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
Sep 17 - Sep 18
Tomorrow
Sep 18 - Sep 19
This weekend
Sep 18 - Sep 20
Next weekend
Sep 25 - Sep 27

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 waterfront property with a multi-story building featuring balconies, a dock, and a landscaped garden with palm trees.
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 $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
$391 nightly
$434 total
Sep 27 - Sep 28
Total with taxes and fees
SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
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 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.

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

SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
$366 nightly
$407 total
Sep 21 - Sep 22
Total with taxes and fees
SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

3. 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
$388 nightly
$433 total
Sep 18 - Sep 19
Total with taxes and fees
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
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.

4. 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 1 - Oct 2
Total with taxes and fees
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
A kitchen with a stainless steel refrigerator, a dining table with chairs, and a view of the street through a window.
A covered outdoor area with wicker furniture and string lights.

5. 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
Sep 18 - Sep 19
Total with taxes and fees
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
A two-story building with a blue exterior, white railings, and a staircase leading to the upper floor.
A compact kitchen with white cabinets, a refrigerator, a stove, and a dining area with a table and chairs.
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.

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

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Cudjoe Key
$496 nightly
$553 total
Sep 22 - Sep 23
Total with taxes and fees
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
A beachfront property with a pool, palm trees, and a two-story building.
A marina with waterfront properties, including a docked boat and a small dock with a table and chairs.
A waterfront view with a marina, a boat docked, and a building with a balcony.
A beachfront property with a large house, a parked bus, and a rocky foreground.

7. Seabreeze Escape WF RV Lot 489

Seabreeze Escape WF RV Lot 489
Cudjoe Key
$251 nightly
$270 total
Sep 18 - Sep 19
Total with taxes and fees
Seabreeze Escape WF RV Lot 489
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.

8. 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
Sep 18 - Sep 19
Total with taxes and fees
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
A waterfront property with a concrete dock extending into calm water, a white building with a covered porch, and a palm tree.
An electrical box with warning labels and a view of a marina with boats and palm trees.
A large, two-story house with a balcony, a patio area with chairs, and a view of the water.
A coastal residential area with white houses, palm trees, and a clear blue sky.

9. Venture Out RV lot 223

Venture Out RV lot 223
Cudjoe key
$220 nightly
$233 total
Sep 18 - Sep 19
Total with taxes and fees
Venture Out RV lot 223
A resort with a swimming pool, beach area, and marina.
A marina with several white mobile homes, a swimming pool, and a trailer.
A coastal residential area with houses, a marina, and a flag.

10. Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
Cudjoe Key
$474 nightly
$526 total
Sep 18 - Sep 19
Total with taxes and fees
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
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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

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

10/10 Excellent
"This is the second year we have stayed here for our annual girl's trip. Everything was as great as it was last year. We plan on staying again next year."
Amanda 7-night trip
Posted less than an hour ago
Hyatt Vacation Club at Windward Pointe, Key West
Ibis Bay Beach Resort

Ibis Bay Beach Resort

10/10 Excellent
"Had a great time here."
Stephanie 2-night trip
Posted 19 hours ago
Ibis Bay Beach Resort
Hampton Inn Key West FL

Hampton Inn Key West FL

10/10 Excellent
"Front desk associate was fantastic as well as the shuttle drivers . Free buffet breakfast kept me full until supper so that helped save money."
Carolyn 5-night trip
Posted 19 hours ago
Hampton Inn Key West FL
Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

8/10 Good
"It was a good experience"
John 1-night trip
Posted 19 hours ago
Hyatt Vacation Club at Beach House, Key West
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

10/10 Excellent
"It was a nice hotel. It was very clean quiet they had two Swimming Pool pools so that made it nice for the kids at one pool primarily and the adults at the other the walk-up bars were nice and close."
christopher 1-night trip
Posted 19 hours ago
Blue Flamingo Resort Key West
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

10/10 Excellent
"Our stay was pleasant except for the rooster in the Palm tree that woke me up at 3;45 AM in the morning."
James 4-night trip
Posted 1 day ago
Hilton Garden Inn Key West / The Keys Collection
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

10/10 Excellent
"Loved it, marina view room"
Bianca 4-night trip
Posted 2 days ago
The Perry Hotel & Marina Key West

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