What are the top rated Cottage Rentals in Florida Keys?

There are a lot of options in Florida Keys. If you plan on staying in the Florida Keys area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Florida Keys: <a href="/property/waterfront-fishing-cottage-dockage-walking-distance-to-world-famous-lorelei/HA-321429859" class="class="static-page-link"">WATERFRONT FISHING COTTAGE/DOCKAGE + Walking distance to world famous Lorelei</a> <a href="/property/middle-florida-keys-bayfront-with-sailboat-or-boat-slip-included/HA-321111897" class="class="static-page-link"">Middle Florida Keys Bayfront with Sailboat or boat slip included</a> <a href="/property/2-bedroom-25-boat-dock-waterfront-atlantic-side-privatetiki-dining-bikes/HA-3211633504" class="class="static-page-link"">2 bedroom &amp; 25&#39; Boat Dock ~ Waterfront Atlantic Side &amp; PrivateTiki dining, bikes</a> <a href="/property/tiny-home-in-key-largo-with-private-dock-tiki-hut-and-boat-lift/HA-3212395428" class="class="static-page-link"">Tiny home in Key Largo with Private Dock, Tiki Hut and Boat Lift</a> <a href="/property/heron-suite-vibrant-retreat-hot-tubs-steps-from-duval-street/HA-3214261510" class="class="static-page-link"">Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!</a> <a href="/property/ann-street-tranquility-a-cozy-and-peaceful-cottage/HA-3213023404" class="class="static-page-link"">Ann Street Tranquility: A cozy and peaceful cottage</a> <a href="/property/pelican-suite-cozy-cottage-hot-tubs-close-to-duval/HA-3214261513" class="class="static-page-link"">Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!</a> <a href="/property/tropical-cottage-by-rent-key-west-vacations-quiet-gated-pool-deck-pet-frien/HA-3214047861" class="class="static-page-link"">TROPICAL COTTAGE by RENT KEY WEST VACATIONS - Quiet &amp; gated. Pool/Deck/Pet frien</a> <a href="/property/charming-bayfront-cottage-in-heart-of-islamorada-with-pool-dockage-beach-kayaks-more/HA-3214718161" class="class="static-page-link"">Charming Bayfront Cottage in Heart of Islamorada with Pool, Dockage, Beach, Kayaks &amp; More</a> <a href="/property/private-cottage-on-bayfront-estate-with-pool-beach-dockage-kayaks-and-more/HA-3214718162" class="class="static-page-link"">Private Cottage on Bayfront Estate with Pool, Beach, Dockage, Kayaks and More</a>

How much does it cost to rent a cottage in Florida Keys?

The average cost for a cottage rental in Florida Keys is $441 per night. 360vacationrentals has a wide list of great cottages near Florida Keys that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Florida Keys that allow pets?

Yes, here are the top cottage rentals in Florida Keys that allow you to bring your pet: "Tranquility " At Ann Street Gardens Steps From Duval Pilar Cottage - Harbor Walk Hideaways Atlantic Paradise by Avantstay Great Location w/Balcony, Outdoor Dining & Shared Pool & Hot Tub! Private Oceanfront Cottage with dockage, pool just minutes to Key West! <a href="/all/usa/florida/florida-keys" class="class="static-page-link"">See all pet-friendly vacation rentals in Florida Keys on 360vacationrentals</a>

Do you have any rental cottages in Florida Keys that are suitable for families?

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Florida Keys to find one that works for you.

Are there quality cottages in Florida Keys that have indoor swimming pools?

As of 2026, the data from 360vacationrentals shows that there are Over 316 private swimming pools or cottages with indoor pools in the Florida Keys area along with other great amenities.

Florida Keys Cottage Rentals By Owner

"Tranquility " At Ann Street Gardens Steps From Duval

From US $1,243

10.0 (80 Reviews)

Cottage

"Tranquility " At Ann Street Gardens Steps From Duval

Air Conditioner
Pool
TV

Florida Keys Cottage Rentals & Holiday Homes

Find the best cottages in Florida Keys - We found 316 exact matches

When do you want to travel?