Cudjoe Key Hotels with Pool, Summerland Key: Cudjoe Key Hotel Guide

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

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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 balcony with a view of neighboring houses, a street, and a clear sky.

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

Cudjoe Key

€371

includes taxes & fees

4 Oct - 5 Oct

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

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

Cudjoe Key

€370

includes taxes & fees

15 Oct - 16 Oct

A kitchen with white cabinets, a stove, and a dining area with chairs and a table.

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

Cudjoe Key

€407

includes taxes & fees

15 Oct - 16 Oct

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.

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

Cudjoe Key

€397

includes taxes & fees

15 Oct - 16 Oct

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

Cudjoe Key

€424

includes taxes & fees

15 Oct - 16 Oct

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

Cudjoe Key

€528

includes taxes & fees

6 Oct - 7 Oct

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

Cudjoe Key

€436

includes taxes & fees

15 Oct - 16 Oct

A marina with boats docked, a clear sky, and a calm waterway.

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

Cudjoe Key

€454

includes taxes & fees

15 Oct - 16 Oct

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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

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent

"Great shuttle service"

Beachside Resort & Residences

10/10 Excellent

"Good"

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 …"

The Perry Hotel & Marina Key West

10/10 Excellent

"Hotel was great. All of the staff were friendly and accommodating"

Hyatt Vacation Club at Windward Pointe, Key West

10/10 Excellent

"We would definitely stay again, it was a beautiful resort.."

Hyatt Vacation Club at Beach House, Key West

10/10 Excellent

"Fantastic"

Hilton Garden Inn Key West / The Keys Collection

8/10 Good

"Thank you"

Room 1

Change your mind

Treat yourself

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Check availability on Cudjoe Key Hotels with Pool

Our top choices for Cudjoe Key hotels with a pool

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

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

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

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

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

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

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

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

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

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

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

Top Cudjoe Key Hotel Reviews