A tropical island with clear blue waters, palm trees, and a thatched-roof hut.

Find Hotels with a Pool in Cudjoe Key, FL

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Check availability on Cudjoe Key Hotels with a Pool

Tonight
Oct 1 - Oct 2
Tomorrow
Oct 2 - Oct 3
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

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 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.

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

SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
$377 nightly
$419 total
Oct 4 - Oct 5
Total with taxes and fees
SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A resort with a swimming pool, beach area, and marina.
Outdoor dining
A coastal residential area with houses, a marina, and a flag.
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

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

Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
Cudjoe Key
$372 nightly
$413 total
Oct 2 - Oct 3
Total with taxes and fees
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
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 waterfront property with a covered porch, a boat dock, and a clear sky.
A covered balcony with a table and chairs, a grill, and a boat docked nearby.

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

SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
$399 nightly
$443 total
Oct 4 - Oct 5
Total with taxes and fees
SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Pool
Outdoor dining
Beach
A kitchen with white cabinets, a stove, and a dining area with chairs and a table.

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

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Cudjoe Key
$409 nightly
$454 total
Oct 2 - Oct 3
Total with taxes and fees
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
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 bathroom with a toilet, sink, and bathtub.
A living room with a television displaying a show, a ceiling fan, and a window with blinds.

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

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Cudjoe Key
$523 nightly
$580 total
Oct 5 - Oct 6
Total with taxes and fees
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Pool
A covered outdoor area with wicker furniture and string lights.
Beach
Sport court

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

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Cudjoe Key
$427 nightly
$475 total
Oct 2 - Oct 3
Total with taxes and fees
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
A resort with a swimming pool, beach area, and marina.
A coastal residential area with houses, a marina, and a flag.
A marina with boats docked, a clear sky, and a calm waterway.
Outdoor dining

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

Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
Cudjoe Key
$457 nightly
$507 total
Oct 2 - Oct 3
Total with taxes and fees
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
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 marina with RVs and mobile homes, a swimming pool, and a view of the ocean.
Outdoor dining

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

Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views
Cudjoe Key
$439 nightly
$487 total
Oct 2 - Oct 3
Total with taxes and fees
Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views
Pool
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.
A coastal residential area with houses, a marina, and a flag.
A living room with a sofa, armchair, TV, and a view of the outdoors.

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

Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
Cudjoe Key
$468 nightly
$520 total
Oct 4 - Oct 5
Total with taxes and fees
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
A resort with a swimming pool, beach area, and marina.
Outdoor dining
A coastal residential area with houses, a marina, and a flag.
A room with a dark blue dresser, a lamp, and a sign reading "OUR HAPPY PLACE".

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

Mahi House #440 Waterfront Retreat with Dock, Pool & Optional Golf Cart
Cudjoe Key
$457 nightly
$507 total
Oct 2 - Oct 3
Total with taxes and fees
Mahi House #440 Waterfront Retreat with Dock, Pool & Optional Golf Cart
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

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

10/10 Excellent
"We would definitely stay again, it was a beautiful resort.."
William 2-night trip
Posted 13 hours ago
Hyatt Vacation Club at Windward Pointe, Key West
Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

10/10 Excellent
"Fantastic"
COOK 1-night trip
Posted 15 hours ago
Hyatt Vacation Club at Beach House, Key West
Beachside Resort & Residences

Beachside Resort & Residences

10/10 Excellent
"The room was clean. No daily housekeeping. The staff were pleasant and quiet helpful. Breakfast was outstanding. It was alacart and you have to pay per item. Over all this was the most relaxing vacation I've been on. Loved it!"
Harry 1-night trip
Posted 15 hours ago
Beachside Resort & Residences
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

10/10 Excellent
"This property is nicer than anything we found closer to Duval Street. This property is 5 stars! Roomy, worth every penny. I loved my king size bed. I loved the properties gardens and the pools. It was quiet, private, and luxurious. I have one critique, valet parking is not needed. $30 for Valet is not needed."
Krystal 1-night trip
Posted 1 day ago
Parrot Key Hotel & Villas
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

8/10 Good
"Thank you"
Agustin 2-night trip
Posted 3 days ago
Hilton Garden Inn Key West / The Keys Collection
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

8/10 Good
"Good place to stay but watch out for the gratuity tax (it's a State of Florida thing). The property was well maintained, and we enjoyed the room. Overall, it was a good place to stay. Most of the staff were hospitable and management was amazing."
April 5-night trip
Posted 3 days ago
The Perry Hotel & Marina Key West

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