The Best Cudjoe Key Hotels with Pools from $275 - 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

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

Cudjoe Key

$365 nightly

$406 total

Sep 8 - Sep 9

Total with taxes and fees

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

Cudjoe Key

$388 nightly

$431 total

Sep 7 - Sep 8

Total with taxes and fees

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

Cudjoe Key

$460 nightly

$511 total

Sep 11 - Sep 12

Total with taxes and fees

Coffee/tea maker, fridge, microwave, oven

4. Canal Front home with easy Ocean access

Cudjoe Key

$341 nightly

$379 total

Sep 9 - Sep 10

Total with taxes and fees

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

Cudjoe Key

$498 nightly

$552 total

Sep 7 - Sep 8

Total with taxes and fees

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

Cudjoe Key

$527 nightly

$585 total

Sep 8 - Sep 9

Total with taxes and fees

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

Cudjoe Key

$545 nightly

$604 total

Sep 12 - Sep 13

Total with taxes and fees

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

Cudjoe Key

$510 nightly

$567 total

Sep 8 - Sep 9

Total with taxes and fees

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Breakfast included

4 stars

5 stars

Hot tub

Spa

Top Cudjoe Key Hotel Reviews

Blue Flamingo Resort Key West

10/10 Excellent

"Saw good reviews of hotel but needed to stay there myself. I must say I was pleasantly surprised. Please note the hotel is about a minute from the entrance into Key West which is OK for us. The lobby from the moment you enter has an amazing smell due to a scent they put out. We loved it. The lobby is gorgeous, staff very friendly at the front desk. The outside with pool, cabana and other things to do like a swing, cornhole etc. also looked nice. We did not use it but others that did looked happy. They do play music and you can purchase food for extra cost. There is a Starbucks located on the first floor which we used once. I thought the hotel rooms were accessed from the inside but it’s the outside which normally I don’t like but truthfully it was not bad. We stayed upper floor 2 rooms down from elevator. Since it has been hot in Florida the elevator can get a bit hot just FYI. Room was small but comfy and quite cute I have to say. The sliding door to bathroom is unique and loved the oval mirror. No closet door, its open but within the bathroom. Bed soft and shower very nice. Be aware the place is remodeled but they did a very nice job. They also have like 3 buildings but I am glad we stayed at the main building where the lobby is at. Parking on side or back, we preferred the back as hotel is accesible. Our trip was short but enough and would definitely consider staying there again. Price was reasonable. Can say we are very happy with the stay and staff."

Ibis Bay Beach Resort

10/10 Excellent

"Continental breakfast. The free busing that was available 2 years ago has stopped. So now you're either paying an Uber or riding the bus. That was a lot of money every trip we went out. The nice thing was having the pool. We definitely will not be staying there again."

Parrot Key Hotel & Villas

8/10 Good

"Nice property management. Several pools."

The Perry Hotel & Marina Key West

8/10 Good

"We expected the rooms to be nicer more modern but they were clean!"

Hampton Inn Key West FL

8/10 Good

"Great location right by the airport. Nice rooms but there's no reason to be in the rooms because Key West is absolutely beautiful and you want to be outside all day."

Hilton Key West Resort & Marina

8/10 Good

"Liked everything but restaurant prices were extremely high for breakfast. Outrageous breakfast prices for simple breakfast. Cannot recommend restaurant."

DoubleTree Resort by Hilton Grand Key - Key West

8/10 Good

"My husband and I joined the hotel. I would definitely recommend this place. I felt like I was in a mini resort."

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

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

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

4. Canal Front home with easy Ocean access

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

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

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

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

9. Seabreeze Escape WF RV Lot 489

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