Fleming Key Holiday Rentals, Key West: Private House Rentals

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Our top choices for Fleming Key hotels

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

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.

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

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

New Town

Brian

฿4,661

฿6,186 total

includes taxes & fees

14 Oct - 15 Oct

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

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

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.

2. Hampton Inn Key West FL

Key West

Andrew

฿5,684

฿6,394 total

includes taxes & fees

25 Oct - 26 Oct

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

A waterfront hotel with multiple balconies, a dock, and boats.

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.

3. Opal Key Resort & Marina, Key West

Old Town Key West

Susan

฿8,684

฿11,090 total

includes taxes & fees

18 Oct - 19 Oct

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

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

4. Hyatt Centric Key West Resort and Spa

Key West Historic District

Jennifer

฿7,971

฿11,313 total

includes taxes & fees

14 Oct - 15 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 modern living room with a sectional sofa, a small round table, and a potted plant.

5. Hilton Garden Inn Key West / The Keys Collection

New Town

Eli

฿4,117

฿5,578 total

includes taxes & fees

25 Oct - 26 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 tall palm tree with a white building in the background.

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

6. Parrot Key Hotel & Villas

Northside Resort

Anthony

฿4,271

฿6,735 total

includes taxes & fees

14 Oct - 15 Oct

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 exterior of the Silver Palms Inn with a two-story structure, a green awning over the entrance, and a palm tree to the right.

7. Silver Palms Inn & Historic Homes

Old Town Key West

sam

฿2,997

฿5,642 total

includes taxes & fees

25 Oct - 26 Oct

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

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.

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

8. Courtyard by Marriott Key West Waterfront

Northside Resort

Everton

฿6,147

฿6,915 total

includes taxes & fees

26 Oct - 27 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.

9. Blue Flamingo Resort Key West

New Town

Esteban

฿3,893

฿6,265 total

includes taxes & fees

14 Oct - 15 Oct

A pool area with lounge chairs and a cabana.

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

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

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

10. Ocean Key Resort - A Noble House Resort

Key West Historic District

Patrick

฿10,517

฿14,547 total

includes taxes & fees

26 Oct - 27 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 front door with purple shutters, a small porch, and a doormat with 'The Artist House Circa 1890' text.

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

11. Artist House Key West

Key West Historic District

Debbie

฿8,087

฿9,098 total

includes taxes & fees

2 Nov - 3 Nov

A balcony with a view of a pool area, palm trees, and outdoor seating.

A sign for Doubletree by Hilton Grand Key Resort surrounded by lush greenery and palm trees.

A conference room with a patterned carpet, multiple tables, chairs, and two chandeliers.

A large conference room with round tables, chairs, and a central carpeted area.

12. DoubleTree Resort by Hilton Grand Key - Key West

Key West

Nancy

฿4,278

฿5,948 total

includes taxes & fees

27 Oct - 28 Oct

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

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

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.

13. The Reach Key West, Curio Collection by Hilton

Old Town Key West

Darlene

฿5,390

฿8,327 total

includes taxes & fees

26 Oct - 27 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.

14. The Perry Hotel & Marina Key West

Stock Island

Jade

฿3,707

฿6,215 total

includes taxes & fees

27 Oct - 28 Oct

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

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

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

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

15. The Marker Key West Harbor Resort

Key West Historic District

Lynne

฿6,548

฿9,479 total

includes taxes & fees

25 Oct - 26 Oct

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 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.

16. Beachside Resort & Residences

Key West

Brenna

฿3,934

฿7,642 total

includes taxes & fees

14 Oct - 15 Oct

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 paved pathway lined with various plants and trees, leading to a building with a beige exterior.

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

17. Authors of Key West Guest House

Key West Historic District

Robbie

฿4,207

฿4,734 total

includes taxes & fees

14 Oct - 15 Oct

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

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

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.

18. Ibis Bay Beach Resort

Northside Resort

Andre

฿3,753

฿5,307 total

includes taxes & fees

14 Oct - 15 Oct

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

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

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.

19. Margaritaville Beach House Key West

Key West

Richard

฿7,008

฿10,000 total

includes taxes & fees

18 Oct - 19 Oct

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

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

A beachside spa with two massage tables under a canopy, overlooking the sea and a pier.

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

20. Casa Marina Key West, Curio Collection by Hilton

Old Town Key West

Rita

฿7,261

฿10,439 total

includes taxes & fees

25 Oct - 26 Oct

View all properties

Hotels recommended for families in Fleming Key

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

New Town

฿4,661

฿6,186 total

includes taxes & fees

14 Oct - 15 Oct

Hampton Inn Key West FL

Key West

฿5,684

฿6,394 total

includes taxes & fees

25 Oct - 26 Oct

Courtyard by Marriott Key West Waterfront

Northside Resort

฿6,147

฿6,915 total

includes taxes & fees

26 Oct - 27 Oct

Hilton Garden Inn Key West / The Keys Collection

New Town

฿4,117

฿5,578 total

includes taxes & fees

25 Oct - 26 Oct

Hyatt Centric Key West Resort and Spa

Key West Historic District

฿7,971

฿11,313 total

includes taxes & fees

14 Oct - 15 Oct

Ibis Bay Beach Resort

Northside Resort

฿3,753

฿5,307 total

includes taxes & fees

14 Oct - 15 Oct

DoubleTree Resort by Hilton Grand Key - Key West

Key West

฿4,278

฿5,948 total

includes taxes & fees

27 Oct - 28 Oct

Silver Palms Inn & Historic Homes

Old Town Key West

฿2,997

฿5,642 total

includes taxes & fees

25 Oct - 26 Oct

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Top Fleming Key Hotel Reviews

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent

"Staff was great"

Beachside Resort & Residences

10/10 Excellent

"Being near the pool was very convenient. There was no A/C in the gym, the walk down the stairs from the balcony to the pool was hazardous. There was no walkway, just rocks. The elevators closest to our apartment was out of order which caused us to walk quite a bit. The floors in the apartment were very dirty. We requested to have them cleaned. They sent someone up while we were gone and they cleaned the apartment however the floors were left untouched. They didn't clean them. We advised the front desk, they apologized but it was never corrected. The shuttle was definitely a plus but get there super early because if there are 12 people before you, you're not going. The pool is beautiful and very clean. The food at the pool side bar was very good. So a lot of plus' but unfortunately some misses. The people at the front desk were always very friendly."

Winslow's Bungalows - Key West Historic Inns

8/10 Good

"Le déjeuner, le service de bar et l’accueil était top. L’attitude des femmes de ménage et la propreté des entretiens dans la chambre étaient très ordinaire."

Parrot Key Hotel & Villas

10/10 Excellent

"We loved this resort! We will definitely be returning here in the future. Great location- not far from Duvall St but close enough that it’s only a 10 minute drive."

Havana Cabana at Key West

10/10 Excellent

"This was our second stay here. We love the low key vibe. The staff is always pleasant to deal with. The rooms are nice and the pool was well maintained. The food was great. All around great experience will be back again and again."

Hilton Key West Resort & Marina

10/10 Excellent

"Friendly Staff Nice Place"

Southernmost Beach Resort and Guesthouses

10/10 Excellent

"We went with 2 other couples 2nd year in a row at Southern Most, that should tell you how much we enjoyed it! Great location, food rooms were always cleaned."

Hilton Garden Inn Key West / The Keys Collection

8/10 Good

"Somewhat disappointed. Sink was stopped up on arrival, however it was repaired rather quickly. WiFi was non-existent. Room was very clean and staff was helpful. I would give it a 7 out of 10 for the price. I would stay again."

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

8/10 Good

"Not applicable."

More cheap stays in Fleming Key

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd Key West FL

฿3,753

฿5,307 total

14 Oct - 15 Oct

includes taxes & fees

Southwinds Motel

1321 Simonton Street Key West FL

฿4,661

฿6,375 total

26 Oct - 27 Oct

includes taxes & fees

8.6/10 Excellent! (1,385 reviews)

Hampton Inn Key West FL

3755 S Roosevelt Blvd Key West FL

฿5,684

฿6,394 total

25 Oct - 26 Oct

includes taxes & fees

Pegasus International Hotel

501 Southard Street Key West FL

฿4,402

฿6,655 total

14 Oct - 15 Oct

includes taxes & fees

8.2/10 Very good! (1,001 reviews)

Alexander Palms Court

715 South St Key West FL

฿6,693

฿7,530 total

14 Oct - 15 Oct

includes taxes & fees

9.4/10 Exceptional! (1,001 reviews)

Tranquility Guest House

302 Angela st Key West FL

฿4,685

฿8,260 total

14 Oct - 15 Oct

includes taxes & fees

9/10 Wonderful! (35 reviews)

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Book Hotels in Fleming Key on Expedia.com

Find hotels in Fleming Key, FL from ฿4,734

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

2. Hampton Inn Key West FL

3. Opal Key Resort & Marina, Key West

4. Hyatt Centric Key West Resort and Spa

5. Hilton Garden Inn Key West / The Keys Collection

6. Parrot Key Hotel & Villas

7. Silver Palms Inn & Historic Homes

8. Courtyard by Marriott Key West Waterfront

9. Blue Flamingo Resort Key West

10. Ocean Key Resort - A Noble House Resort

11. Artist House Key West

12. DoubleTree Resort by Hilton Grand Key - Key West

13. The Reach Key West, Curio Collection by Hilton

14. The Perry Hotel & Marina Key West

15. The Marker Key West Harbor Resort

16. Beachside Resort & Residences

17. Authors of Key West Guest House

18. Ibis Bay Beach Resort

19. Margaritaville Beach House Key West

20. Casa Marina Key West, Curio Collection by Hilton

Hotels recommended for families in Fleming Key

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

Hampton Inn Key West FL

Courtyard by Marriott Key West Waterfront

Hilton Garden Inn Key West / The Keys Collection

Hyatt Centric Key West Resort and Spa

Ibis Bay Beach Resort

DoubleTree Resort by Hilton Grand Key - Key West

Silver Palms Inn & Historic Homes

Top Fleming Key Hotel Reviews

DoubleTree Resort by Hilton Grand Key - Key West

Beachside Resort & Residences

Winslow's Bungalows - Key West Historic Inns

Parrot Key Hotel & Villas

Havana Cabana at Key West

Hilton Key West Resort & Marina

Southernmost Beach Resort and Guesthouses

Hilton Garden Inn Key West / The Keys Collection

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

More cheap stays in Fleming Key

Ibis Bay Beach Resort

Southwinds Motel

Hampton Inn Key West FL

Pegasus International Hotel

Alexander Palms Court

Tranquility Guest House

Explore a world of travel with Expedia

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