Hotel with Pool in Cudjoe Key
Florida
United States of America
Hotel with Pool
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A sign reading "CUDJOE KEY" by a coastal road with a clear sky and calm sea.

Cudjoe Key Hotel with Pool

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your current months are November, 2026 and December, 2026.

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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 $$$ NOV./DEC. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

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

Cudjoe Key

9.6 out of 10, Exceptional, (99 reviews)

9.6/10

Exceptional

(99 reviews)

The price is HK$1,561

HK$1,561

HK$3,862 total

includes taxes & fees

21 Nov - 22 Nov

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

A resort with a swimming pool, beach area, and marina.

A covered outdoor seating area with white chairs and tables, overlooking turquoise waters and distant islands.

A spacious living room with a large TV, comfortable seating, a wooden cabinet, and a view of the sea through large windows.

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

2. Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

Cudjoe Key

9.8 out of 10, Exceptional, (148 reviews)

9.8/10

Exceptional

(148 reviews)

The price is HK$2,966

HK$2,966

HK$5,499 total

includes taxes & fees

13 Nov - 14 Nov

Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

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

A covered outdoor area with a grill, wicker furniture, and a table with drinks, overlooking the sea.

A beachfront property with a large house featuring a balcony and a covered patio area.

A balcony with wicker furniture overlooking turquoise waters and a distant island.

3. Caribbean Blue #517 Oceanfront Retreat with Dock, Pool & Stunning Views

Caribbean Blue #517 Oceanfront Retreat with Dock, Pool & Stunning Views

Cudjoe Key

9.8 out of 10, Exceptional, (25 reviews)

9.8/10

Exceptional

(25 reviews)

The price is HK$3,188

HK$3,188

HK$6,237 total

includes taxes & fees

14 Nov - 15 Nov

Caribbean Blue #517 Oceanfront Retreat with Dock, Pool & Stunning Views

A covered outdoor seating area with turquoise Adirondack chairs and a small round table, overlooking a beach with palm trees and a pier.

A living room with a sofa, chairs, a coffee table, a TV, and large windows overlooking the ocean.

4. Post Card Point #319 - Ocean Views!

Post Card Point #319 - Ocean Views!

Cudjoe Key

10.0 out of 10, Exceptional, (56 reviews)

10/10

Exceptional

(56 reviews)

The price is HK$2,892

HK$2,892

HK$5,881 total

includes taxes & fees

8 Nov - 9 Nov

Post Card Point #319 - Ocean Views!

A view from a balcony overlooking a beach with a clear sky and calm sea.

A kitchen with a view of the sea, a dining table set with plates, and a blue cabinet.

A spacious living area with a view of the ocean, a dining area with a kitchen, and a ceiling fan.

5. Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

Cudjoe Key

10.0 out of 10, Exceptional, (9 reviews)

10/10

Exceptional

(9 reviews)

The price is HK$3,522

HK$3,522

HK$6,164 total

includes taxes & fees

14 Nov - 15 Nov

Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

A living room with a sofa, armchair, TV, and a view of the outdoors.

6. 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

8.8 out of 10, Excellent, (11 reviews)

8.8/10

Excellent

(11 reviews)

The price is HK$1,483

HK$1,483

HK$3,721 total

includes taxes & fees

8 Nov - 9 Nov

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

A swimming pool with palm trees and a cloudy sky.

A covered outdoor deck with a sofa and table, overlooking a marina with boats and palm trees.

A modern living room with a ceiling fan, a sofa, a coffee table, and a TV mounted on the wall.

A modern kitchen with white cabinetry, stainless steel appliances, and a wooden floor.

7. Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath

Cudjoe Key

8.8 out of 10, Excellent, (110 reviews)

8.8/10

Excellent

(110 reviews)

The price is HK$2,236

HK$2,236

HK$4,131 total

includes taxes & fees

14 Nov - 15 Nov

Canal front, dockage, 2 bedroom, 2 bath

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

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

9.4 out of 10, Exceptional, (18 reviews)

9.4/10

Exceptional

(18 reviews)

The price is HK$1,409

HK$1,409

HK$3,630 total

includes taxes & fees

8 Nov - 9 Nov

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

A waterfront property with a pool, a covered outdoor area, and a mobile home labeled 'Premier.'

9. 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

9.6 out of 10, Exceptional, (5 reviews)

9.6/10

Exceptional

(5 reviews)

The price is HK$1,483

HK$1,483

HK$3,745 total

includes taxes & fees

8 Nov - 9 Nov

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

A pool with a view of the ocean, surrounded by palm trees and a white fence.

A wooden deck with a white railing, a house with a grey roof, and a tall palm tree in the background.

A staircase leading to a living area with a sofa, coffee table, and a window with blinds.

A gated residential complex with multiple two-story houses, a central driveway, and palm trees.

10. 105 - Newly renovated house Oceanside and Pool

105 - Newly renovated house Oceanside and Pool

Cudjoe Key

The price is HK$2,524

HK$2,524

HK$5,984 total

includes taxes & fees

6 Dec - 7 Dec

105 - Newly renovated house Oceanside and Pool

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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

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5 Star Hotels in Melody Key
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Robbie's
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Big Pine Key Holidays
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Visit Cow Key
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Fort East Martello Museum and Gallery
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Boca Chica Nude Beach
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Visit Stock Island
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Guerin Rental Cars in Lower Florida Keys
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Things to do in Ramrod Key
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Cudjoe Key Hotel with Pool

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Cudjoe Key hotels with a pool

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

2. Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

3. Caribbean Blue #517 Oceanfront Retreat with Dock, Pool & Stunning Views

4. Post Card Point #319 - Ocean Views!

5. Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

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

7. Canal front, dockage, 2 bedroom, 2 bath

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

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

10. 105 - Newly renovated house Oceanside and Pool

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

Explore a world of travel with Expedia