villa

11. 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 NZ$134
includes taxes & fees
2 Sept - 3 Sept
Hummingbird Room in Guest Home: WiFi, Hot Water AC Montego Bay Live-in Hosts

12. 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 NZ$217
includes taxes & fees
27 Aug - 28 Aug
Unity Villa

13. Serenitys Hideaway Montego Bay

Serenitys Hideaway Montego Bay
3.5 star property
Montego Bay
6.0 out of 10, (4 reviews)
"Very comfortable setting"
United States
dawn Marie
The price is NZ$369
includes taxes & fees
27 Aug - 28 Aug
Serenitys Hideaway Montego Bay

14. 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 NZ$338
includes taxes & fees
27 Aug - 28 Aug
Luxury ocean view villa

15. Unity Villa

Unity Villa
3.0 star property
Montego Bay
5.0 out of 10, (2 reviews)
"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 NZ$155
includes taxes & fees
27 Aug - 28 Aug
Unity Villa

16. Claudeville Condo

Claudeville Condo
3.0 star property
Montego Bay
8.8 out of 10, Excellent, (27 reviews)
"The property was very close to the airport. Bed is comfortable. Only thing is I would av appreciated a kitchen curtain. Apart from that it was great and I love the host she is sweet"
United States
Devine
The price is NZ$186
includes taxes & fees
27 Aug - 28 Aug
Claudeville Condo

17. 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 NZ$350
includes taxes & fees
25 Sept - 26 Sept
Hospitality Expert SWF104 - Pool, Beach, Chef

18. Charming 1-BR solar-equipped villa + pool, gym and backyard sea view in Lucea

Charming 1-BR solar-equipped villa + pool, gym and backyard sea view in Lucea
Lucea
The price is NZ$277
includes taxes & fees
24 Sept - 25 Sept
Charming 1-BR solar-equipped villa + pool, gym and backyard sea view in Lucea

19. Penthouse Suites at Emotions

Penthouse Suites at Emotions
2.5 star property
Montego Bay
The price is NZ$458
includes taxes & fees
31 Aug - 1 Sept
Penthouse Suites at Emotions

20. Seawind F104

Seawind F104
3.5 star property
Montego Bay
6.0 out of 10, (1 review)
"Let me start with the property was very nice including the apartment we stayed in. Very modern and tastefully decorated. Location of this property was perfect as we were visiting family and it was close by. To pay for the cleaning fee prior to check in was a little challenging; when traveling with a cell phone you are unable to pay using the link they provide. We were able to pay cash onsite which helped. I would like to focus on the false advertising of guest laundry, there is no guest laundry...
United States
Rachel
The price is NZ$421
includes taxes & fees
31 Aug - 1 Sept
Seawind F104
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Caledonia holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Caledonia. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Caledonia. Seeing all the best attractions is bound to make you fall in love with Caledonia. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Caledonia short-term rentals, that won’t be hard to do.

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 Bay. YS Falls and Chukka Ocean Outpost at Sandy Bay 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.