Florida Keys Holiday Rentals

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Our top choices for Florida Keys holiday rentals

Yacht Haven Marina

Yacht Haven Marina
3.5 star property
Marathon
9.6 out of 10, Exceptional, (307 reviews)
"We love the accommodations and ability to cook with a full kitchen."
United States
Cheryl
The price is NZ$482
includes taxes & fees
20 May - 21 May
Yacht Haven Marina

Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,192 reviews)
"Ocean view from room balcony."
United States
Brian
The price is NZ$211
includes taxes & fees
1 June - 2 June
Knight's Key Suites

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (671 reviews)
"Place was nicer inside than out. Great location."
United States
Marcos
The price is NZ$236
includes taxes & fees
13 May - 14 May
Breezy Palms Resort

Aqua Lodge Rentals At Coconut Cay

Aqua Lodge Rentals At Coconut Cay
3.5 star property
Marathon
9.6 out of 10, Exceptional, (221 reviews)
"We had a wonderful vacation!"
United States
Yuanfen
The price is NZ$652
includes taxes & fees
25 May - 26 May
Aqua Lodge Rentals At Coconut Cay

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (336 reviews)
"I love the place, for the next time I will stay for more days "
United States
Kenia
The price is NZ$455
includes taxes & fees
31 May - 1 June
Old Wooden Bridge Resort and Marina

Skipjack Resort & Marina

Skipjack Resort & Marina
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,262 reviews)
"The staff was very nice, our room was spacious and comfortable, the area has lots to do"
United States
Carol
The price is NZ$398
includes taxes & fees
1 June - 2 June
Skipjack Resort & Marina

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (153 reviews)
"Amazing stay!"
United States
Amanda
The price is NZ$539
includes taxes & fees
11 May - 12 May
Treasure Harbor

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
9.0 out of 10, Wonderful, (183 reviews)
"Beautiful location, quick reply when you contact them. The bar and restaurant were so nice!! We would definitely stay again. "
United States
Stacy
The price is NZ$527
includes taxes & fees
17 May - 18 May
Aqua Lodges at Hurricane Hole Marina

Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (969 reviews)
"Came here for our honeymoon, we absolutely loved it! Clean, the bar and food truck was perfect."
United States
Izabella
The price is NZ$243
includes taxes & fees
26 May - 27 May
Tropical Cottages

Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!

Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
Old Town Key West
9.6 out of 10, Exceptional, (49 reviews)
"Great location, clean space and comfortable beds. Enjoyed our stay!"
United States
Chasity W.
The price is NZ$646
includes taxes & fees
17 May - 18 May
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!

Anchorage Resort & Yacht Club

Anchorage Resort & Yacht Club
3.0 star property
Key Largo
8.8 out of 10, Excellent, (328 reviews)
"The room was clean and the views from our rooms were amazing!!!"
United States
Elizabeth
The price is NZ$369
includes taxes & fees
17 May - 18 May
Anchorage Resort & Yacht Club

Scott's Cottage - Truman @ Duval | Perfect Spot in Old Town Key West!

Scott's Cottage - Truman @ Duval | Perfect Spot in Old Town Key West!
Old Town Key West
9.8 out of 10, Exceptional, (32 reviews)
"The property was cozy and a great location for walking."
United States
Elizabeth E.
The price is NZ$582
includes taxes & fees
17 May - 18 May
Scott's Cottage - Truman @ Duval | Perfect Spot in Old Town Key West!

Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (47 reviews)
"Condo was very nice and clean. Our host responded when we contacted him. The power strip to WiFi was turned off so took us a while to figure that out so if you rent this condo just check that. The pool was extremely nice and the kids loved it. "
United States
Donna H.
The price is NZ$650
includes taxes & fees
11 May - 12 May
Amazing Ocean view condo

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, (131 reviews)
"Amazing place to stay, excellent experience!!!"
United States
Brad
The price is NZ$818
includes taxes & fees
23 May - 24 May
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

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

Ricky's Retreat - Truman @ Duval | Ideal Getaway!
Old Town Key West
9.8 out of 10, Exceptional, (36 reviews)
"Great location!!"
United States
Julie
The price is NZ$726
includes taxes & fees
9 June - 10 June
Ricky's Retreat - Truman @ Duval | Ideal Getaway!

Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (168 reviews)
"Very nice small resort."
United States
Dan
The price is NZ$546
includes taxes & fees
9 June - 10 June
Island Bay Resort

Paradise in Key Largo, FL

Paradise in Key Largo, FL
Key Largo
9.6 out of 10, Exceptional, (69 reviews)
"We really enjoyed our stay here .. the place was clean — had everything we needed… thanks for sharing your place.."
United States
brenda b.
The price is NZ$490
includes taxes & fees
10 May - 11 May
Paradise in Key Largo, FL

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, (431 reviews)
"Clean room, laundry and great location. Owner/operator was very responsive. "
United States
Ashley
The price is NZ$525
includes taxes & fees
12 May - 13 May
Steps from Duval, Pool on Site & Bikes Included!

Lazy Daze Double King Suite Ocean Pointe 2310

Lazy Daze Double King Suite Ocean Pointe 2310
Tavernier
9.8 out of 10, Exceptional, (31 reviews)
"Everything was exceptionally nice. Would definitely book again."
United States
Sharon
The price is NZ$722
includes taxes & fees
17 May - 18 May
Lazy Daze Double King Suite Ocean Pointe 2310

VanGogh Studio | Updated, Old Town, Heated Pool

VanGogh Studio | Updated, Old Town, Heated Pool
Old Town Key West
8.6 out of 10, Excellent, (45 reviews)
"Room had everything we needed!Owners and staff were very responsive and offered free shuttle to/from the airport!"
United States
Timothy P.
The price is NZ$558
includes taxes & fees
12 May - 13 May
VanGogh Studio | Updated, Old Town, Heated Pool
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$211 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.