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Rockland Key Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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
$253 nightly
The price is $285
Oct 14 - Oct 15
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina
A hot tub with a view of a marina and boats during sunset.

2. 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.
$478 nightly
The price is $531
Oct 13 - Oct 14
Total with taxes and fees
Living the Dream Key West Style
A beachside resort with a wooden deck, palm trees, and a sunset view.

3. 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 13 - Oct 14
Total with taxes and fees
Grand Marina Suite by Brightwild Waterfront
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.
$272 nightly
The price is $302
Oct 13 - Oct 14
Total with taxes and fees
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
A modern living room with a sofa, coffee table, and a painting of a beach scene.

5. The Saint Kitts Suite | Breathtaking View, Heated Pool

The Saint Kitts Suite | Breathtaking View, Heated Pool
Key West
9.6 out of 10, Exceptional, (9 reviews)
"Beautifully decorated and great location. The condo was clean, comfortable, quiet and well stocked. Would recommend and definitely stay there again!"
United States
Linda W.
$451 nightly
The price is $501
Oct 13 - Oct 14
Total with taxes and fees
The Saint Kitts Suite | Breathtaking View, Heated Pool
A wide sandy beach with palm trees and a clear sky.

6. 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.
$421 nightly
The price is $468
Oct 13 - Oct 14
Total with taxes and fees
Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.
A wooden boardwalk leading to a building with a green roof, surrounded by lush greenery and palm trees.

7. 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.
$446 nightly
The price is $496
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.

8. 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
$418 nightly
The price is $464
Oct 13 - Oct 14
Total with taxes and fees
Welcome Matt's - Truman @ Duval | Perfect Hideaway!
A wide sandy beach with palm trees and a clear sky.

9. Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony

Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony
Key West
9.0 out of 10, Wonderful, (49 reviews)
"Great place for our 1 night in key west "
United States
Thadd W.
$426 nightly
The price is $473
Oct 13 - Oct 14
Total with taxes and fees
Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony
A wooden signpost with city names and distances in miles.

10. 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 14 - Oct 15
Total with taxes and fees
Steps from Duval, Pool on Site & Bikes Included!
A beach with lounge chairs, palm trees, and a water body.

11. 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 wooden boardwalk leading to a hotel with a green roof, surrounded by palm trees and a water feature.

12. 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.
$446 nightly
The price is $496
Oct 26 - Oct 27
Total with taxes and fees
The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!
Exterior

13. 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 14 - Oct 15
Total with taxes and fees
Island View 1BR Residence With Balcony
A swimming pool with lounge chairs and a thatched roof structure, surrounded by lush greenery and a brick patio.

14. Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS

Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
Stock Island
9.6 out of 10, Exceptional, (136 reviews)
"I can't say enough about how wonderful this property is or the host."
United States
Linda
$468 nightly
The price is $519
Oct 13 - Oct 14
Total with taxes and fees
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
A wooden deck with rows of green lounge chairs facing the ocean, a rope barrier, and a distant view of the sunset over the water.

15. Luxury Waterfront at Galion Resort in Old Town

Luxury Waterfront at Galion Resort in Old Town
Key West Historic District
9.6 out of 10, Exceptional, (113 reviews)
"A great place for my family to stay on our trip! Lots of room and all the amenities you could need for a perfect trip to Key West."
United States
Katie C.
$771 nightly
The price is $855
Nov 3 - Nov 4
Total with taxes and fees
Luxury Waterfront at Galion Resort in Old Town
A narrow brick pathway flanked by white buildings with potted plants and a bench.

16. Abbey's Attic - Truman @ Duval | Cozy Getaway in the Heart of Key West

Abbey's Attic - Truman @ Duval | Cozy Getaway in the Heart of Key West
Old Town Key West
9.8 out of 10, Exceptional, (27 reviews)
"Awesome location & very helpful host!"
United States
Jay M.
$337 nightly
The price is $374
Oct 13 - Oct 14
Total with taxes and fees
Abbey's Attic - Truman @ Duval | Cozy Getaway in the Heart of Key West
A bedroom with two beds, a ceiling fan, a window with curtains, a wall clock, and a decorative plate.

17. Waterfront Condo Dock Pool Downtown Near Duval

Waterfront Condo Dock Pool Downtown Near Duval
Meadows
9.6 out of 10, Exceptional, (30 reviews)
"Wow, this was one of the best short term rentals we've done. Well appointed, extremely clean, convenient location, and everything pretty much top of the line."
United States
John L.
$436 nightly
The price is $485
Oct 28 - Oct 29
Total with taxes and fees
Waterfront Condo Dock Pool Downtown Near Duval
A fish cleaning station with a sign, wooden structure, and water.

18. Waterfront Dock Pool Key West Near Duval

Waterfront Dock Pool Key West Near Duval
Meadows
10.0 out of 10, Exceptional, (40 reviews)
"We loved our stay! Beautiful room with a wonderful view. We loved how quiet and relaxing it was!"
United States
Jesse B.
$472 nightly
The price is $524
Nov 9 - Nov 10
Total with taxes and fees
Waterfront Dock Pool Key West Near Duval
A wooden deck with a large tree, outdoor seating, and a marina in the background.

19. Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (37 reviews)
"Wonderful stay. Thank you."
United States
shannon b.
$265 nightly
The price is $295
Oct 18 - Oct 19
Total with taxes and fees
Poolside Cottage #412
A living room with a sofa, two chairs, a coffee table, a TV, and a ceiling fan.

20. Hollinsed House Studio - Great Location!!

Hollinsed House Studio - Great Location!!
Old Town Key West
9.6 out of 10, Exceptional, (162 reviews)
"Nice location, clean, & would stay there again"
United States
Karen L.
Hollinsed House Studio - Great Location!!
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

Hilton Garden Inn Key West / The Keys Collection

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."
Barry 3-night trip
Posted 4 hours ago
Hilton Garden Inn Key West / The Keys Collection

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 $208 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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