Fleming Island Cottage Rentals & Holiday Homes

Find the best cottages in Fleming Island - We found 37 exact matches

About Fleming Island Cottage Rentals on PickleTrip

Searching for cottages to rent near Fleming Island? PickleTrip™ features more than 37 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 Fleming Island 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 Fleming Island.

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 37 holiday cottages and places to stay in Fleming Island. 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 Fleming Island Rental Cottages

There are a lot of options in Fleming Island. If you plan on staying in the Fleming Island area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Fleming Island:

The average cost for a cottage rental in Fleming Island is $286 per night. PickleTrip has a wide list of great cottages near Fleming Island 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 Fleming Island that allow you to bring your pet:

See all pet-friendly vacation rentals in Fleming Island on PickleTrip

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Fleming Island to find one that works for you.
As of 2025, the data from PickleTrip shows that there are Over 37 private swimming pools or cottages with indoor pools in the Fleming Island area along with other great amenities.
About 37 cottages in Fleming Island boast of premium hot tubs. Some of the popular places to stay with hot tubs include:See all holiday vacation rentals in Fleming Island on PickleTrip
Yes, there are luxury cottages in Fleming Island. Find more luxury, lakefront, winter, & last-minute cottage rentals near Fleming Island.