Leeward Islands Cottage Rentals & Holiday Homes

Find the best cottages in Leeward Islands - We found 270 exact matches

About Leeward Islands Cottage Rentals on Float Homes

Looking for charming lakeside or dock cottages near Leeward Islands for your next getaway? Float Homes offers more than 270 luxury lakeside and dock cottage and floating home rentals, perfect for your family or group trip. Discover cottages located just a few steps from the water, featuring amenities like hot tubs, kid-friendly accommodations, and easy access to top local attractions. These rentals ensure an exceptional experience on the water, with options that cater to large groups, families, friends, or couples.

Planning a lakeside retreat or a water-based getaway for your group? Float Homes provides a variety of floating home rentals including dock and lakeside cottages, houseboats, floating cabins, and more, connecting you directly with owners to secure the best prices.

Explore 270 lakeside cottages and exceptional water-based accommodations in Leeward Islands with Float Homes. Find unique Airbnb-style and VRBO-style cottages perfect for your weekend escape, spring break, or annual vacation, all within your budget.

Show more
Show less

Frequently Asked Questions About Leeward Islands Rental Cottages

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

The average cost for a cottage rental in Leeward Islands is $322 per night. FloatHomes.com has a wide list of great cottages near Leeward Islands 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 Leeward Islands that allow you to bring your pet:

See all pet-friendly vacation rentals in Leeward Islands on Float Homes

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Leeward Islands to find one that works for you.
As of 2026, the data from Float Homes shows that there are Over 270 private swimming pools or cottages with indoor pools in the Leeward Islands area along with other great amenities.
About 270 cottages in Leeward Islands boast of premium hot tubs. Some of the popular places to stay with hot tubs include:See all holiday vacation rentals in Leeward Islands on Float Homes
Yes, there are luxury cottages in Leeward Islands. Find more luxury, lakefront, winter, & last-minute cottage rentals near Leeward Islands.