
Search Vacation Homes in Rockland Key
- Change your mindBook hotels with free cancellation
- Be pickySearch 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 vacation homes

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, (66 reviews)
The price is ¥216,915
¥377,916 total
includes taxes & fees
Mar 14 - Mar 15

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key WestCudjoe Key
The price is ¥38,829
¥104,308 total
includes taxes & fees
Mar 3 - Mar 4

Starlight Serenity - Hideaway w Stunning Views
Starlight Serenity - Hideaway w Stunning ViewsSummerland Key
The price is ¥79,104
¥143,197 total
includes taxes & fees
Mar 12 - Mar 13

Cudjoe Cottages, swimming pool, just 20 miles from Key West
Cudjoe Cottages, swimming pool, just 20 miles from Key WestCudjoe Key
8.8 out of 10, Excellent, (151 reviews)
The price is ¥58,144
¥113,013 total
includes taxes & fees
Feb 23 - Feb 24

105 - Newly renovated house Oceanside and Pool
105 - Newly renovated house Oceanside and PoolCudjoe Key
The price is ¥59,865
¥131,999 total
includes taxes & fees
Mar 24 - Mar 25

Kelly's Kabin - Adorable Private Summerland Key Cottage
Kelly's Kabin - Adorable Private Summerland Key CottageSummerland Key
9.8 out of 10, Exceptional, (123 reviews)
The price is ¥42,639
¥94,426 total
includes taxes & fees
Mar 1 - Mar 2

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 BEDSCudjoe Key
9.4 out of 10, Exceptional, (104 reviews)
The price is ¥30,855
¥76,634 total
includes taxes & fees
Feb 25 - Feb 26

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key WestCudjoe Key
8.6 out of 10, Excellent, (91 reviews)
The price is ¥55,818
¥119,892 total
includes taxes & fees
Mar 1 - Mar 2
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.
Find vacation rentals that suit your style
Aparthotels
Apartments
Save an average of 15% on thousands of hotels when you're signed in
Top Rockland Key Hotel Reviews

The Perry Hotel & Marina Key West
10/10 Excellent
Find out more about Rockland Key
Rockland Key Vacation Homes information
Number of reviews | 888 |
|---|---|
Accommodation | 806 Vacation Homes |
Lowest Price | ¥76,634 |
Highest Price | ¥403,351 |
Explore a world of travel with Expedia
- Resorts in Bahia Honda Key
- Apartments in Cow Key
- Lodges in Big Pine Key
- Gay friendly Hotels in Key West Historic District
- Scuba Diving Hotels in Old Town Key West
- Shopping Hotels in Sunset Key
- Coral Lagoon Hotels
- Cheap Hotels in Key West
- Hotels near Key West Naval Station
- Ranches in Key West
- Ryokans in Big Pine Key
- Palaces in Key Colony Beach
- Gay friendly Hotels in Key West
- Family Hotels in Grassy Key
- Cheap Hotels in Old Town Key West
- Hotels near Calusa Beach
- Hotels near Harry S. Truman Little White House
- All-Inclusive Hotel Hotels in Key Colony Beach
- Cheap Hotels in Key West Historic District
- Gay friendly Hotels in Old Town Key West
- Riads in Big Pine Key
- All-Inclusive Hotel Hotels in Bahama Village
- Cheap Hotels in Casa Marina
- Holiday Park Resorts in Key West
- Key West Hotels
- Hotels near Southernmost Point
- Guest Houses in Cudjoe Key
- Hotels near Florida Keys Eco - Discovery Center
- Adults Only Resorts & in Key West
- Vacation Homes in Big Pine Key
- Beach Hotels in Downtown Key West
- Resorts & Hotels with Spas in Little Torch Key
- Hotels near Smathers Beach
- Cheap Hotels in Cudjoe Key
- All-Inclusive Hotel Hotels in Downtown Key West
- Big Pine Key Hotels
- Guest Houses in Key West
- Hotels near Fort Zachary Taylor Historic State Park
- Vacation Homes in Marathon
- Farmstay in Marathon
- All-Inclusive Hotel Hotels in Key West
- Hotels near Key West Historic Seaport
- Cow Key Hotels
- Resorts in No Name Key
- Apartments in Big Pine Key
- Condo Resorts in Key Colony Beach
- Marathon Hotels
- Beach Hotels in Key Colony Beach
- Waterpark Hotels in Key West
- Scuba Diving Hotels in Little Torch Key
- Beach Hotels in Key West
- Hotels near Simonton Beach
- Scuba Diving Hotels in Key West
- Resorts in Key West
- Cheap Hotels in Beachside
- Hotels with a Pool in Key West
- Luxury Hotels in Key West
- Rv Parks in Bahia Honda Key
- Beach Hotels in Key West Historic District
- Motels in Lower Florida Keys
- Pet-Friendly Hotels in Key West
- Hotels near Sombrero Beach
- Family Hotels in Lower Keys
- Apartments in Key West
- Hotels near Florida Keys Beaches
- Hotels near Duval Street
- Cheap Hotels in Downtown Key West
- Scuba Diving Hotels in Downtown Key West
- Hotels near Key West Intl.
- Adults Only Resorts & in Marathon
- Beach Hotels in Midtown
- Historic Hotels in Key West
- Cheap Hotels in Lower Florida Keys
- Residences in Summerland Key
- Scuba Diving Hotels in Marathon
- Resorts in Stock Island
- Aparthotels in Key Colony Beach
- Casa Marina Hotels
- Cheap Hotels in Sugarloaf Key
- Hostels in Key West
- Hotels near South Beach
- Resorts & Hotels with Spas in Beachside
- Adults Only Resorts & in Downtown Key West
- Resorts in Little Torch Key
- Romantic Hotels in Sugarloaf Key
- All-Inclusive Hotel Hotels in Sunset Key
- Aparthotels in Key West
- Resorts in Key Colony Beach
- Luxury Hotels in Casa Marina
- Hotels near Florida Keys National Marine Sanctuary
- Hotels near Florida Keys Marathon
- Luxury Hotels in Beachside
- Hotels near Ernest Hemingway Home and Museum
- Inns in Key Colony Beach
- Rv Parks in Key West
- Lodges in Key West















































































