Rockland Key Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Our top choices for Rockland Key holiday 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, (170)
"Location , staff , and aqua lodge were perfect."
United States
William
The price is NZ$669
includes taxes & fees
14 Jan - 15 Jan 2026
Aqua Lodges at Hurricane Hole Marina

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)
"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 NZ$1,759
includes taxes & fees
16 Jan - 17 Jan 2026
Atlantic View Luxury Villa with Pool

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)
"Nice place "
United States
Pawel
The price is NZ$2,059
includes taxes & fees
2 Jan - 3 Jan 2026
Grand Marina Suite by Brightwild Waterfront

Coconut Mallory Marina and Resort Condo

Coconut Mallory Marina and Resort Condo
3.0 star property
Key West
The price is NZ$2,249
includes taxes & fees
2 Jan - 3 Jan 2026
Coconut Mallory Marina and Resort Condo

Contra House Key West

Contra House Key West
3.0 star property
Old Town Key West
The price is NZ$2,900
includes taxes & fees
14 Jan - 15 Jan 2026
Contra House Key West

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
The price is NZ$1,338
includes taxes & fees
6 Jan - 7 Jan 2026
Starlight Serenity - Hideaway w Stunning Views

Waterfront Luxury Home - Tidelands House

Waterfront Luxury Home - Tidelands House
2.0 star property
Raccoon Key
The price is NZ$5,714
includes taxes & fees
20 Jan - 21 Jan 2026
Waterfront Luxury Home - Tidelands House

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)
"Wonderful property, 4 large bedroom and en suite bathroom, private pool we really liked our stay"
France
Karen
The price is NZ$3,309
includes taxes & fees
20 Jan - 21 Jan 2026
Capmar House by Brightwild Huge Home Pool

Island View 1BR Residence With Balcony

Island View 1BR Residence With Balcony
2.0 star property
Key West
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
The price is NZ$986
includes taxes & fees
4 Jan - 5 Jan 2026
Island View 1BR Residence With Balcony

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 NZ$1,711
includes taxes & fees
20 Jan - 21 Jan 2026
Mesa House Uno by Brightwild Perfect Location

The Grenada Suite Pool View Private Balcony

The Grenada Suite Pool View Private Balcony
2.0 star property
Key West
10.0 out of 10, Exceptional, (1)
The Grenada Suite Pool View Private Balcony

Palmgale House in Key West

Palmgale House in Key West
2.0 star property
Raccoon Key
The price is NZ$3,997
includes taxes & fees
4 Jan - 5 Jan 2026
Palmgale House in Key West

The Fairhaven House at Solaire Lunara Bay

The Fairhaven House at Solaire Lunara Bay
2.0 star property
Raccoon Key
The price is NZ$5,985
includes taxes & fees
20 Jan - 21 Jan 2026
The Fairhaven House at Solaire Lunara Bay

Brand New Catchlight House With Private Pool

Brand New Catchlight House With Private Pool
2.5 star property
Raccoon Key
The price is NZ$4,391
includes taxes & fees
20 Jan - 21 Jan 2026
Brand New Catchlight House With Private Pool

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 NZ$1,652
includes taxes & fees
20 Jan - 21 Jan 2026
The Bartlum Luxury Studio In Prime Location

New Waterfront Home - Dreamside House

New Waterfront Home - Dreamside House
2.0 star property
Raccoon Key
The price is NZ$4,783
includes taxes & fees
4 Jan - 5 Jan 2026
New Waterfront Home - Dreamside House

Parking Pool Dock - Shellstone House

Parking Pool Dock - Shellstone House
2.0 star property
Raccoon Key
The price is NZ$5,985
includes taxes & fees
20 Jan - 21 Jan 2026
Parking Pool Dock - Shellstone House

New Waterfront Home - Sunray House

New Waterfront Home - Sunray House
2.0 star property
Raccoon Key
The price is NZ$5,714
includes taxes & fees
20 Jan - 21 Jan 2026
New Waterfront Home - Sunray House

Brand New Build Larkshine House - Pool

Brand New Build Larkshine House - Pool
2.0 star property
Raccoon Key
The price is NZ$5,638
includes taxes & fees
20 Jan - 21 Jan 2026
Brand New Build Larkshine House - Pool

The Joyrise House at Solaire Lunara Bay

The Joyrise House at Solaire Lunara Bay
2.0 star property
Raccoon Key
The price is NZ$4,902
includes taxes & fees
20 Jan - 21 Jan 2026
The Joyrise House at Solaire 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.
Save an average of 15% on thousands of hotels when you're signed in

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 favorite 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 depends 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 NZ$641 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 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.