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

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.

1. Atlantic View Luxury Villa with Pool

Summerland Key

Preetam

฿17,463

฿32,933 total

includes taxes & fees

15 Nov - 16 Nov

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.

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.

2. Sugar Loaf Lodge

Summerland Key

Mariia

฿4,018

฿4,520 total

includes taxes & fees

26 Oct - 27 Oct

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

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

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

A thatched-roof building with a sign for 'Look Reef Resort' and 'Tiki Bar'.

3. Looe Key Reef Resort

Summerland Key

Stephen

฿4,895

฿5,507 total

includes taxes & fees

26 Oct - 27 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.

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

A spacious living area with a flat-screen TV, a wooden coffee table, a sofa with colorful cushions, and a blue chair.

4. Parmer's Resort

Summerland Key

Mireya

฿4,525

฿6,192 total

includes taxes & fees

1 Nov - 2 Nov

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 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.

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

New Town

Jacob

฿3,700

฿5,112 total

includes taxes & fees

1 Nov - 2 Nov

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

A bar area with a thatched roof, wooden chairs, and a poolside view.

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

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

6. Hampton Inn Key West FL

Key West

Heylin

฿4,052

฿4,558 total

includes taxes & fees

25 Oct - 26 Oct

A spacious living area with a kitchen island, a staircase, and large windows offering a view of the outdoors.

A spacious living room with a flat-screen TV, two sofas, a coffee table, and large windows offering a view of the outdoors.

A wooden deck with a swing chair and a view of a lake.

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

7. Starlight Serenity - Hideaway w Stunning Views

Summerland Key

max

฿9,199

฿22,048 total

includes taxes & fees

27 Oct - 28 Oct

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

An outdoor bar area with a poolside view, featuring a bar counter, blue chairs, and a sign reading 'GUMBO LIMBO'.

A hotel room with a bed, a desk, a chair, a TV, and a balcony with a view of buildings.

A hotel with a central fountain, surrounded by palm trees and a well-maintained lawn.

8. DoubleTree Resort by Hilton Grand Key - Key West

Key West

Danee

฿4,007

฿5,648 total

includes taxes & fees

29 Oct - 30 Oct

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 person standing by a window overlooking a beach with palm trees and the ocean.

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

9. Margaritaville Beach House Key West

Key West

Siamak

฿7,390

฿10,447 total

includes taxes & fees

25 Oct - 26 Oct

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

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.

A compact kitchen with wooden beams, a dining area with white chairs, and a TV mounted on the wall.

10. Old Wooden Bridge Resort and Marina

Punta Brisa

Daisybel

฿3,007

฿8,128 total

includes taxes & fees

25 Oct - 26 Oct

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

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

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.

11. Hilton Key West Resort & Marina

Stock Island

Eric A

฿3,936

฿6,403 total

includes taxes & fees

28 Oct - 29 Oct

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

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

A hotel room with a large bed, a desk, a chair, a television, and a ceiling fan.

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

12. The Perry Hotel & Marina Key West

Stock Island

Jade

฿3,354

฿5,749 total

includes taxes & fees

16 Nov - 17 Nov

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

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

A hotel room with a bed, a sofa, a round table with a book, a window with a view, and a radiator.

13. Blue Flamingo Resort Key West

New Town

Jesus

฿3,918

฿6,306 total

includes taxes & fees

25 Oct - 26 Oct

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

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

A tall palm tree with a white building in the background.

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

14. Parrot Key Hotel & Villas

Northside Resort

Anthony

฿3,829

฿6,245 total

includes taxes & fees

25 Oct - 26 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 hotel room with a desk, two beds, a TV, a ceiling fan, and a balcony with curtains.

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

15. Courtyard by Marriott Key West Waterfront

Northside Resort

Patrick

฿5,365

฿6,036 total

includes taxes & fees

28 Oct - 29 Oct

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

A beachfront hotel with multiple colorful buildings, a pool area, and a boat dock.

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.

16. Ibis Bay Beach Resort

Northside Resort

Sebastian

฿4,352

฿5,985 total

includes taxes & fees

25 Oct - 26 Oct

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

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.

A swimming pool with lounge chairs and palm trees, overlooking a sunset over the water.

17. Beachside Resort & Residences

Key West

Deana

฿3,947

฿7,668 total

includes taxes & fees

25 Oct - 26 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 beach volleyball court with a net, surrounded by palm trees and a hotel in the background.

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

18. Hyatt Vacation Club at Windward Pointe, Key West

Key West

Leismy

฿6,533

฿8,869 total

includes taxes & fees

28 Oct - 29 Oct

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

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.

A poolside lounge area with a wicker chair, a straw hat, and a beach bag.

19. Hyatt Vacation Club at Beach House, Key West

Key West

Rachel

฿6,351

฿8,664 total

includes taxes & fees

26 Oct - 27 Oct

A swimming pool with lounge chairs and palm trees.

A modern living room with a sectional sofa, a small round table, and a potted plant.

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

20. Hilton Garden Inn Key West / The Keys Collection

New Town

Eli

฿3,777

฿5,199 total

includes taxes & fees

27 Oct - 28 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

Hilton Key West Resort & Marina

8/10 Good

"Construction underway at the hotel site. Staff and room were fine. Beautiful view."

Sugarloaf Key Hotel at KOA Resort

10/10 Excellent

"Excellent property !"

Hilton Garden Inn Key West / The Keys Collection

10/10 Excellent

"Room was very comfortable, staff was very helpful and breakfast was good"

Havana Cabana at Key West

10/10 Excellent

"We had an excellent stay! The room was clean, close to the pool, and even though we were near the action we did not have a noise issue. The staff was so helpful, friendly, and professional. We also appreciated the shuttles , way better than having to pay the other expensive car services. I would definitely book again with them!"

Margaritaville Beach House Key West

8/10 Good

"Checkin was ok, staff were ok. Room was ok . Main bathroom sink was blocked and ensuite door was broken/off the tracks. Said they would look at it. Directly across the road from the beach. Free shuttle to and from Old Town. Very basic hotel for the price"

Blue Flamingo Resort Key West

10/10 Excellent

"Loved this hotel! Hourly shuttle to town, wish it was later then 10 pm though. Staff very nice and they celebrated my son’s birthday with champagne and snacks in our room!"

Beachside Resort & Residences

10/10 Excellent

"Loved the place. Will definitely be back in the future with the family."

Parrot Key Hotel & Villas

10/10 Excellent

"Parrot Key Hotel & Villas is the place to stay if you are planning a family trip to Key West on a reasonable budget.The rooms are spacious and very clean. Everybody is nice, we had no complaints. The restaurant is under construction at this time but in a few months I believe it will be up and running."

Parmer's Resort

10/10 Excellent

"All Aspects"

More cheap stays in Cudjoe Key

Sugar Loaf Lodge

17001 Overseas Hwy Summerland Key FL

฿4,018

฿4,520 total

26 Oct - 27 Oct

includes taxes & fees

8.2/10 Very good! (1,000 reviews)

Hampton Inn Key West FL

3755 S Roosevelt Blvd Key West FL

฿4,052

฿4,558 total

25 Oct - 26 Oct

includes taxes & fees

Looe Key Reef Resort

27340 Overseas Highway Summerland Key FL

฿4,895

฿5,507 total

26 Oct - 27 Oct

includes taxes & fees

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd Key West FL

฿4,352

฿5,985 total

25 Oct - 26 Oct

includes taxes & fees

Parmer's Resort

565 Barry Avenue Summerland Key FL

฿4,525

฿6,192 total

1 Nov - 2 Nov

includes taxes & fees

9/10 Wonderful! (1,000 reviews)

Old Wooden Bridge Resort and Marina

1791 Bogie Drive Big Pine Key FL

฿3,007

฿8,128 total

25 Oct - 26 Oct

includes taxes & fees

8.6/10 Excellent! (376 reviews)

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Find hotels in Cudjoe Key, FL from ฿4,520

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. Parmer's Resort

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

6. Hampton Inn Key West FL

7. Starlight Serenity - Hideaway w Stunning Views

8. DoubleTree Resort by Hilton Grand Key - Key West

9. Margaritaville Beach House Key West

10. Old Wooden Bridge Resort and Marina

11. Hilton Key West Resort & Marina

12. The Perry Hotel & Marina Key West

13. Blue Flamingo Resort Key West

14. Parrot Key Hotel & Villas

15. Courtyard by Marriott Key West Waterfront

16. Ibis Bay Beach Resort

17. Beachside Resort & Residences

18. Hyatt Vacation Club at Windward Pointe, Key West

19. Hyatt Vacation Club at Beach House, Key West

20. Hilton Garden Inn Key West / The Keys Collection

Learn more about Cudjoe Key

Top Cudjoe Key Hotel Reviews

Hilton Key West Resort & Marina

Sugarloaf Key Hotel at KOA Resort

Hilton Garden Inn Key West / The Keys Collection

Havana Cabana at Key West

Margaritaville Beach House Key West

Blue Flamingo Resort Key West

Beachside Resort & Residences

Parrot Key Hotel & Villas

Parmer's Resort

More cheap stays in Cudjoe Key

Sugar Loaf Lodge

Hampton Inn Key West FL

Looe Key Reef Resort

Ibis Bay Beach Resort

Parmer's Resort

Old Wooden Bridge Resort and Marina

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