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

Our top choices for Cudjoe Key hotels with a pool

A residential property with a swimming pool, a covered patio, and a view of the ocean.
A two-story building with a balcony, surrounded by tropical vegetation.
A bedroom with a bed, a ceiling fan, a balcony with a view, and a nightstand with a lamp.
A two-story beachfront house with a balcony, a covered outdoor seating area, and a small boat dock.

1. Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
Summerland Key
  • Private plunge pool paradise unfolds with Atlantic views and 7 outdoor oases for sun-drenched days.
NT$16,485
NT$31,089 total
includes taxes & fees
Oct 11 - Oct 12
Atlantic View Luxury Villa with Pool
A swimming pool with a surrounding deck, palm trees, and lounge chairs.
A corridor lined with trees and potted plants, leading to a building with a white exterior and windows.
A waterfront building with a flat roof, large windows, and a balcony.
A reception area with a wooden sculpture, a reception desk, a computer, and a television.

2. Sugar Loaf Lodge

Sugar Loaf Lodge
Summerland Key
  • Dive into paradise at this oceanfront retreat with heated pool, marina access, and tennis courts.
NT$3,791
NT$4,265 total
includes taxes & fees
Oct 8 - Oct 9
Sugar Loaf Lodge
A sunset view with a thatched structure and a palm tree by a calm body of water.
A white building with a covered patio area, surrounded by palm trees and a view of the ocean.
Beach chairs and a blue umbrella on a sandy shore with a calm body of water and a palm tree in the background.
A hotel room with a bed, a flat-screen TV, a small kitchenette, and a balcony with a view of palm trees and the ocean.

3. Parmer's Resort

Parmer's Resort
Summerland Key
  • Soak up sun and sea at this coastal oasis with a sparkling pool, private beach, and marina.
NT$4,054
NT$5,606 total
includes taxes & fees
Nov 1 - Nov 2
Parmer's Resort
A swimming pool with blue and white tiles, surrounded by lounge chairs and palm trees.
A rustic wooden structure with a thatched roof, multiple tables and chairs, and flags hanging from the ceiling.
A thatched-roof building with a sign for 'Look Reef Resort' and 'Tiki Bar'.
A sign for Looe Key Reef Resort's tiki bar, surrounded by palm trees and a thatched-roof structure.

4. Looe Key Reef Resort

Looe Key Reef Resort
Summerland Key
  • Sun-dappled pool paradise at Looe Key Reef Resort offers snorkeling adventures nearby.
NT$3,214
NT$3,616 total
includes taxes & fees
Oct 14 - Oct 15
Looe Key Reef Resort
A poolside area with two covered seating areas labeled "Sugarloaf" and "Boca Grande," surrounded by palm trees and a clear blue pool.
A hotel room with a large bed, a wooden nightstand, a desk, a chair, and a window with curtains.
An outdoor patio area with tables and chairs, a bar area with a counter and bar stools, and a TV mounted on the wall.
A modern office space with a reception desk, computer, and seating area.

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

Fairfield by Marriott Inn & Suites Key West at The Keys Collection
New Town
  • Float in a tranquil oasis at this Key West hotel, where the outdoor pool beckons after adventures along nearby hiking trails.
NT$4,109
NT$5,519 total
includes taxes & fees
Oct 4 - Oct 5
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
A fenced pool area with palm trees, a blue and white tiled walkway, and a sign indicating pool hours.
A white building with a sloped roof, a balcony with blue chairs, and a yellow bird sculpture on the roof.
A compact kitchen with wooden beams, a dining area with white chairs, and a TV mounted on the wall.
A floating houseboat with a covered deck and seating area, docked at a marina.

6. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
Punta Brisa
  • Soak in tropical views at the outdoor pool, then paddle away from this waterfront cottage with an onsite marina and private dock.
NT$6,195
NT$11,471 total
includes taxes & fees
Oct 3 - Oct 4
Old Wooden Bridge Resort and Marina
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.
A balcony with wicker furniture and a view of the ocean and palm trees.
A hotel room with a balcony, a bed, a desk, and two chairs.
Breakfast area

7. Hampton Inn Key West FL

Hampton Inn Key West FL
Key West
  • Splash into ocean-view paradise at this poolside haven with loungers, umbrellas, and refreshing cocktail service.
NT$5,275
NT$5,935 total
includes taxes & fees
Oct 6 - Oct 7
Hampton Inn Key West FL
A clear swimming pool with lounge chairs and gazebos, surrounded by palm trees.
An outdoor patio with tables and chairs, umbrellas, and palm trees.
A spacious living area with a high ceiling, a blue accent wall, and a wooden staircase.
A spacious indoor dining area with tables and chairs, ceiling fans, and large windows.

8. DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West
Key West
  • Splash into tropical paradise at this resort's cabana-lined pool with views and poolside cocktails.
NT$3,816
NT$5,373 total
includes taxes & fees
Oct 8 - Oct 9
DoubleTree Resort by Hilton Grand Key - Key West
A dining table with plates of food, a drink, and a view of a pool and palm trees.
A beach with a palm tree and two chairs.
A hotel entrance with a palm tree-lined driveway, a vintage car, and a metal canopy structure.
A person standing by a window overlooking a beach with palm trees and the ocean.

9. Margaritaville Beach House Key West

Margaritaville Beach House Key West
Key West
  • Float in serene waters at this sun-soaked poolside paradise with direct beach access and friendly round-the-clock service.
NT$6,658
NT$9,500 total
includes taxes & fees
Oct 4 - Oct 5
Margaritaville Beach House Key West
A pool area with lounge chairs, palm trees, and a building with a tiled roof.
A modern restaurant with a wooden counter, seating area, and large windows.
A wooden boardwalk with a palm tree and lamp post, leading to a waterfront.
A covered outdoor area with wooden tables and chairs, a view of the water, and a wooden deck with railings.

10. Courtyard by Marriott Key West Waterfront

Courtyard by Marriott Key West Waterfront
Northside Resort
  • Savor the sun in this poolside paradise with tropical gardens and a relaxing hot tub.
NT$6,179
NT$6,952 total
includes taxes & fees
Oct 26 - Oct 27
Courtyard by Marriott Key West Waterfront
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

DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent
"Great shuttle service"
Eric 1-night trip
Posted 12 hours ago
DoubleTree Resort by Hilton Grand Key - Key West
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

8/10 Good
"Valet parking obligatoire ce qui était pour nous plutôt une nuisance qu’un avantage car nous sortions souvent visiter les alentours! Nous ne pouvions pas apporter de boissons alcoolisé au bord de la piscine il fallait les acheter directement au bar de piscine …"
Alexandre 1-night trip
Posted 22 hours ago
Parrot Key Hotel & Villas
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

10/10 Excellent
"Hotel was great. All of the staff were friendly and accommodating"
Kellie 1-night trip
Posted 1 day ago
The Perry Hotel & Marina Key West
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 2 days 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 2 days ago
Hyatt Vacation Club at Beach House, Key West
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 4 days ago
Hilton Garden Inn Key West / The Keys Collection
Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina

10/10 Excellent
"Best stop over before going to Key west. We enjoyed here a lot, parking our trailer was never a problem."
Daisybel 2-night trip
Posted 8 days ago
Old Wooden Bridge Resort and Marina

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