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Our top choices for Rockland Key holiday rentals

Cottage with Pool and Dockage, just minutes to Key West

Cottage with Pool and Dockage, just minutes to Key West
Cudjoe Key
9.2 out of 10, Wonderful, (167 reviews)
"Great place "
United States
David
Cottage with Pool and Dockage, just minutes to Key West

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

SAVE BIG $$$ APRIL! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (87 reviews)
"The rental was super clean and beautiful."
United States
christopher v.
The price is £365
includes taxes & fees
27 Apr - 28 Apr
SAVE BIG $$$ APRIL! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
9.0 out of 10, Wonderful, (182 reviews)
"Great stay better than we expected "
Canada
Jordan
The price is £235
includes taxes & fees
26 Apr - 27 Apr
Aqua Lodges at Hurricane Hole Marina

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 £760
includes taxes & fees
26 Apr - 27 Apr
Atlantic View Luxury Villa with Pool

Authentic 40' Hatteras Yacht Budget Keys Living & Ocean Views

Authentic 40' Hatteras Yacht Budget Keys Living & Ocean Views
Stock Island
8.8 out of 10, Excellent, (8 reviews)
"If you are looking for a fun adventure stay this is the place for you, host was amazing from start to finish. Ocean views at sunset are amazing!"
United States
Barry
The price is £257
includes taxes & fees
27 Apr - 28 Apr
Authentic 40' Hatteras Yacht Budget Keys Living & Ocean Views

Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (124 reviews)
"Great location and Host was very helpful and responsive."
United States
Dennis G.
Kelly's Kabin - Adorable Private Summerland Key Cottage

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 £603
includes taxes & fees
27 Apr - 28 Apr
Old Florida Style, wrap around porch, boat basin for dockage, open water

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

SAVE BIG $$$ APRIL! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (106 reviews)
"Janet and Jerry were excellent hosts and the property was perfect for our trip "
United States
Shayne H.
The price is £411
includes taxes & fees
4 May - 5 May
SAVE BIG $$$ APRIL! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

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

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!
Stock Island
7.6 out of 10, Good, (35 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 £375
includes taxes & fees
19 May - 20 May
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (24 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 £507
includes taxes & fees
27 Apr - 28 Apr
Spanish Queen @Venture Out, Cudjoe Key

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, (98 reviews)
"We had a great time and will be back. "
United States
Michelle K.
The price is £552
includes taxes & fees
27 Apr - 28 Apr
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

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, (7 reviews)
"Gorgeous place! Had an excellent time. Very clean and easy check-in/out process. Highly recommend!"
United States
Susan B.
The price is £686
includes taxes & fees
27 Apr - 28 Apr
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

Yacht in Key West - Hosted by Luxury Sea Charters @ The Perry Marina

Yacht in Key West - Hosted by Luxury Sea Charters @ The Perry Marina
Stock Island
The price is £604
includes taxes & fees
26 Apr - 27 Apr
Yacht in Key West - Hosted by Luxury Sea Charters @ The Perry Marina

Living the Dream Key West Style

Living the Dream Key West Style
Stock Island
10.0 out of 10, Exceptional, (58 reviews)
"everything was perfect"
United States
Kathy A
The price is £296
includes taxes & fees
27 Apr - 28 Apr
Living the Dream Key West Style

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)
"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 £963
includes taxes & fees
17 May - 18 May
One of the very few beach houses with a daily, rental license in the Keys.

The Andros | Incredible Views w/ Shared Pool

The Andros | Incredible Views w/ Shared Pool
Key West
8.8 out of 10, Excellent, (37 reviews)
"Great place, location and reasonable price"
United States
Sujan K.
The price is £475
includes taxes & fees
28 Apr - 29 Apr
The Andros | Incredible Views w/ Shared Pool

The Cat Island Suite | Charmingly Renovated w/ Pool

The Cat Island Suite | Charmingly Renovated w/ Pool
Key West
9.8 out of 10, Exceptional, (44 reviews)
"Every as described, great stay!"
United States
Bryan W.
The price is £491
includes taxes & fees
5 May - 6 May
The Cat Island Suite | Charmingly Renovated w/ Pool

Claude Monet Suite | Cozy Studio with Pool & Patio

Claude Monet Suite | Cozy Studio with Pool & Patio
Old Town Key West
9.4 out of 10, Exceptional, (31 reviews)
"Room was clean and within easy walk to most attractions. Check in and check out was easy. "
United States
Sharon
The price is £427
includes taxes & fees
6 May - 7 May
Claude Monet Suite | Cozy Studio with Pool & Patio

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

ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
Old Town Key West
9.6 out of 10, Exceptional, (102 reviews)
"Nice property, great location, comfortable bed, lovely pool. "
United States
Candice B.
The price is £277
includes taxes & fees
29 Apr - 30 Apr
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!

Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
Old Town Key West
9.8 out of 10, Exceptional, (47 reviews)
"Great place!!! Private with but still in the middle of everything. 5+ stars will be back in November!!!"
United States
Rob
The price is £487
includes taxes & fees
10 May - 11 May
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
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 holiday rentals

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

Rockland Key holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Rockland Key holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Rockland Key holiday rentals we have selected for you start as low as £223 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Rockland Key rentals

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

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.