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

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.

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

Cudjoe Key

$393 nightly

$436 total

Aug 20 - Aug 21

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 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.

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

Cudjoe Key

$393 nightly

$436 total

Aug 20 - Aug 21

Total with taxes and fees

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.

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

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

Cudjoe Key

$512 nightly

$568 total

Aug 20 - Aug 21

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

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

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

Cudjoe Key

$540 nightly

$599 total

Aug 26 - Aug 27

Total with taxes and fees

A marina with several white mobile homes, a swimming pool, and a trailer.

6. Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

Cudjoe Key

$560 nightly

$621 total

Aug 20 - Aug 21

Total with taxes and fees

A living room with a sofa, armchair, TV, and a view of the outdoors.

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

Cudjoe Key

$560 nightly

$621 total

Aug 20 - Aug 21

Total with taxes and fees

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

A covered outdoor area with wicker furniture and string lights.

8. 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

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

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4 stars

5 stars

Hot tub

Spa

Top Cudjoe Key Hotel Reviews

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent

"No complaints."

Hampton Inn Key West FL

8/10 Good

"The free breakfast every morning was filling. They also shuttle you to a designated area that is walking distance from lots of shops and activities. They also pick you up from the same designated spot as at scheduled times. Definitely save money on the UBERING."

The Perry Hotel & Marina Key West

10/10 Excellent

"We had a great stay, staff were very friendly and helpful. The only concern was that since it was “off” season for them the restaurants and bars closed early."

Blue Flamingo Resort Key West

10/10 Excellent

"This resort is amazing. We have stayed here for the past 3 years and plan to go back again next year. The only thing that I would have a small complaint is there is no microwave in the rooms. We wasted alot of leftover food from restaurants because there was no way to heat it back up. After the first couple of meals we learned to eat appetizers or share an entree."

Hilton Garden Inn Key West / The Keys Collection

10/10 Excellent

"Con gusto se puede ir a disfrutar"

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."

Hilton Key West Resort & Marina

10/10 Excellent

"The room was clean and smells clean. Staffs are very helpful and greeted me enthusiastically. It was a place that I was expecting to be in and relax after a long drive. The pool was nice, heated and relaxing. Highly recommended."

Hyatt Vacation Club at Windward Pointe, Key West

8/10 Good

"The property itself was very nice and well kept. The maintenance and cleaning staff were very creepy men and made me feel very uncomfortable during my stay. It’s something to think about if you are solo traveling. The area was nice, amenities were great, but I would not return here."

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

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

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

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

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

6. Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

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

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

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

10. Seabreeze Escape WF RV Lot 489

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

Top Cudjoe Key Hotel Reviews