Rockland Key holiday rentals

We found 2,330 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Rockland Key

Showing deals for:13 Nov - 20 Nov

Living area
Room
Interior
Interior
Wonderful
(12 reviews)

Authentic 40' Hatteras Yacht Budget Keys Living & Ocean Views

Key West

6% off
AU$2,519
for 7 nights, 1 houseboat
AU$360 per night
includes taxes & fees
Authentic 40' Hatteras Yacht Budget Keys Living & Ocean Views
Marina
Pool
Interior
Private kitchen
Exceptional
(62 reviews)

Living the Dream Key West Style

Key West

8% off
AU$4,540
for 7 nights, 1 houseboat
AU$649 per night
includes taxes & fees
Living the Dream Key West Style
Room
Marina
Private kitchen
Beach
Exceptional
(13 reviews)

All Included!!Private 3bedSailboat IncludingAccommodations&AllExcursions up to 6

Key West

8% off
AU$12,949
for 7 nights, 1 houseboat
AU$1,850 per night
includes taxes & fees
All Included!!Private 3bedSailboat IncludingAccommodations&AllExcursions up to 6
Exterior
Living area
Private kitchen
Exterior
Exceptional
(5 reviews)

SEASIDE ESCAPE- 2 Bed/2 Bath Condo With Shared Pool & Parking

Key West

7% off
AU$5,001
for 7 nights, 1 apartment
AU$714 per night
includes taxes & fees
SEASIDE ESCAPE- 2 Bed/2 Bath Condo With Shared Pool & Parking
Private kitchen
Interior
Room
Dining
Wonderful
(198 reviews)

Aug.-Sept. Special@125.lodging Only 129. + extras. From.8-17 to 9-30

Key West

7% off
AU$2,042
for 7 nights, 1 home
AU$292 per night
includes taxes & fees
Aug.-Sept. Special@125.lodging Only 129. + extras. From.8-17 to 9-30
Pool
Golf
Terrace/patio
Dining
Exceptional
(45 reviews)

Key West - Stock Island

Key West

12% off
AU$4,240
for 7 nights, 1 home
AU$606 per night
includes taxes & fees
Key West - Stock Island
Private kitchen
Property grounds
Room
Pool
Wonderful
(9 reviews)

Treehouse Condo 2nd Floor Balcony sleeps 6 free parking

Key West

8% off
AU$6,824
for 7 nights, 1 apartment
AU$975 per night
includes taxes & fees
Treehouse Condo 2nd Floor Balcony sleeps 6 free parking
hang out on your own private full front porch
Varela St Retreat, Historic Old Town Key West
Room
Living area
Exceptional
(256 reviews)

Feb 3-10 $245 off the rates close beach full kitchen & patio

Key West

7% off
AU$2,051
for 7 nights, 1 home
AU$293 per night
includes taxes & fees
Feb 3-10 $245 off the rates close beach full kitchen & patio
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    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Choose a holiday rental for your Rockland Key getaway

Learn about the unique charm of Rockland Key with a stay in a holiday home rental. This city has something for everyone. Florida Keys Beaches and Duval Street are just a couple of the must-see attractions in the area. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Sightseeing in and around Rockland Key

Do you want to find attractions to see while you're in town? Venture out of your holiday home and experience everything that makes Rockland Key a fun place to get away to. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Key West Golf Club (4.3 mi / 7 km)
  • The Kite House (8.1 mi / 13 km)
  • MLK Community Pool & Community Center (8.4 mi / 13.5 km)

Exploring the natural features in Rockland Key

Whether you're looking for fun outdoor activities or just want to take in the scenery, Rockland Key is a great place to get out in nature. These are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Florida Keys Beaches (7.7 mi / 12.5 km)
  • Key West Tropical Forest and Botanical Garden (4.8 mi / 7.7 km)
  • Smathers Beach (6.8 mi / 11 km)
  • Clarence S. Higgs Memorial Beach Park (7.5 mi / 12.1 km)
  • Simonton Beach (8 mi / 12.9 km)
  • South Beach (8.1 mi / 13.1 km)

Frequently asked questions

How much does it cost to rent a holiday home in Rockland Key?
Length of stay, property type and season are among the factors that can affect the price of a holiday home. Simply enter your dates of travel to find your perfect match. From comfy cottages to expansive villas, all Stayz holiday homes provide amazing value.
How much does it cost to rent a beach house in Rockland Key?
When you travel and the size and style of the property will help determine the cost of your beachside holiday home. Click on your Rockland Key travel dates to see all your options on Stayz. Looking for a backyard so the kids can run around, or a pool to keep them busy? Use our filters to pick the amenities and features you want in your home.
What are the top attractions for families in Rockland Key?
Keeping the kids entertained during your holiday in Rockland Key is child's play with these exciting family-friendly attractions:
  • Smathers Beach
  • South Beach
  • Higgs Beach
How old do you have to be to rent a holiday home in Rockland Key?
Age restrictions can differ across properties on Stayz, so be sure to check the rules of the holiday home in Rockland Key you're interested in. But normally, it's 16, 18 or 21.
How long can I rent a holiday home in Rockland Key for?
The amount of time you can rent a Rockland Key holiday home for differs depending on the property. Just put in your dates of travel to see options that offer long-term stays. They feature all you need to make your extended break more comfortable like kitchens and air conditioning. Some properties might also offer weekly or monthly discounted prices, so you can stay longer for less money.

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