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 7 - Oct 8
Tomorrow
Oct 8 - Oct 9
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

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 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 waterfront property with a multi-story building featuring balconies, a dock, and a landscaped garden with palm trees.

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

SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
$377 nightly
$419 total
Oct 9 - Oct 10
Total with taxes and fees
SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A resort with a swimming pool, beach area, and marina.
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.
A room with a sliding glass door, a small table with a 'WELCOME' sign, a refrigerator, and a wicker chair.

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 8 - Oct 9
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 covered balcony with a table and chairs, a grill, and a boat docked nearby.
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.

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

SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
$399 nightly
$443 total
Oct 13 - Oct 14
Total with taxes and fees
SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Pool
Outdoor dining
Sport court
Beach

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
$410 nightly
$455 total
Oct 8 - Oct 9
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 living room with a television displaying a show, a ceiling fan, and a window with blinds.
A compact kitchen with white cabinets, a refrigerator, a stove, and a dining area with a table and chairs.
A bathroom with a toilet, sink, and bathtub.

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
$536 nightly
$595 total
Oct 8 - Oct 9
Total with taxes and fees
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Pool
A kitchen with a stainless steel refrigerator, a dining table with chairs, and a view of the street through a window.
Beach
A covered outdoor area with wicker furniture and string lights.

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 14 - Oct 15
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.
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.

7. 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 8 - Oct 9
Total with taxes and fees
Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views
Pool
Outdoor dining
A living room with a sofa, armchair, TV, and a view of the outdoors.
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

8. 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 14 - Oct 15
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.
A marina with boats docked, a clear sky, and a calm waterway.
Outdoor dining
A coastal residential area with houses, a marina, and a flag.

9. 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 13 - Oct 14
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 room with a dark blue dresser, a lamp, and a sign reading "OUR HAPPY PLACE".
A coastal residential area with houses, a marina, and a flag.
Outdoor dining

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 8 - Oct 9
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 Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

10/10 Excellent
"Excellent"
Anali 1-night trip
Posted 3 hours ago
Hyatt Vacation Club at Beach House, Key West
Ibis Bay Beach Resort

Ibis Bay Beach Resort

10/10 Excellent
"Very nice and staff was great."
Andre 4-night trip
Posted 5 hours ago
Ibis Bay Beach Resort
Fairfield by Marriott Inn & Suites Key West at The Keys Collection

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

10/10 Excellent
"Great place! Rooms were nice. So was staff. Great breakfast with lots of choices."
Walter 3-night trip
Posted 7 hours ago
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

10/10 Excellent
"Great hotel and pool!"
Eli 2-night trip
Posted 8 hours ago
Hilton Garden Inn Key West / The Keys Collection
Hilton Key West Resort & Marina

Hilton Key West Resort & Marina

10/10 Excellent
"Staff at reception are genuinely welcoming."
Nche 1-night trip
Posted 9 hours ago
Hilton Key West Resort & Marina
Hampton Inn Key West FL

Hampton Inn Key West FL

10/10 Excellent
"It was good"
Alliance 4-night trip
Posted 10 hours ago
Hampton Inn Key West FL
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

10/10 Excellent
"Great place definitely staying there next time"
Francisca 4-night trip
Posted 1 day ago
Parrot Key Hotel & Villas
Parmer's Resort

Parmer's Resort

10/10 Excellent
"Just a fantastic property, wonderful staff, great amenities, so many waterfront places to chill. Immaculate grounds with a laid back vibe, loved it!!"
Moira 1-night trip
Posted 3 days ago
Parmer's Resort
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

10/10 Excellent
"The whole experience was fantastic. I wouldn't stay anywhere else!"
james 5-night trip
Posted 3 days ago
The Perry Hotel & Marina Key West

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