Book The Best Hotels in Fleming Key, FL for 2026 from CA $116 - Fully Refundable Options

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Our top choices for Fleming Key hotels

A swimming pool with water splashing, surrounded by palm trees and a building in the background.

A hotel with a pool, bicycles, and lush greenery.

A two-story yellow house with a porch, white railings, and green shutters.

The entrance to Silver Palms Inn with a reception desk, a seating area, and a glass door.

1. Silver Palms Inn & Historic Homes

Old Town Key West

Alexey

CA $111

CA $219 total

includes taxes & fees

Sep 16 - Sep 17

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

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

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

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

2. Ibis Bay Beach Resort

Northside Resort

Roland

CA $141

CA $203 total

includes taxes & fees

Sep 15 - Sep 16

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

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.

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

3. Parrot Key Hotel & Villas

Northside Resort

Anthony

CA $172

CA $273 total

includes taxes & fees

Sep 24 - Sep 25

A building with a white exterior, a large red awning, and a gated entrance.

A spacious kitchen with a dining area, large windows, and a view of the outdoors.

A small, enclosed porch with a chair and a table, surrounded by lush greenery and a white lattice fence.

A pool area with lounge chairs and a lifebuoy.

4. Authors of Key West Guest House

Key West Historic District

Idamis

CA $103

CA $116 total

includes taxes & fees

Sep 28 - Sep 29

A hotel with a swimming pool, balconies, and a view of the sea.

A marina with jet skis docked in front of a hotel with a dock and a boat in the background.

A spacious bar area with a wooden counter and green bar stools, a seating area with a sofa and chairs, and a dining area with a table set for two.

A balcony with a view of the ocean, a table, chairs, and a railing.

5. Hyatt Centric Key West Resort and Spa

Key West Historic District

yendy

CA $276

CA $407 total

includes taxes & fees

Sep 28 - Sep 29

A pool area with lounge chairs and a cabana.

A balcony with a table set for breakfast, overlooking the sea.

A waterfront hotel with a long pier, multiple balconies, and a view of the ocean.

A hotel room with a bed, a sofa, a desk with a computer, a chair, and a view of the sea through large windows.

6. Ocean Key Resort - A Noble House Resort

Key West Historic District

Brian

CA $305

CA $451 total

includes taxes & fees

Sep 28 - Sep 29

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

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

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

A hotel room with a desk, two beds, a TV, a ceiling fan, and a balcony with curtains.

7. Courtyard by Marriott Key West Waterfront

Northside Resort

Everton

CA $214

CA $240 total

includes taxes & fees

Sep 15 - Sep 16

A wooden deck with white railings, surrounded by lush greenery and a staircase leading to a building.

A hallway with a white door, a wooden bench, a blue sofa, and a staircase with a white railing.

A swimming pool with a mural of a dolphin and a butterfly, surrounded by lounge chairs and palm trees.

A lush garden with a variety of tropical plants and a paved walkway.

8. Duval House

Old Town Key West

Robert

CA $135

CA $181 total

includes taxes & fees

Sep 16 - Sep 17

A bedroom with a bed, bedside table, lamp, and a small kitchenette. There is a balcony with wicker chairs and a glass table.

A spacious living area with a gray sofa, wooden staircase, and a kitchen in the background.

A pool area with lounge chairs and umbrellas, surrounded by buildings with balconies and a clear blue sky.

A cozy cabin with a wooden interior, a bed, a TV, and a kitchenette.

9. Eden House

Key West Historic District

Erik

CA $142

CA $179 total

includes taxes & fees

Oct 11 - Oct 12

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.'

10. Hilton Garden Inn Key West / The Keys Collection

New Town

Marian

CA $145

CA $202 total

includes taxes & fees

Sep 22 - Sep 23

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

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.

A beach with a palm tree and two chairs.

11. Margaritaville Beach House Key West

Key West

TRICIA LYNN

CA $247

CA $365 total

includes taxes & fees

Sep 28 - Sep 29

A modern hotel room with a large bed, a nightstand, a bedside table, and a bathroom visible through an open door.

A reception area with a wooden herringbone wall, teal chairs, a wooden bench, and two framed sunset paintings.

A building with a sign reading "ALMOND Frog & Toad Inn" and a "VACANCY" sign below it.

A swimming pool with lounge chairs, surrounded by palm trees and greenery.

12. Almond Tree Inn Hotel - Adults Only

Old Town Key West

John

CA $213

CA $240 total

includes taxes & fees

Sep 20 - Sep 21

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

A hotel room with a large bed, a wooden nightstand, a desk, a chair, and a window with curtains.

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

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

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

New Town

Anais

CA $156

CA $215 total

includes taxes & fees

Sep 20 - Sep 21

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

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

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

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

14. Beachside Resort & Residences

Key West

Jerome

CA $121

CA $269 total

includes taxes & fees

Sep 15 - Sep 16

A large, white, two-story building with a balcony and a sign reading "The Marker Resort."

A covered outdoor area with a pool, palm trees, and lounge chairs.

A marina with various boats docked, including a green and white boat named 'Jolly Roger'.

A resort with a swimming pool, lounge chairs, umbrellas, and palm trees.

15. The Marker Key West Harbor Resort

Key West Historic District

Joelle

CA $262

CA $382 total

includes taxes & fees

Sep 22 - Sep 23

A room with a view of the beach and ocean, a bed with a white and blue blanket, and a small table with a potted plant.

A poolside area with lounge chairs and umbrellas, palm trees, and a view of the sea.

A beachside lounge with chairs and umbrellas, overlooking the ocean.

A beach scene with two people relaxing under a white umbrella, a palm tree, and a clear blue sky.

16. Southernmost Beach Resort and Guesthouses

Old Town Key West

Deaenna

CA $242

CA $374 total

includes taxes & fees

Sep 27 - Sep 28

A poolside area with lounge chairs, a staircase leading to a balcony, and a pool.

A dining area with round tables and wicker chairs, a ceiling fan, and a bar area in the background.

An outdoor patio with tables and chairs, surrounded by trees and a house.

A Southernmost Inn with a porch, a sign indicating vacancy, and a staircase leading to the entrance.

17. The Southernmost Inn - Adults Only

Old Town Key West

Ron

CA $93

CA $167 total

includes taxes & fees

Sep 15 - Sep 16

A swimming pool surrounded by palm trees and a natural rock formation.

A cozy room with wicker furniture, a glass coffee table, and a view of lush greenery outside.

A spacious lobby with a central seating area, two staircases, and multiple potted plants.

A bar setting with a bartender preparing a drink, a counter with various bottles, and a TV screen in the background.

18. Havana Cabana at Key West

New Town

Silvia

CA $153

CA $259 total

includes taxes & fees

Sep 28 - Sep 29

A modern hotel room with a white sofa, a zebra-patterned rug, and a large mirror above the sofa.

A spacious living room with a sofa, chairs, and a dining table. There are large windows with blinds, a door leading to a patio, and a ceiling with exposed beams.

A pool area with lounge chairs, a pool, and a building with a balcony and outdoor seating.

A narrow room with a bed, a potted plant, and a window with blinds.

19. Alexander's Guesthouse - Adult Exclusive

Old Town Key West

Justin

CA $124

CA $191 total

includes taxes & fees

Sep 15 - Sep 16

A covered porch with wicker furniture, potted plants, and a sign for the "Office" at the Palm Hotel.

A row of bicycles parked in front of a building with a white balcony and a palm tree.

A hotel with a white facade, multiple balconies, and lush tropical landscaping.

A compact kitchen with white cabinets, a microwave, and a small dining area with two wicker chairs.

20. The Palms Hotel

Old Town Key West

Zachary

CA $143

CA $192 total

includes taxes & fees

Sep 28 - Sep 29

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Top Fleming Key Hotel Reviews

Casa Marina Key West, Curio Collection by Hilton

10/10 Excellent

"The only problem I had was trying to get ahold of the front desk by phone. Always caught in a loop and was never answered so I had to go downstairs if I needed anything"

Havana Cabana at Key West

10/10 Excellent

"Excellent"

Beachside Resort & Residences

10/10 Excellent

"Pictures do NOT do this property justice. I have beeen ti all 50 states, 6 provinces in Canada and 14 countries and this was the best surprise ever"

Southernmost Beach Resort and Guesthouses

10/10 Excellent

"Pools were well maintained but crowded. Property was beautiful. Staff was helpful. Breakfast was very good."

Margaritaville Beach House Key West

8/10 Good

"The only beach on island is across the road and I love that about this location. Very small beach and not much to it, coming from Tampa we have better beaches. The location of hotel is 20-30 minutes away from the bars and restaurants. Good thing is they have a free shuttle running daily with helps a lot. If you drive parking is about $10 an hour anywhere in town. Down side of hotel is that it’s starting to show signs of wear and tear. Water pressure was low, but the room was clean and overall had a good weekend getaway."

Southwinds Motel

10/10 Excellent

"Excellent price. The location and parking were very convenient."

Blue Flamingo Resort Key West

8/10 Good

"The room was clean but small. It was hard for all of my family to move around in it. The cleaning staff was not friendly. The pool was clean but really warm. The breakfast that you could purchase was to expensive. $20 for an omelet is to much."

Hyatt Vacation Club at Windward Pointe, Key West

10/10 Excellent

"Beautiful property and rooms!!"

Hilton Garden Inn Key West / The Keys Collection

10/10 Excellent

"Good"

More cheap stays in Fleming Key

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd Key West FL

CA $141

CA $203 total

Sep 15 - Sep 16

includes taxes & fees

Hampton Inn Key West FL

3755 S Roosevelt Blvd Key West FL

CA $187

CA $210 total

Sep 22 - Sep 23

includes taxes & fees

Alexander Palms Court

715 South St Key West FL

CA $197

CA $221 total

Sep 15 - Sep 16

includes taxes & fees

9.4/10 Exceptional! (1,000 reviews)

Tranquility Guest House

302 Angela st Key West FL

CA $91

CA $226 total

Sep 16 - Sep 17

includes taxes & fees

Southwinds Motel

1321 Simonton Street Key West FL

CA $173

CA $241 total

Sep 16 - Sep 17

includes taxes & fees

8.6/10 Excellent! (1,375 reviews)

Pegasus International Hotel

501 Southard Street Key West FL

CA $176

CA $268 total

Sep 18 - Sep 19

includes taxes & fees

Hotels in Fleming Key with star rating

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Find hotels in Fleming Key, FL from CA $116

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Fleming Key

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Fleming Key hotels

1. Silver Palms Inn & Historic Homes

2. Ibis Bay Beach Resort

3. Parrot Key Hotel & Villas

4. Authors of Key West Guest House

5. Hyatt Centric Key West Resort and Spa

6. Ocean Key Resort - A Noble House Resort

7. Courtyard by Marriott Key West Waterfront

8. Duval House

9. Eden House

10. Hilton Garden Inn Key West / The Keys Collection

11. Margaritaville Beach House Key West

12. Almond Tree Inn Hotel - Adults Only

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

14. Beachside Resort & Residences

15. The Marker Key West Harbor Resort

16. Southernmost Beach Resort and Guesthouses

17. The Southernmost Inn - Adults Only

18. Havana Cabana at Key West

19. Alexander's Guesthouse - Adult Exclusive

20. The Palms Hotel

Top Fleming Key Hotel Reviews

Casa Marina Key West, Curio Collection by Hilton

Havana Cabana at Key West

Beachside Resort & Residences

Southernmost Beach Resort and Guesthouses

Margaritaville Beach House Key West

Southwinds Motel

Blue Flamingo Resort Key West

Hyatt Vacation Club at Windward Pointe, Key West

Hilton Garden Inn Key West / The Keys Collection

More cheap stays in Fleming Key

Ibis Bay Beach Resort

Hampton Inn Key West FL

Alexander Palms Court

Tranquility Guest House

Southwinds Motel

Pegasus International Hotel

Hotels in Fleming Key with star rating

Explore a world of travel with Expedia

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