Book The Best Hotels in Rockland Key for 2026 from CA $183 - Fully Refundable Options

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Our top choices for Rockland Key hotels

A hotel room with a balcony overlooking a marina and the ocean.

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

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

1. Hilton Key West Resort & Marina

Stock Island

Linda

CA $157

CA $259 total

includes taxes & fees

Sep 7 - Sep 8

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

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

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

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

2. Hampton Inn Key West FL

Key West

Christopher Lynn

CA $163

CA $183 total

includes taxes & fees

Aug 30 - Aug 31

A swimming pool with lounge chairs and palm trees.

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

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

3. Hilton Garden Inn Key West / The Keys Collection

New Town

Thomas

CA $151

CA $208 total

includes taxes & fees

Aug 30 - Aug 31

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 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.

4. Beachside Resort & Residences

Key West

JOSEPH

CA $142

CA $291 total

includes taxes & fees

Aug 25 - Aug 26

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

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

5. Hyatt Vacation Club at Beach House, Key West

Key West

Kailey

CA $276

CA $372 total

includes taxes & fees

Sep 19 - Sep 20

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

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

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

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

6. DoubleTree Resort by Hilton Grand Key - Key West

Key West

Jose

CA $157

CA $223 total

includes taxes & fees

Sep 1 - Sep 2

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

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

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

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

New Town

Marta

CA $160

CA $218 total

includes taxes & fees

Aug 30 - Aug 31

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 resort with a well-maintained lawn, palm trees, a pool area, and a view of the ocean.

8. Hyatt Vacation Club at Windward Pointe, Key West

Key West

Daina

CA $246

CA $338 total

includes taxes & fees

Aug 31 - Sep 1

A hotel with a large pool, multiple balconies, and palm trees.

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.

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

Sabrina

CA $156

CA $253 total

includes taxes & fees

Aug 25 - Aug 26

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

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.

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

10. Parrot Key Hotel & Villas

Northside Resort

Melvin

CA $191

CA $293 total

includes taxes & fees

Aug 30 - Aug 31

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

A marina with numerous yachts docked, surrounded by palm trees and a clear sky.

A marina with boats docked, a building with multiple floors, and palm trees in the background.

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

11. The Perry Hotel & Marina Key West

Stock Island

Boyan

CA $200

CA $310 total

includes taxes & fees

Sep 7 - Sep 8

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.

12. Ibis Bay Beach Resort

Northside Resort

Nicolas

CA $143

CA $205 total

includes taxes & fees

Aug 25 - Aug 26

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 beach with a palm tree and two chairs.

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

13. Margaritaville Beach House Key West

Key West

Ivelisse

CA $278

CA $399 total

includes taxes & fees

Aug 25 - Aug 26

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.

14. Sugar Loaf Lodge

Summerland Key

Marjorie

CA $164

CA $184 total

includes taxes & fees

Aug 25 - Aug 26

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 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.

15. Courtyard by Marriott Key West Waterfront

Northside Resort

Everton

CA $233

CA $262 total

includes taxes & fees

Aug 25 - Aug 26

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

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

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.

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

16. Silver Palms Inn & Historic Homes

Old Town Key West

Shawn

CA $104

CA $210 total

includes taxes & fees

Aug 25 - Aug 26

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

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

An outdoor patio area with wicker furniture, a bar, and a television.

A hotel with a two-story structure, a covered outdoor area, and a well-maintained lawn.

17. Fairfield Inn and Suites by Marriott Key West

New Town

Zachary

CA $164

CA $223 total

includes taxes & fees

Aug 25 - Aug 26

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

18. Casa Marina Key West, Curio Collection by Hilton

Old Town Key West

Dirk

CA $291

CA $421 total

includes taxes & fees

Sep 13 - Sep 14

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 beachfront hotel with multiple-story buildings, palm trees, and beach chairs.

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

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

19. Southernmost Beach Resort and Guesthouses

Old Town Key West

Deaenna

CA $186

CA $310 total

includes taxes & fees

Sep 3 - Sep 4

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

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

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.

20. The Palms Hotel

Old Town Key West

Marcus

CA $177

CA $230 total

includes taxes & fees

Sep 9 - Sep 10

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Top Rockland Key Hotel Reviews

DoubleTree Resort by Hilton Grand Key - Key West

8/10 Good

"Joe at the front desk was very helpful. We did have a few issues with housekeeping and being able to get into our room. On four separate occasions, we had to come and have someone readjust the lock on our door because our keys did not work. We did enjoy the complementary coffee each morning."

Blue Flamingo Resort Key West

10/10 Excellent

"Wonderful experience! We’ll definitely be back!"

Havana Cabana at Key West

10/10 Excellent

"Todo súper"

Parrot Key Hotel & Villas

10/10 Excellent

"The rooms was spacious and immaculate. Check in was very pleasant, we were greeted with mimosas by the staff. The pool and restaurant were amazing as well. Centralized location just minutes form restaurants and activities."

Hampton Inn Key West FL

10/10 Excellent

"outdoor pool"

Hilton Garden Inn Key West / The Keys Collection

10/10 Excellent

"Entire stay was fabulous"

Beachside Resort & Residences

10/10 Excellent

"Nice facilities, excellent rooms."

Margaritaville Beach House Key West

10/10 Excellent

"Excelente estadía, buena limpieza, buen trato el sitio hermoso"

Hyatt Vacation Club at Windward Pointe, Key West

8/10 Good

"So we have stayed here both times coming to Key West. The staff is outstanding and very nice from check in.. to check out. I will say that when you purchase through Expedia make sure you still have enough to pay for the resort fees and tax... they are NOT included."

More cheap stays in Rockland Key

Hampton Inn Key West FL

3755 S Roosevelt Blvd Key West FL

CA $163

CA $183 total

Aug 30 - Aug 31

includes taxes & fees

9/10 Wonderful! (1,483 reviews)

Parmer's Resort

565 Barry Avenue Summerland Key FL

CA $139

CA $201 total

Aug 26 - Aug 27

includes taxes & fees

9/10 Wonderful! (1,007 reviews)

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd Key West FL

CA $143

CA $205 total

Aug 25 - Aug 26

includes taxes & fees

Southwinds Motel

1321 Simonton Street Key West FL

CA $153

CA $218 total

Aug 25 - Aug 26

includes taxes & fees

8.6/10 Excellent! (1,389 reviews)

Simonton Court Historic Inn & Cottages

523 Eaton Street Key West FL

CA $205

CA $231 total

Aug 26 - Aug 27

includes taxes & fees

9.8/10 Exceptional! (1,005 reviews)

Weatherstation Inn

57 Front St Key West FL

CA $246

CA $277 total

Aug 25 - Aug 26

includes taxes & fees

9.4/10 Exceptional! (1,003 reviews)

Hotels in Rockland Key with star rating

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Find hotels in Rockland Key, FL from CA $183

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Rockland Key

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Rockland Key hotels

1. Hilton Key West Resort & Marina

2. Hampton Inn Key West FL

3. Hilton Garden Inn Key West / The Keys Collection

4. Beachside Resort & Residences

5. Hyatt Vacation Club at Beach House, Key West

6. DoubleTree Resort by Hilton Grand Key - Key West

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

8. Hyatt Vacation Club at Windward Pointe, Key West

9. Blue Flamingo Resort Key West

10. Parrot Key Hotel & Villas

11. The Perry Hotel & Marina Key West

12. Ibis Bay Beach Resort

13. Margaritaville Beach House Key West

14. Sugar Loaf Lodge

15. Courtyard by Marriott Key West Waterfront

16. Silver Palms Inn & Historic Homes

17. Fairfield Inn and Suites by Marriott Key West

18. Casa Marina Key West, Curio Collection by Hilton

19. Southernmost Beach Resort and Guesthouses

20. The Palms Hotel

Top Rockland Key Hotel Reviews

DoubleTree Resort by Hilton Grand Key - Key West

Blue Flamingo Resort Key West

Havana Cabana at Key West

Parrot Key Hotel & Villas

Hampton Inn Key West FL

Hilton Garden Inn Key West / The Keys Collection

Beachside Resort & Residences

Margaritaville Beach House Key West

Hyatt Vacation Club at Windward Pointe, Key West

More cheap stays in Rockland Key

Hampton Inn Key West FL

Parmer's Resort

Ibis Bay Beach Resort

Southwinds Motel

Simonton Court Historic Inn & Cottages

Weatherstation Inn

Hotels in Rockland Key with star rating

Explore a world of travel with Expedia

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