Middle Keys vacation rentals
Book unique homes, vacation rentals, and more on Airbnb
Top-rated vacation rentals in Middle Keys
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Middle Keys vacation rentals
Other great vacation rentals in Middle Keys
Apartment in Key West
4.94 out of 5 average rating, 360 reviewsStudio Blu - Key West, FL - Hip Studio in Old Town
Cottage in Cudjoe Key
4.9 out of 5 average rating, 136 reviewsATLANTIS...Ocean Front Cottage Retreat!
Townhouse in Key West
4.91 out of 5 average rating, 109 reviewsPoolside Cottage #411
Houseboat in Key West
4.96 out of 5 average rating, 129 reviewsBeautiful Houseboat in Key West
Villa in Marathon
4.89 out of 5 average rating, 148 reviewsNew Aqua Lodge 2Beds 1 Bath with Full Kitchens
Condo in Key West
4.86 out of 5 average rating, 131 reviewsA Perfect Getaway
Home in Cudjoe Key
4.9 out of 5 average rating, 104 reviewsSunrise Beach Escape
Condo in Key West
4.86 out of 5 average rating, 111 reviewsRooftop Penthouse
Middle Keys beach vacation rentals
Home in Marathon
4.96 out of 5 average rating, 126 reviewsOceanfront Tiny Villa in the Heart of the FL Keys
Tiny home in Key West
4.86 out of 5 average rating, 349 reviewsModern studio half block from Duval with parking
Apartment in Key West
4.8 out of 5 average rating, 127 reviewsMango Hideaway steps off World Famous Duval street
Condo in Key West
4.99 out of 5 average rating, 84 reviewsHidden Beach Duplex, Best Place in Key West
Guest suite in Key Colony Beach
4.99 out of 5 average rating, 84 reviewsTurtle-By-The-Sea: the Best Deal in KCB!
Home in Marathon
4.97 out of 5 average rating, 35 reviewsThe Gulf Cottage at Marathon Key
Camper/RV in Big Pine Key
4.93 out of 5 average rating, 41 reviewsHaving fun in the lower Keys
Apartment in Key West
4.94 out of 5 average rating, 16 reviewsOceanfront Condo in Key West
House rentals in Middle Keys
Home in Marathon
4.91 out of 5 average rating, 159 reviewsBeachfront Villa - Florida Keys
Home in Cudjoe Key
4.97 out of 5 average rating, 124 reviewsCudjoe Key Home with a View
Home in Islamorada
4.97 out of 5 average rating, 167 reviewsFlakey's
Home in Cudjoe Key
4.81 out of 5 average rating, 223 reviewsOCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!
Home in Cudjoe Key
4.87 out of 5 average rating, 46 reviews*Emerald Seas*-Florida Keys Ocean Front Paradise!
Home in Summerland Key
4.86 out of 5 average rating, 7 reviewsBungalows at Sugarloaf Beach - Little Hammock
Home in Key West
4.95 out of 5 average rating, 59 reviewsParadise found
Home in Key West
5.0 out of 5 average rating, 40 reviewsGorgeous Romantic Private Villa, Steps from Duval!
Destinations to explore
- Key West Vacation rentals
- Naples Vacation rentals
- Varadero Vacation rentals
- Havana Vacation rentals
- Miami Vacation rentals
- Miami Beach Vacation rentals
- Fort Lauderdale Vacation rentals
- Boca Raton Vacation rentals
- West Palm Beach Vacation rentals
- Sarasota Vacation rentals
- Anna Maria Island Vacation rentals
- Tampa Vacation rentals
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes