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Rockland Key Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Rockland Key vacation rentals

A marina with boats docked, a small docked boat with a thatched roof, and a restaurant with outdoor seating overlooking the water.

1. Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (199 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
$261 nightly
The price is $293
Oct 11 - Oct 12
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina
A beachside resort with a wooden deck, palm trees, and a sunset view.

2. Grand Marina Suite by Brightwild Waterfront

Grand Marina Suite by Brightwild Waterfront
2.0 star property
Stock Island
10.0 out of 10, Exceptional, (3 reviews)
"Nice place "
United States
Pawel
$566 nightly
The price is $636
Oct 12 - Oct 13
Total with taxes and fees
Grand Marina Suite by Brightwild Waterfront
A hot tub with a view of a marina and boats during sunset.

3. Living the Dream Key West Style

Living the Dream Key West Style
Stock Island
10.0 out of 10, Exceptional, (62 reviews)
"Great would definitely stay again "
United States
Zach C.
$474 nightly
The price is $527
Oct 11 - Oct 12
Total with taxes and fees
Living the Dream Key West Style
A tropical garden pathway leading to a building with a yellow facade and green shutters.

4. SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
Old Town Key West
9.8 out of 10, Exceptional, (138 reviews)
"Great place to stay"
United States
walter l.
$288 nightly
The price is $320
Oct 13 - Oct 14
Total with taxes and fees
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
A wooden signpost with city names and distances in miles.

5. Steps from Duval, Pool on Site & Bikes Included!

Steps from Duval, Pool on Site & Bikes Included!
Old Town Key West
9.6 out of 10, Exceptional, (458 reviews)
"This studio is in a wonderful location and comes with bikes and a pool spa. It is a fabulous place to stay for a relaxing get-away island-style."
United States
Laura D.
$215 nightly
The price is $239
Oct 11 - Oct 12
Total with taxes and fees
Steps from Duval, Pool on Site & Bikes Included!
A modern living room with a sofa, coffee table, and a dining area with a table and chairs. There is a kitchen area with cabinets and appliances.

6. The Grand Cayman | Beautifully Remodeled Key West!

The Grand Cayman | Beautifully Remodeled Key West!
Key West
9.8 out of 10, Exceptional, (21 reviews)
"Great facility and loved the location! "
United States
Matt R.
$447 nightly
The price is $497
Oct 26 - Oct 27
Total with taxes and fees
The Grand Cayman | Beautifully Remodeled Key West!
Living Area

7. Capmar House at Lunara Bay

Capmar House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (29 reviews)
"The Best VRBO I have stayed in "
United States
Wilbert C.
$1,313 nightly
The price is $1,457
Oct 11 - Oct 12
Total with taxes and fees
Capmar House at Lunara Bay
A beach with lounge chairs, palm trees, and a water body.

8. Grand Marina Suite - Poolside & Waterfront Condo

Grand Marina Suite - Poolside & Waterfront Condo
Stock Island
9.6 out of 10, Exceptional, (35 reviews)
"Pool was great! Just far enough from Duval street to get away and relax if needed or jump in the car and head down for live music! "
United States
Brent H.
$569 nightly
The price is $632
Oct 13 - Oct 14
Total with taxes and fees
Grand Marina Suite - Poolside & Waterfront Condo
A living room with a beige sofa, a white coffee table with a plant, and a view through glass doors to an outdoor area.

9. Waterlane House at Lunara Bay

Waterlane House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (38 reviews)
"Everything was great"
United States
Justin S.
$1,313 nightly
The price is $1,457
Oct 11 - Oct 12
Total with taxes and fees
Waterlane House at Lunara Bay
A wooden boardwalk leading to a building with a green roof, surrounded by lush greenery and palm trees.

10. The Cat Island Suite | Charmingly Renovated w/ Pool

The Cat Island Suite | Charmingly Renovated w/ Pool
Key West
9.8 out of 10, Exceptional, (47 reviews)
"I liked that it was pretty centrally located to everything very nice Thank you we had a great time "
United States
Patti E.
$447 nightly
The price is $497
Oct 26 - Oct 27
Total with taxes and fees
The Cat Island Suite | Charmingly Renovated w/ Pool
A narrow alleyway with white buildings, a stone pathway, and various plants.

11. Welcome Matt's - Truman @ Duval | Perfect Hideaway!

Welcome Matt's - Truman @ Duval | Perfect Hideaway!
Old Town Key West
9.8 out of 10, Exceptional, (33 reviews)
"The apartment was perfect for a trip to Key West!! Super good communication with the host. Their bus happened to be at the airport when I landed and even got to enjoy a complimentary ride from the airport! They went the extra mile and I can’t wait to book again!"
United States
John
$419 nightly
The price is $465
Oct 12 - Oct 13
Total with taxes and fees
Welcome Matt's - Truman @ Duval | Perfect Hideaway!
Exterior

12. Island View 1BR Residence With Balcony

Island View 1BR Residence With Balcony
2.0 star property
Key West
10.0 out of 10, Exceptional, (3 reviews)
"Great place it is a full apartment with everything you could need and very clean "
United States
Luis
$305 nightly
The price is $343
Oct 11 - Oct 12
Total with taxes and fees
Island View 1BR Residence With Balcony
A wooden deck with a large tree, outdoor seating, and a marina in the background.

13. Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (37 reviews)
"Definitely would stay here again. Very smooth process. Property was perfect for our family of 5. We loved having access to the pool right at our doorstep. Very accurate photos and description. Excellent value for the money."
United States
Danielle D.
$275 nightly
The price is $305
Oct 18 - Oct 19
Total with taxes and fees
Poolside Cottage #412
Property Overview

14. Aquaria House at Lunara Bay

Aquaria House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (46 reviews)
"Loved the property and the location!! It was perfect for me and the family. Short commute to everything we needed and wanted. I can't wait to go back for the next visit!!"
United States
Chris H.
$1,313 nightly
The price is $1,457
Oct 11 - Oct 12
Total with taxes and fees
Aquaria House at Lunara Bay
A wooden boardwalk leading to a hotel with a green roof, surrounded by palm trees and a water feature.

15. The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!

The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!
Key West
10.0 out of 10, Exceptional, (35 reviews)
"Very nice clean place. Had a minor problem with the beds after checking in but property manager was quick to respond and correct issue. Would stay here again. "
United States
Teri K.
$448 nightly
The price is $498
Oct 11 - Oct 12
Total with taxes and fees
The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!
A wide sandy beach with palm trees and a clear sky.

16. Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.

Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.
Key West
9.2 out of 10, Wonderful, (115 reviews)
"I enjoyed my stay at the resort, highly recommend!"
United States
Michelaine a.
$417 nightly
The price is $464
Oct 11 - Oct 12
Total with taxes and fees
Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.
A beach path leading to the ocean with palm trees and a wooden fence.

17. Magical Ocean Penthouse Top-Floor Ocean View Condo. Feel the magic.

Magical Ocean Penthouse Top-Floor Ocean View Condo. Feel the magic.
Beachside
9.8 out of 10, Exceptional, (236 reviews)
"Condo was clean and beautiful. Pool area was gorgeous. Cannot wait to get back!"
United States
carol c.
$707 nightly
The price is $763
Oct 30 - Oct 31
Total with taxes and fees
Magical Ocean Penthouse Top-Floor Ocean View Condo. Feel the magic.
Property Overview

18. Suncoast House at Lunara Bay

Suncoast House at Lunara Bay
Raccoon Key
9.6 out of 10, Exceptional, (43 reviews)
"Beautiful House, super clean, perfect location "
United States
carlos s.
$1,423 nightly
The price is $1,584
Oct 19 - Oct 20
Total with taxes and fees
Suncoast House at Lunara Bay
A multi-level wooden house with a blue staircase and white railings.

19. Underwater Cabana at Custom House Inn | On Duval!

Underwater Cabana at Custom House Inn | On Duval!
Key West Historic District
9.8 out of 10, Exceptional, (26 reviews)
"Perfect location, spacious room. Our second time staying at this venue."
United States
Colleen L.
$407 nightly
The price is $452
Oct 26 - Oct 27
Total with taxes and fees
Underwater Cabana at Custom House Inn | On Duval!
A covered balcony with wicker chairs, a view of palm trees, and multiple flags.

20. NIGHTCAP ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches!

NIGHTCAP ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches!
Old Town Key West
10.0 out of 10, Exceptional, (15 reviews)
"Wonderful stay, location was great!"
United States
Taffy M.
$289 nightly
The price is $321
Oct 19 - Oct 20
Total with taxes and fees
NIGHTCAP ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Rockland Key Hotel Reviews

Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

8/10 Good
"Enjoyed the beach. Nice ocean view room. Clean and pet friendly. Our neighbors were noisy and annoying and there was a Harley convention our first night. Nice, pleasant resort with many amenities in paradise. Good hike to the Key West action. Key West is expensive."
Mike 4-night trip
Posted 1 hour ago
Casa Marina Key West, Curio Collection by Hilton

Find out more about Rockland Key

Everything you need to know about Rockland Key vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Rockland Key vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Rockland Key vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Rockland Key vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Rockland Key. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Rockland Key in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $206 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Rockland Key rentals

At Expedia, we put the best Rockland Key vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Rockland Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Rockland Key vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Rockland Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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