Rockland Key Vacation Rentals

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Our top choices for Rockland Key vacation rentals

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (175 reviews)
"Unique place to stay! We loved the nature and the location! "
United States
Sara
The price is CA $303
CA $571 total
includes taxes & fees
Mar 1 - Mar 2
Aqua Lodges at Hurricane Hole Marina

SAVE BIG $$FEBRUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$FEBRUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (103 reviews)
"Great location. "
United States
Davian k.
The price is CA $272
CA $683 total
includes taxes & fees
Feb 25 - Feb 26
SAVE BIG $$FEBRUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
8.6 out of 10, Excellent, (52 reviews)
"We were very happy with our stay. Everything was as expected or above. Old Keys vibe was exactly what we wanted. "
United States
Lauren R.
The price is CA $338
CA $629 total
includes taxes & fees
Feb 10 - Feb 11
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cottage with swimming pool and dockage, just minutes to Key West!

Cottage with swimming pool and dockage, just minutes to Key West!
Cudjoe Key
9.0 out of 10, Wonderful, (165 reviews)
"Everything was there that I needed. Very nice area for my dog."
United States
Terry
The price is CA $246
CA $443 total
includes taxes & fees
Feb 15 - Feb 16
Cottage with swimming pool and dockage, just minutes to Key West!

Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Cudjoe Key
8.6 out of 10, Excellent, (165 reviews)
"Everything was nice and clean. Loved the location . Would definitely stay at the property again. "
United States
Shawn M.
Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
3.5 star property
Summerland Key
10.0 out of 10, Exceptional, (1 review)
"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 $892
CA $1,542 total
includes taxes & fees
Feb 10 - Feb 11
Atlantic View Luxury Villa with Pool

Waterfront Home

Waterfront Home
Cudjoe Key
8.6 out of 10, Excellent, (177 reviews)
"Great location if you bring a boat. Secure location. Venture Out is a nice community. "
United States
Georgiana V.
The price is CA $342
CA $668 total
includes taxes & fees
Feb 22 - Feb 23
Waterfront Home

Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (123 reviews)
"We enjoyed our stay! Great little house and location. "
United States
Lisa K.
The price is CA $376
CA $833 total
includes taxes & fees
Mar 1 - Mar 2
Kelly's Kabin - Adorable Private Summerland Key Cottage

Relax by Florida Keys Beaches, just a 7-min drive away

Relax by Florida Keys Beaches, just a 7-min drive away
Cudjoe Key
9.8 out of 10, Exceptional, (201 reviews)
"The cottage was clean and the location was nice and quiet. "
United States
Jaconica B.
The price is CA $376
CA $899 total
includes taxes & fees
Feb 27 - Feb 28
Relax by Florida Keys Beaches, just a 7-min drive away

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 $1,612
CA $2,146 total
includes taxes & fees
Feb 17 - Feb 18
Grand Marina Suite by Brightwild Waterfront

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!
Stock Island
7.8 out of 10, Good, (29 reviews)
"This was exactly what was advertised, it was clean, and in a great location. The on-site restaurant had great food. Also, all staff members we encountered were very friendly and accommodating. I hope it’s available for our next trip."
United States
Julie
The price is CA $342
CA $693 total
includes taxes & fees
Feb 10 - Feb 11
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Private and Exclusive Florida Keys Getaway

Private and Exclusive Florida Keys Getaway
Upper Sugarloaf Key
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful! Pool was amazing!"
United States
Jennifer B.
The price is CA $745
CA $1,584 total
includes taxes & fees
Feb 20 - Feb 21
Private and Exclusive Florida Keys Getaway

Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (19 reviews)
"This is our third time staying here. It is a great property and works perfectly for a three-person family."
United States
Kimberly G.
The price is CA $479
CA $936 total
includes taxes & fees
Feb 16 - Feb 17
Spanish Queen @Venture Out, Cudjoe Key

SAVE BIG $$FEBRUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

SAVE BIG $$FEBRUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (82 reviews)
"The place is clean and convenient for anyone wanting to spend time on the water in the keys"
United States
Ubaldo G.
The price is CA $532
CA $1,012 total
includes taxes & fees
Mar 5 - Mar 6
SAVE BIG $$FEBRUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

The Seagate Estate at Lunara Bay

The Seagate Estate at Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (19 reviews)
"The perfect House , everything was good "
United States
CARLOS G.
The price is CA $1,093
CA $2,338 total
includes taxes & fees
Feb 12 - Feb 13
The Seagate Estate at Lunara Bay

Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly
Cudjoe Key
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful "
United States
Lisa P.
The price is CA $718
CA $1,396 total
includes taxes & fees
Feb 11 - Feb 12
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome

Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome
Key West
8.6 out of 10, Excellent, (143 reviews)
"Clean, easy check-in, great pools, quiet area, comfy beds. Will book again!"
Germany
Julia P.
The price is CA $299
CA $680 total
includes taxes & fees
Mar 4 - Mar 5
Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome

Living the Dream Key West Style

Living the Dream Key West Style
Stock Island
10.0 out of 10, Exceptional, (42 reviews)
"Everything was excellent, awesome host, beautiful vacation!"
United States
Jodi M.
The price is CA $574
CA $728 total
includes taxes & fees
Feb 25 - Feb 26
Living the Dream Key West Style

Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Cottages, swimming pool, just 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (150 reviews)
"Boat access and docking spaces could be improved but overall not terrible. Spent a week here and enjoyed the stay. Quiet decent location. "
United States
bryan c.
The price is CA $513
CA $997 total
includes taxes & fees
Feb 21 - Feb 22
Cudjoe Cottages, swimming pool, just 20 miles from Key West

Suncoast House at Lunara Bay

Suncoast House at Lunara Bay
Raccoon Key
9.6 out of 10, Exceptional, (42 reviews)
"Beautiful House, super clean, perfect location "
United States
carlos s.
The price is CA $1,229
CA $2,745 total
includes taxes & fees
Feb 17 - Feb 18
Suncoast House at Lunara Bay
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.