Chalet Rentals in Florida Keys from 1199 CAD/night in 02 2026

861-880 out of 1062

Located less than 10 minutes' walk from American Outdoors, the beachfront Sea Haven 4 Bedroom Home With Resort Privileges Key Largo is at a 3.3 km distance from YMCA Park.

FromC$ 1 630 /nightSelect

Two J'S ParadiseHoliday home

10.0

Perfect1 total review

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The Two J'S Paradise Key Largo is only 5 minutes' walk from Benwood wreck and has a quick access to Shell Man.

FromC$ 568 /nightSelect

The Ebberly House - Amazing Pool In Gated CommunityHoliday home

Featuring a sunny patio along with 6 bedrooms, this villa is set 1.8 km from Safe Harbor.

FromC$ 6 501 /nightSelect

Waterfront Anchor House With Boat Basin & RampHoliday home

9.5

Perfect2 total reviews

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Little Torch Key and Artists in Paradise Gallery are located 1.2 km and 3.3 km from the Waterfront Anchor House With Boat Basin & Ramp! respectively.

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Waterfront Captain House With Boat Basin & RampHoliday home

Looe Key Reef Resort & Dive Center is also set a 15-minute walk from the Waterfront Captain House With Boat Basin & Ramp!.

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Waterfront Beach Houses With Dock & Heated PoolHoliday home

While staying at the Waterfront Beach House With Dock & Heated Pool! Summerland Key you are invited to discover National Key Deer Refuge, set 25 minutes' walk away, or Grimal Grove, which is around 3.9 km away.

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New The Windrose House - Pool & PetsHoliday home

10.0

Perfect1 total review

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The New The Windrose House by Brightwild - Pool & Pets is set at a 7 km distance from Key West AIDS Memorial and about a 10-minute drive from Fort East Martello Museum.

FromC$ 4 038 /nightSelect

Waterfront Cozy Cottage With Boat Ramp & DockHoliday home

8.0

Great1 total review

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National Key Deer Refuge and Newfound Harbor Keys are located 2.3 km and 4.7 km from the Waterfront Cozy Cottage with Boat Ramp & Dock! respectively.

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Tollgate TidesHoliday home

While staying at the Tollgate Tides Villa Islamorada you are invited to discover Lower Matecumbe Key, set 3.3 km away, or Anne's Beach, which is 150 metres away.

FromC$ 284 /nightSelect

Dune Wind South: Beachside Extended Stay with Pool & Hot TubHoliday home

The Dune Wind South by AvantStay Communal Pool Hot Tub Gated Community Close to Smathers Beach Month Long Stays Only is set at 350 metres of Higgs Beach Dog Park and within 5 minutes' walk of The Key West Nature Preserve.

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Breezy Bungalow By Avantstay Close 2 Zachary Taylor State Park W Shared Pool Month-Long StaysHoliday home

The Breezy Bungalow by AvantStay Close 2 Zachary Taylor State Park Beach w Shared Pool Week Long Stays Key West is only 1.1 km from Mallory Square and has a quick access to Truman Waterfront Park.

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