Rockland Key Vacation Rentals

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Vacation Rentals in Rockland Key

Houseboat in Stock Island

2.0 star property
9.0 out of 10, Wonderful, (169)
"Location , staff , and aqua lodge were perfect."
United States
William
$301 nightly
The price is $339
Dec 14 - Dec 15
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina

Cottage in Cudjoe Key

9.2 out of 10, Wonderful, (161)
"Great property,Great location. Will definitely stay there again."
United States
Roy F.
$285 nightly
The price is $316
Dec 6 - Dec 7
Total with taxes and fees
Cottage with Pool and Dockage, just minutes to Key West

Cottage in Cudjoe Key

8.2 out of 10, Very Good, (48)
"Great area. Quiet and comfortable "
United States
nancy c.
$285 nightly
The price is $316
Dec 9 - Dec 10
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Apartment in Old Town Key West

3.5 star property
8.4 out of 10, Very Good, (317)
"Place was great bed was comfy and the water was HOT!!! "
United States
Angela
$289 nightly
The price is $325
Dec 8 - Dec 9
Total with taxes and fees
Hyatt Vacation Club at Sunset Harbor, Key West

Cottage in Cudjoe Key

8.6 out of 10, Excellent, (151)
"This cottage served our purpose well, very close to our family’s home and was very clean and comfortable for a short stay."
United States
Richard S.
$228 nightly
The price is $253
Dec 15 - Dec 16
Total with taxes and fees
Cottage with Pool and Boat Dockage just minutes to Key West!

Vacation Home in Cudjoe Key

9.4 out of 10, Exceptional, (101)
"Great location. "
United States
Davian k.
$391 nightly
The price is $434
Dec 6 - Dec 7
Total with taxes and fees
DECEMBER SAVE 60% OFF! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Vacation Home in Cudjoe Key

9.8 out of 10, Exceptional, (82)
"The place is clean and convenient for anyone wanting to spend time on the water in the keys"
United States
Ubaldo G.
$504 nightly
The price is $560
Dec 8 - Dec 9
Total with taxes and fees
DECEMBER SAVE 60% OFF OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Vacation Home in Summerland Key

9.8 out of 10, Exceptional, (121)
"We enjoyed our stay! Great little house and location. "
United States
Lisa K.
$489 nightly
The price is $543
Dec 14 - Dec 15
Total with taxes and fees
Kelly's Kabin - Adorable Private Summerland Key Cottage

Vacation Home in Cudjoe Key

2.5 star property
9.6 out of 10, Exceptional, (11)
"Our family had an amazing vacation! We love the house and hope to come back!! "
United States
Tammy G.
$585 nightly
The price is $650
Dec 6 - Dec 7
Total with taxes and fees
Island Time #110 Ocean Views - Cudjoe Key

Houseboat in Stock Island

7.8 out of 10, Good, (26)
"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
$451 nightly
The price is $501
Dec 6 - Dec 7
Total with taxes and fees
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Houseboat in Stock Island

9.8 out of 10, Exceptional, (34)
"Everything was very nice. Staff was friendly and helpful ."
United States
Debra
$306 nightly
The price is $340
Dec 8 - Dec 9
Total with taxes and fees
Living the Dream Key West Style

Vacation Home in Cutthroat Harbor Estates

8.4 out of 10, Very Good, (118)
"Great experience "
United States
Peyton S.
$483 nightly
The price is $536
Dec 6 - Dec 7
Total with taxes and fees
Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Vacation Home in Little Torch Key

9.6 out of 10, Exceptional, (85)
"The secluded dock is a nice feature. The driveway is tricky to exit. "
United States
drywall c.
$792 nightly
The price is $880
Dec 26 - Dec 27
Total with taxes and fees
Old Florida Style, wrap around porch, boat basin for dockage, open water

Cottage in Old Town Key West

10.0 out of 10, Exceptional, (24)
"We had a wonderful stay here with our kids. Can’t beat the location."
United States
Julia P.
$367 nightly
The price is $404
Dec 17 - Dec 18
Total with taxes and fees
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

Vacation Home in Key West

9.8 out of 10, Exceptional, (53)
"Perfect for our family! Recommend 10/10!"
United States
Melissa F.
$274 nightly
The price is $304
Dec 14 - Dec 15
Total with taxes and fees
Poolside Cottage #411

Aparthotel in Key West

2.0 star property
10.0 out of 10, Exceptional, (2)
"Great place it is a full apartment with everything you could need and very clean "
United States
Luis
$377 nightly
The price is $424
Dec 9 - Dec 10
Total with taxes and fees
Island View 1BR Residence With Balcony

Condo in Meadows

10.0 out of 10, Exceptional, (24)
"My husband and I stayed at this property for our anniversary week. "
United States
Claudia S.
Curaçao Key West 2BR Condo w/ Pool&Waterfront Dock

Apartment in Key West

9.8 out of 10, Exceptional, (28)
"I stayed at this property for 3 nights and it was wonderful super clean and very comfortableJust minutes away from all the attractions and far away from the crowds. Really quiet at night A I really recommend this property "
United States
domingo d.
$390 nightly
The price is $429
Dec 8 - Dec 9
Total with taxes and fees
The Cat Island Suite | Beautifully Renovated w/ Pool!

Vacation Home in Summerland Key

8.8 out of 10, Excellent, (65)
"My family and I had an incredible stay. We utilized every available component of the home including the dock. Property manager provided us with 2 available free ramps to drop off our jet-skis. We settled on the ramp located on Blimp Road, which was a 10 minute drive and 15-20 minute ride on the skis. We were able to tie off our skis our whole stay with no issues. Home was exactly as disclosed and worked great for our family. Communication was great, with quick respond time. "
United States
Yissel W.
$1,186 nightly
The price is $1,316
Dec 15 - Dec 16
Total with taxes and fees
One of the very few beach houses with a daily, rental license in the Keys.

Apartment in Key West

9.0 out of 10, Wonderful, (27)
"Good location and clean. Definitely recommend. "
United States
Kim Y.
$390 nightly
The price is $429
Dec 8 - Dec 9
Total with taxes and fees
The Andros | Incredible Views w/ Shared Pool
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

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 $227 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.