Florida Keys Holiday Rentals

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Our top choices for Florida Keys holiday rentals

Cottage in Marathon

Tropical Cottages
3.0 star property
8.6 out of 10, Excellent, (911)
"Decent stay, easy check in and contactless checkout. Very quiet and nice place! "
United States
Swastik
The price is NZ$260
includes taxes & fees
8 Jan - 9 Jan 2026
Tropical Cottages

Aparthotel in Marathon

Knight's Key Suites
3.0 star property
9.0 out of 10, Wonderful, (1157)
"Very good location.. Clean room."
United States
Leonor
The price is NZ$277
includes taxes & fees
15 Jan - 16 Jan 2026
Knight's Key Suites

Houseboat in Marathon

Yacht Haven Marina
3.5 star property
9.8 out of 10, Exceptional, (242)
"Friendly staff and extremely clean."
United States
Travis
Yacht Haven Marina

Houseboat in Islamorada

Treasure Harbor
3.0 star property
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
2.5 star property
8.6 out of 10, Excellent, (281)
"Enjoyed the duplex, instead of a standard hotel room. Full kitchen, nice bathroom, and bedroom. "
United States
Alejandra
Old Wooden Bridge Resort and Marina
3.5 star property
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

Aparthotel in Matecumbe

Breezy Palms Resort
2.5 star property
8.8 out of 10, Excellent, (591)
"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 NZ$395
includes taxes & fees
11 Jan - 12 Jan 2026
Breezy Palms Resort

Aparthotel in Marathon

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

Aparthotel in Key Largo

Anchorage Resort & Yacht Club
3.0 star property
8.6 out of 10, Excellent, (297)
"Really good place to stay "
United States
Elier
The price is NZ$481
includes taxes & fees
5 Jan - 6 Jan 2026
Anchorage Resort & Yacht Club

Mobile Home in Big Pine Key

Sunshine Key RV Resort & Marina
2.0 star property
8.8 out of 10, Excellent, (160)
"Staff was great. Room so clean! Loved the shower. Bed comfy and the property was beautiful! "
United States
brenda
The price is NZ$587
includes taxes & fees
4 Jan - 5 Jan 2026
Sunshine Key RV Resort & Marina

Holiday Home in Key Largo

Charming Home in 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.
The price is NZ$782
includes taxes & fees
4 Jan - 5 Jan 2026
Charming Home in Key Largo

Condo in Tavernier

Amazing Ocean view condo
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 NZ$645
includes taxes & fees
4 Jan - 5 Jan 2026
Amazing Ocean view condo
10.0 out of 10, Exceptional, (108)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
The price is NZ$817
includes taxes & fees
5 Jan - 6 Jan 2026
Serenity In The Sun Condo Fabulous Ocean View
9.6 out of 10, Exceptional, (123)
"Great stay!! Location was perfect view of the canal and close to the pool. Unit was very clean and would definitely stay again!!"
United States
Brad T.
The price is NZ$867
includes taxes & fees
7 Jan - 8 Jan 2026
Waterfront Beach, Pool, Dock, Kayaks, Paddleboards
3.0 star property
8.2 out of 10, Very good, (821)
"The staff goes above and beyond very, very warm and nice people"
United States
erik
Coconut Mallory Resort And Marina By Kees Vacations
10.0 out of 10, Exceptional, (122)
"We enjoyed our stay!"
United States
Halley R.
The price is NZ$861
includes taxes & fees
7 Jan - 8 Jan 2026
Modern and Coastal Ocean Pointe 2307
8.8 out of 10, Excellent, (42)
"The condo was renovated, and very nicely decorated, very clean and cozy. We enjoyed our short stay. Community and pool were good too. "
United States
Lina
The price is NZ$733
includes taxes & fees
4 Jan - 5 Jan 2026
Ocean view condo with balcony/marina view
9.8 out of 10, Exceptional, (26)
"Everything was exceptionally nice. Would definitely book again."
United States
Sharon
The price is NZ$791
includes taxes & fees
21 Jan - 22 Jan 2026
Lazy Daze Double King Suite Ocean Pointe 2310

Aparthotel in Tavernier

Island Bay Resort
2.5 star property
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 NZ$815
includes taxes & fees
1 Jan - 2 Jan 2026
Island Bay Resort

Houseboat in Stock Island

Aqua Lodges at Hurricane Hole Marina
2.0 star property
8.8 out of 10, Excellent, (170)
"Location , staff , and aqua lodge were perfect."
United States
William
The price is NZ$680
includes taxes & fees
7 Jan - 8 Jan 2026
Aqua Lodges at Hurricane Hole Marina
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$260 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.