
Holiday rentals with outdoor seating in Windley Key
Find and book unique rentals with outdoor seating on Airbnb
Top-rated rentals with outdoor seating in Windley Key
Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.

Island Sanctuary Islamorada
Stay aboard the eco-friendly two-story 63 ft River Queen with a 360 degree view with beautiful sunrises and sets, mored 1/8 mi offshore in a quite harbor close to shopping center, movie theater, hospital, bars & restaurants. A 10-foot dinghy with small outboard to come & go from shore "ONLY", nowhere else. I also offer Personal Training, deep tissue work & Life Coach sessions. I live on the vessel about a hundred yards from you so if there are any questions, etc. I will be there to assist you.

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

Sugar Cane - Florida Keys tropical retreat
We have just completely renovated this condo at Ocean Pointe Resort and it's Insta-worthy. Every detail has been designed and considered. Sugar Cane is conveniently located near the best of the Florida Keys - close to Islamorada and Key Largo. The property boasts a large outdoor pool with a pool bar, hot tub, oceanfront beach and boardwalk, boat ramp, marina, tennis courts and children's play area. We manage Sugar Cane ourselves and live nearby so we have local knowledge and are very responsive

Seaside Vista - Ocean Front 2/1 with dockage
The Seaside Vista is a luxurious ocean front retreat located in Key Largo. Only 1 hour from Miami International Airport, we are located in the heart of the fishing and diving areas of the Florida Keys. From great dining, to water sports, to eco tours, to parasail, to museums, shopping and beaches, allow us to be your base for all of your Florida Keys activities. Freshly remodeled , enjoy our little piece of paradise...minutes from all that the Upper Keys has to offer. MC Permit #: 21302180

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.

Romantic cozy peaceful Guesthouse beach Sunsets.
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"

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!!!

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.

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.

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.

2br/1ba w heated pool, 1 mile to robbies marina
Your slice of Islamorada awaits at the Key Lime Cottage! Step inside this charming 2 bedroom cottage and you will instantly feel at home. Located in the heart of the Florida Keys yet nestled in a serene neighborhood, it offers the perfect blend of comfort and relaxation. With a full kitchen, access to a gorgeous pool shared with only 6 other homes, outside seating with grill and a fire pit, beach chairs and key lime treats - there is something for everyone!

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!
Popular amenities for outdoor seating rentals in Windley Key
House rentals with outdoor seating

Waterfront Cozy Modern Retreat w/Deep Canal

Pristine pool front home w/ocean views Anglers 148

Paradise found!Key Colony Beach,Cabana Club.

NEW! CASA PALMA - Golf Cart, 2 King-Size Beds, Pool, Kayaks

Spacious, 70ft Dock, Near Beach VACA23-16

Large Waterfront Home, w/Efficiency, Pool, Kayaks

Waterfront Home 37.5-ft dock, Cabana Club Included

Waterfront Haven House with Boat Basin & Ramp!
Apartment rentals with outdoor seating

Beachside Unit 22 - Private Beach on Atlantic

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

The HMH House

Key's Cottage Escape

Ocean Pointe Condo | Beach, Pool, Hot Tub & Tennis

Little Peace of Haven

Boho FL Keys Condo

Waterfront Studio 1| Kayaks | Pool |Bay View |Wifi
Apartment rentals with outdoor seating

Oceanfront Sunrise Condo Private Beach Heated Pool

2BR - Key Largo Sunshine Getaway

Mariner's Club 522 - Don't worry Beach Happy!

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

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

Enjoy sunsets & sunrise in your home away home.

Slip, Ramp, Pool, Trailer Parking, Bait Freezer

🏝 Oceanfront Paradise Awaits You
Destinations to explore
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- Rentals with outdoor seating Islamorada
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- Everglades National Park
- Sombrero Beach
- Zoo Miami
- John Pennekamp Coral Reef State Park
- Biscayne National Park
- Coral Castle
- Cocoa Plum Beach
- Calusa Beach & Loggerhead Beach
- Cannon Beach
- Conch Key
- Theater of the Sea
- Monkey Jungle
- Deering Estate
- Far Beach
- Sea Oats Beach
- Everglades Alligator Farm
- Horseshoe Beach
- Long Key State Park
- EAA Air Museum
- Windley Key Fossil Reef Geological State Park
- Schnebly Redland's Winery & Brewery
- Sandspur Beach
- Bahia Honda State Park
- Keys' Meads




