Book The Best Hotels in Rockland Key, FL for 2026 from CA $190 - Fully Refundable Options

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Our top choices for Rockland Key hotels

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.

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

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

New Town

Brian

CA $178

CA $241 total

includes taxes & fees

Oct 15 - Oct 16

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 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.

2. Hilton Garden Inn Key West / The Keys Collection

New Town

Eli

CA $170

CA $231 total

includes taxes & fees

Oct 11 - Oct 12

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 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.

3. Hilton Key West Resort & Marina

Stock Island

Molly

CA $170

CA $274 total

includes taxes & fees

Oct 15 - Oct 16

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

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

4. The Perry Hotel & Marina Key West

Stock Island

Jade

CA $157

CA $263 total

includes taxes & fees

Oct 25 - Oct 26

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 indoor dining area with tables and chairs, ceiling fans, and large windows.

5. DoubleTree Resort by Hilton Grand Key - Key West

Key West

Nancy

CA $181

CA $252 total

includes taxes & fees

Oct 27 - Oct 28

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.

6. Hampton Inn Key West FL

Key West

Jaycie

CA $258

CA $290 total

includes taxes & fees

Oct 13 - Oct 14

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

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.

A beach with palm trees, clear blue water, and a pier extending into the sea.

7. Beachside Resort & Residences

Key West

James

CA $137

CA $290 total

includes taxes & fees

Oct 27 - Oct 28

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 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.

8. Sugar Loaf Lodge

Summerland Key

Richard

CA $169

CA $190 total

includes taxes & fees

Oct 13 - Oct 14

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

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.

9. Blue Flamingo Resort Key West

New Town

Esteban

CA $168

CA $269 total

includes taxes & fees

Oct 13 - Oct 14

A spacious living room with a balcony, a ceiling fan, and a large window offering a view of the ocean.

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

A multi-story hotel with balconies and a well-lit entrance.

A hotel room with two beds, a balcony with a view of the ocean, and a large wave painting on the wall.

10. The Laureate Key West

New Town

Eileen

CA $226

CA $294 total

includes taxes & fees

Oct 25 - Oct 26

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.

11. Hyatt Vacation Club at Windward Pointe, Key West

Key West

Tina

CA $270

CA $368 total

includes taxes & fees

Oct 26 - Oct 27

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

12. Ibis Bay Beach Resort

Northside Resort

Andre

CA $163

CA $229 total

includes taxes & fees

Oct 11 - Oct 12

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 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.

13. Courtyard by Marriott Key West Waterfront

Northside Resort

Everton

CA $226

CA $254 total

includes taxes & fees

Oct 13 - Oct 14

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

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

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.

14. Havana Cabana at Key West

New Town

Stephanie

CA $201

CA $317 total

includes taxes & fees

Oct 25 - Oct 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 two-story building with a balcony, arched windows, and a green roof.

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

15. Hyatt Vacation Club at Beach House, Key West

Key West

Rachel

CA $307

CA $410 total

includes taxes & fees

Oct 29 - Oct 30

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

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

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.

16. Parrot Key Hotel & Villas

Northside Resort

Anthony

CA $180

CA $285 total

includes taxes & fees

Oct 13 - Oct 14

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 pool area with lounge chairs and a lifebuoy.

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

CA $178

CA $201 total

includes taxes & fees

Oct 11 - Oct 12

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

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

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

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

18. The Reach Key West, Curio Collection by Hilton

Old Town Key West

Darlene

CA $252

CA $380 total

includes taxes & fees

Oct 25 - Oct 26

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

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

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

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

19. Casa Marina Key West, Curio Collection by Hilton

Old Town Key West

Coni

CA $307

CA $441 total

includes taxes & fees

Oct 25 - Oct 26

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 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.

20. Margaritaville Beach House Key West

Key West

James Joseph

CA $297

CA $424 total

includes taxes & fees

Oct 13 - Oct 14

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Top Rockland Key Hotel Reviews

Hampton Inn Key West FL

10/10 Excellent

"I took my kids on an end of summer trip to Key West. I travel a lot and have never stayed at a Hampton Inn, so we weren’t sure what to expect. Check in was easy and the front desk staff explained everything in detail. Our room was clean and spacious and the balcony was a nice add on. We also enjoyed the pool, which was clean and a the water was a good temperature. The bar was amazing and the food at rheir restaurant was good and a good value for the price. We loved the amenities such as their shuttle and the activities desk, where we learned about a lot of fun options and ended up choosing the day-long Extreme Adventure (excellent by the way). It made it easy to find activities and ideas of things to do; plus she had coupons for basically everything. The breakfast was also awesome. My kids loved that they constantly changed out the waffle batter. We had a blast and look forward to staying here again next year!!"

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!"

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 Rockland Key

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd Key West FL

CA $163

CA $229 total

Oct 11 - Oct 12

includes taxes & fees

Alexander Palms Court

715 South St Key West FL

CA $242

CA $273 total

Oct 11 - Oct 12

includes taxes & fees

9.4/10 Exceptional! (1,003 reviews)

Southwinds Motel

1321 Simonton Street Key West FL

CA $204

CA $278 total

Oct 12 - Oct 13

includes taxes & fees

8.6/10 Excellent! (1,390 reviews)

Parmer's Resort

565 Barry Avenue Summerland Key FL

CA $216

CA $290 total

Nov 1 - Nov 2

includes taxes & fees

Hampton Inn Key West FL

3755 S Roosevelt Blvd Key West FL

CA $258

CA $290 total

Oct 13 - Oct 14

includes taxes & fees

9/10 Wonderful! (1,548 reviews)

Pegasus International Hotel

501 Southard Street Key West FL

CA $205

CA $303 total

Oct 12 - Oct 13

includes taxes & fees

Hotels in Rockland Key with star rating

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Find hotels in Rockland Key, FL from CA $190

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

2. Hilton Garden Inn Key West / The Keys Collection

3. Hilton Key West Resort & Marina

4. The Perry Hotel & Marina Key West

5. DoubleTree Resort by Hilton Grand Key - Key West

6. Hampton Inn Key West FL

7. Beachside Resort & Residences

8. Sugar Loaf Lodge

9. Blue Flamingo Resort Key West

10. The Laureate Key West

11. Hyatt Vacation Club at Windward Pointe, Key West

12. Ibis Bay Beach Resort

13. Courtyard by Marriott Key West Waterfront

14. Havana Cabana at Key West

15. Hyatt Vacation Club at Beach House, Key West

16. Parrot Key Hotel & Villas

17. Authors of Key West Guest House

18. The Reach Key West, Curio Collection by Hilton

19. Casa Marina Key West, Curio Collection by Hilton

20. Margaritaville Beach House Key West

Top Rockland Key Hotel Reviews

Hampton Inn Key West FL

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

Havana Cabana at Key West

More cheap stays in Rockland Key

Ibis Bay Beach Resort

Alexander Palms Court

Southwinds Motel

Parmer's Resort

Hampton Inn Key West FL

Pegasus International Hotel

Hotels in Rockland Key with star rating

Explore a world of travel with Expedia

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