Rockland Key Vacation Rentals

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November 2026

December 2026

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Our top choices for Rockland Key vacation rentals

A row of floating houses with balconies, connected by walkways, on calm water.

1. Aqua Lodges at Hurricane Hole Marina

Stock Island

Kagni

₩398,293 total

includes taxes & fees

Nov 11 - Nov 12

A wooden boardwalk leading to a building with a green roof, surrounded by palm trees and a body of water.

2. The Grenada Suite Pool View Private Balcony

Key West

Luis

₩759,571 total

includes taxes & fees

Nov 30 - Dec 1

A pool area with a wooden deck, lounge chairs, and a waterfall feature.

3. Lighthouse Suites Collection

Old Town Key West

Melissa

₩1,011,628 total

includes taxes & fees

Nov 13 - Nov 14

A modern house with a swimming pool, a balcony, and a well-maintained garden.

4. Contra House Key West

Old Town Key West

Rosalie

₩1,632,034 total

includes taxes & fees

Dec 8 - Dec 9

A two-story beachfront house with a balcony, a covered outdoor seating area, and a small boat dock.

5. Atlantic View Luxury Villa with Pool

Summerland Key

Preetam

₩1,311,571 total

includes taxes & fees

Nov 15 - Nov 16

A wooden pedestrian bridge over a water body, surrounded by lush greenery and palm trees.

6. Tortuga Suite Sparkling Pool Hot Tub

Key West

₩767,471 total

includes taxes & fees

Dec 1 - Dec 2

A waterfront property with a large building featuring balconies and a covered area, boats docked in front, and palm trees in the background.

7. Grand Marina Suite by Brightwild Waterfront

Stock Island

Pawel

₩915,357 total

includes taxes & fees

Nov 11 - Nov 12

A view through white blinds of a swimming pool area with a hot tub, surrounded by palm trees and a white fence.

8. Poolside Retreat by Brightwild Cottage w Pool

Old Town Key West

"My boyfriend and I booked this for our first anniversary together and I cannot stress enough to not book this listing. There was trash from people before us, back door was broken to get to the pool, air conditioning didn’t work (it was so hot inside that the glass was all fogged up it was like a sauna), and the blow dryer in the bathroom SHOCKED ME when I tried to plug it in, my boyfriend heard the sound of the shock loudly from two rooms away. Horrifying to say the least and when I reached out...

Julia

₩617,419 total

includes taxes & fees

Dec 9 - Dec 10

A wooden deck with a hanging hammock and a view of a green landscape.

9. Starlight Serenity - Hideaway w Stunning Views

Summerland Key

max

₩969,646 total

includes taxes & fees

Nov 19 - Nov 20

A modern kitchen with white cabinets, stainless steel appliances, and a wooden door.

10. The Bartlum Luxury Studio In Prime Location

Key West Historic District

₩797,424 total

includes taxes & fees

Nov 23 - Nov 24

A covered porch with a table and chairs, overlooking a street with houses and cars.

11. Banana Split by Brightwild Pool Grill

Key West Historic District

₩726,916 total

includes taxes & fees

Nov 23 - Nov 24

A porch with a white railing, a pink door, and a white fence.

12. New Rose Petal Petite Suite - Pool Parking

Key West Historic District

A white house with a porch, palm trees, and a white picket fence.

13. Mesa House Uno by Brightwild Perfect Location

Key West Historic District

₩840,088 total

includes taxes & fees

Dec 1 - Dec 2

A spacious foyer with a wooden staircase, a console table with decorative items, and a view of the outdoors through a glass door.

14. Evershore House Pool Parking Dock

Raccoon Key

₩2,092,743 total

includes taxes & fees

Nov 24 - Nov 25

A white house with a porch, surrounded by tropical plants and a stone pathway.

15. New The Cottage at James House

Key West Historic District

Pamela

₩798,898 total

includes taxes & fees

Nov 30 - Dec 1

A white two-story house with a balcony and a swimming pool.

16. Capmar House by Brightwild Huge Home Pool

Raccoon Key

Karen

₩2,126,035 total

includes taxes & fees

Nov 11 - Nov 12

A two-story house with a swimming pool, surrounded by greenery and palm trees.

17. Seagate House by Brightwild Waterfront w Dock

Raccoon Key

A spacious living area with a large sofa, a coffee table, and a view of a balcony with a railing.

18. Mastway House by Brightwild Pool Dock

Raccoon Key

₩2,126,035 total

includes taxes & fees

Nov 11 - Nov 12

A modern kitchen with a large island, bar stools, and pendant lighting.

19. The Joyrise House at Solaire Lunara Bay

Raccoon Key

A white two-story house with a central archway and a paved driveway.

20. Palmgale House in Key West

Raccoon Key

₩3,180,643 total

includes taxes & fees

Nov 30 - Dec 1

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Find vacation rentals that suit your style

Top Rockland Key Hotel Reviews

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

Hilton Key West Resort & Marina

Stock Island

10/10 Excellent

Jesse

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

Hampton Inn Key West FL

Key West

10/10 Excellent

Karen

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

Hyatt Vacation Club at Windward Pointe, Key West

Key West

10/10 Excellent

Lindsay

A resort pool with clear blue water, surrounded by palm trees and lounge chairs.

Havana Cabana at Key West

New Town

10/10 Excellent

Eliana

A swimming pool with lounge chairs and palm trees.

Hilton Garden Inn Key West / The Keys Collection

New Town

10/10 Excellent

Charity

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

The Laureate Key West

New Town

10/10 Excellent

We stayed two nights in the 3-bedroom suite. Everything, from the moment of arrival, was top rate. The front desk attendant was in contact with me via text to ensure a smooth and efficient check in before arrival and was a great help with local recommendations at check in. Departure took 30 seconds yet the desk attendant took the time to ask how everything was, if I needed anything, wished me well, etc. The suite was beautiful appointed and the furniture very functional and comfortable. Our...

Shannon

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

DoubleTree Resort by Hilton Grand Key - Key West

Key West

10/10 Excellent

Hector

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

Hyatt Vacation Club at Beach House, Key West

Key West

10/10 Excellent

Sonia

A wooden boardwalk with a palm tree and lamp post, leading to a waterfront.

Courtyard by Marriott Key West Waterfront

Northside Resort

10/10 Excellent

Ased

A dining table with plates of food, a drink, and a view of a pool and palm trees.

Margaritaville Beach House Key West

Key West

10/10 Excellent

We traveled as a family with 3 small children, so we liked having a hotel away from Duval street. It was convenient being a 5 min shuttle drive from the airport to the hotel. The grounds are beautiful and the pool was a good size. We liked that the pool was heated too. We ate breakfast at the hotel most days, and the food was pretty good with attentive service. The shuttle to the downtown area was about 10-15 mins away and dropped off/picked up at a good location around a lot of good...

Kristen

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

Parrot Key Hotel & Villas

Northside Resort

10/10 Excellent

Great for a relaxing weekend, quiet hotel not too far from the main tourist center. We love the shuttle service provided by the hotel and his driver Gerry who guided us in every short trips. The only advice to the hotel is to provide the housekeeping service everyday without being requested by the guest, we expected this service to be included since the hotel charged an extra 51.00 usd per night!

CARLOS

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

Sugar Loaf Lodge

Summerland Key

10/10 Excellent

Upon our arrival, the sight of 2 iguanas on the lounging on the bridge by the pristine water at the back of the property had my entire family out of the minivan at lightning speed. They followed one, which lead them to trees full of these beautiful lizards. The front desk personnel, a very amiable gentleman, was very friendly and welcoming. Our room was in the middle of the 2nd floor, and had a fantastic view of the bay. And yes, there were more iguanas looking at us from the first floor, some...

Momi

Aqua Lodges at Hurricane Hole Marina

Stock Island

10/10 Excellent

Abigail

A compact living space with a dining area, kitchenette, and a bedroom.

The Grand Guesthouse

Old Town Key West

10/10 Excellent

The Grand Guesthouse is a gem in Key West! The host was outstanding and the facility was lovely. Breakfast was simple but nice, and the Happy Hour was an added bonus. We had a nice suite- a bedroom and a living/kitchen area. The room was nicely appointed and it was straightened by the staff each day. The room was very clean! Overall, my wife and I were impressed! Two small improvements... the mattress was too firm. Also, the wifi was not strong enough in our room to stream anything. ...

Anonymous traveler

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

Silver Palms Inn & Historic Homes

Old Town Key West

10/10 Excellent

Janice

A hotel room with a bed, a view of the beach, a hammock, and beach chairs.

Ibis Bay Beach Resort

Northside Resort

10/10 Excellent

I read some bad reviews.... and I think those people are probably just snobs lol. This is a quirky, unique hotel that feels very "Key West"y. It isn't a 5 star hotel, it's old and cute but clean, funky, and an experience you won't get anywhere else. The vibe of the place is very islandy and different than any chain you'll find. I would definitely stay there again if I was looking for an experience and not just a room. Loved the tortoises, the hammocks everywhere, the natural beach, the trees,...

Amy

Find out more about Rockland Key

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Look no further and take a look at our great range of rental properties in Rockland Key!

Rockland Key Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Rockland Key vacation rentals

1. Aqua Lodges at Hurricane Hole Marina

2. The Grenada Suite Pool View Private Balcony

3. Lighthouse Suites Collection

4. Contra House Key West

5. Atlantic View Luxury Villa with Pool

6. Tortuga Suite Sparkling Pool Hot Tub

7. Grand Marina Suite by Brightwild Waterfront

8. Poolside Retreat by Brightwild Cottage w Pool

9. Starlight Serenity - Hideaway w Stunning Views

10. The Bartlum Luxury Studio In Prime Location

11. Banana Split by Brightwild Pool Grill

12. New Rose Petal Petite Suite - Pool Parking

13. Mesa House Uno by Brightwild Perfect Location

14. Evershore House Pool Parking Dock

15. New The Cottage at James House

16. Capmar House by Brightwild Huge Home Pool

17. Seagate House by Brightwild Waterfront w Dock

18. Mastway House by Brightwild Pool Dock

19. The Joyrise House at Solaire Lunara Bay

20. Palmgale House in Key West

Find vacation rentals that suit your style

Top Rockland Key Hotel Reviews

Hilton Key West Resort & Marina

10/10 Excellent

Find out more about Rockland Key