Waterfront vacation rentals in Windley Key
Find and book unique waterfront rentals on Airbnb
Top-rated waterfront rentals in Windley Key
Guests agree: these waterfront 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 Windley Key waterfront rentals
Waterfront apartment rentals
Apartment in Tavernier
4.83 out of 5 average rating, 255 reviewsBreathtaking Oceanfront Views at Tropical Daze
Jan 12 – 19
Apartment in Key Largo
4.98 out of 5 average rating, 126 reviewsKey Largo Kawama Lagoon Free Cancel Deutsch Spain
Aug 15 – 22
Apartment in Key Largo
4.75 out of 5 average rating, 186 reviewsHideaway with Picturesque Canal View Apt 3
Jul 10 – 17
Apartment in Key Largo
4.78 out of 5 average rating, 137 reviewsEscape to the Seaside!
Jul 28 – Aug 2
Apartment in Tavernier
5.0 out of 5 average rating, 17 reviewsTurtles Nest 2 Ocean Point condo
Nov 17 – 24
Apartment in Key Largo
5.0 out of 5 average rating, 21 reviewsStudio apartment in Calusa Resort & Campgrounds
Oct 10 – 17
Apartment in Tavernier
5.0 out of 5 average rating, 8 reviewsModern-Coastal Suite with Vast Ocean views
Sep 28 – Oct 5
Apartment in Marathon
5.0 out of 5 average rating, 8 reviewsGated Oceanfront Heated Pool
Dec 3 – 10
Waterfront house rentals
Home in Marathon
4.91 out of 5 average rating, 159 reviewsBeachfront Villa - Florida Keys
Mar 22 – 29
Home in Key Largo
4.96 out of 5 average rating, 136 reviewsKey Largo Waterfront Home with Tiki & Boat Dock
Sep 26 – Oct 3
Home in Islamorada
4.98 out of 5 average rating, 140 reviewsPorter’s Corner
Jun 26 – Jul 3
Home in Key Largo
4.9 out of 5 average rating, 127 reviewsBlue House Marine in Key Largo
Jan 15 – 22
Home in Marathon
4.99 out of 5 average rating, 107 reviewsSea Ray Cove , 75’ boat dock, 1 block from beach!
Sep 14 – 21
Home in Marathon
4.97 out of 5 average rating, 119 reviewsMarathon one-level home on the Marina - with slip!
Dec 20 – 27
Home in Key Largo
4.88 out of 5 average rating, 165 reviewsOutdoor Paradise - Beach, Boats, Snorkeling & Sun!
Oct 23 – 30
Home in Islamorada
4.94 out of 5 average rating, 18 reviews3 Lux Ensuites Walk/Boat Island! - Villa Plátano
Jul 13 – 20
Waterfront condo rentals
Condo in Tavernier
4.91 out of 5 average rating, 111 reviews500 Burton Drive Tavernier, Key Largo
Oct 7 – 14
Condo in Key Colony Beach
4.96 out of 5 average rating, 171 reviewsOceanfront Sunrise Condo Private Beach Heated Pool
Nov 18 – 25
Condo in Key Largo
4.98 out of 5 average rating, 117 reviewsOceanfront Condo w/Lake, Kayak, Paddleboard & Bike
Nov 2 – 9
Condo in Tavernier
4.87 out of 5 average rating, 126 reviewsReel Large END Unit in Ocean Point Suites
Oct 9 – 16
Condo in Tavernier
4.93 out of 5 average rating, 108 reviewsKeys Life Ocean Pointe Pool Jacuzzi Beach Crib
Feb 11 – 18
Condo in Key Largo
4.97 out of 5 average rating, 148 reviewsKEYS BEACH RETREAT WITH CAPTIVATING WATERVIEW!
Nov 11 – 18
Condo in Tavernier
4.8 out of 5 average rating, 130 reviewsTROPICAL PARADISE Ocean Condo - Cabana Daydreamin'
Oct 28 – Nov 4
Condo in Key Colony Beach
4.91 out of 5 average rating, 112 reviewsBeachside Unit 39 Tiki Huts, Private Beach & Pool
Oct 27 – Nov 3
Destinations to explore
- Miami Vacation rentals
- Miami Beach Vacation rentals
- Key West Vacation rentals
- Fort Lauderdale Vacation rentals
- Boca Raton Vacation rentals
- Naples Vacation rentals
- West Palm Beach Vacation rentals
- Varadero Vacation rentals
- Havana Vacation rentals
- Nassau Vacation rentals
- Sarasota Vacation rentals
- Anna Maria Island Vacation rentals
- Waterfront rentals Miami
- Waterfront rentals United States
- Waterfront rentals Miami Beach
- Waterfront rentals Florida
- Waterfront rentals Fort Lauderdale
- Waterfront rentals Monroe County
- Rentals with pools Windley Key
- Family-friendly rentals Windley Key
- Fitness-friendly rentals Windley Key
- Monthly Rentals Windley Key
- Pet-friendly rentals Windley Key
- House rentals Windley Key
- Rentals with outdoor seating Windley Key
- Rentals with beach access Windley Key
- Rentals with a patio Windley Key
- Rentals with a washer and dryer Windley Key
- 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