The Best Ski Hotels in Florida Keys from ￥27,259 in 2026 | Expedia

A beach with palm trees, people relaxing on chairs, and colorful kayaks.

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Check availability on Florida Keys Ski Hotels

Tonight

Sep 22 - Sep 23

Tomorrow

Sep 23 - Sep 24

This weekend

Sep 25 - Sep 27

Next weekend

Our top choices for Florida Keys ski hotels

A swimming pool with lounge chairs and a thatched roof structure, surrounded by lush greenery and a brick patio.

A living room with a sofa, armchair, coffee table, and a cabinet with decorative items.

A two-story house with a front porch, a staircase, and a garage.

A bar with a signboard listing various destinations.

1. Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS

Stock Island

￥33,271

￥81,005 total

includes taxes & fees

Sep 23 - Sep 24

A covered outdoor seating area with white chairs and tables, overlooking turquoise waters and distant islands.

A spacious living room with a large TV, comfortable seating, a wooden cabinet, and a view of the sea through large windows.

A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

A resort with a swimming pool, beach area, and marina.

2. Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

Cudjoe Key

￥61,941

￥117,291 total

includes taxes & fees

Sep 23 - Sep 24

A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

A living room with a sofa, chairs, a coffee table, a TV, and large windows overlooking the ocean.

A covered outdoor seating area with turquoise Adirondack chairs and a small round table, overlooking a beach with palm trees and a pier.

A coastal residential area with houses, a marina, and a flag.

3. Post Card Point #319 - Ocean Views!

Cudjoe Key

￥64,418

￥130,814 total

includes taxes & fees

Sep 23 - Sep 24

A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

A resort with a swimming pool, beach area, and marina.

A coastal residential area with houses, a marina, and a flag.

4. Mahi House #440 Waterfront Retreat with Dock, Pool & Optional Golf Cart

Cudjoe Key

￥31,298

￥77,196 total

includes taxes & fees

Sep 24 - Sep 25

A beach with a thatched-roof table and benches, surrounded by trees and a calm body of water.

A compact kitchen with a microwave, stove, and refrigerator.

A dock with a wooden walkway leading to a building with a flat roof, surrounded by water and palm trees.

A calm river at sunset with a dock and boats.

5. RV by the Sea - Glamping in the Keys

Key Largo

￥9,242

￥40,150 total

includes taxes & fees

Sep 27 - Sep 28

A poolside area with lounge chairs and a gazebo overlooking the ocean.

A balcony with a wooden table, white cushioned seating, and a view of the beach and ocean.

A modern bedroom with a large window, a wooden headboard, a bedside table with a plant, and a TV on the wall.

A modern living room with a wooden dining table, wicker chairs, and a view of the ocean.

6. 1 Hotel South Beach

South Beach

￥76,311

￥98,831 total

includes taxes & fees

Oct 4 - Oct 5

A beach with a clear view of the ocean, a sandy beach, and palm trees.

A modern hotel lobby with a long reception desk, comfortable seating, and a wall adorned with framed photographs.

A rooftop pool with lounge chairs and a view of the city skyline.

A rooftop terrace with outdoor seating, a large planter with a tree, and a view of the city skyline at dusk.

7. Gale South Beach, Curio Collection by Hilton

South Beach

￥17,619

￥27,259 total

includes taxes & fees

Sep 24 - Sep 25

A beachside view with a thatched umbrella, a lounge chair, and a rocky shoreline.

A compact RV kitchen with a central island, a dining area with a sofa, and a TV mounted on the wall.

A modern kitchen with wooden cabinets, stainless steel appliances, and a central island.

A dock with a thatched roof structure, a small boat, and a blue building with a white door.

8. Ocean Front with Dock, Key Largo, FL., Pirate's Cove

Key Largo

￥17,186

￥49,145 total

includes taxes & fees

Oct 4 - Oct 5

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