Rockland Key Holiday Rentals, Key West: Private House Rentals

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Our top choices for Rockland Key hotels

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 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.

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

New Town

Patricia

฿3,997

฿5,440 total

includes taxes & fees

1 Oct - 2 Oct

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

Jaycie

฿5,562

฿6,257 total

includes taxes & fees

6 Oct - 7 Oct

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

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

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.

3. DoubleTree Resort by Hilton Grand Key - Key West

Key West

Nancy

฿4,406

฿6,090 total

includes taxes & fees

7 Oct - 8 Oct

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.'

4. Hilton Garden Inn Key West / The Keys Collection

New Town

Walt

฿3,552

฿4,941 total

includes taxes & fees

6 Oct - 7 Oct

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.

5. Courtyard by Marriott Key West Waterfront

Northside Resort

Everton

฿6,483

฿7,293 total

includes taxes & fees

27 Oct - 28 Oct

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.

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

6. Blue Flamingo Resort Key West

New Town

Esteban

฿3,685

฿6,035 total

includes taxes & fees

1 Oct - 2 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 hotel room with a large bed, a desk, a chair, a television, and a ceiling fan.

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

7. The Perry Hotel & Marina Key West

Stock Island

Jade

฿3,576

฿6,068 total

includes taxes & fees

26 Oct - 27 Oct

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

8. Beachside Resort & Residences

Key West

James

฿2,641

฿6,183 total

includes taxes & fees

1 Oct - 2 Oct

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.

9. Parrot Key Hotel & Villas

Northside Resort

Anthony

฿4,433

฿6,914 total

includes taxes & fees

6 Oct - 7 Oct

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 waterfront hotel with a pool, palm trees, and a wooden dock.

10. Hilton Key West Resort & Marina

Stock Island

Molly

฿4,243

฿6,738 total

includes taxes & fees

12 Oct - 13 Oct

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

11. Margaritaville Beach House Key West

Key West

TRICIA LYNN

฿7,019

฿10,016 total

includes taxes & fees

1 Oct - 2 Oct

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

12. Ibis Bay Beach Resort

Northside Resort

Stephanie

฿4,397

฿6,030 total

includes taxes & fees

1 Oct - 2 Oct

A hotel with a swimming pool, balconies, and a view of the sea.

A marina with jet skis docked in front of a hotel with a dock and a boat in the background.

A beach wedding setup with white chairs, a wooden arch, and lanterns.

A spacious bar area with a wooden counter and green bar stools, a seating area with a sofa and chairs, and a dining area with a table set for two.

13. Hyatt Centric Key West Resort and Spa

Key West Historic District

yendy

฿7,825

฿11,146 total

includes taxes & fees

4 Oct - 5 Oct

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

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 hotel with a pool, bicycles, and lush greenery.

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

14. Silver Palms Inn & Historic Homes

Old Town Key West

sam

฿3,597

฿6,314 total

includes taxes & fees

5 Oct - 6 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.

15. Casa Marina Key West, Curio Collection by Hilton

Old Town Key West

Coni

฿7,964

฿11,227 total

includes taxes & fees

7 Oct - 8 Oct

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

฿6,680

฿9,782 total

includes taxes & fees

8 Oct - 9 Oct

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

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

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

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

17. Havana Cabana at Key West

New Town

Gustavo

฿3,728

฿6,314 total

includes taxes & fees

1 Oct - 2 Oct

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 pool area with lounge chairs and a lifebuoy.

A spacious kitchen with a dining area, large windows, and a view of the outdoors.

18. Authors of Key West Guest House

Key West Historic District

Avamarie

฿2,997

฿3,372 total

includes taxes & fees

4 Oct - 5 Oct

A modern hotel room with a large bed, a nightstand, a bedside table, and a bathroom visible through an open door.

A building with a sign reading "ALMOND Frog & Toad Inn" and a "VACANCY" sign below it.

A breakfast table with various food items and drinks, a pool in the background, and a tiled wall.

A reception area with a wooden herringbone wall, teal chairs, a wooden bench, and two framed sunset paintings.

19. Almond Tree Inn Hotel - Adults Only

Old Town Key West

John

฿6,250

฿7,031 total

includes taxes & fees

5 Oct - 6 Oct

A bottle of Marc's Reserve 12 FL. OZ. on a coaster with a metal table.

A patio area with white metal tables and chairs, surrounded by potted plants and palm trees.

A pool with a lion head sculpture in the center.

A potted yellow orchid plant in a garden setting with a brick pathway, palm trees, and a white building in the background.

20. Artist House Key West

Key West Historic District

NATHAN

฿7,383

฿8,306 total

includes taxes & fees

21 Oct - 22 Oct

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Top Rockland Key Hotel Reviews

Parrot Key Hotel & Villas

10/10 Excellent

"This property is nicer than anything we found closer to Duval Street. This property is 5 stars! Roomy, worth every penny. I loved my king size bed. I loved the properties gardens and the pools. It was quiet, private, and luxurious. I have one critique, valet parking is not needed. $30 for Valet is not needed."

Ibis Bay Beach Resort

10/10 Excellent

"Good service"

Winslow's Bungalows - Key West Historic Inns

10/10 Excellent

"The property offered striking beauty and an ideal location. The staff we spoke with throughout our stay were consistently friendly and welcoming. I appreciated the amenities. The complimentary continental breakfast and two welcome drinks were excellent. I would gladly return for another visit."

Beachside Resort & Residences

10/10 Excellent

"Beautiful"

Hampton Inn Key West FL

10/10 Excellent

"This is our 8th stay at The Hampton Inn key west. Great property, awesome staff especially Kim at the front desk. Very clean property and nice rooms .we always stay ocean front, beautiful view, peaceful.Cant wait to go again."

Casa Marina Key West, Curio Collection by Hilton

10/10 Excellent

"Amazing place to stay for vacation."

Southernmost Beach Resort and Guesthouses

10/10 Excellent

"Property was amazing, our second time here. Staff was very accommodating! Pools were clean and the atmosphere at the pools was perfect. We will definitely be returning."

Southwinds Motel

10/10 Excellent

"Me and my fiancé had a great time"

Havana Cabana at Key West

10/10 Excellent

"Excellent place, beautiful decor, rooms, pool, will stay again. Well recommended place."

More cheap stays in Rockland Key

Alexander Palms Court

715 South St Key West FL

฿4,005

฿4,506 total

6 Oct - 7 Oct

includes taxes & fees

9.4/10 Exceptional! (1,005 reviews)

Pegasus International Hotel

501 Southard Street Key West FL

฿3,682

฿5,843 total

1 Oct - 2 Oct

includes taxes & fees

8.2/10 Very good! (1,007 reviews)

Southwinds Motel

1321 Simonton Street Key West FL

฿4,332

฿6,007 total

1 Oct - 2 Oct

includes taxes & fees

8.6/10 Excellent! (1,391 reviews)

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd Key West FL

฿4,397

฿6,030 total

1 Oct - 2 Oct

includes taxes & fees

8.2/10 Very good! (2,400 reviews)

Hampton Inn Key West FL

3755 S Roosevelt Blvd Key West FL

฿5,562

฿6,257 total

6 Oct - 7 Oct

includes taxes & fees

9/10 Wonderful! (1,534 reviews)

Parmer's Resort

565 Barry Avenue Summerland Key FL

฿4,824

฿6,523 total

4 Oct - 5 Oct

includes taxes & fees

Find hotels in Rockland Key, FL from ฿3,372

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Rockland Key

Check prices for these dates

Filter by

Star rating

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Our top choices for Rockland Key hotels

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

2. Hampton Inn Key West FL

3. DoubleTree Resort by Hilton Grand Key - Key West

4. Hilton Garden Inn Key West / The Keys Collection

5. Courtyard by Marriott Key West Waterfront

6. Blue Flamingo Resort Key West

7. The Perry Hotel & Marina Key West

8. Beachside Resort & Residences

9. Parrot Key Hotel & Villas

10. Hilton Key West Resort & Marina

11. Margaritaville Beach House Key West

12. Ibis Bay Beach Resort

13. Hyatt Centric Key West Resort and Spa

14. Silver Palms Inn & Historic Homes

15. Casa Marina Key West, Curio Collection by Hilton

16. The Reach Key West, Curio Collection by Hilton

17. Havana Cabana at Key West

18. Authors of Key West Guest House

19. Almond Tree Inn Hotel - Adults Only

20. Artist House Key West

Top Rockland Key Hotel Reviews

Parrot Key Hotel & Villas

Ibis Bay Beach Resort

Winslow's Bungalows - Key West Historic Inns

Beachside Resort & Residences

Hampton Inn Key West FL

Casa Marina Key West, Curio Collection by Hilton

Southernmost Beach Resort and Guesthouses

Southwinds Motel

Havana Cabana at Key West

More cheap stays in Rockland Key

Alexander Palms Court

Pegasus International Hotel

Southwinds Motel

Ibis Bay Beach Resort

Hampton Inn Key West FL

Parmer's Resort

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