The Best Cudjoe Key Hotels with Pools from $270 - 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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Sep 10 - Sep 11

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Sep 11 - Sep 13

Next weekend

Sep 18 - Sep 20

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 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.

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

Cudjoe Key

$365 nightly

$406 total

Sep 13 - Sep 14

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

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

Cudjoe Key

$373 nightly

$415 total

Sep 10 - Sep 11

Total with taxes and fees

A swimming pool with blue and white tiled edges, surrounded by palm trees and white lounge chairs.

A balcony with white chairs and a table, overlooking a pool and a marina with boats.

A white building with large windows and a balcony, featuring outdoor furniture and a covered area.

A stone sculpture with a face, surrounded by rocks and palm trees.

3. Canal Front home with easy Ocean access

Cudjoe Key

$338 nightly

$376 total

Sep 10 - Sep 11

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.

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

Cudjoe Key

$457 nightly

$508 total

Sep 11 - Sep 12

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 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.

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

Cudjoe Key

$521 nightly

$578 total

Sep 14 - Sep 15

Total with taxes and fees

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

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

Cudjoe Key

$494 nightly

$548 total

Sep 10 - Sep 11

Total with taxes and fees

A covered outdoor area with wicker furniture and string lights.

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

Cudjoe Key

$506 nightly

$563 total

Sep 10 - Sep 11

Total with taxes and fees

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

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

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

Cudjoe Key

$548 nightly

$609 total

Sep 10 - Sep 11

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

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

10/10 Excellent

"good , will come back again with my family"

Ibis Bay Beach Resort

Ibis Bay Beach Resort

10/10 Excellent

"Todo bien pero la playa no era playa era un pantano todo lo demás muy bueno"

Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

10/10 Excellent

"Beautiful hotel to relax and enjoy Key West"

Beachside Resort & Residences

Beachside Resort & Residences

10/10 Excellent

"Very happy with this stay. The location is perfect with shopping food coffee The hotel area and the room were so clean the staff were very friendly and gave us everything we needed it was very quiet until the morning Loved hearing the chicken arlam and the shuttle are very services."

Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

10/10 Excellent

"Beautiful updated condo!!! Chris was so helpful and kind and would respond so quickly!"

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

10/10 Excellent

"Excellent location"

DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent

"We arrive early and our room was ready,clean and spacious, personnal very attentive. Great Stay"

The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

8/10 Good

"We loved that Matt's Stockyard cooked our Fresh Lobsters !"

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