274 Properties in Islamorada, Florida, United States of America. May 16, 2026 through May 17, 2026

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Stays within a 15-minute walk to the beach

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Hurricane Monument

Bud n' Mary's Dive Center

Theater of the Sea

History of Diving Museum

Founders Park

Anne's Beach

Windley Key Fossil Reef Geological State Park

Fiesta Key

Matecumbe United Methodist Church

Sunset Drive Beach

Florida Keys Brewing Co.

Islamorada County Park

Indian Key Historic State Park

Islamorada Brewery & Distillery

Keys History & Discovery Center

Robbie’s of Islamorada

beach near Islamorada

Hog Heaven

Rain Barrel Village

Lorelei Restaurant & Cabana Bar

Neighborhood

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Islamorada

Lower Matecumbe Beach

Venetian Shores

Seabreeze Trailer Park

Matecumbe

Property brand

CR Managers LLC

Vacasa

TravelStaytion

Equity Lifestyle

Hampton Inn

CoralTree Hospitality

Ocean Properties Hotels Resorts & Affiliate

Trademark

Great Ocean Condos and Homes

Autograph Collection Hotels & Resorts

Lodgable

eviivo NORAM

Curio Collection

InnRoad

Fairfield Inn and Suites

Key West Inns

Holiday Inn

Courtyard

Tribute Portfolio

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Museums

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Winter activities

Enjoy the season with activities like ice skating, snowmobiling, or sledding.

Scuba diving or snorkeling

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Shopping

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Casino

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274 properties

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A thatched-roof hut surrounded by lush greenery and vibrant red flowers.

A beach with palm trees, a dock, and a boat named "STYX".

The Pelican Key Largo Cottages

On the beach

Fully refundable

9.09.0 out of 10

Wonderfulwonderful

1,010 reviews(1,010 reviews)

$32 off

$115 nightly

The current price is $129 total

$129 total

Total with taxes and fees

We have 2 left at this price

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A kitchen with a microwave, coffee maker, and a TV on the wall. There's a window with a view of a thatched-roof structure.

A beach with thatched umbrellas, wooden chairs, and a wooden pier extending into the water.

Sunset Cove Beach Resort

On the beach

Breakfast included

9.29.2 out of 10

Wonderfulwonderful

1,012 reviews(1,012 reviews)

$15 off

$117 nightly

The current price is $132 total

$132 total

Total with taxes and fees

We have 1 left at this price

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A kitchen with white cabinets, a sink, a stove, and a window overlooking a deck.

A beach hut with a thatched roof, surrounded by lounge chairs and a picnic table, overlooking a calm sea.

Rock Reef Resort

On the beach

Pool

9.29.2 out of 10

Wonderfulwonderful

1,171 reviews(1,171 reviews)

$50 off

$134 nightly

The current price is $151 total

$151 total

Total with taxes and fees

We have 1 left at this price

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Photo gallery for The Pelican Key Largo Cottages

The Pelican Key Largo Cottages

Photo gallery for Sunset Cove Beach Resort

Sunset Cove Beach Resort

Photo gallery for Rock Reef Resort

Rock Reef Resort