Holiday Rentals in Florida Keys

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Florida Keys holiday rentals

Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (910)
"Decent stay, easy check in and contactless checkout. Very quiet and nice place! "
United States
Swastik
The price is €130
includes taxes & fees
8 Jan - 9 Jan 2026
Tropical Cottages

Skipjack Resort & Marina

Skipjack Resort & Marina
3.0 star property
Marathon
8.6 out of 10, Excellent, (1218)
"Beautiful location clean rooms friendly staff "
United States
Tiffany
Skipjack Resort & Marina

Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1157)
"Very good location.. Clean room."
United States
Leonor
The price is €126
includes taxes & fees
23 Dec - 24 Dec
Knight's Key Suites

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (117)
"I am obsessed with tiny houses and this one floats! It was so relaxing to sit on the deck and enjoy the view. The bed was very comfy and the gentle motion of the water put me right to sleep. The staff are friendly and helpful. Islamorada is beautiful and fun to explore."
United States
Mary
Treasure Harbor

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (280)
"Enjoyed the duplex, instead of a standard hotel room. Full kitchen, nice bathroom, and bedroom. "
United States
Alejandra
Old Wooden Bridge Resort and Marina

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (589)
"we stayed in the beach front cottage kitchen was stocked room was clean and the views were great friendly staff "
United States
Terry
The price is €188
includes taxes & fees
24 Dec - 25 Dec
Breezy Palms Resort

Yacht Haven Marina

Yacht Haven Marina
3.5 star property
Marathon
9.8 out of 10, Exceptional, (239)
"Friendly staff and extremely clean."
United States
Travis
Yacht Haven Marina

Aqua Lodge Rentals At Coconut Cay

Aqua Lodge Rentals At Coconut Cay
3.5 star property
Marathon
9.6 out of 10, Exceptional, (199)
"A unique and interesting place to vacation. Relaxing yet close enough to things to do. I highly recommend the Aqua Loge rentals as a place to stay."
United States
Keith
Aqua Lodge Rentals At Coconut Cay

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (170)
"Location , staff , and aqua lodge were perfect."
United States
William
The price is €367
includes taxes & fees
5 Jan - 6 Jan 2026
Aqua Lodges at Hurricane Hole Marina

Anchorage Resort & Yacht Club

Anchorage Resort & Yacht Club
3.0 star property
Key Largo
8.6 out of 10, Excellent, (297)
"Really good place to stay "
United States
Elier
The price is €240
includes taxes & fees
5 Jan - 6 Jan 2026
Anchorage Resort & Yacht Club

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

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
8.2 out of 10, Very good, (51)
"Great area. Quiet and comfortable "
United States
nancy c.
The price is €303
includes taxes & fees
23 Dec - 24 Dec
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (42)
"Exceeded expectations, exceptionally clean, great for kids (they loved the pool), perfect for our Keys trip"
United States
Natalie M.
Amazing Ocean view condo

Charming cottages, dockage, pool, just minutes to Key West

Charming cottages, dockage, pool, just minutes to Key West
Cudjoe Key
8.6 out of 10, Excellent, (120)
"Jennifer was very nice and accommodating."
United States
Randy G.
The price is €289
includes taxes & fees
23 Dec - 24 Dec
Charming cottages, dockage, pool, just minutes to Key West

Serenity In The Sun Condo Fabulous Ocean View

Serenity In The Sun Condo Fabulous Ocean View
Tavernier
10.0 out of 10, Exceptional, (108)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
Serenity In The Sun Condo Fabulous Ocean View

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, (33)
"Good place to stay loved it"
United States
Charles I.
The price is €521
includes taxes & fees
9 Jan - 10 Jan 2026
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!

Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (141)
"Very quiet and the outdoor spaces are very nice. Staff was very friendly also."
United States
Jacob
The price is €337
includes taxes & fees
23 Dec - 24 Dec
Island Bay Resort

Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Cudjoe Key
8.6 out of 10, Excellent, (164)
"Beautiful serene, location, located close enough to Key West and also nice restaurants in the area and close to Bahia Honda State Park, which was beautiful and the key deer areas."
United States
Andrea S.
The price is €250
includes taxes & fees
23 Dec - 24 Dec
Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (28)
"It was clean and a very nice place to stay. Plenty of room and awesome amenities."
United States
Eric M.
Charming Home in Key Largo

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

SUGAR PALM STUDIO ~ Adult Only Studio w/Community Pool & Close to Town!
Old Town Key West
9.8 out of 10, Exceptional, (110)
"Great value stay"
United States
Mike B.
The price is €460
includes taxes & fees
20 Jan - 21 Jan 2026
SUGAR PALM STUDIO ~ Adult Only Studio w/Community Pool & Close to Town!

Modern and Coastal 3212 is Across from Pool

Modern and Coastal 3212 is Across from Pool
Tavernier
9.8 out of 10, Exceptional, (150)
"Great stay lovely home "
United States
Yezenia
The price is €420
includes taxes & fees
12 Jan - 13 Jan 2026
Modern and Coastal 3212 is Across from 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.
Save an average of 15% on thousands of hotels when you're signed in

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, 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 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 €126 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.