Skip to content

Vacation rentals in Middle Keys

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Middle Keys

Guests agree: these stays are highly rated for location, cleanliness, and more.

Private room in Key Colony Beach
Turtle-By-The-Sea: the Best Deal in KCB!
A perfect get-away for couples or budget travelers, Turtle-by-the-Sea is the best priced vacation rental or hotel room in the middle-keys. Together with its prime location and amenities there simply isn’t a better deal to be had! Bursting with Keys charm, this cozy retreat is the perfect place to relax & escape. Newly rebuilt & reimagined, owners Mallory & Steve infused their love of the Keys & its surrounding ocean into every aspect of their waterside home.
$129 per night
SUPERHOST
Home in Key West
La Casita- Waterfront, Hot Tub & Dock
Welcome to La Casita - a beautiful and serene escape on the outskirts of Key West. This waterfront little gem offers waterfront views, a hot tub and private parking - the perfect getaway for your next vacation to paradise. Located on Stock Island in a manufactured home small community called "Bone Island", La Casita is just a short 10-15 minute drive from downtown Key West and all of the famous attractions.
$297 per night
Home in Key West
Casa Tranquility- Waterfront, King Suite & Hot Tub
Tranquility awaits you at this island oasis. With elevated views of the Atlantic Ocean and private hot tub, this waterfront property is perfect for your next family getaway. Located on Stock Island in a gated manufactured home small community called "Bone Island", Casa Tranquility is just a short 10-15 minute drive from downtown Key West and all of the famous attractions.
$365 per night

Other great vacation rentals in Middle Keys

Houseboat in Key West
Live the real Key West- Entire Houseboat at Marina
$261 per night
SUPERHOST
Condo in Key Colony Beach
Oceanfront Sunrise Condo Private Beach Heated Pool
$319 per night
SUPERHOST
Condo in Key Colony Beach
Beachside Unit 39 Tiki Huts, Private Beach & Pool
$253 per night
SUPERHOST
Private room in Big Pine Key
Old Island Life
$83 per night
Home in Cudjoe Key
Sea Haven - Waterfront "Venture Out" Home w/ Dock!
$348 per night
Condo in Key Colony Beach
Beachside Unit 27 - The Beach is Calling You!
$208 per night
SUPERHOST
Condo in Marathon
Tropical Paradise
$143 per night
Guest suite in Key West
STUDIO / APARTMENT
$271 per night
SUPERHOST
Condo in Key Colony Beach
Coastal Keys Condo, Oceanfront Complex Sleeps 4
$220 per night
SUPERHOST
Cottage in Cudjoe Key
ATLANTIS...Ocean Front Cottage Retreat!
$399 per night
SUPERHOST
Home in Cudjoe Key
NEW! 2BR,2BA Waterfront UPDATED w 35' Seawall! WOW
$353 per night
SUPERHOST
Boat in Key West
Unique Couples Retreat at Private Yacht Club
$152 per night

Other types of stays on Airbnb

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Middle Keys