Holiday Rentals in Florida Keys

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Our top choices for Florida Keys holiday rentals

Tropical Cottages

3.0 star property
Marathon
8.6 out of 10, Excellent, (907)
"Beautiful place, conveniently located "
United States
Clifton
The price is €92
includes taxes & fees
10 Dec - 11 Dec
Tropical Cottages

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 €103
includes taxes & fees
14 Dec - 15 Dec
Knight's Key Suites

Old Wooden Bridge Resort and Marina

2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (276)
"We loved it here. So beautiful and quiet."
United Kingdom
Mark
Old Wooden Bridge Resort and Marina

Aqua Lodge Rentals At Coconut Cay

3.5 star property
Marathon
9.6 out of 10, Exceptional, (198)
"Kitchen was very well equipped and the property was very pet friendly. "
United States
Tomas
Aqua Lodge Rentals At Coconut Cay

Yacht Haven Marina

3.5 star property
Marathon
9.8 out of 10, Exceptional, (232)
"Nice Lodge nice area close to grocery store & shops, will love to stay there again."
United States
Xiomeidy
Yacht Haven Marina

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

Breezy Palms Resort

2.5 star property
Matecumbe
8.8 out of 10, Excellent, (584)
"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 €142
includes taxes & fees
11 Dec - 12 Dec
Breezy Palms Resort

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 €266
includes taxes & fees
19 Dec - 20 Dec
Anchorage Resort & Yacht Club

Skipjack Resort & Marina

3.0 star property
Marathon
8.6 out of 10, Excellent, (1214)
"Stayed just one night but have a great experience. The staff nice and helpful. Room was clean and comfy and spacious. "
United States
Esther
Skipjack Resort & 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 €274
includes taxes & fees
10 Dec - 11 Dec
Aqua Lodges at Hurricane Hole Marina

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

Cudjoe Key
8.2 out of 10, Very good, (49)
"Great area. Quiet and comfortable "
United States
nancy c.
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Island Bay Resort

2.5 star property
Tavernier
10.0 out of 10, Exceptional, (139)
"Buutifull and cozy place "
United States
DILIA
The price is €245
includes taxes & fees
10 Dec - 11 Dec
Island Bay Resort

Beachside Retreat w/ Pool, Boat Ramp Dock for Rent

Key Largo
9.6 out of 10, Exceptional, (45)
"We absolutely loved it! "
United States
Emily B.
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent

Charming Home in Key Largo

Key Largo
9.8 out of 10, Exceptional, (27)
"It was clean and a very nice place to stay. Plenty of room and awesome amenities."
United States
Eric M.
The price is €419
includes taxes & fees
28 Dec - 29 Dec
Charming Home in Key Largo

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.
The price is €380
includes taxes & fees
9 Jan - 10 Jan 2026
Amazing Ocean view condo

Modern and Coastal 3212 is Across from Pool

Tavernier
9.8 out of 10, Exceptional, (150)
"Great stay lovely home "
United States
Yezenia
Modern and Coastal 3212 is Across from Pool

Poolside Cottage #411

Key West
9.8 out of 10, Exceptional, (53)
"Perfect for our family! Recommend 10/10!"
United States
Melissa F.
The price is €259
includes taxes & fees
14 Dec - 15 Dec
Poolside Cottage #411

Serenity In The Sun Condo Fabulous Ocean View

Tavernier
10.0 out of 10, Exceptional, (107)
"Good clean condo, great pool and little private beach "
United Kingdom
Nicola W.
Serenity In The Sun Condo Fabulous Ocean View

Cottage with Pool and Dockage, just minutes to Key West

Cudjoe Key
9.2 out of 10, Wonderful, (161)
"Great property,Great location. Will definitely stay there again."
United States
Roy F.
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, 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 €92 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.