𝗧𝗢𝗣 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Rockland Key from S$128 (2026) - Fully Refundable Options - Expedia

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Go beyond your typical stay in Rockland Key

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16 Oct - 18 Oct

Our top choices for Rockland Key hotels

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

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.

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

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

New Town

United States

Brian

S$216

includes taxes & fees

14 Oct - 15 Oct

A marina with boats docked, a pool area, and a building with a white facade.

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

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.

2. Hilton Key West Resort & Marina

Stock Island

United States

Molly

S$244

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 bar area with a thatched roof, wooden chairs, and a poolside view.

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

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

3. Hampton Inn Key West FL

Key West

United States

Jaycie

S$243

includes taxes & fees

25 Oct - 26 Oct

A swimming pool with lounge chairs and palm trees.

Sports facility

A modern living room with a sectional sofa, a small round table, and a potted plant.

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

4. Hilton Garden Inn Key West / The Keys Collection

New Town

United States

Eli

S$200

includes taxes & fees

13 Oct - 14 Oct

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

5. DoubleTree Resort by Hilton Grand Key - Key West

Key West

United States

Nancy

S$209

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

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

6. The Perry Hotel & Marina Key West

Stock Island

United States

Jade

S$246

includes taxes & fees

26 Oct - 27 Oct

A balcony with wicker furniture and a view of the water.

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

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

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

7. Beachside Resort & Residences

Key West

United States

James

S$257

includes taxes & fees

8 Oct - 9 Oct

Pool

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

8. Blue Flamingo Resort Key West

New Town

United States

Esteban

S$242

includes taxes & fees

11 Oct - 12 Oct

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 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.

9. Sugar Loaf Lodge

Summerland Key

United States

Richard

S$171

includes taxes & fees

8 Oct - 9 Oct

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

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.

A swimming pool surrounded by palm trees and lounge chairs, with a clear view of the ocean in the background.

10. Hyatt Vacation Club at Windward Pointe, Key West

Key West

United States

Tina

S$355

includes taxes & fees

27 Oct - 28 Oct

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 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.

11. Ibis Bay Beach Resort

Northside Resort

United States

Stephanie

S$219

includes taxes & fees

8 Oct - 9 Oct

A spacious living room with a balcony, a ceiling fan, and a large window offering 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.

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.

12. The Laureate Key West

New Town

United States

Eileen

S$264

includes taxes & fees

25 Oct - 26 Oct

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 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.

13. Courtyard by Marriott Key West Waterfront

Northside Resort

United States

Everton

S$264

includes taxes & fees

26 Oct - 27 Oct

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.

14. Parrot Key Hotel & Villas

Northside Resort

United States

Anthony

S$252

includes taxes & fees

14 Oct - 15 Oct

Two wooden Adirondack chairs on a sandy beach with a view of the sea and a sailboat in the distance.

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

A poolside lounge area with a wicker chair, a straw hat, and a beach bag.

A wooden deck with two wooden chairs and a small table, surrounded by white railings and palm trees.

15. Hyatt Vacation Club at Beach House, Key West

Key West

United States

Rachel

S$336

includes taxes & fees

28 Oct - 29 Oct

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

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

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.

16. Havana Cabana at Key West

New Town

United States

Stephanie

S$284

includes taxes & fees

25 Oct - 26 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 small, enclosed porch with a chair and a table, surrounded by lush greenery and a white lattice fence.

A pool area with lounge chairs and a lifebuoy.

17. Authors of Key West Guest House

Key West Historic District

United States

Robbie

S$128

includes taxes & fees

8 Oct - 9 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 resort with a pool leading to a beach, surrounded by palm trees and white buildings.

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

18. Casa Marina Key West, Curio Collection by Hilton

Old Town Key West

United States

Coni

S$397

includes taxes & fees

25 Oct - 26 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 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.

19. The Reach Key West, Curio Collection by Hilton

Old Town Key West

United States

Darlene

S$332

includes taxes & fees

19 Oct - 20 Oct

A bedroom with a four-poster bed, a wooden desk, wicker chairs, and a view of the outdoors.

A wooden door with glass panels, leading to an interior space with furniture and plants.

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

A breakfast buffet with a variety of fruits, pastries, and beverages on a wooden deck with a view of a lush garden and a pool.

20. Tropical Inn

Old Town Key West

United States

Natalie

S$187

includes taxes & fees

8 Oct - 9 Oct

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Top Rockland Key Hotel Reviews

Havana Cabana at Key West

Havana Cabana at Key West

10/10 Excellent

"The only thing that I didn’t like was the bar staff"

Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

10/10 Excellent

"I did hear roosters, but that's part of the charm of Key West. There was occasional chicken poop on the floors outside, so that's why I gave a 4 for cleanliness, but they do seem to clean it up fairly quickly. Overall I loved the stay. I will go again."

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

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

10/10 Excellent

"Great place! Rooms were nice. So was staff. Great breakfast with lots of choices."

Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

10/10 Excellent

"Great hotel and pool!"

Hilton Key West Resort & Marina

Hilton Key West Resort & Marina

10/10 Excellent

"Staff at reception are genuinely welcoming."

Hampton Inn Key West FL

Hampton Inn Key West FL

10/10 Excellent

"It was good"

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent

"Perfect! Great surroundings, staff & people! Convenient to get to everything!"

Margaritaville Beach House Key West

Margaritaville Beach House Key West

10/10 Excellent

"Staff was great! Rooms were clean! Had a great stay!"

Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

10/10 Excellent

"Great place definitely staying there next time"

More cheap stays in Rockland Key

Alexander Palms Court

Alexander Palms Court

715 South St Key West FL

S$204

11 Oct - 12 Oct

includes taxes & fees

9.4/10 Exceptional! (1,001 reviews)

Ibis Bay Beach Resort

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd Key West FL

S$219

8 Oct - 9 Oct

includes taxes & fees

Pegasus International Hotel

Pegasus International Hotel

501 Southard Street Key West FL

S$235

8 Oct - 9 Oct

includes taxes & fees

Hampton Inn Key West FL

Hampton Inn Key West FL

3755 S Roosevelt Blvd Key West FL

S$243

25 Oct - 26 Oct

includes taxes & fees

9/10 Wonderful! (1,547 reviews)

Southwinds Motel

Southwinds Motel

1321 Simonton Street Key West FL

S$249

12 Oct - 13 Oct

includes taxes & fees

8.6/10 Excellent! (1,388 reviews)

Parmer's Resort

Parmer's Resort

565 Barry Avenue Summerland Key FL

S$260

1 Nov - 2 Nov

includes taxes & fees

9/10 Wonderful! (1,002 reviews)

Hotels in Rockland Key with star rating

4 Star Hotels

3 Star Hotels

2 Star Hotels

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