Florida Keys Vacation Rentals

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Our top choices for Florida Keys vacation rentals

Yacht Haven Marina

Yacht Haven Marina
3.5 star property
Marathon
9.6 out of 10, Exceptional, (314 reviews)
"We love the accommodations and ability to cook with a full kitchen."
United States
Cheryl
$270 nightly
The price is $304
May 19 - May 20
Total with taxes and fees
Yacht Haven Marina

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (153 reviews)
"Amazing stay!"
United States
Amanda
$259 nightly
The price is $292
May 21 - May 22
Total with taxes and fees
Treasure Harbor

Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,193 reviews)
"Good value for money. Would definitely stay again "
Canada
Raghavan
$104 nightly
The price is $115
Jun 3 - Jun 4
Total with taxes and fees
Knight's Key Suites

Skipjack Resort & Marina

Skipjack Resort & Marina
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,264 reviews)
"Room was very nice and roomy. Breakfast was very good and pool area/bar relaxing. Good options for restaurants nearby."
United States
Krista
$224 nightly
The price is $252
May 31 - Jun 1
Total with taxes and fees
Skipjack Resort & Marina

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (337 reviews)
"I love the place, for the next time I will stay for more days "
United States
Kenia
$254 nightly
The price is $286
May 21 - May 22
Total with taxes and fees
Old Wooden Bridge Resort and Marina

Aqua Lodge Rentals At Coconut Cay

Aqua Lodge Rentals At Coconut Cay
3.5 star property
Marathon
9.6 out of 10, Exceptional, (222 reviews)
"This was an amazing experience and would stay in a houseboat again! It was so clean, quaint and cozy. The deck off the back was beautiful and we can’t wait to return!!"
United States
Stephanie
$352 nightly
The price is $397
May 19 - May 20
Total with taxes and fees
Aqua Lodge Rentals At Coconut Cay

Anchorage Resort & Yacht Club

Anchorage Resort & Yacht Club
3.0 star property
Key Largo
8.8 out of 10, Excellent, (330 reviews)
"The kitchen was completely equipped, everything ready for us to have a wonderful time."
United States
Geysi
$196 nightly
The price is $220
May 19 - May 20
Total with taxes and fees
Anchorage Resort & Yacht Club

Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (973 reviews)
"Came here for our honeymoon, we absolutely loved it! Clean, the bar and food truck was perfect."
United States
Izabella
$125 nightly
The price is $141
May 31 - Jun 1
Total with taxes and fees
Tropical Cottages

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
9.0 out of 10, Wonderful, (186 reviews)
"Beautiful location, quick reply when you contact them. The bar and restaurant were so nice!! We would definitely stay again. "
United States
Stacy
$283 nightly
The price is $319
May 27 - May 28
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (677 reviews)
"Easy parking and great clean kitchen"
United States
JoAnn
$143 nightly
The price is $160
May 21 - May 22
Total with taxes and fees
Breezy Palms Resort

Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (169 reviews)
"Very nice small resort."
United States
Dan
$289 nightly
The price is $325
Jun 10 - Jun 11
Total with taxes and fees
Island Bay Resort

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (114 reviews)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
$394 nightly
The price is $438
May 19 - May 20
Total with taxes and fees
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

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, (224 reviews)
"Loved our stay. Great pool, our three kids couldn’t get enough of it! Would stay again"
United States
Erik E.
$372 nightly
The price is $413
May 20 - May 21
Total with taxes and fees
Two Spectacular Ocean Views from the Living Room and Master Bedroom of the 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
$256 nightly
The price is $284
May 20 - May 21
Total with taxes and fees
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
Old Town Key West
9.6 out of 10, Exceptional, (104 reviews)
"Loved it! Quiet, clean, good amenities, close to Duval street. Would 100% go back."
United States
Ian G.
$276 nightly
The price is $306
May 25 - May 26
Total with taxes and fees
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

May Special 9-13 & 17 -19 & 29-1st 30$ off a ngt @169 lod + extras

May Special 9-13 & 17 -19 & 29-1st 30$ off a ngt @169 lod + extras
Old Town Key West
9.6 out of 10, Exceptional, (250 reviews)
"The condo/room was very clean and put together, the location is a nice neighborhood."
United States
Bonnie R.
$316 nightly
The price is $351
May 19 - May 20
Total with taxes and fees
May Special 9-13 & 17 -19 & 29-1st 30$ off a ngt @169 lod + extras

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
9.0 out of 10, Wonderful, (62 reviews)
"The location was very good and the host was responsive. "
United States
Lilly A.
$359 nightly
The price is $398
May 20 - May 21
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (166 reviews)
"Very nice place. Clean and easy to contact the host."
United States
Bonnie H.
$389 nightly
The price is $432
May 19 - May 20
Total with taxes and fees
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

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
$236 nightly
The price is $262
May 19 - May 20
Total with taxes and fees
Steps from Duval, Pool on Site & Bikes Included!

Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen

Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen
Tavernier
10.0 out of 10, Exceptional, (18 reviews)
"Perfect Stay."
United States
suhaela s.
$405 nightly
The price is $450
May 25 - May 26
Total with taxes and fees
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Florida Keys vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Florida Keys vacation 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 low season months. For more hustle and bustle, you may prefer to visit Florida Keys in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $115 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Florida Keys rentals

At Expedia, we put the best Florida Keys vacation 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 vacation.

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.

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