Find the best vacation rental

ACCOMMODATION TYPES

Save Up To 73%

Airbnb, Vacation rentals and hotel deals in Middle Keys, FL

Excellent Choice! Three Family-friendly Rooms, Fantastic View, Outdoor Pool
Holiday home · 2 Guests · 1 Bedroom
$1,465 /night*
View deal
9.4 (7 reviews)
Key West Luxury Houseboat
House boat · 2 Guests · 1 Bedroom
$799 /night*
View deal
DoubleTree by Hilton Grand Key Resort
Resort · 2 Guests · 1 Bedroom
$426 /night
View deal
9.2 (1013 reviews)
The Perry Hotel & Marina Key West
Resort · 2 Guests · 1 Bedroom
$426 /night
View deal
7.9 (967 reviews)
Fairfield Inn & Suites by Marriott Key West
Hotel · 2 Guests · 1 Bedroom
$396 /night
View deal
Bayview Retreat
Condo · 2 Guests · 1 Bedroom
$16,471 /night
View deal
8.5 (823 reviews)
Fairfield Inn & Suites by Marriott Key West at The Keys Collection
Hotel · 2 Guests · 1 Bedroom
$362 /night
View deal
7.5 (1482 reviews)
24 North Hotel Key West
Hotel · 2 Guests · 1 Bedroom
$368 /night
View deal
10 (1 review)
Hyatt Windward Pointe, Key West, Fl - 2 Bedroom Unit
Condo · 2 Guests · 1 Bedroom
$1,299 /night*
View deal
9.4 (7 reviews)
BEAUTIFUL SANTUARY PRIVATE ISLAND CONNECTED BY BRIDGE TO KEY WEST
Holiday home · 2 Guests · 1 Bedroom
$2,248 /night*
View deal
8.5 (524 reviews)
Courtyard by Marriott Key West Waterfront
Hotel · 2 Guests · 1 Bedroom
$438 /night
View deal
7.7 (1032 reviews)
The Gates Hotel Key West
Hotel · 2 Guests · 1 Bedroom
$365 /night
View deal
The Laureate Key West
Hotel · 2 Guests · 1 Bedroom
$469 /night
View deal
7.7 (1720 reviews)
Ibis Bay Resort
Resort · 2 Guests · 1 Bedroom
$404 /night
View deal
Southern Comfort
Holiday home · 2 Guests · 1 Bedroom
$2,645 /night
View deal
Beautiful Houseboat in Key West
Boat · 2 Guests · 1 Bedroom
$450 /night
View deal
Best Spot For Your Next Trip! Deluxe Room w/ 2 Queen Beds, Onsite Pool
Holiday home · 2 Guests · 1 Bedroom
$499 /night*
View deal
Hilton Garden Inn Key West / The Keys Collection
Hotel · 2 Guests · 1 Bedroom
$359 /night
View deal
8.6 (4 reviews)
Cozy Houseboat
House boat · 2 Guests · 1 Bedroom
$500 /night*
View deal
9.4 (184 reviews)
Peaceful 2 BR Condo with All Amenities
Condo · 2 Guests · 1 Bedroom
$485 /night*
View deal

Airbnb, Holiday Beachfront House with Pool in Middle Keys, FL

Southern Comfort
Holiday home · 2 Guests · 1 Bedroom
$2,645 /night
View deal
9.4 (7 reviews)
BEAUTIFUL SANTUARY PRIVATE ISLAND CONNECTED BY BRIDGE TO KEY WEST
Holiday home · 2 Guests · 1 Bedroom
$2,248 /night*
View deal
Amazing Room with Stunning Ocean View Close to Beach! w/ Outdoor Swimming Pool
Holiday home · 2 Guests · 1 Bedroom
$480 /night*
View deal
What Are The Best Rental Amenities in Middle Keys, FL?
Top Rental Amenities in Middle Keys, FL
+
Check above for the most common and the least popular rental amenities in Middle Keys, and pick the one that fits your preference easily. In Middle Keys, 1653 rentals offer Air Conditioning, 1653 rentals offer Internet or Wifi, 1636 rentals offer TV. So, if you need Air Conditioning during your vacation, use the Air Conditioning filter to compare these properties. Two amenities that are not typical are Fireplace, Garden or Backyard.
How Does The Vacation Home Rental Price Look Like in Middle Keys, FL?
Vacation House & Condo Rental Price Information in Middle Keys, FL
+
The graph shows the percentages of vacation homes in each price bucket. Middle Keys has the largest percentage (18.69%) of homes in $150 - $200 price range.
$0 to 50
$0 to 50
$50 to 100
$50 to 100
$100 to 150
$100 to 150
$150 to 200
$150 to 200
$200 to 250
$200 to 250
$250 to 300
$250 to 300
$300 to 350
$300 to 350
$350 to 400
$350 to 400
$400 to 450
$400 to 450
$450 to 500
$450 to 500
$500 +
$500 +
Which Accommodations Should I Pick in Middle Keys, FL?
Rental Property Types in Middle Keys, FL
+
In Middle Keys, 50.20% of listings are House, which is the most popular accommodation out of 19 total accommodation types. Avg price per night for House is around $303. And the most searched amenities for House accommodation is Fireplace.The least popular accommodation in Middle Keys is Recreational Vehicle rentals
How Many Accommodations Are Pets Allowed in Middle Keys, FL?
Pets Allowed vs Not Allowed in Middle Keys, FL
+
34.27% of vacation homes in Middle Keys are pet friendly. Either you bring your loved pets on vacation or you have pet allergies, make sure to select the homes by applying the right filters.
Best Tourist Attractions in Middle Keys, FL?
Points of Interests In Middle Keys, FL
+

The most common & popular places (a.k.a points of interests) here in Middle Keys are:

Which Airports Should I Choose To Get To Middle Keys, FL?
Suggested Airports in Middle Keys, FL
+

Here are the airports that located near Middle Keys:

Airbnb, Vacation Condo with Full Kitchen, and Other Rental Options in Middle Keys, FL

Island Chic
Condo · 2 Guests · 1 Bedroom
$2,320 /night
View deal
9.0 (19 reviews)
The Trinidad by Brightwild | Pool View & Parking
Condo · 2 Guests · 1 Bedroom
$642 /night*
View deal
9.0 (18 reviews)
Classic Dog-Friendly Condo with Shared Pool, Central AC, and High-Speed WiFi
Condo · 2 Guests · 1 Bedroom
$569 /night*
View deal
* The displayed nightly rate may be estimated based on a future travel date. Narrow down your search with checkin and checkout dates to see the exact price.
See all offers