Rockland Key Holiday Rentals

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Holiday Rentals in Rockland Key

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (161)
"The stay was beautiful "
The price is AU$403
includes taxes & fees
2 Sept - 3 Sept
Aqua Lodges at Hurricane Hole Marina

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
8.4 out of 10, Very good, (312)
"EXCELENT LOCATION AND SUNSET VIEW"
The price is AU$453
includes taxes & fees
7 Sept - 8 Sept
Hyatt Vacation Club at Sunset Harbor, Key West

COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!

9.6 out of 10, Exceptional, (140)
"This property was great, it had everything needed, extremely clean and walking distance to Davual st.The pool area is wonderful and it was the perfect temperature!Would highly recommend."
The price is AU$357
includes taxes & fees
2 Sept - 3 Sept
COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (399)
"Great location. The bike was an awesome way to get around. Pool was very clean and refreshing. "
The price is AU$345
includes taxes & fees
4 Sept - 5 Sept
Steps from Duval, Pool on Site & Bikes Included!

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

9.6 out of 10, Exceptional, (78)
"Took the team down to the keys for a little R&R"
Old Florida Style, wrap around porch, boat basin for dockage, open water

RIPTIDES ~Stylish Studio Located in a Central Location Near All the Action!

9.6 out of 10, Exceptional, (188)
"The location was perfect for exploring and getting places in key West. It had a relaxing vibe that was perfect for vacation. "
RIPTIDES ~Stylish Studio Located in a Central Location Near All the Action!

TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

9.2 out of 10, Wonderful, (181)
"Great location; excellent property management "
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property
8.2 out of 10, Very good, (818)
"Great place really nice rooms"
Coconut Mallory Resort And Marina By Kees Vacations

THE TRUMAN ROOM @ Inn on Fleming ~ ADULTS ONLY 2nd Floor Queen & Shared Pool

9.6 out of 10, Exceptional, (19)
"Great place will rent again "
The price is AU$360
includes taxes & fees
2 Sept - 3 Sept
THE TRUMAN ROOM @ Inn on Fleming ~ ADULTS ONLY 2nd Floor Queen & Shared Pool

Heart of Downtown Key West Cottage With Off-Street Parking

10.0 out of 10, Exceptional, (134)
"May not be a better location"
Heart of Downtown Key West Cottage With Off-Street Parking

Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

10.0 out of 10, Exceptional, (20)
"We had a wonderful stay here with our kids. Can’t beat the location."
The price is AU$484
includes taxes & fees
9 Sept - 10 Sept
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

Holly's Hideaway - Truman @ Duval | Two-Bedroom Prime Location!

9.6 out of 10, Exceptional, (15)
"Great place to stay! Very clean and steps to Duval Ave."
The price is AU$584
includes taxes & fees
10 Sept - 11 Sept
Holly's Hideaway - Truman @ Duval | Two-Bedroom Prime Location!

ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

8.8 out of 10, Excellent, (55)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: great place, great location! we'll be back year after year!"
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

GEIGER SUITE @ Inn on Fleming~ADULTS ONLY 2 BR 3rd Floor Suite w/Shared Pool!

9.2 out of 10, Wonderful, (16)
"I was initially worried because I normally would only book with a property that had quite a bit of reviews. I'm glad I trusted my instincts to go with the Inn on Fleming! The room looked exactly as pictured. The whole lodge had a cute charm to it. Perfect place to stay when visiting the keys."
The price is AU$446
includes taxes & fees
2 Sept - 3 Sept
GEIGER SUITE @ Inn on Fleming~ADULTS ONLY 2 BR 3rd Floor Suite w/Shared Pool!

NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location

10.0 out of 10, Exceptional, (3)
"This was the perfect cottage for our stay. Very clean, nicely remodeled, great location to everything. It had everything we needed for or stay."
The price is AU$736
includes taxes & fees
10 Sept - 11 Sept
NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location

Southernmost Retreat | On Duval! With Hot Tub, Patio, & Private Parking

9.6 out of 10, Exceptional, (8)
"Great location ! "
The price is AU$1,269
includes taxes & fees
7 Sept - 8 Sept
Southernmost Retreat | On Duval! With Hot Tub, Patio, & Private Parking

HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!

9.6 out of 10, Exceptional, (142)
"We had a great stay places is amazing"
The price is AU$348
includes taxes & fees
2 Sept - 3 Sept
HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!

WHITEHEAD ROOM @ Inn on Fleming ~ ADULTS ONLY 2nd Floor Queen & Shared Pool

9.4 out of 10, Exceptional, (11)
"Great time staying there "
The price is AU$360
includes taxes & fees
2 Sept - 3 Sept
WHITEHEAD ROOM @ Inn on Fleming ~ ADULTS ONLY 2nd Floor Queen & Shared Pool

Duval Delight | Recently Remodeled Condo on Duval!

9.8 out of 10, Exceptional, (30)
"Very nice, clean, comfortable!"
The price is AU$682
includes taxes & fees
8 Sept - 9 Sept
Duval Delight | Recently Remodeled Condo on Duval!

Oversized home for the whole family w/private pool & dock

9.8 out of 10, Exceptional, (134)
"Beautiful home with everything needed for a fun family vacation"
Oversized home for the whole family w/private pool & dock
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

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, 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 favourite 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 depend 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 AU$345 per night. Entering your travel dates in the search wizard might find you 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.