Top 10 Hotels in Rockland Key (from $114) 2026 - Competitive Prices

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Our top choices for Rockland Key hotels

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.'

1. Hilton Garden Inn Key West / The Keys Collection

New Town

Walt

$134 nightly

$151 total

Oct 27 - Oct 28

Total with taxes and fees

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.

2. Hilton Key West Resort & Marina

Stock Island

Molly

$178 nightly

$201 total

Oct 12 - Oct 13

Total with taxes and fees

A waterfront building with a flat roof, large windows, and a balcony.

A swimming pool with a surrounding deck, palm trees, and lounge chairs.

A corridor lined with trees and potted plants, leading to a building with a white exterior and windows.

A reception area with a wooden sculpture, a reception desk, a computer, and a television.

3. Sugar Loaf Lodge

Summerland Key

Richard

$119 nightly

$134 total

Oct 6 - Oct 7

Total with taxes and fees

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

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

New Town

Patricia

$159 nightly

$179 total

Oct 12 - Oct 13

Total with taxes and fees

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

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

5. DoubleTree Resort by Hilton Grand Key - Key West

Key West

Nancy

$153 nightly

$172 total

Oct 12 - Oct 13

Total with taxes and fees

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 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.

6. Hampton Inn Key West FL

Key West

Jaycie

$169 nightly

$190 total

Oct 6 - Oct 7

Total with taxes and fees

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

A modern kitchen with white cabinets and a built-in microwave. There is a dining area with a table set for two, a sofa, and a balcony with a view of the ocean.

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

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

7. The Laureate Key West

New Town

Mailyn

$184 nightly

$207 total

Oct 25 - Oct 26

Total with taxes and fees

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.

8. Havana Cabana at Key West

New Town

Stephanie

$190 nightly

$214 total

Nov 1 - Nov 2

Total with taxes and fees

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

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

9. Beachside Resort & Residences

Key West

James

$185 nightly

$208 total

Oct 6 - Oct 7

Total with taxes and fees

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

A beach volleyball court with a net, surrounded by palm trees and a hotel in the background.

10. Hyatt Vacation Club at Windward Pointe, Key West

Key West

Tina

$232 nightly

$261 total

Oct 26 - Oct 27

Total with taxes and fees

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

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

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.

11. Authors of Key West Guest House

Key West Historic District

Robbie

$101 nightly

$114 total

Oct 8 - Oct 9

Total with taxes and fees

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

12. Courtyard by Marriott Key West Waterfront

Northside Resort

Everton

$193 nightly

$217 total

Oct 26 - Oct 27

Total with taxes and fees

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.

13. Hyatt Vacation Club at Beach House, Key West

Key West

Rachel

$248 nightly

$279 total

Oct 28 - Oct 29

Total with taxes and fees

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

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

14. Parrot Key Hotel & Villas

Northside Resort

Anthony

$183 nightly

$206 total

Oct 12 - Oct 13

Total with taxes and fees

A modern cafe with a wooden counter, seating area, and shelves stocked with beverages.

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.

15. Blue Flamingo Resort Key West

New Town

Esteban

$168 nightly

$189 total

Oct 6 - Oct 7

Total with taxes and fees

A rustic wooden structure with a thatched roof, multiple tables and chairs, and flags hanging from the ceiling.

A canal with boats docked on both sides, surrounded by lush greenery and trees.

A sign for Looe Key Reef Resort's tiki bar, surrounded by palm trees and a thatched-roof structure.

A spacious indoor dining area with multiple tables and chairs, ceiling fans, and a bar area.

16. Looe Key Reef Resort

Summerland Key

Stephen

$101 nightly

$114 total

Oct 14 - Oct 15

Total with taxes and fees

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 hotel room with a bed, a TV, a coffee table, a sofa, and a view of the ocean.

17. Margaritaville Beach House Key West

Key West

TRICIA LYNN

$265 nightly

$298 total

Oct 6 - Oct 7

Total with taxes and fees

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.

18. The Perry Hotel & Marina Key West

Stock Island

Jade

$181 nightly

$203 total

Oct 8 - Oct 9

Total with taxes and fees

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 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.

19. Ibis Bay Beach Resort

Northside Resort

Stephanie

$172 nightly

$193 total

Oct 6 - Oct 7

Total with taxes and fees

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.

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

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

20. The Reach Key West, Curio Collection by Hilton

Old Town Key West

Darlene

$280 nightly

$315 total

Oct 25 - Oct 26

Total with taxes and fees

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Top Rockland Key Hotel Reviews

Winslow's Bungalows - Key West Historic Inns

10/10 Excellent

"This was a great property! Not expensive but with all the amenities. Close to Duvall. The only drawback were the roosters! But I think that’s everywhere in Key West."

Beachside Resort & Residences

10/10 Excellent

"I like the location, they do not have a clean beach!"

Margaritaville Beach House Key West

10/10 Excellent

"The staff were friendly and extremely helpful. The shuttle provided an excellent means for transportation to Duval Street as well as the ferry. The beaches in Key West are not the greatest so if your decision is based on proximity to the beach, it may not be worthwhile. The pool at the resort was awesome and the pool/bar/restaurant service really made this tropical destination pop!"

Pier House Resort & Spa

10/10 Excellent

"Love pier house resort"

Parrot Key Hotel & Villas

10/10 Excellent

"Absolutely fabulous!"

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

10/10 Excellent

"Clean room. Amazing staff"

Blue Flamingo Resort Key West

8/10 Good

"Great rooms and property. But the elevators need work. slow and only one wroking."

Ibis Bay Beach Resort

10/10 Excellent

"I love this place. It is the most adorable hotel. Super clean and well maintained. The staff is very friendly and they seem to take pride in their work. All day you see staff around the property making sure everything is running smooth. This place is super relaxing, enough space for everyone to relax by the water. This is my go to hotel when staying in Key West."

Hilton Garden Inn Key West / The Keys Collection

10/10 Excellent

"The room was super clean and the staff was super courteous. I recommend the hotel and visit it again."

More cheap stays in Rockland Key

Alexander Palms Court

715 South St Key West FL

$135 nightly

$152 total

Oct 6 - Oct 7

Total with taxes and fees

9.4/10 Exceptional! (1,001 reviews)

Parmer's Resort

565 Barry Avenue Summerland Key FL

$156 nightly

$175 total

Nov 1 - Nov 2

Total with taxes and fees

9/10 Wonderful! (1,001 reviews)

Pegasus International Hotel

501 Southard Street Key West FL

$159 nightly

$179 total

Oct 7 - Oct 8

Total with taxes and fees

Hampton Inn Key West FL

3755 S Roosevelt Blvd Key West FL

$169 nightly

$190 total

Oct 6 - Oct 7

Total with taxes and fees

Southwinds Motel

1321 Simonton Street Key West FL

$169 nightly

$190 total

Oct 6 - Oct 7

Total with taxes and fees

8.6/10 Excellent! (1,384 reviews)

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd Key West FL

$172 nightly

$193 total

Oct 6 - Oct 7

Total with taxes and fees

8.2/10 Very Good! (2,402 reviews)

Hotels in Rockland Key with star-rating

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Find hotels in Rockland Key, FL from $114

Upfront pricing

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 Garden Inn Key West / The Keys Collection

2. Hilton Key West Resort & Marina

3. Sugar Loaf Lodge

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

5. DoubleTree Resort by Hilton Grand Key - Key West

6. Hampton Inn Key West FL

7. The Laureate Key West

8. Havana Cabana at Key West

9. Beachside Resort & Residences

10. Hyatt Vacation Club at Windward Pointe, Key West

11. Authors of Key West Guest House

12. Courtyard by Marriott Key West Waterfront

13. Hyatt Vacation Club at Beach House, Key West

14. Parrot Key Hotel & Villas

15. Blue Flamingo Resort Key West

16. Looe Key Reef Resort

17. Margaritaville Beach House Key West

18. The Perry Hotel & Marina Key West

19. Ibis Bay Beach Resort

20. The Reach Key West, Curio Collection by Hilton

Top Rockland Key Hotel Reviews

Winslow's Bungalows - Key West Historic Inns

Beachside Resort & Residences

Margaritaville Beach House Key West

Pier House Resort & Spa

Parrot Key Hotel & Villas

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

Blue Flamingo Resort Key West

Ibis Bay Beach Resort

Hilton Garden Inn Key West / The Keys Collection

More cheap stays in Rockland Key

Alexander Palms Court

Parmer's Resort

Pegasus International Hotel

Hampton Inn Key West FL

Southwinds Motel

Ibis Bay Beach Resort

Hotels in Rockland Key with star-rating

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