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A sign reading "CUDJOE KEY" by a coastal road with a clear sky and calm sea.

Find Hotels with a Pool in Cudjoe Key, FL

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    Check prices for these dates, December 12 – 13, 2026

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    Our top choices for Cudjoe Key hotels with a pool

    1. Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

    Pool

    2. Affordable Dog Friendly Keys Retreat in Venture Out Near Key West

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

    3. Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

    Pool

    4. Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views

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

    5. Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West

    Pool

    6. SAVE BIG $$$ NOV./DEC. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

    A marina with boats, a dock, and a white building with a balcony.

    7. SAVE BIG $$$ NOV./DEC. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

    A beach with a thatched-roof hut, palm trees, and a pebbled walkway leading to the water.

    8. Canal-Front Retreat with Dock, Pool & Open Ocean Views

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

    9. Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

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

    10. Waterfront 2BR/2BA with 35' Dock – Island Breeze Keys Escape

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

    Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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    Choose what matters most at hotels with a pool in Cudjoe Key

    Breakfast included

    4 stars

    5 stars

    Hot tub

    Spa

    Top Cudjoe Key Hotel Reviews

    Parmer's Resort

    A sunset view with a thatched structure and a palm tree by a calm body of water.

    Hampton Inn Key West FL

    A pool area with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.

    Sugar Loaf Lodge

    A swimming pool with a surrounding deck, palm trees, and lounge chairs.

    Hyatt Vacation Club at Beach House, Key West

    A poolside lounge area with a wicker chair, a straw hat, and a beach bag.

    Hyatt Vacation Club at Windward Pointe, Key West

    A swimming pool surrounded by palm trees and lounge chairs, with a clear view of the ocean in the background.

    Courtyard by Marriott Key West Waterfront

    A pool area with lounge chairs, palm trees, and a building with a tiled roof.

    DoubleTree Resort by Hilton Grand Key - Key West

    A pool area with lounge chairs and gazebos, surrounded by palm trees.

    Hilton Key West Resort & Marina

    A marina with boats docked, a pool area, and a building with a white facade.

    Margaritaville Beach House Key West

    A dining table with plates of food, a drink, and a view of a pool and palm trees.

    Havana Cabana at Key West

    A swimming pool surrounded by palm trees and a natural rock formation.

    Old Wooden Bridge Resort and Marina

    A fenced pool area with palm trees, a blue and white tiled walkway, and a sign indicating pool hours.

    The Laureate Key West

    A swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean at dusk.

    Parrot Key Hotel & Villas

    A wooden archway leading to a pool area surrounded by lush tropical vegetation.

    Looe Key Reef Resort

    A swimming pool with blue and white tiles, surrounded by lounge chairs and palm trees.

    Blue Flamingo Resort Key West

    A hotel with a swimming pool, sun loungers, and palm trees.

    Ibis Bay Beach Resort

    A pool area with blue lounge chairs, a hot tub, and a covered seating area.

    Hilton Garden Inn Key West / The Keys Collection

    A swimming pool with lounge chairs and palm trees.

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