Search Vacation Homes in Rockland Key

  • 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

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)
"If you are looking to see spectacular sunrises in the Keys, this location is great. Kitchen is well stocked with everything you need. "
United States
Paula D.
The price is ¥216,915
¥377,916 total
includes taxes & fees
Mar 14 - Mar 15
One of the very few beach houses with a daily, rental license in the Keys.

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

Starlight Serenity - Hideaway w Stunning Views

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

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 ¥58,144
¥113,013 total
includes taxes & fees
Feb 23 - Feb 24
Cudjoe Cottages, swimming pool, just 20 miles from Key West

105 - Newly renovated house Oceanside and Pool

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

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 ¥42,639
¥94,426 total
includes taxes & fees
Mar 1 - Mar 2
Kelly's Kabin - Adorable Private Summerland Key Cottage

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

SAVE BIG $$FEBRUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (104 reviews)
"Janet was great; quick to respond and very kind. Also the kayaks were fun and the beds were super comfy. "
United States
Lauren D.
The price is ¥30,855
¥76,634 total
includes taxes & fees
Feb 25 - Feb 26
SAVE BIG $$FEBRUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

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, (91 reviews)
"We had a great time and will be back. "
United States
Michelle K.
The price is ¥55,818
¥119,892 total
includes taxes & fees
Mar 1 - Mar 2
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

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

SAVE BIG $$FEBRUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (83 reviews)
"The place is clean and convenient for anyone wanting to spend time on the water in the keys"
United States
Ubaldo G.
The price is ¥38,607
¥86,285 total
includes taxes & fees
Mar 5 - Mar 6
SAVE BIG $$FEBRUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
Cudjoe Key
7.8 out of 10, Good, (14 reviews)
"Good experience. The property is well place and the Venture is really nice and quiet."
United States
Primeau J.
The price is ¥38,375
¥79,144 total
includes taxes & fees
Mar 7 - Mar 8
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool
Cudjoe Key
9.8 out of 10, Exceptional, (143 reviews)
"Super relaxing! Great location! Wonderful views! "
United States
Allicia W.
The price is ¥77,331
¥153,051 total
includes taxes & fees
Mar 11 - Mar 12
Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

Fun in the Sun in Cudjoe Key! #51

Fun in the Sun in Cudjoe Key! #51
Cudjoe Key
8.6 out of 10, Excellent, (9 reviews)
"This was a beautiful"
United States
Debbie A.
The price is ¥35,662
¥107,256 total
includes taxes & fees
Mar 9 - Mar 10
Fun in the Sun in Cudjoe Key! #51

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 ¥54,268
¥106,132 total
includes taxes & fees
Feb 24 - Feb 25
Spanish Queen @Venture Out, Cudjoe Key

Private and Exclusive Beach Getaway

Private and Exclusive Beach Getaway
Sugarloaf Key
10.0 out of 10, Exceptional, (10 reviews)
"The location of the home is great, beautiful and peaceful.Enjoyed the pool."
United States
Rachel N.
The price is ¥230,249
¥373,039 total
includes taxes & fees
Mar 9 - Mar 10
Private and Exclusive Beach Getaway

Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock

Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock
Cudjoe Key
9.2 out of 10, Wonderful, (29 reviews)
"Close to Key West and lots of great boating"
United States
Simon S.
The price is ¥52,911
¥120,615 total
includes taxes & fees
Mar 6 - Mar 7
Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock

Post Card Point #319 - Ocean Views!

Post Card Point #319 - Ocean Views!
Cudjoe Key
10.0 out of 10, Exceptional, (52 reviews)
"New furniture, and outfitting. Great view. Possibly the best location in the community. Steps from the boat ramp. "
United States
Matthew K.
The price is ¥65,121
¥147,415 total
includes taxes & fees
Feb 28 - Mar 1
Post Card Point #319 - Ocean Views!

Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community

Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community
Cudjoe Key
10.0 out of 10, Exceptional, (14 reviews)
"outstanding views and house is spotless!"
United States
Virginia L.
The price is ¥65,121
¥145,710 total
includes taxes & fees
Mar 7 - Mar 8
Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community

Waterfront Luxury Home - Tidelands House

Waterfront Luxury Home - Tidelands House
2.0 star property
Raccoon Key
The price is ¥218,370
¥403,351 total
includes taxes & fees
Feb 22 - Feb 23
Waterfront Luxury Home - Tidelands House

Tiki Time in Cudjoe Key 136

Tiki Time in Cudjoe Key 136
Cudjoe Key
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful well maintained property. You just cannot beat the view on the extra large deck. Sit back relax and enjoy a coffee.I absolutely love this property."
Canada
Rachel H.
The price is ¥53,492
¥129,797 total
includes taxes & fees
Mar 13 - Mar 14
Tiki Time in Cudjoe Key 136

The Hemingway - Beach Houses Key West

The Hemingway - Beach Houses Key West
Upper Sugarloaf Key
9.6 out of 10, Exceptional, (8 reviews)
"Perfect location way off the path if you like seclusion."
United States
Jonathan L.
The price is ¥152,647
¥277,904 total
includes taxes & fees
Feb 22 - Feb 23
The Hemingway - Beach Houses Key West
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

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