
Waterfront holiday rentals in Windley Key
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Top-rated waterfront rentals in Windley Key
Guests agree: these waterfront rentals are highly rated for location, cleanliness and more.

4. Cozy Waterfront Apartment in Key Largo!
Enjoy water front living in Key Largo! Watch the boats go by with fresh catch served daily at the local restaurants. See manatees, nurse sharks and fish swim by the canal all day. Dock your boat at the Pilot House Marina just down the street. Our unit is Modern, Spacious and Spotless with Private Parking, Fast Wifi, Netflix, Cold AC, Plush Pillows and a Cozy bed. We are on a main canal to open ocean. Near Rodriguez Key, Mosquito Bank, Christ of the Abyss and many sunken shipwrecks for exploring.

Florida Keys Dockside Paradise, Luxury Houseboat
Escape to the laid-back luxury of the Florida Keys aboard your own floating oasis. This fully equipped houseboat offers a unique blend of comfort, adventure, and waterfront living. Wake up to breathtaking sunrises, sip your morning coffee with all the marine life, and fall asleep to the gentle movement of the boat. Whether your celebrating something special or simply want a one of a kind getaway-it's the perfect home base for Keys adventures or peaceful retreats. An amazing experience Free park

Condo in the Keys, Peaceful ocean view retreat!
Newly renovated ocean view condo in beautiful Tavernier, FL! Ideally situated in the Upper Keys, between Miami and Key West, this condo is close to state parks and coral reefs great for diving, fishing, and snorkeling. Relax on the private beach where kayak and paddle board rentals are available. Then enjoy a stroll on the pier to the gazebo. Splash around in the beautifully renovated heated pool and hot tub with mermaid bar! You can also enjoy food and beverages in the on-site cafe and bar

Captainβs Quarters Ahoy Mateys! Florida, Keys
This is located at the Florida Keys in Key Colony, Marathon. It is a spacious two bedroom, two bathroom duplex surrounded by water. It is a renovated beauty and close to the best restaurants and the tranquility of this city. It is the perfect getaway where you can recharge your exhausted batteries. Captainβs Quarters is a clean and spacious base camp location for the many adventures that await you in this amazing location. Water views and the accessibility to the best fishing in the world.

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. β 5 STAR β Get what you pay for.

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.

Waterfront, GROUND LEVEL, Awesome Sunsets!!!
This ground level unique location is close to everything. Walk to some of the most iconic restaurants and bars Key Largo has to offer for fresh seafood and awesome drinks! We Do Not allow fishing on our Property! Dockage Available for additional fee! Enjoy the amazing sunsets over the water from your private porch and dock. John Pennekamp Coral Reef State Park close by. Walk to dolphin research center!! 28 day rental I am a licensed charter boat captain and offer discounts for all guests

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. 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.

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.

Ocean views at βSangria Sunriseβ 10% off Charters
Welcome to Sangria Sunrise at Ocean Pointe Suites in the beautiful Tavernier Key Florida. Relax and enjoy all of the options offered such as Jr. Olympic sized pool, beach, marina, kayak rentals, tennis courts, and so much more! We invite you to come stay at this cozy and updated one bedroom and one bathroom top floor condo with the most amazing ocean views. We offer a very comfortable queen sized bed and also a queen sleeper sofa that's equally as comfortable.

Turtles Nest 2 Beach, Pool, Restaurant 2bed 2bath
Turtle lovers rejoyce! Enjoy this Two Bedroom/Two Bath Condo with the perfect blend of style, comfort and convenience. Featuring a spacious living room and a fully stocked Kitchen. The Master bedroom features a King size bed and ensuite master bathroom. The guest bedroom features a Queen bed with a unattached bathroom. Both bathrooms feature a walk-in shower. The balcony offers views of the nature preserve and peek-a-boo views of the Atlantic Ocean!

SaltSpray Bungalow Oceanside, 1 bedroom
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.
Popular amenities for waterfront rentals in Windley Key
Waterfront apartment rentals

Oceanfront Bliss β’ Wall-to-Wall Water Views + Pool

Beachside Unit 22 - Private Beach on Atlantic

Ocean View 2br/2ba w/pool, bar, gym + dockage 28ft

Kawama Lagoon, 3D corner chickee 2bdr , 2 baths

Amazing Oceanview @Ocean Pointe

Hidden Gem Islamorada | 1st Floor

Panoramic Ocean Views, Ocean Pointe Condo

Ocean Pointe Condo | Beach, Pool, Hot Tub & Tennis
Waterfront house rentals

Waterfront Cozy Modern Retreat w/Deep Canal

Heart of Islamorada ~ Private Boat Slip

Islamorada Cay Home Elegant Canal home Christmas-

Large Waterfront Home, w/Efficiency, Pool, Kayaks

Luxury Boating Paradise+Pool+Sailing Kayaks

Bay Sunsets Free Kayaks/Paddleboard Jacuzzi

NEW! CASA AZUL - Golf Cart, 2 Kings, Pool, Kayaks

Waterfront House with 37 ft Dock & Cabana Club
Waterfront apartment rentals

Reel Large END Unit in Ocean Point Suites

Your Happy Place - Oceanfront

Enjoy sunsets & sunrise in your home away home.

Tequila Sunrise

2026 Jan-Feb Islamorada Sandy Sunset Beach+Pool

Waterfront Apt Key Largo #1, 10% Off 7+, 5% Off 4+

Modern and Coastal 3212 is Across from Pool

Sugar Cane - Florida Keys tropical retreat
Destinations to explore
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- Rentals with a washing machine and dryerΒ Windley Key
- Rentals with poolsΒ Windley Key
- Fitness-friendly rentalsΒ Windley Key
- Rentals with a kayakΒ Windley Key
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- Rentals with beach accessΒ Windley Key
- Rentals with outdoor seatingΒ Windley Key
- Waterfront rentalsΒ Islamorada
- Waterfront rentalsΒ Monroe County
- Waterfront rentalsΒ Florida
- Waterfront rentalsΒ United States
- Everglades National Park
- Sombrero Beach
- Zoo Miami
- John Pennekamp Coral Reef State Park
- Biscayne National Park
- Cocoa Plum Beach
- Coral Castle
- Calusa Beach & Loggerhead Beach
- Cannon Beach
- Far Beach
- Everglades Alligator Farm
- Theater of the Sea
- Deering Estate
- Conch Key
- Sea Oats Beach
- Monkey Jungle
- Horseshoe Beach
- Long Key State Park
- EAA Air Museum
- Windley Key Fossil Reef Geological State Park
- Schnebly Redland's Winery & Brewery
- Bahia Honda State Park
- Sandspur Beach
- Keys' Meads




