Florida Keys Holiday Rentals

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Our top choices for Florida Keys holiday rentals

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (129 reviews)
"Very peaceful and comfortable stay! Dallas and Hannah were amazing hosts! Thank you so much !"
United States
Nick
Treasure Harbor

Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (927 reviews)
"Room was great and clean. Had a sweet cat that roamed the premises. Parking is limited to 1 vehicle but that was fine. Definitely would stay there again!"
United States
James
The price is NZ$346
includes taxes & fees
9 Feb - 10 Feb
Tropical Cottages

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (299 reviews)
"Great stay in Bug Pine Key! Clean and spacious room, excellent staff and Beautiful views!"
United States
Peter
Old Wooden Bridge Resort and Marina

Anchorage Resort & Yacht Club

Anchorage Resort & Yacht Club
3.0 star property
Key Largo
8.6 out of 10, Excellent, (304 reviews)
"Quaint and very convenient. Beautiful views of the marina and water. Staff was very helpful and recommended a great restaurant. "
United States
Michelle
The price is NZ$421
includes taxes & fees
9 Feb - 10 Feb
Anchorage Resort & Yacht Club

Yacht Haven Marina

Yacht Haven Marina
3.5 star property
Marathon
9.8 out of 10, Exceptional, (266 reviews)
"Great place. "
Canada
Elizabeth
Yacht Haven Marina

Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,169 reviews)
"Very a nice place clean nice location good price"
United States
Pawel
The price is NZ$357
includes taxes & fees
8 Feb - 9 Feb
Knight's Key Suites

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (616 reviews)
"Friendly staff, beautiful peaceful beach, great room with a big comfy bed and all that you might need. "
United States
Alexander
The price is NZ$478
includes taxes & fees
12 Feb - 13 Feb
Breezy Palms Resort

Sunshine Key RV Resort & Marina

Sunshine Key RV Resort & Marina
2.0 star property
Big Pine Key
8.8 out of 10, Excellent, (160 reviews)
"Staff was great. Room so clean! Loved the shower. Bed comfy and the property was beautiful! "
United States
brenda
The price is NZ$570
includes taxes & fees
22 Feb - 23 Feb
Sunshine Key RV Resort & Marina

Aqua Lodge Rentals At Coconut Cay

Aqua Lodge Rentals At Coconut Cay
3.5 star property
Marathon
9.6 out of 10, Exceptional, (208 reviews)
"Room was clean, staff was friendly, view from deck was amazing, took the free kayaks out and saw a Manatee, convenient location. Great experience!"
United States
Wendy
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, (175 reviews)
"Unique place to stay! We loved the nature and the location! "
United States
Sara
The price is NZ$684
includes taxes & fees
1 Mar - 2 Mar
Aqua Lodges at Hurricane Hole Marina

Skipjack Resort & Marina

Skipjack Resort & Marina
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,224 reviews)
"Beautiful location clean rooms friendly staff "
United States
Tiffany
Skipjack Resort & Marina

Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (43 reviews)
"Exceeded expectations, exceptionally clean, great for kids (they loved the pool), perfect for our Keys trip"
United States
Natalie M.
Amazing Ocean view condo

Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.6 out of 10, Exceptional, (20 reviews)
"Everything was just as described in the condo listing. We enjoyed the pool and hot tub. Wonderful location to explore the Keys. "
United States
Michele G.
The price is NZ$734
includes taxes & fees
25 Feb - 26 Feb
Florida Keys Getaway - Slps 4 - Ocean View

Cottage with swimming pool and dockage, just minutes to Key West!

Cottage with swimming pool and dockage, just minutes to Key West!
Cudjoe Key
9.0 out of 10, Wonderful, (165 reviews)
"Everything was there that I needed. Very nice area for my dog."
United States
Terry
The price is NZ$533
includes taxes & fees
15 Feb - 16 Feb
Cottage with swimming pool and dockage, just minutes to Key West!

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
8.8 out of 10, Excellent, (90 reviews)
"Nice place to vacation "
United States
Kevin D.
The price is NZ$759
includes taxes & fees
23 Feb - 24 Feb
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

3212 Across from Pool * King & Queen/Twin Bunk Bed

3212 Across from Pool * King & Queen/Twin Bunk Bed
Tavernier
9.8 out of 10, Exceptional, (152 reviews)
"Great stay lovely home "
United States
Yezenia
3212 Across from Pool * King & Queen/Twin Bunk Bed

Relax by Florida Keys Beaches, just a 7-min drive away

Relax by Florida Keys Beaches, just a 7-min drive away
Cudjoe Key
9.8 out of 10, Exceptional, (201 reviews)
"Will definitely stay here again "
United States
Jeannine R.
The price is NZ$1,083
includes taxes & fees
27 Feb - 28 Feb
Relax by Florida Keys Beaches, just a 7-min drive away

Blue Haven Key Largo | Ocean Pointe 1315

Blue Haven Key Largo | Ocean Pointe 1315
Tavernier
9.6 out of 10, Exceptional, (15 reviews)
"Loved this condo. Had all the amenities we needed and was super clean and tidy. Will definitely be staying here again. "
United States
Rodney B.
The price is NZ$839
includes taxes & fees
4 Mar - 5 Mar
Blue Haven Key Largo | Ocean Pointe 1315

Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR

Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR
Tavernier
9.8 out of 10, Exceptional, (26 reviews)
"Accommodation and location are excellent! Listing is accurate and the resort amenities are very enjoyable after a day out exploring the Keys (or just having at least one whole day at the resort, as we did). "
United States
Jenny G.
The price is NZ$706
includes taxes & fees
8 Feb - 9 Feb
Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR

Paradise Palms 2 Bedroom Condo Ocean Pointe 1206

Paradise Palms 2 Bedroom Condo Ocean Pointe 1206
Tavernier
9.8 out of 10, Exceptional, (6 reviews)
"Thanks for your great hospitality."
United States
richard
The price is NZ$716
includes taxes & fees
8 Feb - 9 Feb
Paradise Palms 2 Bedroom Condo Ocean Pointe 1206
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$346 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.