Florida Keys Holiday Rentals

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Holiday Rentals in Florida Keys

Yacht Haven Marina

3.5 star property
Marathon
9.8 out of 10, Exceptional, (223)
"Nice Lodge nice area close to grocery store & shops, will love to stay there again."
United States
Xiomeidy
Yacht Haven Marina

Aqua Lodge Rentals At Coconut Cay

3.5 star property
Marathon
9.6 out of 10, Exceptional, (190)
"Clean room, spacious, nice and quiet. "
United States
Douglas
Aqua Lodge Rentals At Coconut Cay

Breezy Palms Resort

2.5 star property
Matecumbe
8.8 out of 10, Excellent, (560)
"Everything was perfect, recently remodeled, the best hotel for the price I've stayed at so far"
United States
franklin
The price is NZ$202
includes taxes & fees
11 Nov - 12 Nov
Breezy Palms Resort

Knight's Key Suites

3.0 star property
Marathon
9.0 out of 10, Wonderful, (1155)
"Room were clean and staff was very helpful "
United States
Leonard
The price is NZ$207
includes taxes & fees
10 Nov - 11 Nov
Knight's Key Suites

Tropical Cottages

3.0 star property
Marathon
8.6 out of 10, Excellent, (896)
"The room was very clean. The staff was friendly and helpful. "
United States
Charles
The price is NZ$180
includes taxes & fees
18 Nov - 19 Nov
Tropical Cottages

Old Wooden Bridge Resort and Marina

2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (267)
"I love this place!!!"
United States
Greg
Old Wooden Bridge Resort and Marina

Treasure Harbor

3.0 star property
Islamorada
9.0 out of 10, Wonderful, (109)
"Unique House boat experience, friendly staff. "
United States
Luis
Treasure Harbor

Anchorage Resort & Yacht Club

3.0 star property
Key Largo
8.6 out of 10, Excellent, (297)
"It’s a good place to stay with family"
United States
Cody
The price is NZ$390
includes taxes & fees
30 Nov - 1 Dec
Anchorage Resort & Yacht Club

Skipjack Resort & Marina

3.0 star property
Marathon
8.6 out of 10, Excellent, (1209)
"Great stay"
United States
sharon
Skipjack Resort & Marina

Island Bay Resort

2.5 star property
Tavernier
10.0 out of 10, Exceptional, (135)
"Amazing property and wonderful owners. Super nice people and definitely will be returning."
United States
Daniel
The price is NZ$493
includes taxes & fees
13 Nov - 14 Nov
Island Bay Resort

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
Old Town Key West
8.4 out of 10, Very good, (314)
"Good location "
United States
Paula
The price is NZ$513
includes taxes & fees
19 Nov - 20 Nov
Hyatt Vacation Club at Sunset Harbor, Key West

Beachside Retreat w/ Pool, Boat Ramp Dock for Rent

Key Largo
9.6 out of 10, Exceptional, (43)
"This is the second time we stay in this property in less than a year and we couldn’t been happier. It is clean, spacious; it has all you need and location is great!. Host is very responsive and accomodaring. We cannot wait to come back hopefully before the end of the year. "
United States
MAIDELIS F.
The price is NZ$529
includes taxes & fees
1 Dec - 2 Dec
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent

Amazing Ocean view condo

Tavernier
9.6 out of 10, Exceptional, (42)
"The listing accurately describes this property and the location is great"
United States
Brandon B.
The price is NZ$646
includes taxes & fees
14 Nov - 15 Nov
Amazing Ocean view condo

CORTEZ ~ Adults Only, King Room w/Pool View at Azul Mansion!

Old Town Key West
9.6 out of 10, Exceptional, (141)
"Wonderful and quiet property but in walking distance to the excitement. Great communication and easy check in and check out. We will be back!"
United States
Krista
The price is NZ$466
includes taxes & fees
12 Nov - 13 Nov
CORTEZ ~ Adults Only, King Room w/Pool View at Azul Mansion!

Aqua Lodges at Hurricane Hole Marina

2.0 star property
Stock Island
8.8 out of 10, Excellent, (165)
"The stay was beautiful "
United States
Jennifer
The price is NZ$518
includes taxes & fees
11 Nov - 12 Nov
Aqua Lodges at Hurricane Hole Marina

Serenity In The Sun Condo Fabulous Ocean View

Tavernier
10.0 out of 10, Exceptional, (106)
"Good clean condo, great pool and little private beach "
United Kingdom
Nicola W.
The price is NZ$726
includes taxes & fees
10 Nov - 11 Nov
Serenity In The Sun Condo Fabulous Ocean View

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

Old Town Key West
9.8 out of 10, Exceptional, (108)
"Great stay at the property."
United States
Ira V.
The price is NZ$472
includes taxes & fees
19 Nov - 20 Nov
SUGAR PALM STUDIO ~ Adult Only Studio w/Community Pool & Close to Town!

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.
The price is NZ$596
includes taxes & fees
10 Nov - 11 Nov
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

GOLDEN NUGGET ~ Adult Only, 1st Floor Queen Bedroom w/ Shared Pool!

Old Town Key West
9.8 out of 10, Exceptional, (98)
"Everything you need to explore Key West"
United States
Stephanie P.
The price is NZ$548
includes taxes & fees
12 Nov - 13 Nov
GOLDEN NUGGET ~ Adult Only, 1st Floor Queen Bedroom w/ Shared Pool!

Cottage with Pool and Dockage, just minutes to Key West

Cudjoe Key
9.2 out of 10, Wonderful, (157)
"Great location and very happy with our accommodations."
United States
Carrie B.
The price is NZ$564
includes taxes & fees
13 Nov - 14 Nov
Cottage with Pool and Dockage, just minutes to Key West
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 Florida Keys Hotel Reviews

Find out more about Florida Keys

Everything you need to know about Florida Keys 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 Florida Keys 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 Florida Keys holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Florida Keys holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Florida Keys. 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 Florida Keys 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 Florida Keys holiday rentals we have selected for you start as low as NZ$180 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Florida Keys rentals

At Expedia, we put the best Florida Keys 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 Florida Keys 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 Florida Keys 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 Florida Keys. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.