The Best Cudjoe Key Hotels with Pools from $416 - 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 resort with a swimming pool, beach area, and marina.

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

A room with a sliding glass door, a small table with a 'WELCOME' sign, a refrigerator, and a wicker chair.

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

Cudjoe Key

$375 nightly

$416 total

Oct 10 - Oct 11

Total with taxes and fees

A beach with a thatched-roof hut, palm trees, and a pebbled walkway leading to the water.

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

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.

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

Cudjoe Key

$388 nightly

$431 total

Oct 12 - Oct 13

Total with taxes and fees

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

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

Cudjoe Key

$412 nightly

$457 total

Oct 10 - Oct 11

Total with taxes and fees

A beachside area with palm trees, picnic tables, and a view of the sea.

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

4. 2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.

Cudjoe Key

$489 nightly

$543 total

Oct 10 - Oct 11

Total with taxes and fees

A two-story building with a blue exterior, white railings, and a staircase leading to the upper floor.

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

A living room with a television displaying a show, a ceiling fan, and a window with blinds.

A bathroom with a toilet, sink, and bathtub.

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

Cudjoe Key

$552 nightly

$612 total

Oct 10 - Oct 11

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 ceiling fan, a television, and a seating area with a sofa and chairs.

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

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

Cudjoe Key

$399 nightly

$443 total

Oct 13 - Oct 14

Total with taxes and fees

7. Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views

Cudjoe Key

$442 nightly

$490 total

Oct 10 - Oct 11

Total with taxes and fees

8. Mahi House #440 Waterfront Retreat with Dock, Pool & Optional Golf Cart

Cudjoe Key

$460 nightly

$510 total

Oct 10 - Oct 11

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

Hampton Inn Key West FL

10/10 Excellent

"Amazing stay, no complaints, clean rooms, and great pool area."

Parrot Key Hotel & Villas

10/10 Excellent

"Great place!!!"

Hyatt Vacation Club at Windward Pointe, Key West

10/10 Excellent

"Clean room"

Parmer's Resort

10/10 Excellent

"Fishing charter guide pick up from dock every morning. G"

Hilton Key West Resort & Marina

10/10 Excellent

"We arrived late around 8PM so difficult to see vista from room. However next morning a stunning view of sea was apparent. Nice balcony but a lttle warm to sit out"

Hyatt Vacation Club at Beach House, Key West

8/10 Good

"We had a great stay, everyone was pleasant and accommodating. I would only say the claim for a private beach was misleading. There was very little waterfront beach and only two Adirondack chairs on the entire beach area. Otherwise it was a wonderful stay"

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

10/10 Excellent

"This is an excellent property i every way. Staff are outstanding. The free shuttle to downtown every hour is a huge plus!"

The Perry Hotel & Marina Key West

10/10 Excellent

"Wonderful hotel, good food/restaurant on site, bar too. Great view of marina and pool on site. Will definitely go back. Staff was very helpful whenever we needed anything."

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

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

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

4. 2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.

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

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

7. Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views

8. Mahi House #440 Waterfront Retreat with Dock, Pool & Optional Golf Cart

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

10. Seabreeze Escape WF RV Lot 489

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