The Best Cudjoe Key Hotels with Pools from $264 - Hotels with indoor pools in Cudjoe Key, FL

A tropical island with clear blue waters, palm trees, and a thatched-roof hut.

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Our top choices for Cudjoe Key hotels with a pool

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

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

A room with a sliding glass door, a small table with a 'WELCOME' sign, a refrigerator, and a wicker chair.

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

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

Cudjoe Key

$351 nightly

$392 total

Oct 1 - Oct 2

Total with taxes and fees

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

A waterfront property with a two-story building, a covered outdoor area, and a dock.

A balcony with a view of neighboring houses, a street, and a clear sky.

A marina with RVs docked along a waterway, surrounded by palm trees and buildings.

2. SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Cudjoe Key

$345 nightly

$386 total

Sep 30 - Oct 1

Total with taxes and fees

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

A spacious living area with a ceiling fan, a television, and a seating area with a sofa and chairs.

A covered balcony with a table and chairs, a grill, and a boat docked nearby.

A kitchen with white cabinets, stainless steel appliances, and a wooden ceiling.

3. SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Cudjoe Key

$345 nightly

$386 total

Sep 30 - Oct 1

Total with taxes and fees

A two-story building with a blue exterior, white railings, and a staircase leading to the upper floor.

A compact kitchen with white cabinets, a refrigerator, a stove, and a dining area with a table and chairs.

A living room with a television displaying a show, a ceiling fan, and a window with blinds.

A bathroom with a toilet, sink, and bathtub.

4. Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

Cudjoe Key

$488 nightly

$545 total

Sep 30 - Oct 1

Total with taxes and fees

A kitchen with white cabinets, a stove, and a dining area with chairs and a table.

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

Cudjoe Key

$386 nightly

$431 total

Sep 30 - Oct 1

Total with taxes and fees

A swimming pool with a tiled edge, surrounded by lounge chairs and umbrellas, under a cloudy sky.

A beachside view with palm trees and white lounge chairs along the shoreline.

A waterfront property with a view of the sea, a dock, and a building with balconies.

A marina with bicycles parked near the water, a boat docked, and a building with a balcony.

6. Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Cudjoe Key

$434 nightly

$484 total

Sep 30 - Oct 1

Total with taxes and fees

A covered outdoor area with wicker furniture and string lights.

A kitchen with a stainless steel refrigerator, a dining table with chairs, and a view of the street through a window.

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

Cudjoe Key

$403 nightly

$451 total

Sep 30 - Oct 1

Total with taxes and fees

A marina with boats docked, a clear sky, and a calm waterway.

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

Cudjoe Key

$431 nightly

$481 total

Sep 30 - Oct 1

Total with taxes and fees

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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

Blue Flamingo Resort Key West

8/10 Good

"Beautiful view,clean rooms nice staff"

Ibis Bay Beach Resort

8/10 Good

"The hotel is outside of town. The beach on the edge of the property is not very nice so it’s definitely not a pro. The restaurant and bar was closed for remodel when we went and being so far away from town we had to drive to find food. I feel like I over paid for the reservation. However, the rooms are nice and clean, the vending machines are stocked. There is plenty of parking and the pool seemed thumping."

Parrot Key Hotel & Villas

10/10 Excellent

"⭐️⭐️⭐️⭐️⭐️ Tuvimos una excelente experiencia en Parrot Key Hotel & Villas. El hotel es hermoso, tranquilo y perfecto para disfrutar unos días en Key West. Las instalaciones están muy bien cuidadas, las habitaciones son cómodas y limpias, y las áreas exteriores con las piscinas y la vegetación tropical crean un ambiente espectacular. Nos hospedamos para celebrar el cumpleaños de mi hijo y realmente disfrutamos nuestra estadía. El personal fue amable y atento, y nos sentimos muy cómodos durante todo el fin de semana. La ubicación también es conveniente para disfrutar de Key West y luego regresar a un lugar más relajado. Definitivamente volveríamos a hospedarnos aquí y lo recomendamos para familias, parejas o cualquier persona que quiera disfrutar Key West en un ambiente bonito y tranquilo."

Hilton Garden Inn Key West / The Keys Collection

8/10 Good

"Thank you"

Hampton Inn Key West FL

8/10 Good

"Staff was great, shuttles were timely and helpful, rooms were clean, pool was nice."

Hyatt Vacation Club at Windward Pointe, Key West

10/10 Excellent

"I loved the outdoor area and pool! We utilized the grill area as we had a big party and it was great!! I would have game 5 stars for everything but I was not advised during check in that cleaning staff do not come in daily. I had to call every day for towels (they were delivered quickly) but the old towels and trash were not removed from the room, even after I requested it from the front desk."

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent

"Close to everything, comfortable stay"

The Perry Hotel & Marina Key West

8/10 Good

"Good place to stay but watch out for the gratuity tax (it's a State of Florida thing). The property was well maintained, and we enjoyed the room. Overall, it was a good place to stay. Most of the staff were hospitable and management was amazing."

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Treat yourself

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Check availability on Cudjoe Key Hotels with a Pool

Our top choices for Cudjoe Key hotels with a pool

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

2. SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

3. SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

4. Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

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

6. Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

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

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

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

10. Seabreeze Escape WF RV Lot 489

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