Florida Keys Holiday Rentals

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Holiday Rentals in Florida Keys

Old Wooden Bridge Resort and Marina

2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (267)
"I love this place!!!"
United States
Greg
Old Wooden Bridge Resort and Marina

Yacht Haven Marina

3.5 star property
Marathon
9.8 out of 10, Exceptional, (222)
"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, (109)
"Unique House boat experience, friendly staff. "
United States
Luis
Treasure Harbor

Breezy Palms Resort

2.5 star property
Matecumbe
8.8 out of 10, Excellent, (558)
"Love this resort. Friendly check-in, room is always spotless and lovely outside area with beautiful views of the water. We have stayed here multiple times now - best spot in the keys! "
United States
Gemma
The price is NZ$202
includes taxes & fees
11 Nov - 12 Nov
Breezy Palms Resort

Skipjack Resort & Marina

3.0 star property
Marathon
8.6 out of 10, Excellent, (1208)
"Great stay"
United States
sharon
Skipjack Resort & Marina

Cabins at Bonefish Bay

3.0 star property
Marathon
9.6 out of 10, Exceptional, (74)
"I love this place definitely I will go back there soon, rooms clean staff friendly, ocean view amazing the Floating Aqua Lodge was more than amazing. Thank you for making my vacation so special "
United States
Beatrice
Cabins at Bonefish Bay

Tropical Cottages

3.0 star property
Marathon
8.6 out of 10, Excellent, (892)
"The room was very clean. The staff was friendly and helpful. "
United States
Charles
The price is NZ$180
includes taxes & fees
18 Nov - 19 Nov
Tropical Cottages

The Islands of Islamorada

4.0 star property
Matecumbe
9.8 out of 10, Exceptional, (68)
"Beautiful property!"
United States
Betty
The price is NZ$1,494
includes taxes & fees
9 Dec - 10 Dec
The Islands of Islamorada

Island Bay Resort

2.5 star property
Tavernier
10.0 out of 10, Exceptional, (135)
"Amazing property and wonderful owners. Super nice people and definitely will be returning."
United States
Daniel
The price is NZ$493
includes taxes & fees
13 Nov - 14 Nov
Island Bay Resort

The Hammocks at Marathon

2.5 star property
Marathon
9.0 out of 10, Wonderful, (109)
"We arrived early but were able to use the pool. Lovely cannon firing ceremony at sunset with a sunset shot from the bar. We ate wings and a pretzel from the bar which were both delicious. Room was large and the bed was really comfortable."
United Kingdom
Janet
The Hammocks at Marathon

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 NZ$207
includes taxes & fees
10 Nov - 11 Nov
Knight's Key Suites

Aqua Lodge Rentals At Coconut Cay

3.5 star property
Marathon
9.6 out of 10, Exceptional, (190)
"Clean room, spacious, nice and quiet. "
United States
Douglas
Aqua Lodge Rentals At Coconut Cay

Waterfront home with dock, pool table & private pool - walk to Sombrero Beach

Marathon
9.0 out of 10, Wonderful, (32)
"We loved the pool area. The home was very well appointed. Great location, near the beach and shopping."
United States
Tania K.
Waterfront home with dock, pool table & private pool - walk to Sombrero Beach

Sunshine Key RV Resort & Marina

2.0 star property
Big Pine Key
8.8 out of 10, Excellent, (156)
"I loved staying at Sunshine key"
United States
Miriam
Sunshine Key RV Resort & Marina

Key Largo Cottages

2.5 star property
Key Largo
9.6 out of 10, Exceptional, (26)
"Tropical paradise the way it's supposed to be! The staff are super friendly and helpful. They make you feel at home."
United States
Pamela P
Key Largo Cottages

Kings Kamp

2.5 star property
Key Largo
8.8 out of 10, Excellent, (23)
"Listing did not give the full picture. The room was in a small apartment in the middle of a large and busy RV park."
United Kingdom
Rosemary
Kings Kamp

Charming 3-bedroom house in Big Pine Key near Beach and Key West

Sands
The price is NZ$1,005
includes taxes & fees
11 Nov - 12 Nov
Charming 3-bedroom house in Big Pine Key near Beach and Key West

New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

Key Largo
9.4 out of 10, Exceptional, (80)
"Very cozy tiny home"
United States
Kristen H.
The price is NZ$648
includes taxes & fees
11 Nov - 12 Nov
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

Marlin Bay Resort & Marina

4.0 star property
Marathon
Marlin Bay Resort & Marina

Anchorage Resort & Yacht Club

3.0 star property
Key Largo
8.6 out of 10, Excellent, (297)
"It’s a good place to stay with family"
United States
Cody
The price is NZ$390
includes taxes & fees
30 Nov - 1 Dec
Anchorage Resort & Yacht Club
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$180 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.