Rockland Key Holiday Rentals

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Our top choices for Rockland Key holiday rentals

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 AU$1,441
includes taxes & fees
22 Feb - 23 Feb
Atlantic View Luxury Villa with Pool

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

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 AU$1,496
includes taxes & fees
4 Mar - 5 Mar
Grand Marina Suite by Brightwild Waterfront

Charming cottages, dockage, pool, just minutes to Key West

Charming cottages, dockage, pool, just minutes to Key West
Cudjoe Key
8.6 out of 10, Excellent, (122 reviews)
"Amazing place for a getaway. Very calm quiet area and close to 2 nice beaches. "
United States
ANJANA
The price is AU$567
includes taxes & fees
15 Feb - 16 Feb
Charming cottages, dockage, pool, just minutes to Key West

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (177 reviews)
"Unique place to stay! We loved the nature and the location! "
United States
Sara
The price is AU$573
includes taxes & fees
3 Mar - 4 Mar
Aqua Lodges at Hurricane Hole Marina

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)
"Great location and Host was very helpful and responsive."
United States
Dennis G.
The price is AU$840
includes taxes & fees
1 Mar - 2 Mar
Kelly's Kabin - Adorable Private Summerland Key Cottage

One of the very few beach houses with a daily, rental license in the Keys.

One of the very few beach houses with a daily, rental license in the Keys.
Summerland Key
8.8 out of 10, Excellent, (65 reviews)
"Excellent secluded location but near everything Thanks!!!!!"
United States
Gary D.
The price is AU$2,304
includes taxes & fees
14 Mar - 15 Mar
One of the very few beach houses with a daily, rental license in the Keys.

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

SAVE BIG $$FEBRUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (83 reviews)
"The place is clean and convenient for anyone wanting to spend time on the water in the keys"
United States
Ubaldo G.
The price is AU$1,023
includes taxes & fees
5 Mar - 6 Mar
SAVE BIG $$FEBRUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

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 AU$959
includes taxes & fees
16 Feb - 17 Feb
Spanish Queen @Venture Out, Cudjoe Key

Waterfront Home

Waterfront Home
Cudjoe Key
8.6 out of 10, Excellent, (178 reviews)
"Great location if you bring a boat. Secure location. Venture Out is a nice community. "
United States
Georgiana V.
The price is AU$676
includes taxes & fees
22 Feb - 23 Feb
Waterfront Home

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)
"Will definitely stay here again "
United States
Jeannine R.
Relax by Florida Keys Beaches, just a 7-min drive away

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 AU$1,604
includes taxes & fees
20 Feb - 21 Feb
Private and Exclusive Florida Keys Getaway

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 AU$947
includes taxes & fees
2 Mar - 3 Mar
Resort View 1BR Suite With Direct Pool Access

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 AU$757
includes taxes & fees
2 Mar - 3 Mar
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

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, (151 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 AU$1,014
includes taxes & fees
21 Feb - 22 Feb
Cudjoe Cottages, swimming pool, just 20 miles from Key West

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 AU$2,944
includes taxes & fees
8 Mar - 9 Mar
The Seagate Estate at Lunara Bay

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Cudjoe Key
8.6 out of 10, Excellent, (90 reviews)
"We had a great time and will be back. "
United States
Michelle K.
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

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

SAVE BIG $$FEBRUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (104 reviews)
"Great location. "
United States
Davian k.
The price is AU$692
includes taxes & fees
25 Feb - 26 Feb
SAVE BIG $$FEBRUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Comfortable Condo with Pool, Private Balcony, & Beach Access

Comfortable Condo with Pool, Private Balcony, & Beach Access
Beachside
8.6 out of 10, Excellent, (140 reviews)
"Beautiful property! Pool was phenomenal. There is a men’s and a Womens sauna separately. The common area greenery is beautiful. Thank you"
United States
Amanda G.
The price is AU$1,413
includes taxes & fees
11 Mar - 12 Mar
Comfortable Condo with Pool, Private Balcony, & Beach Access

Capmar House at Lunara Bay

Capmar House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (29 reviews)
"The property had all the comforts of home. Plus, being able to enjoy the heated pool even through the overcast and windy conditions! The tropical landscaping and the dock on the bay was awesome!Would definitely recommend!!!"
United States
Anonymous traveller
The price is AU$2,211
includes taxes & fees
17 Feb - 18 Feb
Capmar 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

Everything you need to know about Rockland Key holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Rockland Key holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Rockland Key holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Rockland Key holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Rockland Key holiday rentals we have selected for you start as low as AU$439 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Rockland Key rentals

At Expedia, we put the best Rockland Key holiday 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 holiday.

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.