Vacation rentals in Windley Key

A sandy beach area is lined with turquoise lounge chairs, oriented towards sparkling waters. Tall palm trees provide shade in parts, while a wooden pier extends into the ocean on the right. The bright sun adds warmth to the tranquil scene.

4.94 out of 5 average rating, 146 reviews

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

Welcome to our remodeled costal 1BR 1 Bath condo nestled in the premier oceanfront complex in Tavernier, FL. Escape to paradise and enjoy the wonderful Ocean views from the private balcony while just a few steps away from the sunny private beach, marina, minutes away from restaurants, shops, and attractions. ✔ Comfortable Queen BR ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Balcony ✔ Smart TVs/WI FI ✔ Complex Amenities (Pool, Hot Tub, Marina, BBQ, Sports, Free Parking) Learn more below!

The image features a sandy beach area bordered by turquoise waters under a bright sky. Lounge chairs are arranged in neat rows on the beach, with palm trees providing shade. A wooden pier extends into the sea, while gentle waves lap against the shore.

4.95 out of 5 average rating, 190 reviews

Tiki Time! Ocean Pointe Top Floor King 1 Br/1Ba

Stay at our tropical hideaway rated one the “Coolest Airbnb’s in the Keys” by Trips to Discover! Our romantic condominium (sleeps 4) is located at the gated Ocean Pointe resort in the nature isle of Tavernier. You'll love the colorful mid-century modern decor that reflects the shades of this Keys paradise in the American Caribbean. With 60+ pristine acres, Ocean Pointe is the perfect blend of natural beauty and modern-day luxury and convenience for a great couples or small family getaway .

4.97 out of 5 average rating, 145 reviews

A serene outdoor space features a dining table with comfortable green cushions, set against a backdrop of the sunset over the water. Two chaise lounges and a hammock are visible, alongside palm trees, creating a relaxed atmosphere by the waterfront.

Tiny home in Key Largo

Oceanfront Lookout Point w/two Kayaks & Deck

Lookout Point is Wide open breathtaking Water View , Amazing Sunrises with a cup of Morning coffee, Refreshing breeze, Sound of water and Rustle of palm trees will start your day… Fishing right from the property, Kayaking. Taking sunbath on Chaise lounges or Reading books or just sitting under Tiki having a nice conversations and enjoying beautiful scenery of the view. You will see fishes jumping out of water, seagulls trying to catch up it , you might see manatee swimming by or dolphins.

4.87 out of 5 average rating, 443 reviews

Two wooden lounge chairs, positioned under a large red umbrella, face a serene body of water. A wooden dock extends into the bay, with a colorful sunset reflecting off the water's surface in the background.

Guesthouse in Key Largo

Romantic Cabin/Guesthouse, beach Sunsets, fishing.

Private Romantic Bayside Cabin/Guesthouse, peaceful settings, lovely sunsets, beach, fishing pier, lush gardens surrounded by nature and wildlife, birds, iguanas, manatees, dolphin’s, eagles, the beach is just a short walk away from the Guesthouse enjoying a cocktail, fishing, boats cruising by, kayaking, snorkeling or an amazing sunset. *This Guesthouse is on bayside not Bayfront ! Same property but private from the residence! "No pets, Airbnb-granted pets Exemption cus allergies reasons"

4.99 out of 5 average rating, 182 reviews

A wide balcony overlooks a serene harbor, featuring several boats docked in the water. Two tall chairs are positioned against the railing, offering a view of the vibrant blue sky and surrounding marina.

Home in Key Largo

Waterfront Sunsets, Great Price, Relaxing Spot!!!

Beautiful Waterfront, Modern Coastal Décor, Spacious !! Enjoy your vacation in this beautiful recently renovated home. Views from almost every window and door of the harbor. Walk to many local restaurants and bars for fresh local seafood and a cold draft beer!! Enjoy the sunsets from your private porch. Easy access to Atlantic Ocean. We Do Not Allow Fishing on our Property! 28 day I am a licensed charter captain and offer discounts to guests! Fishing, Sandbar or a Sunset Cruise!!!

Superhost

A modern houseboat is anchored on calm waters during sunset. The structure features large windows and a spacious front deck with a grill station. The warm glow of the setting sun illuminates the exterior, reflecting off the water, creating a serene atmosphere.

Boat in Marathon

4.8 out of 5 average rating, 270 reviews

Paradise awaits on this cozy houseboat!

Our vision is for you to kick back, relax, and find your home away from home! Wether you want to celebrate with your loved one or retreat by yourself this floating home offers comfortable space for 2 adults. Located near the 7 mile bridge in Marathon Florida on the Atlantic Ocean nestled in a quiet, reserved mangrove area. This spot is fantastic because you have unparalleled access to out of this world sunset/sunrise views. Kayak through the mangrove and explore the surrounding areas.

4.97 out of 5 average rating, 192 reviews

A vibrant garden area features colorful picnic tables and chairs arranged under lush greenery. A winding stone pathway leads through the space, surrounded by tropical plants and flowers. The lively atmosphere is enhanced by decorative lighting elements hanging nearby.

Home in Islamorada

Flakey's

Flakeys, short for Florida Keys is everything you would expect to find on the small Caribbean island. Its paradise! Located in the heart of Islamorada there is no need for a car. You can walk or bike to the best restaurants, bars, beaches and shops this island has to offer. On Morada Way in the middle of the Art and Culture district. Everything at Flakeys is brand NEW! All new appliances, furniture and decor. Shabby Island Chic! Affordable, super clean and you can't beat the location.

4.93 out of 5 average rating, 133 reviews

A vibrant dock area is shown with lined jet skis ready for rental. A thatched-roof building offers shaded seating with colorful umbrellas. Lush palm trees sway gently in the backdrop, enhancing the waterfront experience under a clear blue sky.

Guesthouse in Key Largo

Seaside Bungalow

Very private entire Cottage brand new walking distance to world famous Tiki Bar jet ski rentals kayaks Extremely private surrounded by exotic flowers and orchids.Less than 2 miles from Baker's Cay and close to the Key Largo and Islamorada wedding venues. We have a fully stocked home size kitchen. All the condiments coffee creamers sugar ketchup mustard etc. Giant stone shower with shampoos and conditioner and plenty of plush towels. Beach towels and chairs as well as 2 bicycles.

4.96 out of 5 average rating, 139 reviews

Ocean View Corner Penthouse Ocean Pointe 5416

Coastal decor greets you in this serene Penthouse unit with all around views of the Atlantic ocean. This end unit is located in fabulous Ocean Pointe Suites, complete with small beach, pier, marina, large pool, jacuzzi, tennis and pickle ball court and even basket ball hoop. This unit is smack dab in the middle between Key Largo and Islamorada in the Florida Keys. Very close to amazing waterfront dining, snorkeling, diving, fishing, paddle boarding and kayaking. Must stay to believe!

4.93 out of 5 average rating, 349 reviews

A houseboat is anchored in calm waters, surrounded by lush greenery under a soft sunlit sky. The vessel features a roof deck and a solar panel, reflecting a commitment to sustainable living. Gentle ripples on the water create a serene atmosphere.

Boat in Islamorada

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.

4.96 out of 5 average rating, 133 reviews

A sunset view is captured from a covered outdoor seating area, showcasing a tranquil waterway. Silhouettes of kayaks and a table are visible, while the setting sun creates a warm glow across the horizon. Natural textures are evident in the thatched roof above.

Tiny home in Key Largo

Oasis2 in Key Largo With a million dollar view

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, And most importantly a super comfortable queen size bed, There is also a community pool for your enjoyment The property is located on a residential island, restaurants, bars, stores and grocery stores are within a 15 minute drive from the property.

Superhost

The exterior view of the bungalow showcases a light-colored façade with white trim. Two wooden steamer chairs sit invitingly on a concrete porch, alongside a decorative potted plant. A turquoise door adds a pop of color, complemented by large windows adorned with shutters.

Guesthouse in Key Largo

4.89 out of 5 average rating, 252 reviews

Oceanside, 1 bedroom, Bungalow in Key Largo

Canal front bungalow with beautiful views of the ocean. Private water front and pergola with steamer chairs and hammock. BBQ your fresh catch while lounging on the back porch, relaxing in the tropical landscape. One bedroom with Queen bed. Queen size pull-out couch in the living-room. Full kitchen boasting high-end appliances. One Car Parking by unit. Centrally located between shopping centers and destination activities.

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Popular amenities for Windley Key vacation rentals

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Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Windley Key

5 out of 5 average rating, 34 reviews

A shaded pavilion with a white, peaked roof offers a view of the ocean through tall palm trees. Lush greenery surrounds the area, and lounge chairs are visible in the distance, inviting relaxation near the beach.

Villa in Islamorada

Anglers Reef Islamorada

DeborahRating, 5 stars1 month ago

We had never been to the Keys before and were not sure where to stay. Islamorada ended up being an excellent choice. There was a great variety of activities nearby, and within a 30-45 minute drive there were even more unique places to visit. The private community where Gina's house is located feels like a mini-resort that The Mouse would be proud of. The community was clean, the staff were extremely friendly, and the other people we met were all gracious. Gina's house was well located - close to the entrance and a 1-minute walk to the pool. The house was super clean, comfortable, and the few things we had questions about were immediately dealt with by Gina. We're considering another trip to the Keys and would not hesitate to stay here again or recommend it to another group.

A sandy beach area is seen, featuring lounge chairs arranged under palm trees and a straw thatched gazebo. A volleyball net stands nearby, with a view of the water and a dock visible in the distance.

Apartment in Tavernier

5 out of 5 average rating, 4 reviews

Superb Ocean View w/heated pool, beach, tennis

JustinRating, 5 stars2 months ago

Great location. It felt very quiet and peaceful. We didn't have the best weather so we didn't get to enjoy all the amenities of the property but it felt walkable.

An open living area features a modern kitchen with blue cabinetry and a patterned backsplash. A round dining table is set nearby, accompanied by four chairs. A comfortable sofa faces a wall-mounted television. Natural light enters through large windows adorned with blue floral curtains.

Apartment in Islamorada

4.78 out of 5 average rating, 46 reviews

Poolside 2 queen Apartment

ElizabethRating, 5 stars1 week ago

We had a great time at Breezy Palms with just me and my daughter! The poolside apartment was so squeaky clean, tidy, and just lovely. The bed was very comfortable. We had everything we needed. We will definitely be back with the entire family.

The entrance features a set of white double doors leading into the villa, framed by yellow siding. A covered porch with several chairs sits to the side, while a charcoal grill is positioned adjacent to the porch, surrounded by greenery.

Home in Islamorada

4.93 out of 5 average rating, 27 reviews

Islamorada 131 Anglers Reef Ocean Community 2/2.5

JaredRating, 5 stars2 months ago

We really enjoyed our stay at 131 Anglers Reef. The neighborhood was quiet and beautiful, and the community pool was a great bonus. The house itself was clean, well-maintained, and spacious enough for our family. During our stay, we rented a boat for the day from A1 Watersports — definitely one of the highlights of our trip! We also took a day trip to Key West and visited Fort Zachary Taylor State Park. The beach there was perfect for snorkeling and offered a fun change of scenery. Founders Park was just down the road. It’s a fantastic beach for all ages, especially for families with small kids.

5 out of 5 average rating, 20 reviews

Home in Key Largo

Oceanside Paradise - Pool, HotTub, Kayaks, Pets OK

HannahRating, 5 stars2 weeks ago

Awesome modern home in a little, upcoming community. Pool was great place to relax. If you're up early enough to catch the sunrise they are breathtaking! You might spot a small nurse shark or tarpon in the water!

5 out of 5 average rating, 9 reviews

A spacious outdoor patio features comfortable seating areas overlooking the ocean. Bright blue waters extend into the distance, while a pool and lush greenery are visible below. The serene atmosphere is enhanced by the clear sky and ample natural light.

Townhouse in Islamorada

NEW Oceanfront, Gameroom, Dockage - Paradise Palms

AndreaRating, 5 stars6 days ago

This house was so comfortable and accommodating! The weather was bad the first 4 days of our trip and it was so nice to have the game room to keep us entertained! Everything you need and more!

A wide view of the sandy beach reveals several colorful umbrellas and lounge chairs arranged under palm trees, alongside Tiki huts offering shade. The clear blue ocean extends to the horizon under a partly cloudy sky, enhancing the peaceful beachfront setting.

5 out of 5 average rating, 5 reviews

Oceanfront 2 bdrm, 2 bath, View, Pool, Islamorada

MichalRating, 5 stars6 months ago

We stayed here for the Thanksgiving week. The place was nice, clean, and quiet. My kids enjoyed the playroom and the pool. The condo had plenty of board games to keep the kids entertained. The Keys have lots to offer, so there is always plenty to do. Donna was very responsive, the check-in was very simple, and we had a great time. Thank you for hosting us.