Cudjoe Key Holiday Rentals, Summerland Key: Private House Rentals

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

A two-story beachfront house with a balcony, a covered outdoor seating area, and a small boat dock.

A bedroom with a large bed, a ceiling fan, and a balcony with a view of greenery.

A residential property with a swimming pool, a covered patio, and a view of the ocean.

A concrete pathway flanked by lush green foliage, leading to a shaded area.

1. Atlantic View Luxury Villa with Pool

Summerland Key

Preetam

฿17,367

฿32,751 total

includes taxes & fees

4 Oct - 5 Oct

A waterfront building with a flat roof, large windows, and a balcony.

A beachside dining area with thatched umbrellas, white plastic chairs, and tables.

A corridor lined with trees and potted plants, leading to a building with a white exterior and windows.

A swimming pool with a surrounding deck, palm trees, and lounge chairs.

2. Sugar Loaf Lodge

Summerland Key

Richard

฿3,322

฿3,738 total

includes taxes & fees

4 Oct - 5 Oct

A rustic wooden structure with a thatched roof, multiple tables and chairs, and flags hanging from the ceiling.

A spacious indoor dining area with multiple tables and chairs, ceiling fans, and a bar area.

A sign for Looe Key Reef Resort's tiki bar, surrounded by palm trees and a thatched-roof structure.

A canal with boats docked on both sides, surrounded by lush greenery and trees.

3. Looe Key Reef Resort

Summerland Key

Stephen

฿3,386

฿3,809 total

includes taxes & fees

5 Oct - 6 Oct

A wooden deck with a railing, wicker chairs, and a view of greenery.

A modern kitchen with a large island, white cabinetry, and three wicker bar stools.

A two-story house with a balcony and a staircase leading to the upper level.

A modern bedroom with a large bed, two windows, a ceiling fan, and a green bench.

4. Starlight Serenity - Hideaway w Stunning Views

Summerland Key

max

฿7,808

฿21,035 total

includes taxes & fees

5 Oct - 6 Oct

A white building with a covered patio area, surrounded by palm trees and a view of the ocean.

A sunset view with a thatched structure and a palm tree by a calm body of water.

Beach chairs and a blue umbrella on a sandy shore with a calm body of water and a palm tree in the background.

A dining area with a table and chairs, a ceiling fan, a television, and a window with a view of the outdoors.

5. Parmer's Resort

Summerland Key

Mireya

฿4,250

฿5,877 total

includes taxes & fees

1 Nov - 2 Nov

A cozy room with a brown leather sofa, a white table, and a ceiling fan.

A white building with a sloped roof, a balcony with blue chairs, and a yellow bird sculpture on the roof.

A row of houseboats docked at a marina with clear reflections in the water.

A floating houseboat with a covered deck and seating area, docked at a marina.

6. Old Wooden Bridge Resort and Marina

Punta Brisa

Daisybel

฿4,500

฿9,782 total

includes taxes & fees

4 Oct - 5 Oct

A pool area with lounge chairs and umbrellas, surrounded by palm trees.

A modern office space with a reception desk, computer, and seating area.

A wooden outdoor dining table set with glassware, candles, and lanterns, surrounded by lush greenery.

An outdoor patio area with tables and chairs, a bar area with a counter and bar stools, and a TV mounted on the wall.

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

New Town

Patricia

฿4,329

฿5,814 total

includes taxes & fees

4 Oct - 5 Oct

A pool area with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.

A hotel room with a balcony, a bed, a desk, and two chairs.

A hotel room with a large bed, a TV mounted on a wooden cabinet, and a balcony with a view of palm trees.

A modern kitchen with a marble island, wooden cabinets, and pendant lighting.

8. Hampton Inn Key West FL

Key West

Jaycie

฿5,104

฿5,742 total

includes taxes & fees

7 Oct - 8 Oct

A clear swimming pool with lounge chairs and gazebos, surrounded by 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.

A hotel with a central courtyard, palm trees, and a fountain.

9. DoubleTree Resort by Hilton Grand Key - Key West

Key West

Nancy

฿4,134

฿5,784 total

includes taxes & fees

11 Oct - 12 Oct

A marina with boats docked, a pool area, and a building with a white facade.

A breakfast setting with a table, chairs, a vase with flowers, and a city view.

A covered outdoor seating area with tables and chairs, overlooking a marina with boats.

A clear view of turquoise ocean water and a blue sky with clouds.

10. Hilton Key West Resort & Marina

Stock Island

Molly

฿4,238

฿6,731 total

includes taxes & fees

12 Oct - 13 Oct

Two wooden Adirondack chairs on a sandy beach with a view of the sea and a sailboat in the distance.

A spacious living area with a large window, a dining table, and comfortable seating.

A wooden deck with two wooden chairs and a small table, surrounded by white railings and palm trees.

A two-story building with a balcony, arched windows, and a green roof.

11. Hyatt Vacation Club at Beach House, Key West

Key West

Rachel

฿6,983

฿9,366 total

includes taxes & fees

28 Oct - 29 Oct

A balcony with wicker furniture, a view of the sea, and a spiral staircase.

A beach with palm trees, clear blue water, and a pier extending into the sea.

A spacious lobby with a marble floor, leather sofas, and large potted plants.

A modern dining area with a glass table, four chairs, and a ceiling fan.

12. Beachside Resort & Residences

Key West

James

฿2,929

฿6,505 total

includes taxes & fees

4 Oct - 5 Oct

A pool area with lounge chairs and palm trees, surrounded by boats and a sunset in the background.

A balcony with a wooden table and chairs, overlooking a swimming pool and palm trees.

A restaurant with wooden tables and chairs, a counter with seafood signs, and large windows.

A marina with boats docked, a swimming pool, and palm trees.

13. The Perry Hotel & Marina Key West

Stock Island

Jade

฿3,911

฿6,451 total

includes taxes & fees

26 Oct - 27 Oct

A dining table with plates of food, a drink, and a view of a pool and palm trees.

A hotel room with a bed, a TV, a coffee table, a sofa, and a view of the ocean.

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.

14. Margaritaville Beach House Key West

Key West

TRICIA LYNN

฿7,014

฿10,008 total

includes taxes & fees

4 Oct - 5 Oct

A couple holding hands in a tropical setting with palm trees and greenery.

A modern cafe with a wooden counter, seating area, and shelves stocked with beverages.

A spacious living area with a sofa, chairs, a coffee table, and a foosball table. Large windows offer a view of the outdoor area.

15. Blue Flamingo Resort Key West

New Town

Esteban

฿3,965

฿6,348 total

includes taxes & fees

4 Oct - 5 Oct

A hammock in a garden with a wooden pergola, palm trees, and a view of the ocean.

A swimming pool surrounded by palm trees and lounge chairs, with a clear view of the ocean in the background.

A two-story building with a central entrance, surrounded by palm trees and a wooden walkway.

A beach volleyball court with a net, surrounded by palm trees and a hotel in the background.

16. Hyatt Vacation Club at Windward Pointe, Key West

Key West

Tina

฿6,983

฿9,366 total

includes taxes & fees

26 Oct - 27 Oct

A wooden boardwalk with a palm tree and lamp post, leading to a waterfront.

A pool area with lounge chairs, palm trees, and a building with a tiled roof.

A covered outdoor area with wooden tables and chairs, a view of the water, and a wooden deck with railings.

A modern restaurant with a wooden counter, seating area, and large windows.

17. Courtyard by Marriott Key West Waterfront

Northside Resort

Everton

฿6,478

฿7,288 total

includes taxes & fees

26 Oct - 27 Oct

A wooden archway leading to a pool area surrounded by lush tropical vegetation.

A beach with palm trees, a sandy shore, and a calm sea under a clear sky.

A beach with palm trees, lounge chairs, and umbrellas.

A large, two-story building with a symmetrical facade, a central entrance with a double door, and a balcony on the upper floor.

18. Parrot Key Hotel & Villas

Northside Resort

Anthony

฿4,430

฿6,909 total

includes taxes & fees

12 Oct - 13 Oct

A swimming pool with lounge chairs and palm trees.

A covered outdoor seating area with a central bar, patterned chairs, and a decorative sign.

A bar area with a wooden counter, bar stools, and a sign that reads 'So we BEATON.'

19. Hilton Garden Inn Key West / The Keys Collection

New Town

Walt

฿3,751

฿5,163 total

includes taxes & fees

8 Oct - 9 Oct

A hotel room with a bed, a view of the beach, a hammock, and beach chairs.

A marina with boats docked, a beach resort building, and palm trees.

A pool area with blue lounge chairs, a hot tub, and a covered seating area.

A beachfront restaurant with outdoor seating, a seafood sign, and a market sign.

20. Ibis Bay Beach Resort

Northside Resort

Stephanie

฿4,274

฿5,891 total

includes taxes & fees

4 Oct - 5 Oct

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Learn more about Cudjoe Key

Venture to Florida Keys Beaches—just one of the popular sights around Cudjoe Key, a city also known for cycling trails and boating.

See all hotels in Cudjoe Key

A sign reading "CUDJOE KEY" by a coastal road with a clear sky and calm sea.

Top Cudjoe Key Hotel Reviews

The Laureate Key West

10/10 Excellent

"I really appreciate this hôtel, my wife and my kids was very happy.... Great staff!"

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent

"I enjoyed my stay. It was a very nice place. I would stay again"

Blue Flamingo Resort Key West

10/10 Excellent

"Registration staff very personable. Constant text to check if all is good or need anything."

Hilton Garden Inn Key West / The Keys Collection

10/10 Excellent

"I left several rings when I checked out. The staff called me and held them at the front desk. These rings were worth quite a lot of money. I am so thankful and grateful that they did this."

The Perry Hotel & Marina Key West

10/10 Excellent

"The whole experience was fantastic. I wouldn't stay anywhere else!"

Hilton Key West Resort & Marina

10/10 Excellent

"This was our second time to stay here and this place never disappoints. Staff is wonderful too"

Hyatt Vacation Club at Beach House, Key West

8/10 Good

"The room was beautiful and spacious. I was disappointed by such a big beautiful bathroom that still had black mold spots on floor tile even after the tile was dry. It was surprising. Also, disappointing that the balconies were closed and then the pool was closed our last day. Even though it rained, there were parts of the day it didn’t. All in all it was a nice stay, but wasn’t worth the money."

Sugarloaf Key Hotel at KOA Resort

10/10 Excellent

"Room was clean, we used the pool, hot tub, marina boat rental, bar, store and the beach area. Everything was very nice. It’s a short ride to Bahia Honda beaches and Key West. The bar, marina and store were all very nice and useful."

Hampton Inn Key West FL

10/10 Excellent

"Wonderful"

More cheap stays in Cudjoe Key

Sugar Loaf Lodge

17001 Overseas Hwy Summerland Key FL

฿3,322

฿3,738 total

4 Oct - 5 Oct

includes taxes & fees

Looe Key Reef Resort

27340 Overseas Highway Summerland Key FL

฿3,386

฿3,809 total

5 Oct - 6 Oct

includes taxes & fees

7.8/10 Good! (1,001 reviews)

Hampton Inn Key West FL

3755 S Roosevelt Blvd Key West FL

฿5,104

฿5,742 total

7 Oct - 8 Oct

includes taxes & fees

9/10 Wonderful! (1,541 reviews)

Parmer's Resort

565 Barry Avenue Summerland Key FL

฿4,250

฿5,877 total

1 Nov - 2 Nov

includes taxes & fees

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd Key West FL

฿4,274

฿5,891 total

4 Oct - 5 Oct

includes taxes & fees

Old Wooden Bridge Resort and Marina

1791 Bogie Drive Big Pine Key FL

฿4,500

฿9,782 total

4 Oct - 5 Oct

includes taxes & fees

8.6/10 Excellent! (373 reviews)

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Find hotels in Cudjoe Key, FL from ฿3,738

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Cudjoe Key

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Cudjoe Key hotels

1. Atlantic View Luxury Villa with Pool

2. Sugar Loaf Lodge

3. Looe Key Reef Resort

4. Starlight Serenity - Hideaway w Stunning Views

5. Parmer's Resort

6. Old Wooden Bridge Resort and Marina

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

8. Hampton Inn Key West FL

9. DoubleTree Resort by Hilton Grand Key - Key West

10. Hilton Key West Resort & Marina

11. Hyatt Vacation Club at Beach House, Key West

12. Beachside Resort & Residences

13. The Perry Hotel & Marina Key West

14. Margaritaville Beach House Key West

15. Blue Flamingo Resort Key West

16. Hyatt Vacation Club at Windward Pointe, Key West

17. Courtyard by Marriott Key West Waterfront

18. Parrot Key Hotel & Villas

19. Hilton Garden Inn Key West / The Keys Collection

20. Ibis Bay Beach Resort

Learn more about Cudjoe Key

Top Cudjoe Key Hotel Reviews

The Laureate Key West

DoubleTree Resort by Hilton Grand Key - Key West

Blue Flamingo Resort Key West

Hilton Garden Inn Key West / The Keys Collection

The Perry Hotel & Marina Key West

Hilton Key West Resort & Marina

Hyatt Vacation Club at Beach House, Key West

Sugarloaf Key Hotel at KOA Resort

Hampton Inn Key West FL

More cheap stays in Cudjoe Key

Sugar Loaf Lodge

Looe Key Reef Resort

Hampton Inn Key West FL

Parmer's Resort

Ibis Bay Beach Resort

Old Wooden Bridge Resort and Marina

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