Rockland Key Vacation Rentals

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Vacation Rentals in Rockland Key

Aqua Lodges at Hurricane Hole Marina

2.0 star property
Stock Island
8.8 out of 10, Excellent, (168)
"Location , staff , and aqua lodge were perfect."
United States
William
$256 nightly
The price is $288
Nov 30 - Dec 1
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina

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

Cudjoe Key
8.2 out of 10, Very Good, (48)
"Very quiet place close to restaurants of all source we would like to come back and stay in the 3/2 cabin on the water with our grown children"
United States
Nathalie F.
$286 nightly
The price is $317
Nov 30 - Dec 1
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cottage with Pool and Dockage, just minutes to Key West

Cudjoe Key
9.2 out of 10, Wonderful, (159)
"Great property,Great location. Will definitely stay there again."
United States
Roy F.
$285 nightly
The price is $316
Dec 6 - Dec 7
Total with taxes and fees
Cottage with Pool and Dockage, just minutes to Key West

Cottage with Pool and Boat Dockage just minutes to Key West!

Cudjoe Key
8.6 out of 10, Excellent, (151)
"This cottage served our purpose well, very close to our family’s home and was very clean and comfortable for a short stay."
United States
Richard S.
$228 nightly
The price is $253
Dec 15 - Dec 16
Total with taxes and fees
Cottage with Pool and Boat Dockage just minutes to Key West!

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
Old Town Key West
8.4 out of 10, Very Good, (317)
"Place was great bed was comfy and the water was HOT!!! "
United States
Angela
$263 nightly
The price is $295
Dec 2 - Dec 3
Total with taxes and fees
Hyatt Vacation Club at Sunset Harbor, Key West

Kelly's Kabin - Adorable Private Summerland Key Cottage

Summerland Key
9.8 out of 10, Exceptional, (121)
"We enjoyed our stay! Great little house and location. "
United States
Lisa K.
$489 nightly
The price is $543
Dec 14 - Dec 15
Total with taxes and fees
Kelly's Kabin - Adorable Private Summerland Key Cottage

DECEMBER SAVE 50% OFF! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Cudjoe Key
9.6 out of 10, Exceptional, (100)
"Great location. "
United States
Davian k.
$413 nightly
The price is $459
Dec 1 - Dec 2
Total with taxes and fees
DECEMBER SAVE 50% OFF! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Island Time #110 Ocean Views - Cudjoe Key

2.5 star property
Cudjoe Key
9.6 out of 10, Exceptional, (11)
"Our family had an amazing vacation! We love the house and hope to come back!! "
United States
Tammy G.
$558 nightly
The price is $619
Nov 30 - Dec 1
Total with taxes and fees
Island Time #110 Ocean Views - Cudjoe Key

DECEMBER SAVE 50% OFF OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Cudjoe Key
9.8 out of 10, Exceptional, (82)
"The place is clean and convenient for anyone wanting to spend time on the water in the keys"
United States
Ubaldo G.
$504 nightly
The price is $560
Dec 3 - Dec 4
Total with taxes and fees
DECEMBER SAVE 50% OFF OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Updated 2BR,2BA w KING Master,35' SeaWall-Bikes,Kayaks,SUPs, Extra Frig/Bait Frz

Cudjoe Key
9.8 out of 10, Exceptional, (26)
"Very nicely remodeled Vrbo, excellent location for a quick drive down to Key West or exploring the other Keys!"
United States
Patrick M.
$566 nightly
The price is $628
Dec 13 - Dec 14
Total with taxes and fees
Updated 2BR,2BA w KING Master,35' SeaWall-Bikes,Kayaks,SUPs, Extra Frig/Bait Frz

Comfortable Condo with Pool, Private Balcony, & Beach Access

Beachside
8.6 out of 10, Excellent, (137)
"Nice area, location, and wonderful apartment!"
United States
Harald P.
$518 nightly
The price is $574
Nov 30 - Dec 1
Total with taxes and fees
Comfortable Condo with Pool, Private Balcony, & Beach Access

Poolside Cottage #411

Key West
9.8 out of 10, Exceptional, (53)
"Clean and as advertised "
United States
John H.
$276 nightly
The price is $306
Dec 4 - Dec 5
Total with taxes and fees
Poolside Cottage #411

Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Cutthroat Harbor Estates
8.4 out of 10, Very Good, (118)
"Great experience "
United States
Peyton S.
$486 nightly
The price is $539
Nov 28 - Nov 29
Total with taxes and fees
Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!

Old Town Key West
9.8 out of 10, Exceptional, (21)
"Great little place, perfect for southernmost area."
United States
Lee G.
$289 nightly
The price is $319
Nov 30 - Dec 1
Total with taxes and fees
Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Stock Island
7.8 out of 10, Good, (26)
"This was exactly what was advertised, it was clean, and in a great location. The on-site restaurant had great food. Also, all staff members we encountered were very friendly and accommodating. I hope it’s available for our next trip."
United States
Julie
$451 nightly
The price is $501
Nov 27 - Nov 28
Total with taxes and fees
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Cozy Cottage with Private Hot Tub, Tranquil Garden & Parking - Dogs OK

Old Town Key West
9.0 out of 10, Wonderful, (100)
"Nice place, accurate description. "
United States
Sean F.
$325 nightly
The price is $361
Nov 30 - Dec 1
Total with taxes and fees
Cozy Cottage with Private Hot Tub, Tranquil Garden & Parking - Dogs OK

Living the Dream Key West Style

Stock Island
9.8 out of 10, Exceptional, (34)
"Everything was very nice. Staff was friendly and helpful ."
United States
Debra
$307 nightly
The price is $341
Dec 8 - Dec 9
Total with taxes and fees
Living the Dream Key West Style

Downtown Key West 2BR/2BA•Pool, Dock, Pet "Aruba"

Meadows
9.2 out of 10, Wonderful, (15)
"Great location"
United States
Angie j.
$389 nightly
The price is $432
Dec 4 - Dec 5
Total with taxes and fees
Downtown Key West 2BR/2BA•Pool, Dock, Pet "Aruba"

Island View 1BR Residence With Balcony

2.0 star property
Key West
10.0 out of 10, Exceptional, (1)
"The room was excellent, no complaints at all."
United States
Tonya
$366 nightly
The price is $412
Dec 1 - Dec 2
Total with taxes and fees
Island View 1BR Residence With Balcony

VanGogh Studio | Updated, Old Town, Heated Pool

Old Town Key West
8.8 out of 10, Excellent, (35)
"Great communication, great location, and nice pool."
United States
Lauren S.
$283 nightly
The price is $311
Nov 29 - Nov 30
Total with taxes and fees
VanGogh Studio | Updated, Old Town, Heated 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

Everything you need to know about Rockland Key vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Rockland Key vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Rockland Key vacation 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 low season months. For more hustle and bustle, you may prefer to visit Rockland Key in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $277 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Rockland Key rentals

At Expedia, we put the best Rockland Key vacation 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 vacation.

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.