
Beachfront vacation rentals in Windley Key
Find and book unique beachfront homes on Airbnb
Top-rated beachfront rentals in Windley Key
Guests agree: these beachfront homes are highly rated for location, cleanliness, and more.

Best View Ocean Pointe Pool Beach King Bed, Gated
***IMPORTANT*** The pictures you see here are of OUR unit. What you see is what YOU GET. No surprise when you arrive at Ocean Pointe. NO bait and switch. We own in the Prominent Building #3 just steps from the Pool & Jacuzzi. Wireless Internet Netflix & Cable TV, XBOX ONE. ***Most of our guests (99%) claim this is the cleanest Airbnb they have ever stayed in.*** You will get a TRUE UNIMPEDED OCEAN VIEW in our unit. Read our reviews, our past guests tell it all. ⭐ 5 STAR ⭐ Get what you pay for.
4.97 out of 5 average rating, 234 reviews
NEW luxury RV, Marina, 6 beds&1.5 baths, 2 pools!
This hidden gem is anything but ordinary!!! Come enjoy a piece of paradise in Key Largo while you relax in this spacious NEW luxury RV. It has a BOAT RAMP, indoor/outdoor kitchen with a TV, outdoor speakers, 2 hammock chairs, outdoor sofa, outdoor dining, separate bedrooms including a bunk room that can sleep 5-6, 1.5 baths, 2 heated pools, 2 beaches, volleyball court, playground, & shuffleboard. There are so many outdoor activities to enjoy right at the Kampground, you'll never want to leave!
4.96 out of 5 average rating, 306 reviews
Amazing Ocean Front Views Key Colony Beach
Everything is brand new in this gorgeous condo with amazing oceanfront views. #40 has two queen beds, well equipped kitchen with full-size appliances and everything you need to cook & serve meals. Fast, reliable WiFi, large SmartTV. Super cold new A/C unit Enjoy stunning views of sunrise from your private balcony & sunsets next door at Sunset Park. Heated pool, beach BBQs & tiki huts for guest use We are centrally located to awesome Keys adventures just a few miles drive from the condo.
4.96 out of 5 average rating, 285 reviews
2 bedroom & 25' Boat Dock Waterfront Atlantic Side
ACTUAL LOCATION: within KeyLargoKampground.com Gated Community Lot #66 with BOAT DOCK for 25' OUTSIDE: ~ Large deck/ dock, Grill, Swim Ladder, tiki hut with swing and dining and Pub table. Parking for 1 truck & 1 car. ~ steps from the cottage Dock out back in 30' deep 100' wide Deep water swim canal with tropical fish along the banks, occasional Manatee, tarpon and finger mullet in cooler months. Maybe a porpoise. Kayack, board or Fish off dock. Walk to moon lit beaches in the park.
4.93 out of 5 average rating, 104 reviews
Kawama Yacht Club and Molasses Reef Marine
Vacation in paradise. Beautiful sunsets. Swim at the salt water lagoon or at the beach plus two pools. Our villa is fully equipped, 3 bedrooms wish tv and 3 full baths First floor: garage, 1 bedroom, full bathroom, game room, pool table, bar, family room with TV, and terrace with barbecue and swing. Second floor 2 bedrooms and 2 full bathrooms, fully equipped kitchen and living a big TV, outside balcony with outdoor furniture . Tennis courts available. Optional 24' ft boat slip available.
4.93 out of 5 average rating, 126 reviews
🏝 Oceanfront Paradise Awaits You
Bring your boat to next vacation in tropical paradise surrounded by mangrove forest, coconut trees and the pristine turquoise waters. Welcome to the most visited resort in the beautiful Florida Keys. Ocean Pointe is one of the most luxurious resorts in Tavernier, Florida Keys. The resort offers a private sandy beach, heated swimming pool, jacuzzi, tennis courts, restaurant, bar, marina with boat ramp and dockage, boat & trailer storage, and more - all situated on 60 lush tropical acres.
4.85 out of 5 average rating, 126 reviews
My Little Oasis2 Waterfront Retreat, Key Largo
Million Dollar view at a fraction of the price! This property is on the water with amazing bay views. It includes one kayak for 2 people, paddle board, fishing rod, washer and dryer, kitchen with all cooking utensils. Note: The upstairs room is not comfortable for seniors or adults, the ceiling height is 4 feet (an adult has to walk on his knees). The property is located on a residential island, restaurants, bars, stores and grocery stores are within a 15 minute drive from the property.
4.97 out of 5 average rating, 236 reviews
Tropical Getaway
This light, airy two bedroom condo is located in the community of Kawama. Overlooks a small lake, where people swim, kayak and paddleboard. The condo community features two pools, tennis courts, playground, fishing, beach and marina. A long jetty extends out in the ocean where you can watch the beautiful sunrises or sunsets in the afternoons. Centrally located in Key Largo near restaurants, shopping and attractions. Come down and enjoy the peaceful atmosphere of our tropical area.
4.9 out of 5 average rating, 197 reviews
Vibrant Beachfront Villa
Welcome to Beachfront Villa that has recently been renovated. The 2 bedroom 1.5 bath luxury villa is located in the popular area of Duck key alongside of Hawks Cay Resort. Duck Key marina is located across the street where you can dock your boat or charter a boat for the day. Enjoy stunning sunset views from the back porch. Kitchen includes all amenities including silverware ,plates , cups , and pots. Linens and towels provided. *** Pets welcome with host approval and pet fee. ****
4.81 out of 5 average rating, 238 reviews
360 DEGREE WATERVIEW HOUSEBOAT
IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.
4.93 out of 5 average rating, 394 reviews
Turtle Nest 1 Private beach,Pool, 2bed 2bath
Ocean Pointe Suite is located on the Atlantic. Featuring ocean views from living room, master bedroom and balconies. King bed in master bedroom, Queen bed in guest bedroom, pull out queen sofa, 2 bathrooms, Smart TV's with cable WIFI. Completely stocked kitchen with all appliances. Amenities include heated swimming pool, private beach, marina with boat launch & dockage for extra fee book through marine info in pictures. Tennis courts, gazebo, located on 60 tropical acres.
4.91 out of 5 average rating, 144 reviews
Oceanfront Resort W/Indoor Pickleball - Speakeasy!
An island paradise situated in the heart of Key Largo, adjacent to John Pennekamp Coral Reef State Park and Molasses Reef. The property is located in Key Largo's most upscale oceanfront community. The area has the distinction of being Key Largo's newest oceanfront gated destination, with some of the most unique amenities in all of the keys. It caters to those who simple desire the very best in luxury accommodations. Unique amenities include a Speakeasy Themed Rec. Area.
4.82 out of 5 average rating, 126 reviewsPopular amenities for Windley Key beachfront rentals
Pet-friendly beachfront home rentals

Houseboat Getaway In Marathon
4.87 out of 5 average rating, 142 reviews
Relaxing Town home with great water views
4.89 out of 5 average rating, 143 reviews
Villa 5027 on Duck Key BOAT SLIP available
4.88 out of 5 average rating, 120 reviews
Sunset Catch Gulf Front, Pool, Dock, Kayaks, Fish
4.92 out of 5 average rating, 49 reviews
Deckhouse
4.78 out of 5 average rating, 86 reviews
Luna Light ~ Waterfront ~ Pool ~ Dock ~ Views!
4.96 out of 5 average rating, 26 reviews
SeaEsta! Bring your boat & 1 block to the beach!
4.88 out of 5 average rating, 16 reviews
Boaters delight! 1 min to open water, Dock & Beach
4.92 out of 5 average rating, 24 reviewsBeachfront home rentals with a pool

NEW! Casa Azul - Golf Cart, 2 King, Pool, Kayaks
4.89 out of 5 average rating, 119 reviews
2BR - Key Largo Sunshine Getaway
4.88 out of 5 average rating, 181 reviews
Beachside Unit 33-Private Tropical Beach Plus Pool
4.88 out of 5 average rating, 168 reviews
Closest Oceanfront Home - 3 Stories and Boat Dock
5.0 out of 5 average rating, 23 reviews
Exceptional vaca in Angler's Reef Islamorada
5.0 out of 5 average rating, 28 reviews
5-Star Sandy Beach Sunsets & Pool in Best Location
5.0 out of 5 average rating, 19 reviews
The Villa by the Bay Pool/Boat Dock, Islamorada Fl
5.0 out of 5 average rating, 12 reviews
Islamorada Oceanfront 2 bdrm, 2 bath, View, Pool
4.89 out of 5 average rating, 19 reviewsPrivate beachfront home rentals

Treetops Apt.Sleep1-4 Beach Steps Away
4.54 out of 5 average rating, 628 reviews
*New* Turtles Pace-Private Beach
5.0 out of 5 average rating, 23 reviews
Key Largo Tiny House, Marina, Beach + Pool Access
5.0 out of 5 average rating, 8 reviews
*NEW* Private Beach, pool & fully loaded kitchen
4.93 out of 5 average rating, 41 reviews
Private Beach in Marathons Key Colony Beach
5.0 out of 5 average rating, 29 reviews
Grouper Getaway @ Ocean Isles Fishing Village
4.99 out of 5 average rating, 76 reviews
2 Bdrm Oceanfront Complex Private Beach & Pool
4.93 out of 5 average rating, 41 reviews
Bayside view Cottage , Free kayaks and sailboat
4.77 out of 5 average rating, 13 reviewsDestinations to explore
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- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Biscayne National Park
- Schnebly Redland's Winery & Brewery
- Homestead-Miami Speedway
- Coral Castle
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