Florida Keys Holiday Rentals

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Our top choices for Florida Keys holiday rentals

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (348 reviews)
"Very nice, clean and cozy, with the deers walking around."
United States
Sofia
The price is NZ$434
includes taxes & fees
30 June - 1 July
Old Wooden Bridge Resort and Marina

Yacht Haven Marina

Yacht Haven Marina
3.5 star property
Marathon
9.6 out of 10, Exceptional, (328 reviews)
"We love the accommodations and ability to cook with a full kitchen."
United States
Cheryl
The price is NZ$501
includes taxes & fees
30 June - 1 July
Yacht Haven Marina

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (158 reviews)
"Amazing stay!"
United States
Amanda
The price is NZ$512
includes taxes & fees
29 June - 30 June
Treasure Harbor

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (700 reviews)
"Enjoyed this place."
United States
Christopher
The price is NZ$312
includes taxes & fees
1 July - 2 July
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, (225 reviews)
"Cleanness relaxing location, nice views, good air conditioning"
United States
Hakan
The price is NZ$564
includes taxes & fees
5 July - 6 July
Aqua Lodge Rentals At Coconut Cay

Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,206 reviews)
"Great view of the 7 mile bridge, great restaurant close by"
United States
Eric
The price is NZ$203
includes taxes & fees
29 June - 30 June
Knight's Key Suites

Skipjack Resort & Marina

Skipjack Resort & Marina
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,273 reviews)
"I love the staff, really helping me when we need The place is excellent location, the bungalow was in pristine condition, and the area outside was wonderful"
United States
Ysabel
The price is NZ$394
includes taxes & fees
28 June - 29 June
Skipjack Resort & Marina

Caloosa Cove Resort by CoolVacay

Caloosa Cove Resort by CoolVacay
3.0 star property
Matecumbe
9.8 out of 10, Exceptional, (6 reviews)
"Easy check in if you come After business hours. Kayaks and sport equipment available. Has a small beach which is unique to the Keys. Pool pretty much vacant at all times. Great views. Highly recommend."
United States
Dana
The price is NZ$477
includes taxes & fees
30 June - 1 July
Caloosa Cove Resort by CoolVacay

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (188 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$528
includes taxes & fees
28 June - 29 June
Aqua Lodges at Hurricane Hole Marina

Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (981 reviews)
"It was a very enjoyable stay, highly recommend."
United States
Andrea
The price is NZ$253
includes taxes & fees
12 July - 13 July
Tropical Cottages

Anchorage Resort & Yacht Club

Anchorage Resort & Yacht Club
3.0 star property
Key Largo
8.8 out of 10, Excellent, (337 reviews)
"It was nice! Difficulty getting in but they weee fast to answer and solve problem. Very nice place will be back !"
United States
Maggie
The price is NZ$451
includes taxes & fees
1 July - 2 July
Anchorage Resort & Yacht Club

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (115 reviews)
"Everything was wonderful! We enjoyed our stay very much. "
United States
Colleen D.
The price is NZ$757
includes taxes & fees
24 June - 25 June
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

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, (140 reviews)
"This was the perfect place, right on the ocean and a full kitchen so you can cook your own meals. The room was very clean, I loved that they had a laundry basket and laundry detergent in the room for you, came in handy seeing as we stayed for 7 days. Amazing place to watch the sunset from a hammock and we got lucky enough to see some nurse sharks at the docks right outside of our hotel."
United States
Andrew Jackson
The price is NZ$437
includes taxes & fees
1 July - 2 July
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

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, (132 reviews)
"Great place to stay"
United States
walter l.
The price is NZ$542
includes taxes & fees
7 July - 8 July
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

Two Spectacular Ocean Views from the Living Room and Master Bedroom of the Condo

Two Spectacular Ocean Views from the Living Room and Master Bedroom of the Condo
Tavernier
9.6 out of 10, Exceptional, (227 reviews)
"Great location, lovely pool area, and the owner was very easy to communicate with answering our questions!"
United States
Cathy M.
The price is NZ$771
includes taxes & fees
23 July - 24 July
Two Spectacular Ocean Views from the Living Room and Master Bedroom of the Condo

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, (439 reviews)
"Great location within walking distance to both ends of Duval. The bikes were nice as well and the unit was very clean. Enjoyed our stay."
United States
Jeff T.
The price is NZ$508
includes taxes & fees
20 July - 21 July
Steps from Duval, Pool on Site & Bikes Included!

Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (32 reviews)
"A comfortable little condo, conveniently located for exploring the Keys. There’s a nice pool and small beach area with a bar/restaurant that are well maintained."
United States
Stephen
The price is NZ$580
includes taxes & fees
7 July - 8 July
Florida Keys Getaway - Slps 4 - Ocean View

Carey's Corner | Updated Studio with Heated Pool

Carey's Corner | Updated Studio with Heated Pool
Old Town Key West
8.6 out of 10, Excellent, (45 reviews)
" It was a nice and cozy place in a very convenient location, close to everything. I really enjoyed my stay."
United States
Karen
The price is NZ$577
includes taxes & fees
29 June - 30 June
Carey's Corner | Updated Studio with Heated Pool

Paradise in Key Largo, FL

Paradise in Key Largo, FL
Key Largo
9.8 out of 10, Exceptional, (72 reviews)
"Clean, comfortable place. The RV park very nice. Great place to use as base for exploring upper keys with your dog."
United States
andrea k.
The price is NZ$506
includes taxes & fees
25 June - 26 June
Paradise in Key Largo, FL

Cottage with Pool and Boat Dockage just minutes to Key West!

Cottage with Pool and Boat Dockage just minutes to Key West!
Cudjoe Key
8.6 out of 10, Excellent, (166 reviews)
"Quite location, nice amenities and directions for check in/out were clear."
United States
Kasey M.
Cottage with Pool and Boat Dockage just minutes to Key West!
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Florida Keys holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Florida Keys. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Florida Keys. Seeing all the best attractions is bound to make you fall in love with Florida Keys. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Florida Keys short-term rentals, that won’t be hard to do.