A pier with a boat rental sign, a colorful building, and a calm sea.

Long Key cottage rentals

We found 18 cottage rentals — enter your dates for availability

Explore Long Key cottage rentals

Image of Escape to a Charming 2-Bedroom Cottage in Long Key – Your Perfect Getaway!

Escape to a Charming 2-Bedroom Cottage in Long Key – Your Perfect Getaway!

Sleeps 8 · 2 bedrooms · 2 bathrooms

Image of BRING YOUR BOAT! Perfect Florida Keys Family Getaway with Activities Galore!

BRING YOUR BOAT! Perfect Florida Keys Family Getaway with Activities Galore!

Sleeps 10 · 2 bedrooms · 1 bathroom

Image of Middle Florida Keys Bayfront with Sailboat or boat slip included

Premier Host

Middle Florida Keys Bayfront with Sailboat or boat slip included

Sleeps 8 · 2 bedrooms · 1 bathroom

Image of WATERFRONT COTTAGE W/MOTHER IN LAW TREETOP SUITE &SAILBOAT OR BOAT SLIP INCLUDED

WATERFRONT COTTAGE W/MOTHER IN LAW TREETOP SUITE &SAILBOAT OR BOAT SLIP INCLUDED

Sleeps 8 · 4 bedrooms · 1 bathroom

Image of 2BR/1BA Serene Cozy Cottage of Shady Palms in Islamorada With Heated Pool

2BR/1BA Serene Cozy Cottage of Shady Palms in Islamorada With Heated Pool

Sleeps 4 · 2 bedrooms · 1 bathroom

Image of Oceanfront Cottage With Stunning Pool & Dockage in Islamorada

Oceanfront Cottage With Stunning Pool & Dockage in Islamorada

Sleeps 4 · 2 bedrooms · 2 bathrooms

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Enjoy full kitchens, laundry, pools, gardens and more
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