The Best Cudjoe Key Hotels with Pools from $112 - 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

Coffee/tea maker, fridge, microwave, oven

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

Cudjoe Key

$371 nightly

$412 total

Aug 30 - Aug 31

Total with taxes and fees

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

Cudjoe Key

$460 nightly

$511 total

Sep 4 - Sep 5

Total with taxes and fees

3. Canal Front home with easy Ocean access

Cudjoe Key

$343 nightly

$381 total

Sep 9 - Sep 10

Total with taxes and fees

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

Cudjoe Key

$523 nightly

$580 total

Aug 31 - Sep 1

Total with taxes and fees

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

Cudjoe Key

$497 nightly

$551 total

Sep 1 - Sep 2

Total with taxes and fees

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

Cudjoe Key

$450 nightly

$499 total

Aug 31 - Sep 1

Total with taxes and fees

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

Cudjoe Key

$514 nightly

$571 total

Sep 1 - Sep 2

Total with taxes and fees

8. Venture Out RV lot 223

Cudjoe key

$229 nightly

$242 total

Aug 31 - Sep 1

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

Blue Flamingo Resort Key West

10/10 Excellent

"All of it"

The Perry Hotel & Marina Key West

10/10 Excellent

"After an issue with our first room, the staff was very accommodating by moving us to a new room. The new room and our stay was excellent. Thank you!"

Hyatt Vacation Club at Beach House, Key West

10/10 Excellent

"Property was clean. Room was spacious. Watch charges from the Tiki bar. Not run by the hotel but offer drinks and food by the pool. The prices seemed higher on my bill than advertized."

Parmer's Resort

8/10 Good

"The staff at Parmer’s is excellent from the check-in person to everyone that works on the grounds. However, this place had to grow on me because my initial reaction was one of disappointment. I think the pictures look much better than what’s actually there. The beach that’s advertised and looks like a sandy oasis with a clean shoreline is actually about sandy to mid calf and then algae and seaweed. A nice place to catch some rays with nice loungers but sitting on the waters edge but not for swimming or wading. The furniture is straight out of the 60’s or 70’s, but is clean and well kept. The A/C is enough to keep the cottage type bungalow cool but too far from the bathroom to keep that area cool. The pool is super clean and well maintained but water too hot during summer and would benefit from the pump keeping water flowing longer. Having said all this I found Parmer’s growing on us because of the staff, the light breakfast, eagerness of staff to please providing a fan to keep the bath cooler, the boat ramp, kayaks, shaded sitting areas by the water, fishing on property and the overall laid back feeling made me forget what wasn’t perfect and remember what hotel stays were like when I was young. No fancy Marriott’s or Sheraton, but just a place where you felt you hadn’t left home, but gained a water view with a summer breeze."

Hampton Inn Key West FL

10/10 Excellent

"Stayed for 1 night while traveling. Was very clean and comfortable. Staff were very friendly and helpful. We enjoyed the pool. Free breakfast the next morning was great."

Hilton Garden Inn Key West / The Keys Collection

8/10 Good

"IS WAS OK"

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent

"Room was very clean, pool was great! Bravin and Billy at the pool bar are the best! This was our second stay and will definitely be back soon!"

Parrot Key Hotel & Villas

10/10 Excellent

"So spacious, perfect for groups. The room was very clean and the staff were helpful! 10/10 would stay again They were doing what seemed like a clorox cleaning of the common area sidewalks, which I thought would have been better scheduled during a week day when there werent many guests but other than that the stay was perfect"

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

3. Canal Front home with easy Ocean access

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

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

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