Top Guest Houses in Rockland Key in 2026

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Our top choices for Rockland Key guest houses

A narrow outdoor pathway flanked by potted plants and a wooden staircase leading to a white door with shutters.

1. The Grand Guesthouse

Old Town Key West

Travis

Rp2.731.619 total

includes taxes & fees

1 Oct - 2 Oct

A covered porch with wicker furniture, potted plants, and a sign for the "Office" at the Palm Hotel.

2. The Palms Hotel

Old Town Key West

Zachary

Rp2.776.229 total

includes taxes & fees

1 Oct - 2 Oct

A gated entrance with a gazebo, palm trees, and a brick pathway leading to a building with a red roof.

3. Duval Inn

Old Town Key West

Arnold J

Rp2.955.921 total

includes taxes & fees

1 Oct - 2 Oct

A wooden boardwalk leading to a beach with palm trees and a clear sky.

4. Amsterdam's Curry Mansion Inn

Key West Historic District

Tiffany N

Rp2.912.922 total

includes taxes & fees

5 Oct - 6 Oct

A white building with green shutters, surrounded by a white picket fence and palm trees.

5. Kona Kai Oasis

Old Town Key West

Leah

Rp3.777.696 total

includes taxes & fees

4 Oct - 5 Oct

A swimming pool with a blue mosaic wall and a waterfall feature.

6. Colors on White

Old Town Key West

Harvey

Rp2.715.217 total

includes taxes & fees

1 Oct - 2 Oct

A living room with a ceiling fan, a sofa, a TV, and a bookshelf.

7. The Independent Inn - Formerly Heron House Court

Key West Historic District

Michael

Rp2.944.995 total

includes taxes & fees

4 Oct - 5 Oct

A breakfast setup with wine bottles, fruits, and pastries on a tray by a door with a view of a staircase and greenery.

8. The Cabana Inn Key West - Adults Only

Old Town Key West

Donna

Rp3.521.624 total

includes taxes & fees

1 Oct - 2 Oct

A pool area with lounge chairs, a white fence, and tropical plants.

9. Wicker Guesthouse

Old Town Key West

michael

Rp3.322.529 total

includes taxes & fees

1 Oct - 2 Oct

A tropical outdoor area with palm trees, hanging plants, and string lights.

10. Douglas House - Adults Only

Old Town Key West

michael

Rp2.974.284 total

includes taxes & fees

1 Oct - 2 Oct

A room with a bed, a ceiling fan, and a window with blinds.

11. The Mermaid & Alligator

Old Town Key West

Adam

Rp5.097.614 total

includes taxes & fees

5 Oct - 6 Oct

A covered porch with white railings, a ceiling fan, and a table with chairs.

12. The Porch on Frances Inn

Old Town Key West

Marcos

A green house with a white porch, a flag, and a sign advertising a property for sale.

13. L'Habitation Guest House - Adults Only

Key West Historic District

Richard

Rp3.440.450 total

includes taxes & fees

27 Oct - 28 Oct

A gated entrance with lush green foliage and a white picket fence.

14. Coco Plum Inn

Old Town Key West

Riley

Rp3.625.443 total

includes taxes & fees

1 Oct - 2 Oct

A covered outdoor seating area with wicker chairs and a glass table, overlooking a lush garden with palm trees and a pool.

15. Curry House

Old Town Key West

donald

Rp4.825.746 total

includes taxes & fees

6 Oct - 7 Oct

A pool area with a blue table and chairs, surrounded by palm trees and a white building.

16. Banana's Foster Guesthouse

Key West Historic District

michael

Rp5.517.448 total

includes taxes & fees

8 Oct - 9 Oct

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Top Rockland Key Hotel Reviews

Southernmost Beach Resort and Guesthouses

8/10 Good

"Its good but I wish the pool and ac was working."

Beachside Resort & Residences

10/10 Excellent

"Pros - The room was beautiful! Very clean and felt like a home away from home. Basically, a fully furnished condo with everything you'd need in the kitchen if you're the type to cook on vacation. Covered parking was a plus! Hourly shuttle to the Duval Street area provided which saves $$$ on parking! Cons - Walkway area around pool has many loose and raised blocks that were a tripping hazard. Beach is a bit small and if it's sunsets you're looking for, they are best viewed at the other end of the island. Front desk staff, while friendly, left out important info (such as availability of shuttle and pool bar hours). For first time visitors, signage is non-existent as far as where the check-in lobby is (no sign outside saying such, either) and the way the property is configured, it's not an easy determination. Certainly not complaining as we had a great time. Just offering our experience and observations."

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."

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."

Hyatt Centric Key West Resort and Spa

10/10 Excellent

"We had a wonderful stay at Hyatt Centric Key West Resort & Spa! The pool was a perfect place to relax, and we especially loved seeing the rescued turtles - such a unique and memorable part of the property. The location could not be better: everything we wanted to explore in Key West was within easy walking distance. It was incredibly convenient to enjoy the sights, restaurants, and lively atmosphere without needing a car. We would gladly stay here again!"

Find out more about Rockland Key

Rockland Key Guest Houses information

Number of reviews	6,227
Accommodation	26 Guest Houses
Lowest Price	Rp2.715.217
Highest Price	Rp5.517.448

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Rockland Key guest houses

1. The Grand Guesthouse

2. The Palms Hotel

3. Duval Inn

4. Amsterdam's Curry Mansion Inn

5. Kona Kai Oasis

6. Colors on White

7. The Independent Inn - Formerly Heron House Court

8. The Cabana Inn Key West - Adults Only

9. Wicker Guesthouse

10. Douglas House - Adults Only

11. The Mermaid & Alligator

12. The Porch on Frances Inn

13. L'Habitation Guest House - Adults Only

14. Coco Plum Inn

15. Curry House

16. Banana's Foster Guesthouse

Top Rockland Key Hotel Reviews

Southernmost Beach Resort and Guesthouses

Beachside Resort & Residences

Parrot Key Hotel & Villas

Winslow's Bungalows - Key West Historic Inns

Hampton Inn Key West FL

Casa Marina Key West, Curio Collection by Hilton

Southwinds Motel

Havana Cabana at Key West

Hyatt Centric Key West Resort and Spa

Find out more about Rockland Key

Rockland Key Guest Houses information

Explore a world of travel with Expedia

Search Guest Houses in Rockland Key

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Rockland Key guest houses

1. The Grand Guesthouse

2. The Palms Hotel

3. Duval Inn

4. Amsterdam's Curry Mansion Inn

5. Kona Kai Oasis

6. Colors on White

7. The Independent Inn - Formerly Heron House Court

8. The Cabana Inn Key West - Adults Only

9. Wicker Guesthouse

10. Douglas House - Adults Only

11. The Mermaid & Alligator

12. The Porch on Frances Inn

13. L'Habitation Guest House - Adults Only

14. Coco Plum Inn

15. Curry House

16. Banana's Foster Guesthouse

Top Rockland Key Hotel Reviews

Southernmost Beach Resort and Guesthouses

Find out more about Rockland Key

Rockland Key Guest Houses information

Explore a world of travel with Expedia