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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 15 – 16, 2026

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Our top choices for Cudjoe Key hotels with a pool

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

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

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

Pool

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

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

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

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

5. 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.

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

Pool

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

Pool

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

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

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

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.

Sugar Loaf Lodge

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

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.

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.

Hilton Key West Resort & Marina

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

Havana Cabana at Key West

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

Hampton Inn Key West FL

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

Hyatt Vacation Club at Beach House, Key West

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

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.

DoubleTree Resort by Hilton Grand Key - Key West

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

Hilton Garden Inn Key West / The Keys Collection

A swimming pool with lounge chairs and palm trees.

Courtyard by Marriott Key West Waterfront

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

Margaritaville Beach House Key West

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

Ibis Bay Beach Resort

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

Grand Marina Suite by Brightwild Waterfront

Room

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