The Best Cudjoe Key Hotels with Pools from $103 - 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 beach with a thatched-roof hut, palm trees, and a pebbled walkway leading to the water.

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.

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

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

Cudjoe Key

$351 nightly

$392 total

Sep 27 - Sep 28

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

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

Cudjoe Key

$373 nightly

$416 total

Sep 28 - Sep 29

Total with taxes and fees

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

Cudjoe Key

$410 nightly

$455 total

Sep 25 - Sep 26

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 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

$498 nightly

$555 total

Sep 28 - Sep 29

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

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

Cudjoe Key

$372 nightly

$413 total

Oct 1 - Oct 2

Total with taxes and fees

A covered outdoor area with wicker furniture and string lights.

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

Cudjoe Key

$430 nightly

$478 total

Sep 26 - Sep 27

Total with taxes and fees

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

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

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

Cudjoe Key

$439 nightly

$489 total

Sep 28 - Sep 29

Total with taxes and fees

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

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

Cudjoe Key

$450 nightly

$502 total

Sep 27 - Sep 28

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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Top Cudjoe Key Hotel Reviews

The Perry Hotel & Marina Key West

10/10 Excellent

"Everything was great! Staff was super friendly and helpful. 10/10"

Hyatt Vacation Club at Beach House, Key West

10/10 Excellent

"The Hyatt was awesome. There were two things that were bothersome. The bartender at Jimmy's was very brash almost rude at times. We asked for a late checkout on Sunday, because our boat did not leave until 6:00pm. We was told no because they were closing the following week for an extensive cleaning.No apology just basically tough. This ended up costing us $25.00 each. If we had been told this when we booked we would have chosen another place. They were nice enough to let us check in early. We will not be staying here again."

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent

"Our room was always clean with clean towels. The night person (Michelle) was very personable! The only thing that was an inconvenient was the elevator being out of order to where out room was. It was a long walk for me to go to the other side to get in the elevator. My legs don't work very well. It was like that for 3 days"

Blue Flamingo Resort Key West

8/10 Good

"Wish there were more options as far as eating, the staff was helpful in some ways, I think they were training a lot of them which is fine, I get it. Room was very clean. Would have been nice if there was an indoor eating area not just the outdoor bar areas but it was fine. Never were able to locate the other sister options to eat but that was ok. Food was very tasty. Beds were comfortable and pillows were firm and soft, great options, mini fridge and coffee w/water in the room, oh and the ear plugs were so cute!!!"

Beachside Resort & Residences

10/10 Excellent

"We loved this resort. Room mix up at first. Was moved to beautiful suite with walk in shower. Handicap was needed. Restaurant awesome. Tapas breakfast. Great happy hour with piano bar. Pool a d private beach. 👍 all the way. Thanks for a wonderful vacation."

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

10/10 Excellent

"Nice place"

Ibis Bay Beach Resort

8/10 Good

"Great"

Hilton Key West Resort & Marina

10/10 Excellent

"Nice and comfortable"

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Upfront pricing

Treat yourself

Be picky

Check availability on Cudjoe Key Hotels with a Pool

Our top choices for Cudjoe Key hotels with a pool

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

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

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

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

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

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

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

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

9. Salty Breeze #161 Canal-Front Retreat with Dock, Pool & Ocean Views

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

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