Rockland Key Vacation Rentals

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Our top choices for Rockland Key vacation rentals

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
9.0 out of 10, Wonderful, (61 reviews)
"The location was very good and the host was responsive. "
United States
Lilly A.
The price is CA $277
CA $549 total
includes taxes & fees
May 14 - May 15
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Waterfront Home

Waterfront Home
Cudjoe Key
8.8 out of 10, Excellent, (185 reviews)
"Clean, great view, wonderful porch, comfortable bed"
United States
Karen H.
The price is CA $302
CA $614 total
includes taxes & fees
May 13 - May 14
Waterfront Home

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
9.0 out of 10, Wonderful, (184 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 CA $166
CA $416 total
includes taxes & fees
May 17 - May 18
Aqua Lodges at Hurricane Hole Marina

Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath
Cudjoe Key
8.8 out of 10, Excellent, (98 reviews)
"We stayed one night, everything was as described"
United States
Anonymous traveller
The price is CA $277
CA $579 total
includes taxes & fees
May 18 - May 19
Canal front, dockage, 2 bedroom, 2 bath

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

SAVE BIG $$$ MAY!!! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (87 reviews)
"The rental was super clean and beautiful."
United States
christopher v.
The price is CA $341
CA $763 total
includes taxes & fees
May 18 - May 19
SAVE BIG $$$ MAY!!! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
3.5 star property
Summerland Key
10.0 out of 10, Exceptional, (2 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 CA $769
CA $1,404 total
includes taxes & fees
May 13 - May 14
Atlantic View Luxury Villa with Pool

Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (25 reviews)
"Everything about our stay was simply wonderful. It was very Clean and quiet. It is in a very nice neighborhood and pet friendly. We loved the pool and the privacy. I will be back!"
United States
Marie
The price is CA $479
CA $925 total
includes taxes & fees
May 18 - May 19
Spanish Queen @Venture Out, Cudjoe Key

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (168 reviews)
"Great location with a great staff. The Bug House is very spacious and clean. I would recommend it as a great place to stay and relax with family. "
United States
Phillip
The price is CA $479
CA $954 total
includes taxes & fees
Jun 3 - Jun 4
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Old Florida Style, wrap around porch, boat basin for dockage, open water

Old Florida Style, wrap around porch, boat basin for dockage, open water
Little Torch Key
9.6 out of 10, Exceptional, (105 reviews)
"Wonderful family getaway"
United States
Anthony V.
The price is CA $547
CA $1,127 total
includes taxes & fees
Jun 3 - Jun 4
Old Florida Style, wrap around porch, boat basin for dockage, open water

47ft Viking Yacht · 2 Pools · Perry Marina · Key West

47ft Viking Yacht · 2 Pools · Perry Marina · Key West
Stock Island
7.6 out of 10, Good, (37 reviews)
"The location was fabulous, due to the hotel’s amenities. Ie the hourly transport to downtown.pools and restaurants. The accommodations were a bit dated but adequate. The host responded immediately to our request! "
United States
Leigh P.
The price is CA $342
CA $691 total
includes taxes & fees
May 13 - May 14
47ft Viking Yacht · 2 Pools · Perry Marina · Key West

Private and Exclusive Florida Keys Getaway

Private and Exclusive Florida Keys Getaway
Upper Sugarloaf Key
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful! Pool was amazing!"
United States
Jennifer B.
The price is CA $790
CA $1,643 total
includes taxes & fees
May 26 - May 27
Private and Exclusive Florida Keys Getaway

SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
Old Town Key West
9.8 out of 10, Exceptional, (131 reviews)
"Amazing place to stay, excellent experience!!!"
United States
Brad
The price is CA $211
CA $472 total
includes taxes & fees
May 13 - May 14
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

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, (68 reviews)
"Such a beautiful home, the view is to die for. It could definitely use some upgrades like the washer and dryer, but can’t beat the location and the fact that its beachfront. "
United States
LIZ
The price is CA $682
CA $1,742 total
includes taxes & fees
May 18 - May 19
One of the very few beach houses with a daily, rental license in the Keys.

Living the Dream Key West Style

Living the Dream Key West Style
Stock Island
10.0 out of 10, Exceptional, (60 reviews)
"Friendly host and unique location"
United States
Scott
The price is CA $438
CA $553 total
includes taxes & fees
May 13 - May 14
Living the Dream Key West Style

House of the Rising Sun - VO479

House of the Rising Sun - VO479
Cudjoe Key
8.8 out of 10, Excellent, (14 reviews)
"We rented a boat, fished and snorkeled. Really enjoyed the patio right on the sea wall. One of the best parts of property was the stunning view of the morning sunrise!"
United States
Matt W.
The price is CA $479
CA $1,175 total
includes taxes & fees
May 18 - May 19
House of the Rising Sun - VO479

Waterfront Condo Dock Pool Near Duval St

Waterfront Condo Dock Pool Near Duval St
Meadows
9.8 out of 10, Exceptional, (26 reviews)
"Great location!Breeze in the balcony while sitting in chairs or taking a nap in the hammock were amazing!Everything was nearby and easily accessible. Views are wonderful!We had a great time spending holidays as a family. "
United States
PARESH J.
The price is CA $302
CA $704 total
includes taxes & fees
May 20 - May 21
Waterfront Condo Dock Pool Near Duval St

Pelican Suite | Cozy Cottage, Hot Tubs, Close to D

Pelican Suite | Cozy Cottage, Hot Tubs, Close to D
Old Town Key West
9.8 out of 10, Exceptional, (37 reviews)
"Clean place, felt safe and the location was convenient to our vacation activities. Would recommend to others."
United States
Shannon L.
The price is CA $132
CA $515 total
includes taxes & fees
May 28 - May 29
Pelican Suite | Cozy Cottage, Hot Tubs, Close to D

Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly
Cudjoe Key
10.0 out of 10, Exceptional, (8 reviews)
"Gorgeous place! Had an excellent time. Very clean and easy check-in/out process. Highly recommend!"
United States
Susan B.
The price is CA $610
CA $1,260 total
includes taxes & fees
May 25 - May 26
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

Scott's Cottage - Truman @ Duval | Perfect Spot in Old Town Key West!

Scott's Cottage - Truman @ Duval | Perfect Spot in Old Town Key West!
Old Town Key West
9.8 out of 10, Exceptional, (33 reviews)
"The property was cozy and a great location for walking."
United States
Elizabeth E.
The price is CA $132
CA $461 total
includes taxes & fees
May 13 - May 14
Scott's Cottage - Truman @ Duval | Perfect Spot in Old Town Key West!

The Cat Island Suite | Charmingly Renovated w/ Pool

The Cat Island Suite | Charmingly Renovated w/ Pool
Key West
9.8 out of 10, Exceptional, (45 reviews)
"Every as described, great stay!"
United States
Bryan W.
The price is CA $223
CA $663 total
includes taxes & fees
May 13 - May 14
The Cat Island Suite | Charmingly Renovated w/ Pool
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.
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Top Rockland Key Hotel Reviews

Find out more about Rockland Key

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Rockland Key. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.