The Best Cudjoe Key Hotels with Pools from $276 - 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 kitchen with white cabinets, a stove, and a dining area with chairs and a table.

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

Cudjoe Key

$512 nightly

$568 total

Aug 22 - Aug 23

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

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

Cudjoe Key

$463 nightly

$514 total

Sep 4 - Sep 5

Total with taxes and fees

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

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

A spacious living area with a wooden ceiling, a ceiling fan, a TV, a glass coffee table, a sofa, a chair, and a kitchen area with a refrigerator and bar stools.

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

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

Cudjoe Key

$449 nightly

$498 total

Aug 29 - Aug 30

Total with taxes and fees

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

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.

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

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

Cudjoe Key

$531 nightly

$589 total

Aug 24 - Aug 25

Total with taxes and fees

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

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

Cudjoe Key

$518 nightly

$575 total

Aug 22 - Aug 23

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.

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

Cudjoe Key

$518 nightly

$575 total

Sep 1 - Sep 2

Total with taxes and fees

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 waterfront property with a multi-story building featuring balconies, a dock, and a landscaped garden with palm trees.

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

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

Cudjoe Key

$473 nightly

$525 total

Aug 26 - Aug 27

Total with taxes and fees

A beachfront property with a pool, palm trees, and a two-story building.

A beachfront property with a large house, a parked bus, and a rocky foreground.

A residential street with houses, a driveway, and a gravel path.

A waterfront view with a marina, a boat docked, and a building with a balcony.

8. Seabreeze Escape WF RV Lot 489

Cudjoe Key

$257 nightly

$276 total

Aug 22 - Aug 23

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

Hilton Key West Resort & Marina

10/10 Excellent

"The room was magnificent"

Hyatt Vacation Club at Windward Pointe, Key West

8/10 Good

"The property was very clean and well kept by staff. Outdoor pool area was very clean and the pool was clean and nice. We didn’t have a car but it looked like there was plenty of parking available. The managers concierge staff and cleaning personnel were extremely friendly and helpful."

The Perry Hotel & Marina Key West

10/10 Excellent

"very good better than hotel on key west main island"

Hampton Inn Key West FL

8/10 Good

"Good"

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent

"Awesome"

Fairfield Inn and Suites by Marriott Key West

10/10 Excellent

"Small but clean room, staff was ok. Breakfast was eggs and biscuit which was ok."

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

8/10 Good

"We stayed at this hotel for one night and the room was very clean, staff were friendly and helpful, air conditioning was set at a very comfortable temperature. The pool area was great and so relaxing! Breakfast selection could have been a bit better but we loved how early they served it. Also, we were told that the bicycle rental was only until 5 pm. We initially planned to bike to old town and therefore weren’t able to do that."

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Check availability on Cudjoe Key Hotels with a Pool

Our top choices for Cudjoe Key hotels with a pool

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

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

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

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

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

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