Fleming Key Holiday Rentals, Key West: Private House Rentals

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Our top choices for Fleming Key hotels

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

A beach wedding setup with white chairs, a wooden arch, and lanterns.

1. Hyatt Centric Key West Resort and Spa

Key West Historic District

yendy

6.264.554 ₫

8.860.704 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A hotel with a covered entrance, multiple balconies, and palm trees.

A restaurant interior with wooden beams, a bar area, and a colorful ceiling mural.

A room with a stone wall, a wooden bench, a cactus, and a framed painting.

A covered balcony with white Adirondack chairs and a small table with flowers, overlooking a turquoise sea and distant shoreline.

2. Opal Key Resort & Marina, Key West

Old Town Key West

Susan

6.732.446 ₫

8.597.776 ₫ total

includes taxes & fees

11 Oct - 12 Oct

A beach with a wooden pier, palm trees, and beach umbrellas.

An outdoor dining area with tables set for guests, overlooking a calm sea and a pier.

A modern bar area with a central island, white bar stools, and a view of the ocean.

An outdoor dining area with tables and chairs, overlooking the ocean.

3. The Reach Key West, Curio Collection by Hilton

Old Town Key West

Darlene

4.617.834 ₫

6.949.658 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A pool area with lounge chairs and a cabana.

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

A dining area with a glass table, clear glass bottles, a bowl of fruit, and a wicker chair.

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

4. Ocean Key Resort - A Noble House Resort

Key West Historic District

Patrick

8.148.627 ₫

11.271.586 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A wooden deck with wicker furniture and a glass balustrade overlooking a beach.

A resort with a pool leading to a beach, surrounded by palm trees and white buildings.

A beach with white lounge chairs and umbrellas, a sandy shore, and a calm sea under a partly cloudy sky.

A spacious lobby with green sofas, a coffee table, and a dining area.

5. Casa Marina Key West, Curio Collection by Hilton

Old Town Key West

Coni

5.612.105 ₫

8.068.212 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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

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

A covered outdoor seating area with a pool in the background.

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

6. Havana Cabana at Key West

New Town

Stephanie

3.665.154 ₫

5.772.877 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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

A tropical setting with palm trees and a building with a white facade and dark roof.

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.

7. The Marker Key West Harbor Resort

Key West Historic District

Keith

5.258.586 ₫

7.553.532 ₫ total

includes taxes & fees

26 Oct - 27 Oct

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.

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

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

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

New Town

Brian

3.251.849 ₫

4.389.281 ₫ total

includes taxes & fees

14 Oct - 15 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 tall palm tree with a white building in the background.

9. Parrot Key Hotel & Villas

Northside Resort

Anthony

3.037.442 ₫

4.907.855 ₫ total

includes taxes & fees

14 Oct - 15 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 hotel room with a bed, a sofa, a round table with a book, a window with a view, and a radiator.

10. Blue Flamingo Resort Key West

New Town

Esteban

3.069.537 ₫

4.914.604 ₫ total

includes taxes & fees

11 Oct - 12 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 bar area with a thatched roof, wooden chairs, and a poolside view.

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

11. Hampton Inn Key West FL

Key West

Jaycie

4.711.473 ₫

5.300.407 ₫ 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 person standing by a window overlooking a beach with palm trees and the ocean.

A hotel entrance with a palm tree-lined driveway, a vintage car, and a metal canopy structure.

12. Margaritaville Beach House Key West

Key West

James Joseph

5.432.746 ₫

7.752.094 ₫ total

includes taxes & fees

13 Oct - 14 Oct

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

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

An outdoor patio with tables and chairs, umbrellas, and palm trees.

A spacious living area with a high ceiling, a blue accent wall, and a wooden staircase.

13. DoubleTree Resort by Hilton Grand Key - Key West

Key West

Nancy

3.098.485 ₫

4.363.095 ₫ total

includes taxes & fees

14 Oct - 15 Oct

A beachfront hotel with a covered patio, palm trees, and a boat on the sand.

A balcony with a view of the ocean, a sofa, and a massage table.

A view through a white-framed window with a decorative white fence, leading to a tiled patio area with a round table.

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

14. Pier House Resort & Spa

Key West Historic District

Richard

8.632.607 ₫

11.524.764 ₫ total

includes taxes & fees

12 Oct - 13 Oct

A two-story building with a covered entrance, palm trees, and a bench outside.

A white picket fence, a wooden bench with cushions, and a concrete pathway surrounded by lush greenery.

A bright room with a staircase, two windows overlooking a pool area, and two wicker chairs with cushions.

A poolside area with lounge chairs, umbrellas, and a covered seating area with hanging lights.

15. Winslow's Bungalows - Key West Historic Inns

Old Town Key West

Mackenzie

5.196.000 ₫

7.160.867 ₫ total

includes taxes & fees

14 Oct - 15 Oct

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

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

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

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

16. The Perry Hotel & Marina Key West

Stock Island

Jade

2.872.245 ₫

4.815.796 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A multi-story hotel with a pink facade, multiple balconies, and a prominent 'LA CONCHA' sign.

A beach with clear turquoise water, snorkelers, and a large building in the background.

A spacious lobby with a checkered floor, a central seating area with wicker chairs, a large potted plant, and a staircase with a metal railing.

A modern hotel entrance with a black and white striped curtain, wicker furniture, potted plants, and a sign for the Autograph Collection.

17. La Concha Key West, Autograph Collection

Key West Historic District

THOMAS

5.689.620 ₫

7.277.647 ₫ total

includes taxes & fees

13 Oct - 14 Oct

A bottle of Marc's Reserve 12 FL. OZ. on a coaster with a metal table.

A patio area with white metal tables and chairs, surrounded by potted plants and palm trees.

A potted yellow orchid plant in a garden setting with a brick pathway, palm trees, and a white building in the background.

A pool with a lion head sculpture in the center.

18. Artist House Key West

Key West Historic District

NATHAN

4.687.498 ₫

5.273.663 ₫ total

includes taxes & fees

2 Nov - 3 Nov

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

A resort with a well-maintained lawn, palm trees, a pool area, 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.

19. Hyatt Vacation Club at Windward Pointe, Key West

Key West

Tina

5.408.832 ₫

7.254.665 ₫ total

includes taxes & fees

26 Oct - 27 Oct

A deck with sun loungers and a railing overlooking the sea.

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

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

A beachside hotel with rows of blue lounge chairs and white umbrellas, palm trees, and a clear blue sky.

20. Southernmost Beach Resort and Guesthouses

Old Town Key West

Krystle

3.800.874 ₫

6.175.900 ₫ total

includes taxes & fees

11 Oct - 12 Oct

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Top Fleming Key Hotel Reviews

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

10/10 Excellent

"This is an excellent property i every way. Staff are outstanding. The free shuttle to downtown every hour is a huge plus!"

Beachside Resort & Residences

10/10 Excellent

"We were extremely pleased with our room, the staff and the facilities. We had a 1 bedroom suite with an ocean view and it was all we could have hoped for. Our only minor issue was the availability of luggage carts could have been more accessible. Overall, an Outstanding property and stay."

Hilton Key West Resort & Marina

10/10 Excellent

"All was good"

Parrot Key Hotel & Villas

10/10 Excellent

"We had a beautiful room with a gorgeous view. The pillows were LOVELY! The pools were enjoyable and the food truck was great! It is a great place to stay and we will be back!"

The Perry Hotel & Marina Key West

10/10 Excellent

"Wonderful hotel, good food/restaurant on site, bar too. Great view of marina and pool on site. Will definitely go back. Staff was very helpful whenever we needed anything."

Pier House Resort & Spa

8/10 Good

"Guest BEWARE, didn't think there would be a surcharge, but there was. A total of $262. and no one said anything. When we checked in and the asked for a credit card, I asked why, they said for unexpectedly occurred charges, nothing about surcharges. So PLEASE beware"

Winslow's Bungalows - Key West Historic Inns

10/10 Excellent

"Felt like a resort. Everyone was helpful and amazing!"

Opal Key Resort & Marina, Key West

10/10 Excellent

"Overall, nice stay. Some of the rooms and hotel areas are showing some age, but the property appeared to be very clean. The location of the hotel is fantastic. Within walking distance of all that Duvall St. has to offer and a great coffee shop very close by. The hotel restaurant was fantastic and the room pricing is very reasonable. I would definitely stay at this property again."

Havana Cabana at Key West

10/10 Excellent

"Awesome pool, great service & very comfy beds. We will 100% stay there again. Highly recommend!"

More cheap stays in Fleming Key

Alexander Palms Court

715 South St Key West FL

3.684.650 ₫

4.145.524 ₫ total

11 Oct - 12 Oct

includes taxes & fees

9.4/10 Exceptional! (1,003 reviews)

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd Key West FL

3.306.436 ₫

4.558.306 ₫ total

11 Oct - 12 Oct

includes taxes & fees

Southwinds Motel

1321 Simonton Street Key West FL

3.725.967 ₫

5.069.011 ₫ total

12 Oct - 13 Oct

includes taxes & fees

8.6/10 Excellent! (1,390 reviews)

Hampton Inn Key West FL

3755 S Roosevelt Blvd Key West FL

4.711.473 ₫

5.300.407 ₫ total

26 Oct - 27 Oct

includes taxes & fees

9/10 Wonderful! (1,547 reviews)

Pegasus International Hotel

501 Southard Street Key West FL

3.732.027 ₫

5.513.768 ₫ total

12 Oct - 13 Oct

includes taxes & fees

Tranquility Guest House

302 Angela st Key West FL

2.897.083 ₫

5.569.435 ₫ total

14 Oct - 15 Oct

includes taxes & fees

Hotels in Fleming Key with star rating

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Find hotels in Fleming Key, FL from 4.091.261 ₫

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. Hyatt Centric Key West Resort and Spa

2. Opal Key Resort & Marina, Key West

3. The Reach Key West, Curio Collection by Hilton

4. Ocean Key Resort - A Noble House Resort

5. Casa Marina Key West, Curio Collection by Hilton

6. Havana Cabana at Key West

7. The Marker Key West Harbor Resort

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

9. Parrot Key Hotel & Villas

10. Blue Flamingo Resort Key West

11. Hampton Inn Key West FL

12. Margaritaville Beach House Key West

13. DoubleTree Resort by Hilton Grand Key - Key West

14. Pier House Resort & Spa

15. Winslow's Bungalows - Key West Historic Inns

16. The Perry Hotel & Marina Key West

17. La Concha Key West, Autograph Collection

18. Artist House Key West

19. Hyatt Vacation Club at Windward Pointe, Key West

20. Southernmost Beach Resort and Guesthouses

Top Fleming Key Hotel Reviews

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

Beachside Resort & Residences

Hilton Key West Resort & Marina

Parrot Key Hotel & Villas

The Perry Hotel & Marina Key West

Pier House Resort & Spa

Winslow's Bungalows - Key West Historic Inns

Opal Key Resort & Marina, Key West

Havana Cabana at Key West

More cheap stays in Fleming Key

Alexander Palms Court

Ibis Bay Beach Resort

Southwinds Motel

Hampton Inn Key West FL

Pegasus International Hotel

Tranquility Guest House

Hotels in Fleming Key with star rating

Explore a world of travel with Expedia

Go further with the Expedia app