Top 10 Hotels in Rockland Key (from $134) 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

Eli

$141 nightly

$159 total

Oct 28 - Oct 29

Total with taxes and fees

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

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.

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

2. Hilton Key West Resort & Marina

Stock Island

Eric A

$182 nightly

$205 total

Oct 26 - Oct 27

Total with taxes and fees

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

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

3. Hampton Inn Key West FL

Key West

Andrew

$169 nightly

$190 total

Oct 25 - Oct 26

Total with taxes and fees

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

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.

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

4. Sugar Loaf Lodge

Summerland Key

morgan

$119 nightly

$134 total

Oct 14 - Oct 15

Total with taxes and fees

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.

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

New Town

Brian

$164 nightly

$185 total

Oct 14 - Oct 15

Total with taxes and fees

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

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

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.

6. The Perry Hotel & Marina Key West

Stock Island

Jade

$188 nightly

$211 total

Oct 28 - Oct 29

Total with taxes and fees

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

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

7. DoubleTree Resort by Hilton Grand Key - Key West

Key West

Nancy

$157 nightly

$177 total

Oct 27 - Oct 28

Total with taxes and fees

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

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

8. Beachside Resort & Residences

Key West

Brenna

$202 nightly

$227 total

Oct 14 - Oct 15

Total with taxes and fees

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.

A couple holding hands in a tropical setting with palm trees and greenery.

9. Blue Flamingo Resort Key West

New Town

Esteban

$166 nightly

$187 total

Oct 14 - Oct 15

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 marina with boats docked, a beach resort building, and palm trees.

A beachfront hotel with multiple colorful buildings, a pool area, and a boat dock.

10. Ibis Bay Beach Resort

Northside Resort

Andre

$172 nightly

$193 total

Oct 14 - Oct 15

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

11. The Laureate Key West

New Town

Eileen

$184 nightly

$207 total

Oct 14 - Oct 15

Total with taxes and fees

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 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.

12. Courtyard by Marriott Key West Waterfront

Northside Resort

Everton

$183 nightly

$206 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 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.

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

13. Hyatt Vacation Club at Beach House, Key West

Key West

Rachel

$251 nightly

$282 total

Oct 29 - Oct 30

Total with taxes and fees

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

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.

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

14. Parrot Key Hotel & Villas

Northside Resort

Anthony

$178 nightly

$200 total

Oct 14 - Oct 15

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 two-story building with a central entrance, surrounded by palm trees and a wooden walkway.

15. Hyatt Vacation Club at Windward Pointe, Key West

Key West

Tina

$239 nightly

$269 total

Oct 26 - Oct 27

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.

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

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

16. The Reach Key West, Curio Collection by Hilton

Old Town Key West

Darlene

$157 nightly

$176 total

Oct 26 - Oct 27

Total with taxes and fees

A large, ornate hotel with a pool, palm trees, and a view of the ocean.

A grand staircase with ornate railings and a chandelier.

A large, two-story house with a prominent tower and a covered porch.

A balcony with white railings and a table, overlooking a beach with palm trees and a clear blue sky.

17. Southernmost House - Adult Exclusive

Old Town Key West

Amy

$261 nightly

$294 total

Oct 28 - Oct 29

Total with taxes and fees

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

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

18. Casa Marina Key West, Curio Collection by Hilton

Old Town Key West

Rita

$215 nightly

$242 total

Oct 16 - Oct 17

Total with taxes and fees

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

A thatched-roof building with a sign for 'Look Reef Resort' and 'Tiki Bar'.

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.

19. Looe Key Reef Resort

Summerland Key

Stephen

$103 nightly

$116 total

Oct 14 - Oct 15

Total with taxes and fees

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

A covered outdoor seating area with a pool in the background.

A bar setting with a bartender preparing a drink, a counter with various bottles, and a TV screen in the background.

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

20. Havana Cabana at Key West

New Town

Stephanie

$205 nightly

$231 total

Oct 14 - Oct 15

Total with taxes and fees

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Top Rockland 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 Rockland Key

Hampton Inn Key West FL

3755 S Roosevelt Blvd Key West FL

$169 nightly

$190 total

Oct 25 - Oct 26

Total with taxes and fees

Southwinds Motel

1321 Simonton Street Key West FL

$169 nightly

$190 total

Oct 14 - Oct 15

Total with taxes and fees

8.6/10 Excellent! (1,385 reviews)

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd Key West FL

$172 nightly

$193 total

Oct 14 - Oct 15

Total with taxes and fees

Pegasus International Hotel

501 Southard Street Key West FL

$174 nightly

$196 total

Oct 14 - Oct 15

Total with taxes and fees

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

Parmer's Resort

565 Barry Avenue Summerland Key FL

$198 nightly

$223 total

Nov 1 - Nov 2

Total with taxes and fees

9/10 Wonderful! (1,002 reviews)

Alexander Palms Court

715 South St Key West FL

$199 nightly

$224 total

Oct 14 - Oct 15

Total with taxes and fees

9.4/10 Exceptional! (1,001 reviews)

Hotels in Rockland Key with star-rating

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Find hotels in Rockland Key, FL from $134

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. Hampton Inn Key West FL

4. Sugar Loaf Lodge

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

6. The Perry Hotel & Marina Key West

7. DoubleTree Resort by Hilton Grand Key - Key West

8. Beachside Resort & Residences

9. Blue Flamingo Resort Key West

10. Ibis Bay Beach Resort

11. The Laureate Key West

12. Courtyard by Marriott Key West Waterfront

13. Hyatt Vacation Club at Beach House, Key West

14. Parrot Key Hotel & Villas

15. Hyatt Vacation Club at Windward Pointe, Key West

16. The Reach Key West, Curio Collection by Hilton

17. Southernmost House - Adult Exclusive

18. Casa Marina Key West, Curio Collection by Hilton

19. Looe Key Reef Resort

20. Havana Cabana at Key West

Top Rockland 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 Rockland Key

Hampton Inn Key West FL

Southwinds Motel

Ibis Bay Beach Resort

Pegasus International Hotel

Parmer's Resort

Alexander Palms Court

Hotels in Rockland Key with star-rating

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