Search Holiday Rentals in Rockland Key

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Save instantly and earn perks with One Key
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Rockland Key holiday rentals

Ocean Front One Bedroom Residence

Ocean Front One Bedroom Residence
2.0 star property
Key West
The price is £323
includes taxes & fees
10 Jun - 11 Jun
Ocean Front One Bedroom Residence

Lighthouse Suites Collection

Lighthouse Suites Collection
4.0 star property
Old Town Key West
The price is £861
includes taxes & fees
11 Jun - 12 Jun
Lighthouse Suites Collection

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
9.0 out of 10, Wonderful, (187 reviews)
"Beautiful location, quick reply when you contact them. The bar and restaurant were so nice!! We would definitely stay again. "
United States
Stacy
The price is £239
includes taxes & fees
22 Jun - 23 Jun
Aqua Lodges at Hurricane Hole Marina

Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
3.5 star property
Summerland Key
7.4 out of 10, Good, (3 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 £845
includes taxes & fees
14 Jun - 15 Jun
Atlantic View Luxury Villa with Pool

Contra House Key West

Contra House Key West
3.0 star property
Old Town Key West
8.0 out of 10, Very good, (1 review)
"Pool and outside was undesirable"
United States
Rosalie
The price is £1,095
includes taxes & fees
22 Jun - 23 Jun
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 £602
includes taxes & fees
1 Jul - 2 Jul
Starlight Serenity - Hideaway w Stunning Views

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 £303
includes taxes & fees
10 Jun - 11 Jun
Resort View 1BR Suite With Direct Pool Access

The Fairhaven House at Solaire Lunara Bay

The Fairhaven House at Solaire Lunara Bay
2.0 star property
Raccoon Key
The price is £2,640
includes taxes & fees
10 Jun - 11 Jun
The Fairhaven House at Solaire Lunara Bay

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 review)
"Wonderful property, 4 large bedroom and en suite bathroom, private pool we really liked our stay"
France
Karen
The price is £1,462
includes taxes & fees
10 Jun - 11 Jun
Capmar House by Brightwild Huge Home Pool

Resort View 3BR Residence

Resort View 3BR Residence
2.0 star property
Key West
The price is £720
includes taxes & fees
17 Jun - 18 Jun
Resort View 3BR Residence

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 £455
includes taxes & fees
21 Jun - 22 Jun
Grand Marina Suite by Brightwild Waterfront

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 £458
includes taxes & fees
10 Jun - 11 Jun
Poolside Suite by Brightwild Pvt Pool Parking

Mirador House by Brightwild Pool Dock

Mirador House by Brightwild Pool Dock
2.0 star property
Raccoon Key
The price is £2,403
includes taxes & fees
6 Jul - 7 Jul
Mirador House by Brightwild Pool Dock

Aquaria House by Brightwild Pool Boat Dock

Aquaria House by Brightwild Pool Boat Dock
2.0 star property
Raccoon Key
The price is £1,851
includes taxes & fees
8 Jul - 9 Jul
Aquaria House by Brightwild Pool Boat Dock

Seagate House by Brightwild Waterfront w Dock

Seagate House by Brightwild Waterfront w Dock
2.0 star property
Raccoon Key
The price is £1,430
includes taxes & fees
10 Jun - 11 Jun
Seagate House by Brightwild Waterfront w Dock

Mastway House by Brightwild Pool Dock

Mastway House by Brightwild Pool Dock
2.0 star property
Raccoon Key
The price is £1,523
includes taxes & fees
10 Jun - 11 Jun
Mastway House by Brightwild Pool Dock

New Waterfront Home - Sunray House

New Waterfront Home - Sunray House
2.0 star property
Raccoon Key
The price is £2,573
includes taxes & fees
10 Jun - 11 Jun
New Waterfront Home - Sunray House

Waterlane House by Brightwild Pool Boat Dock

Waterlane House by Brightwild Pool Boat Dock
2.0 star property
Raccoon Key
The price is £1,699
includes taxes & fees
28 Jun - 29 Jun
Waterlane House by Brightwild Pool Boat Dock

The Joyrise House at Solaire Lunara Bay

The Joyrise House at Solaire Lunara Bay
2.0 star property
Raccoon Key
The price is £2,534
includes taxes & fees
7 Jul - 8 Jul
The Joyrise House at Solaire Lunara Bay

New Waterfront Home - Dreamside House

New Waterfront Home - Dreamside House
2.0 star property
Raccoon Key
New Waterfront Home - Dreamside House
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, apart-hotels, 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 £214 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. 

Explore a world of travel with Expedia