1. Jamaica
  2. Cottage Rentals

Jamaica Cottage Rentals & Holiday Homes

Find the best cottages in Jamaica - We found 185 exact matches

About Jamaica Cottage Rentals on PickleTrip

Searching for cottages to rent near Jamaica? PickleTrip™ features more than 185 cottages that are perfect for your next pickleball getaway. Plan your ultimate holiday and discover luxury cottage rentals that are a few miles away from the lake or beach and have access to private courts or nearby facilities. These cottage rentals in Jamaica have hot baths, are kid-friendly & family-friendly, and are near top local attraction spots, to give guests the best travel experience they could ever wish for. PickleTrip™’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Jamaica.

Are you planning to travel to the lakeside, beach, or mountain area? PickleTrip™’s cottage rentals offers a wide selection, giving you direct access to the owners of these cottage rentals, and offering you the best opportunity to find a good price.

PickleTrip™ boasts of 185 holiday cottages and places to stay in Jamaica. The site provides unique Airbnb, VRBO, pickleball-ready cottages to fit your trip or get away with your friends and family. This can be a weekend getaway, spring break, summer vacation, or annual holiday — all fitting within your budget.

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Frequently Asked Questions About Jamaica Rental Cottages

The average cost for a cottage rental in Jamaica is $234 per night. PickleTrip has a wide list of great cottages near Jamaica that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Yes, here are the top cottage rentals in Jamaica that allow you to bring your pet:

See all pet-friendly vacation rentals in Jamaica on PickleTrip

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Jamaica to find one that works for you.
As of 2025, the data from PickleTrip shows that there are Over 185 private swimming pools or cottages with indoor pools in the Jamaica area along with other great amenities.
About 185 cottages in Jamaica boast of premium hot tubs. Some of the popular places to stay with hot tubs include:See all holiday vacation rentals in Jamaica on PickleTrip
Yes, there are luxury cottages in Jamaica. Find more luxury, lakefront, winter, & last-minute cottage rentals near Jamaica.