A beach with palm trees, people relaxing on chairs, and colorful kayaks.

Holiday Rentals in Florida Keys

  • 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

1. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (777 reviews)
"Such a great place to stay!!"
United States
Gavin
The price is €116
includes taxes & fees
3 Nov - 4 Nov
Breezy Palms Resort

2. Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,244 reviews)
"We had the pool view..Excellent!"
United States
Brandy
The price is €111
includes taxes & fees
29 Nov - 30 Nov
Knight's Key Suites

3. Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,013 reviews)
"The family running the food truck and tiki hut were great. Felt like we were guests in their home."
United States
Douglas
The price is €96
includes taxes & fees
3 Nov - 4 Nov
Tropical Cottages

4. Aqua Lodge Rentals At Coconut Cay

Aqua Lodge Rentals At Coconut Cay
3.5 star property
Marathon
9.6 out of 10, Exceptional, (237 reviews)
"Never stayed in a houseboat before. It was a novel experience!"
United States
Susan
The price is €219
includes taxes & fees
4 Nov - 5 Nov
Aqua Lodge Rentals At Coconut Cay

5. Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (201 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
The price is €261
includes taxes & fees
3 Nov - 4 Nov
Aqua Lodges at Hurricane Hole Marina

6. Yacht Haven Marina

Yacht Haven Marina
3.5 star property
Marathon
9.6 out of 10, Exceptional, (380 reviews)
"Loved staying in the aqua lodges, such a relaxing place."
United States
Lauren
The price is €222
includes taxes & fees
4 Nov - 5 Nov
Yacht Haven Marina

7. Skipjack Resort & Marina

Skipjack Resort & Marina
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,296 reviews)
"Great spot"
Canada
Justin
The price is €197
includes taxes & fees
3 Nov - 4 Nov
Skipjack Resort & Marina

8. Anchorage Resort & Yacht Club

Anchorage Resort & Yacht Club
3.0 star property
Key Largo
8.8 out of 10, Excellent, (351 reviews)
"Very nice room"
United States
Sabrina
The price is €160
includes taxes & fees
3 Nov - 4 Nov
Anchorage Resort & Yacht Club

9. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (379 reviews)
"Great view , clean room and excellent staff ( Mr. shaggy )"
United States
Jordan
The price is €243
includes taxes & fees
8 Nov - 9 Nov
Old Wooden Bridge Resort and Marina

10. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (180 reviews)
"Had a very enjoyable stay at Hemingway House. The place was spotless! All staff were very friendly and helpful. Would highly recommend staying here!"
United States
Diane
The price is €234
includes taxes & fees
3 Nov - 4 Nov
Treasure Harbor

11. Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
2.5 star property
Marathon
9.2 out of 10, Wonderful, (147 reviews)
"It is an excellent place."
United States
Arianna
The price is €204
includes taxes & fees
2 Dec - 3 Dec
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

12. Aqua Lodges at 47th Street Gulfside

Aqua Lodges at 47th Street Gulfside
3.0 star property
Marathon
8.8 out of 10, Excellent, (60 reviews)
"Loved our stay at the aqua lodges 10/10 would do it again"
United States
Lauren
The price is €270
includes taxes & fees
3 Nov - 4 Nov
Aqua Lodges at 47th Street Gulfside

13. Steps from Duval, Pool on Site & Bikes Included!

Steps from Duval, Pool on Site & Bikes Included!
Old Town Key West
9.6 out of 10, Exceptional, (463 reviews)
"This studio is in a wonderful location and comes with bikes and a pool spa. It is a fabulous place to stay for a relaxing get-away island-style."
United States
Laura D.
The price is €261
includes taxes & fees
2 Dec - 3 Dec
Steps from Duval, Pool on Site & Bikes Included!

14. Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (43 reviews)
"great stay and value! glad we went with this place for our trip, everyone loved it! beautiful, clean and the pool was great too!"
Canada
Nick
The price is €292
includes taxes & fees
3 Nov - 4 Nov
Florida Keys Getaway - Slps 4 - Ocean View

15. Ricky's Retreat - Truman @ Duval | Ideal Getaway!

Ricky's Retreat - Truman @ Duval | Ideal Getaway!
Old Town Key West
9.8 out of 10, Exceptional, (40 reviews)
"Ricky’s Retreat is in a fantastic location. The room was all you need in Key West. Highly recommend it and will definitely stay there again."
United States
Brian R.
The price is €345
includes taxes & fees
3 Nov - 4 Nov
Ricky's Retreat - Truman @ Duval | Ideal Getaway!

16. Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (37 reviews)
"Wonderful stay. Thank you."
United States
shannon b.
The price is €253
includes taxes & fees
9 Nov - 10 Nov
Poolside Cottage #412

17. SAVE BIG $$$ NOV./DEC. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ NOV./DEC. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (113 reviews)
"Our family had an amazing time staying here! Our hosts were quick to answer any questions we had and the house was clean and fully stocked with everything you might need. Our favorite part was being able to sit out on the deck by the canal and see all the marine wildlife. We even had a little family of manatees hang out for awhile. Definitely would recommend staying here!"
United States
Mckayla S.
The price is €374
includes taxes & fees
9 Nov - 10 Nov
SAVE BIG $$$ NOV./DEC. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

18. 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, (139 reviews)
"Great place to stay"
United States
walter l.
The price is €332
includes taxes & fees
10 Nov - 11 Nov
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

19. Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (116 reviews)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
The price is €338
includes taxes & fees
19 Nov - 20 Nov
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

20. Paradise in Key Largo, FL

Paradise in Key Largo, FL
Key Largo
9.8 out of 10, Exceptional, (77 reviews)
"This was a neat place to stay and the host was very helpful when I had questions!"
United States
Anonymous traveller
The price is €264
includes taxes & fees
3 Nov - 4 Nov
Paradise in Key Largo, FL
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 €96 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.