Rockland Key Vacation Rentals

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Our top choices for Rockland Key vacation rentals

Ocean Front One Bedroom Residence

Ocean Front One Bedroom Residence
2.0 star property
Key West
The price is CA $875
CA $1,099 total
includes taxes & fees
Mar 29 - Mar 30
Ocean Front One Bedroom Residence

Contra House Key West

Contra House Key West
3.0 star property
Old Town Key West
The price is CA $1,906
CA $2,698 total
includes taxes & fees
Apr 23 - Apr 24
Contra House Key West

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
9.0 out of 10, Wonderful, (181 reviews)
"Great stay better than we expected "
Canada
Jordan
The price is CA $181
CA $436 total
includes taxes & fees
Mar 29 - Mar 30
Aqua Lodges at Hurricane Hole Marina

Lighthouse Suites Collection

Lighthouse Suites Collection
4.0 star property
Old Town Key West
The price is CA $772
CA $1,318 total
includes taxes & fees
Mar 29 - Mar 30
Lighthouse Suites Collection

Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
3.5 star property
Summerland Key
10.0 out of 10, Exceptional, (2 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 $777
CA $1,418 total
includes taxes & fees
Apr 12 - Apr 13
Atlantic View Luxury Villa with Pool

Resort View 1BR Suite With Direct Pool Access

Resort View 1BR Suite With Direct Pool Access
2.0 star property
Key West
The price is CA $593
CA $782 total
includes taxes & fees
Mar 29 - Mar 30
Resort View 1BR Suite With Direct Pool Access

Poolside Suite by Brightwild Pvt Pool Parking

Poolside Suite by Brightwild Pvt Pool Parking
2.0 star property
Old Town Key West
The price is CA $864
CA $1,341 total
includes taxes & fees
Apr 9 - Apr 10
Poolside Suite by Brightwild Pvt Pool Parking

Sea Breeze by Brightwild Off-street Parking

Sea Breeze by Brightwild Off-street Parking
2.0 star property
Old Town Key West
The price is CA $1,135
CA $1,709 total
includes taxes & fees
Apr 21 - Apr 22
Sea Breeze by Brightwild Off-street Parking

Mesa House Uno by Brightwild Perfect Location

Mesa House Uno by Brightwild Perfect Location
2.0 star property
Key West Historic District
Mesa House Uno by Brightwild Perfect Location

Resort View 3BR Residence

Resort View 3BR Residence
2.0 star property
Key West
The price is CA $1,339
CA $2,021 total
includes taxes & fees
Apr 13 - Apr 14
Resort View 3BR Residence

New Coastal Rose - Bright Loft With High Ceilings

New Coastal Rose - Bright Loft With High Ceilings
2.0 star property
Key West Historic District
The price is CA $668
CA $1,161 total
includes taxes & fees
Apr 12 - Apr 13
New Coastal Rose - Bright Loft With High Ceilings

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 $691
CA $1,105 total
includes taxes & fees
Apr 27 - Apr 28
Grand Marina Suite by Brightwild Waterfront

Commodore s Cove by Brightwild Epic Location

Commodore s Cove by Brightwild Epic Location
2.0 star property
Key West Historic District
The price is CA $1,663
CA $2,606 total
includes taxes & fees
Apr 21 - Apr 22
Commodore s Cove by Brightwild Epic Location

Ocean Front 2BR Residence

Ocean Front 2BR Residence
2.0 star property
Key West
The price is CA $1,248
CA $1,755 total
includes taxes & fees
Mar 29 - Mar 30
Ocean Front 2BR Residence

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
The price is CA $590
CA $1,112 total
includes taxes & fees
Apr 14 - Apr 15
Starlight Serenity - Hideaway w Stunning Views

Sky Suite on Duval by Brightwild Condo w Balcony

Sky Suite on Duval by Brightwild Condo w Balcony
2.0 star property
Old Town Key West
The price is CA $1,074
CA $1,657 total
includes taxes & fees
Apr 21 - Apr 22
Sky Suite on Duval by Brightwild Condo w Balcony

Duval Dream Loft by Brightwild Right on Duval

Duval Dream Loft by Brightwild Right on Duval
2.0 star property
Old Town Key West
10.0 out of 10, Exceptional, (1 review)
The price is CA $730
CA $1,272 total
includes taxes & fees
Apr 22 - Apr 23
Duval Dream Loft by Brightwild Right on Duval

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
The price is CA $650
CA $846 total
includes taxes & fees
Mar 29 - Mar 30
Island View 1BR Residence With Balcony

Kamp by Brightwild Rooftop Penthouse On Duval

Kamp by Brightwild Rooftop Penthouse On Duval
2.0 star property
Old Town Key West
The price is CA $1,129
CA $1,721 total
includes taxes & fees
Apr 7 - Apr 8
Kamp by Brightwild Rooftop Penthouse On Duval

Tortuga Suite Sparkling Pool Hot Tub

Tortuga Suite Sparkling Pool Hot Tub
2.0 star property
Key West
The price is CA $544
CA $979 total
includes taxes & fees
Mar 29 - Mar 30
Tortuga Suite Sparkling Pool Hot Tub
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

Find out more about Rockland Key

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Rockland Key. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.