Rockland Key Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 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, (202 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
The price is CA $145
CA $405 total
includes taxes & fees
Nov 10 - Nov 11
Aqua Lodges at Hurricane Hole Marina
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

The Grenada Suite Pool View Private Balcony
2.0 star property
Key West
9.0 out of 10, Wonderful, (2 reviews)
"A little dated, but clean and well located."
United States
Luis
The price is CA $343
CA $786 total
includes taxes & fees
Nov 30 - Dec 1
The Grenada Suite Pool View Private Balcony
A pool area with a wooden deck, lounge chairs, and a waterfall feature.

3. Lighthouse Suites Collection

Lighthouse Suites Collection
4.0 star property
Old Town Key West
10.0 out of 10, Exceptional, (2 reviews)
"My favorite place now. Won’t stay anywhere else. Lost track of the amount of my Key West stays, but this place has been the the most memorable."
United States
Melissa
The price is CA $732
CA $1,064 total
includes taxes & fees
Nov 13 - Nov 14
Lighthouse Suites Collection
A modern house with a swimming pool, a balcony, and a well-maintained garden.

4. Contra House Key West

Contra House Key West
3.0 star property
Old Town Key West
8.0 out of 10, Very good, (1 review)
"Pool and outside was undesirable"
United States
Rosalie
The price is CA $999
CA $1,689 total
includes taxes & fees
Nov 10 - Nov 11
Contra House Key West
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

Atlantic View Luxury Villa with Pool
3.5 star property
Summerland Key
7.4 out of 10, Good, (3 reviews)
"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "
United States
Preetam
The price is CA $731
CA $1,379 total
includes taxes & fees
Nov 15 - Nov 16
Atlantic View Luxury Villa with Pool
A wooden pedestrian bridge over a water body, surrounded by lush greenery and palm trees.

6. Tortuga Suite Sparkling Pool Hot Tub

Tortuga Suite Sparkling Pool Hot Tub
2.0 star property
Key West
The price is CA $350
CA $794 total
includes taxes & fees
Dec 1 - Dec 2
Tortuga Suite Sparkling Pool Hot Tub
A beachside resort with a wooden deck, palm trees, and a sunset view.

7. 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
The price is CA $550
CA $962 total
includes taxes & fees
Nov 10 - Nov 11
Grand Marina Suite by Brightwild Waterfront
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

Poolside Retreat by Brightwild Cottage w Pool
3.0 star property
Old Town Key West
2.0 out of 10, (2 reviews)
"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...
United States
Julia
The price is CA $331
CA $639 total
includes taxes & fees
Dec 9 - Dec 10
Poolside Retreat by Brightwild Cottage w Pool
A wooden deck with a hanging hammock and a view of a green landscape.

9. Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
10.0 out of 10, Exceptional, (1 review)
"The host team is amazing and very responsive. The house is very beautiful inside and out. We loved grilling downstairs, so much room down there. We loved our stay here because it was very secluded, unlike Key West, where you are on top of each other. The location is perfect because you can still make it down to Key West in 25 minutes for activities and food."
United States
max
The price is CA $471
CA $1,019 total
includes taxes & fees
Nov 19 - Nov 20
Starlight Serenity - Hideaway w Stunning Views
A modern kitchen with white cabinets, stainless steel appliances, and a wooden door.

10. The Bartlum Luxury Studio In Prime Location

The Bartlum Luxury Studio In Prime Location
2.0 star property
Key West Historic District
The price is CA $409
CA $790 total
includes taxes & fees
Nov 11 - Nov 12
The Bartlum Luxury Studio In Prime Location
A covered porch with a table and chairs, overlooking a street with houses and cars.

11. Banana Split by Brightwild Pool Grill

Banana Split by Brightwild Pool Grill
2.0 star property
Key West Historic District
The price is CA $371
CA $711 total
includes taxes & fees
Nov 30 - Dec 1
Banana Split by Brightwild Pool Grill
A porch with a white railing, a pink door, and a white fence.

12. New Rose Petal Petite Suite - Pool Parking

New Rose Petal Petite Suite - Pool Parking
2.0 star property
Key West Historic District
The price is CA $353
CA $638 total
includes taxes & fees
Nov 29 - Nov 30
New Rose Petal Petite Suite - Pool Parking
A white house with a porch, palm trees, and a white picket fence.

13. Mesa House Uno by Brightwild Perfect Location

Mesa House Uno by Brightwild Perfect Location
2.0 star property
Key West Historic District
The price is CA $480
CA $869 total
includes taxes & fees
Dec 1 - Dec 2
Mesa House Uno by Brightwild Perfect Location
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

Evershore House Pool Parking Dock
2.0 star property
Raccoon Key
The price is CA $1,085
CA $2,200 total
includes taxes & fees
Nov 24 - Nov 25
Evershore House Pool Parking Dock
A white house with a porch, surrounded by tropical plants and a stone pathway.

15. New The Cottage at James House

New The Cottage at James House
2.0 star property
Key West Historic District
8.0 out of 10, Very good, (2 reviews)
"The best thing about this property is location. Short walk to everything - short walk to Sloppy Joes. It is overpriced for the accommodations but you pay for location. "
United States
Pamela
The price is CA $577
CA $827 total
includes taxes & fees
Nov 30 - Dec 1
New The Cottage at James House
A white two-story house with a balcony and a swimming pool.

16. Capmar House by Brightwild Huge Home Pool

Capmar House by Brightwild Huge Home Pool
2.0 star property
Raccoon Key
10.0 out of 10, Exceptional, (1 review)
"Wonderful property, 4 large bedroom and en suite bathroom, private pool we really liked our stay"
France
Karen
The price is CA $1,085
CA $2,200 total
includes taxes & fees
Nov 10 - Nov 11
Capmar House by Brightwild Huge Home Pool
A two-story house with a swimming pool, surrounded by greenery and palm trees.

17. Seagate House by Brightwild Waterfront w Dock

Seagate House by Brightwild Waterfront w Dock
2.0 star property
Raccoon Key
The price is CA $1,448
CA $2,608 total
includes taxes & fees
Nov 16 - Nov 17
Seagate House by Brightwild Waterfront w Dock
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

Mastway House by Brightwild Pool Dock
2.0 star property
Raccoon Key
The price is CA $1,085
CA $2,200 total
includes taxes & fees
Nov 10 - Nov 11
Mastway House by Brightwild Pool Dock
A modern kitchen with a large island, bar stools, and pendant lighting.

19. The Joyrise House at Solaire Lunara Bay

The Joyrise House at Solaire Lunara Bay
2.5 star property
Raccoon Key
The price is CA $2,172
CA $3,868 total
includes taxes & fees
Nov 10 - Nov 11
The Joyrise House at Solaire Lunara Bay
A white two-story house with a central archway and a paved driveway.

20. Palmgale House in Key West

Palmgale House in Key West
2.5 star property
Raccoon Key
The price is CA $1,448
CA $2,964 total
includes taxes & fees
Nov 10 - Nov 11
Palmgale House in Key West
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

A pool area with lounge chairs and palm trees, surrounded by boats and a sunset in the background.
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West
Stock Island

10/10 Excellent

Lovely boutique hotel located in a marina. Very romantic spot. Really nice pool area and a good gym. Staff is very friendly. Restaurants were quite good as well The only reason I am not giving 5 stars is because there was a really funky smell in the rooms and halls that really bothered us. Not sure what it was. Also the beds were not comfortable and seemed “worn out”. They need to be replaced/upgraded.
Canada
Trisha
Reviewed December 5, 2024
The Perry Hotel & Marina Key West

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, cottages, cabins, villas... 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Rockland Key vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Rockland Key vacation rentals we have selected for you start as low as CA $145 per night. Entering your travel dates in the search wizard 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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