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Caledonia Vacation Rentals

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Caledonia vacation rentals

Beach

1. Awesome 1-bedroom apartment with AC in Montego Bay

Awesome 1-bedroom apartment with AC in Montego Bay
Montego Bay
10.0 out of 10, Exceptional, (2 reviews)
"Great host, great amenities on the property."
United States
Nancy B.
$148 nightly
The price is $149
Sep 19 - Sep 20
Total with taxes and fees
Awesome 1-bedroom apartment with AC in Montego Bay
Smart TV

2. Modern 1BR Getaway near Beaches, Airport, and popular entertainment spots.

Modern 1BR Getaway near Beaches, Airport, and popular entertainment spots.
Montego Bay
$244 nightly
The price is $244
Aug 25 - Aug 26
Total with taxes and fees
Modern 1BR Getaway near Beaches, Airport, and popular entertainment spots.
Exterior

3. Entire townhouse in Montego Bay, Jamaica

Entire townhouse in Montego Bay, Jamaica
Montego Bay
$251 nightly
The price is $269
Aug 24 - Aug 25
Total with taxes and fees
Entire townhouse in Montego Bay, Jamaica
Deluxe Suite, Pool View | Pool | 2 outdoor pools

4. Penthouse Suites at Emotions

Penthouse Suites at Emotions
2.5 star property
Montego Bay
$237 nightly
The price is $274
Aug 24 - Aug 25
Total with taxes and fees
Penthouse Suites at Emotions
House | Beach

5. 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
$203 nightly
The price is $235
Aug 25 - Aug 26
Total with taxes and fees
Seawind F104
Exterior detail

6. MAJORVILLA@WEST VILLAGE_Cozy 1-bedroom apartment in adorable Montego Bay with AC

MAJORVILLA@WEST VILLAGE_Cozy 1-bedroom apartment in adorable Montego Bay with AC
Montego bay
$116 nightly
The price is $116
Aug 24 - Aug 25
Total with taxes and fees
MAJORVILLA@WEST VILLAGE_Cozy 1-bedroom apartment in adorable Montego Bay with AC
Beach

7. Seawind E202

Seawind E202
2.0 star property
Montego Bay
$203 nightly
The price is $234
Aug 30 - Aug 31
Total with taxes and fees
Seawind E202
Property grounds

8. 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.
$70 nightly
The price is $70
Aug 24 - Aug 25
Total with taxes and fees
The Artist cabin is a mountain cabin overlooking the sea and coastline
Property grounds

9. 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
$83 nightly
The price is $83
Aug 24 - Aug 25
Total with taxes and fees
Dragon fly Cottage
Outdoor dining

10. 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.
$79 nightly
The price is $79
Aug 28 - Aug 29
Total with taxes and fees
Firefly cottage with Ocean view
Property grounds

11. 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.
$133 nightly
The price is $133
Aug 24 - Aug 25
Total with taxes and fees
Muris Light Sanctuary
1 bedroom, WiFi, bed sheets

12. 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.
$80 nightly
The price is $80
Aug 24 - Aug 25
Total with taxes and fees
Kimoya's cottage is a mountain cottage overlooking the sea and coastline
Terrace/patio

13. Serene 1-bedroom apartment in Montego Bay perfect for relaxing stays

Serene 1-bedroom apartment in Montego Bay perfect for relaxing stays
Montego Bay
$2,886 nightly
The price is $2,886
Aug 24 - Aug 25
Total with taxes and fees
Serene 1-bedroom apartment in Montego Bay perfect for relaxing stays
Living area

14. 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.
$80 nightly
The price is $80
Aug 30 - Aug 31
Total with taxes and fees
Hummingbird Room in Guest Home: WiFi, Hot Water AC Montego Bay Live-in Hosts
Rafting

15. 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
$189 nightly
The price is $218
Aug 24 - Aug 25
Total with taxes and fees
Serenitys Hideaway Montego Bay
Restaurant

16. 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
$97 nightly
The price is $108
Aug 24 - Aug 25
Total with taxes and fees
Sky Beach Rooms
Outdoor pool, sun loungers

17. Turquoise Sea Villa

Turquoise Sea Villa
3.5 star property
Montego Bay
$176 nightly
The price is $188
Aug 24 - Aug 25
Total with taxes and fees
Turquoise Sea Villa
Basic Loft | View from room

18. 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
$96 nightly
The price is $111
Aug 24 - Aug 25
Total with taxes and fees
Claudeville Condo
Outdoor pool

19. 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.
$155 nightly
The price is $155
Aug 24 - Aug 25
Total with taxes and fees
Charming Seaview Studio with Private Pool & Complimentary Airport Transfer!
Outdoor dining

20. Come on Home to Paradise, Your Montego Bay Escape.

Come on Home to Paradise, Your Montego Bay Escape.
Paradise Acres
10.0 out of 10, Exceptional, (1 review)
"Beautiful property in a great location! Everything was spotless, comfortable, and exactly as described. The host was incredibly welcoming, responsive, and made our stay effortless. We had a fantastic experience and would happily stay here again. Highly recommend!"
United States
Dionna
$160 nightly
The price is $181
Aug 24 - Aug 25
Total with taxes and fees
Come on Home to Paradise, Your Montego Bay Escape.
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

Hotel 39 Jamaica

Hotel 39 Jamaica

10/10 Excellent
"Convenient location. Clean hotel, will certainly return"
Dominique 2-night trip
Posted less than an hour ago
Hotel 39 Jamaica

Find out more about Caledonia

Everything you need to know about Caledonia 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 Caledonia 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 Caledonia vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Caledonia vacation 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 low season months. For more hustle and bustle, you may prefer to visit Caledonia 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 Caledonia rentals

At Expedia, we put the best Caledonia 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 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 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 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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Caledonia?

Yes, we give you a choice of vacation rentals close to top sights in Caledonia, or you can select a more secluded option if you're looking for relaxation.

What's the top vacation rental in Caledonia?

5 bed villa, gated community, private pool, fully staffed, private chauffeur: Visitors like this Caledonia vacation home rental. It is located next to a golf course and has an outdoor pool, a balcony, and a barbecue grill 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 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 Freeport Peninsula are a couple of places you'll find in the larger area.

What’s a vacation rental in Caledonia like?

A vacation rental is a private property you can book for a few weeks or just a few days in Caledonia. Vacation rentals feature extras like laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a clean environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for small groups.