The Best Cudjoe Key Hotels with Pools from $413 - Hotels with indoor pools in Cudjoe Key, FL | Expedia

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

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Check availability on Cudjoe Key Hotels with a Pool

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Oct 16 - Oct 18

Our top choices for Cudjoe Key hotels with a pool

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

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

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

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

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

Cudjoe Key

$377 nightly

$419 total

Oct 4 - Oct 5

Total with taxes and fees

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

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.

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

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

Cudjoe Key

$372 nightly

$413 total

Oct 4 - Oct 5

Total with taxes and fees

Pool

Beach

Sport court

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

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

Cudjoe Key

$409 nightly

$454 total

Oct 4 - Oct 5

Total with taxes and fees

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

A waterfront property with a covered porch, a boat dock, and a clear sky.

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

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

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

Cudjoe Key

$399 nightly

$443 total

Oct 4 - Oct 5

Total with taxes and fees

Pool

A covered outdoor area with wicker furniture and string lights.

Beach

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

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

Cudjoe Key

$427 nightly

$475 total

Oct 4 - Oct 5

Total with taxes and fees

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

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

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

Outdoor dining

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

Cudjoe Key

$457 nightly

$507 total

Oct 4 - Oct 5

Total with taxes and fees

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

A bathroom with a toilet, sink, and bathtub.

A bedroom with a bed, a ceiling fan, a window with curtains, and a framed picture on the wall.

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

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

Cudjoe Key

$526 nightly

$583 total

Oct 6 - Oct 7

Total with taxes and fees

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

Outdoor dining

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

A marina with RVs and mobile homes, a swimming pool, and a view of the ocean.

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

Cudjoe Key

$439 nightly

$487 total

Oct 4 - Oct 5

Total with taxes and fees

View all properties

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

Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

10/10 Excellent

"Staff was very nice. Pool was great as well as the hot tub."

Fairfield by Marriott Inn & Suites Key West at The Keys Collection

Fairfield by Marriott Inn & Suites Key West at The Keys Collection

10/10 Excellent

"Great customer service and very clean!!!"

Hampton Inn Key West FL

Hampton Inn Key West FL

10/10 Excellent

"Great experience even with the rain. Great place to stay."

DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent

"Great shuttle service"

Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

8/10 Good

"Valet parking obligatoire ce qui était pour nous plutôt une nuisance qu’un avantage car nous sortions souvent visiter les alentours! Nous ne pouvions pas apporter de boissons alcoolisé au bord de la piscine il fallait les acheter directement au bar de piscine …"

The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

10/10 Excellent

"Hotel was great. All of the staff were friendly and accommodating"

Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

10/10 Excellent

"Fantastic"

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