Holiday Rentals in Rockland Key

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Our top choices for Rockland Key holiday rentals

9.0 out of 10, Wonderful, (56 reviews)
"Clean rooms, clear guidelines, completely no contact experience without facing any trouble."
United States
Raj
The price is €393
includes taxes & fees
12 Mar - 13 Mar
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
8.6 out of 10, Excellent, (165 reviews)
"Everything was nice and clean. Loved the location . Would definitely stay at the property again. "
United States
Shawn M.
The price is €301
includes taxes & fees
12 Mar - 13 Mar
Private Oceanfront Cottage with dockage, pool just minutes to Key West!
9.0 out of 10, Wonderful, (166 reviews)
"Everything was there that I needed. Very nice area for my dog."
United States
Terry
The price is €276
includes taxes & fees
26 Mar - 27 Mar
Cottage with swimming pool and dockage, just minutes to Key West!
8.6 out of 10, Excellent, (196 reviews)
"Great location"
United States
Kimberly W.
The price is €352
includes taxes & fees
15 Mar - 16 Mar
Direct Oceanfront Cottage-Sunrise View- #2,

Cottage in Cudjoe Key

Waterfront Home
8.6 out of 10, Excellent, (178 reviews)
"Great location if you bring a boat. Secure location. Venture Out is a nice community. "
United States
Georgiana V.
The price is €390
includes taxes & fees
12 Mar - 13 Mar
Waterfront Home
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 €528
includes taxes & fees
30 Mar - 31 Mar
SAVE BIG $$$ MARCH! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Houseboat in Stock Island

Aqua Lodges at Hurricane Hole Marina
2.0 star property
9.0 out of 10, Wonderful, (181 reviews)
"Unique place to stay! We loved the nature and the location! "
United States
Sara
The price is €327
includes taxes & fees
24 Mar - 25 Mar
Aqua Lodges at Hurricane Hole Marina
9.8 out of 10, Exceptional, (123 reviews)
"Great location and Host was very helpful and responsive."
United States
Dennis G.
The price is €455
includes taxes & fees
5 Apr - 6 Apr
Kelly's Kabin - Adorable Private Summerland Key Cottage
8.8 out of 10, Excellent, (162 reviews)
"Great location , clear communications and listing accuracy. Will be coming back again "
United States
Kirk D.
The price is €570
includes taxes & fees
25 Mar - 26 Mar
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Holiday Home in Cudjoe Key

Spanish Queen @Venture Out, 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 €584
includes taxes & fees
17 Mar - 18 Mar
Spanish Queen @Venture Out, Cudjoe Key
8.8 out of 10, Excellent, (92 reviews)
"Nice place to vacation "
United States
Kevin D.
The price is €393
includes taxes & fees
16 Mar - 17 Mar
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
8.6 out of 10, Excellent, (53 reviews)
"We were very happy with our stay. Everything was as expected or above. Old Keys vibe was exactly what we wanted. "
United States
Lauren R.
The price is €393
includes taxes & fees
12 Mar - 13 Mar
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
9.0 out of 10, Wonderful, (150 reviews)
"Enjoyed the area. Not to far from Key West but far enough there wasn't a crowd"
United States
Donna P.
The price is €376
includes taxes & fees
19 Mar - 20 Mar
Quaint cottage, pool, dockage just minutes to Key West!
9.6 out of 10, Exceptional, (97 reviews)
"Loved the location, good communication!"
United States
Cindy P.
The price is €773
includes taxes & fees
29 Mar - 30 Mar
Old Florida Style, wrap around porch, boat basin for dockage, open water
8.8 out of 10, Excellent, (153 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 €634
includes taxes & fees
14 Mar - 15 Mar
Cudjoe Cottages, swimming pool, just 20 miles from Key West
8.6 out of 10, Excellent, (124 reviews)
"host answered our question. Did not know w& d was coin washer and dryer"
United States
Robin D.
The price is €352
includes taxes & fees
13 Mar - 14 Mar
Charming cottages, dockage, pool, just minutes to Key West

Houseboat in Stock Island

Living the Dream Key West Style
9.8 out of 10, Exceptional, (49 reviews)
"Everything was excellent, awesome host, beautiful vacation!"
United States
Jodi M.
The price is €558
includes taxes & fees
5 Apr - 6 Apr
Living the Dream Key West Style
8.6 out of 10, Excellent, (77 reviews)
"It was a nice location. 30” from Key West. "
United States
Linda N.
The price is €393
includes taxes & fees
14 Mar - 15 Mar
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
9.2 out of 10, Wonderful, (164 reviews)
"Very convenient to Restaurants & nice drive to Key West"
United States
Kim V.
The price is €376
includes taxes & fees
14 Mar - 15 Mar
Cottage with Pool and Dockage, just minutes to Key West
8.4 out of 10, Very good, (124 reviews)
"Great experience "
United States
Peyton S.
Just 20 miles from Key West! Oceanfront, dockage, swimming 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 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 €271 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.