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Pet-friendly vacation rentals in Windley Key

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Windley Key

Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite
Houseboat in Islamorada Tavernier
4.89 out of 5 average rating, 245 reviews

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

Guest favorite
A serene sunset view showcases a circle of white Adirondack chairs positioned around a fire pit. The calm waters reflect vibrant hues of orange and purple from the sky, creating a peaceful atmosphere.
Townhouse in Key Largo
4.87 out of 5 average rating, 150 reviews

Sunrise Escape - Ocean Front Villa - Sleeps 10

Enjoy the sunrise while sitting on one of two terraces and sipping your morning coffee in the exclusive part of Kawama Yacht Club overlooking the Marina and Ocean. Enjoy the many choices for the day: Kayaking/paddle boarding just 20 steps from your door, walking to the south beach just 100 yards away, or walking to the beach jetty just across the marina. Or take a swim/snorkel in our swimmable lagoon or one of our two pools. Then bring a glass of wine to watch the breathtaking sunsets from our o

Superhost
A collage showcases four images: A serene sunrise over water, a cozy bedroom with a flat-screen TV, an open-concept living area with a kitchen and dining space, and a tranquil view of the evening sun reflected on the bay, complete with a kayak along the shoreline.
Home in Key Largo
4.9 out of 5 average rating, 165 reviews

Tiny Home on Waterfront | Bay Views | Deck | Pool

Down by the waters of Manatee Bay, you’ll find this idyllic tiny home for 6. With a full kitchen, three comfy beds,and access to a community pool, this is a prime location to enjoy the best of Key Largo. Sit on the deck and dip your toes in the water or explore the bay using the available kayaks and paddle boards. 10 Min Drive to the Gilbert’s Resort 15 Min Drive to John Pennekamp Coral Reef State Park 22 Min Drive to African Queen Canal Cruise Experience Key Largo With Us & Learn More Below!

A modern kitchen features white cabinetry and stainless steel appliances. A wooden cutting board is placed on the counter, complemented by cooking utensils. Soft lighting illuminates the space, enhancing the clean and functional design. A window with shutters allows natural light to enter.
Condo in Key Largo
4.92 out of 5 average rating, 123 reviews

Gorgeous lagoon-front 2BR Townhouse with 2 pools

Kawama Yacht Club is situated between an extension of John Pennekamp Coral Reef State Park and a salt-water, filtered, tidal snorkeling lagoon! Two pools, tennis courts, private beach, a waterfront (lagoon) will keep you busy on site, while the neighborhood offers boating, many great restaurants and you may even swim with dolphins just outside the gates to the community. The townhouse comes equipped with two bicycles and two kayaks. All brand new appliances throughout + extra lg washer/dryer.

Top guest favorite
A serene view of a canal populated by several pelicans floating on the water's surface. Palm trees line the shore, and colorful houses are visible in the background. A boat is docked nearby, enhancing the peaceful coastal scene.
Home in Key Colony Beach
4.98 out of 5 average rating, 113 reviews

Waterfront House with 37 ft Dock & Cabana Club

Right in the middle of the action between Miami and Key West. This 2/2 house has been nicely renovated and furnished with new stainless kitchen appliances and a gorgeous granite countertop. Comfortable outside/inside living space perfect for a getaway in paradise. Walk out to the porch and backyard, and you will be engulfed by the beauty of the sunset views while lying on the cozy hammock. It features lots of outdoor entertaining: fishing, paddling, BBQ or just plain hanging out in the shade.

Guest favorite
A cozy living area features a light-colored sofa with decorative pillows, complemented by a coffee table and a patterned area rug. Expansive glass sliding doors provide natural light and views of palm trees outside, while a small dining table adds functionality to the space.
Apartment in Key Largo
4.89 out of 5 average rating, 299 reviews

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

Guest favorite
A charming cabin is nestled among lush greenery, featuring a cozy porch with comfortable seating. The pathway is lined with vibrant tropical plants and palms, creating a serene and inviting entrance. Sunlight filters through the canopy, illuminating the peaceful surroundings.
Guesthouse in Key Largo
4.87 out of 5 average rating, 460 reviews

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"

Top guest favorite
The living area features a comfortable light blue sofa and a glass-top coffee table, complemented by tropical-themed decor. A ceiling fan circulates air above, while a kitchen bar with high chairs is visible in the background. Natural light enters through multiple windows, enhancing the welcoming atmosphere.
Home in Islamorada
4.97 out of 5 average rating, 200 reviews

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.

Top guest favorite
A paved outdoor patio features two lounge chairs and a small round table, surrounded by tropical plants and palms. The tranquil canal is visible in the background, offering a serene waterfront view.
Home in Key Colony Beach
4.95 out of 5 average rating, 126 reviews

Waterfront Home 37.5-ft dock, Cabana Club Included

Bright, Open Floor Plan with new floors & kitchen. East facing for sunny mornings and shady afternoons on the great screened porch. Two roomy bedrooms and 2 full baths. Plenty of parking on the paved driveway. Perfectly located with the boater and angler in mind on a 37. 5 ft concrete dock, on deep & wide canal. Here on Key Colony Beach you can walk or bike the entire city to the marina, Sunset Park, 3 restaurants, play golf, tennis, pickle ball, bocce ball, horseshoes & basketball.

Guest favorite
Three modern Aqua Lodges are positioned on water, featuring white exteriors and blue roofs. Each lodge has a furnished deck with chairs, providing relaxed seating options. A smooth, concrete path runs alongside the lodges, leading to a marina setting with sailboats in the background.
Villa in Marathon
4.9 out of 5 average rating, 377 reviews

New Aqua Lodge 2Beds 1 Bath with Full Kitchens

This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!

Guest favorite
The image captures a serene night view of a canal lined with thatched-roof structures. The still water reflects the moonlight and surrounding greenery, creating a peaceful atmosphere. A boat is seen in the foreground, offering a vantage point over the tranquil scene.
Camper/RV in Key Largo
4.93 out of 5 average rating, 120 reviews

Paradise in Key Largo, FL

Enjoy your vacation in this brand new recreational vehicle with great taste in interior design. This unit has an extended air-conditioned porch with a full kitchen and living room This amazing unit accommodates a total of 6 guests with 2 bedrooms with queen sized memory foam mattress in each bedroom and a sofa bed if required. Lot 170 is one of the largest lots in Key Largo Kampground and is located very close to the pool with nature at this unforgettable escape.

Guest favorite
Condo in Key Largo
4.85 out of 5 average rating, 110 reviews

Lagoon View Free Kayaks Pool Playground Pickle Bal

Two story condo just steps away from one of the two pools and salt water lagoon. Enjoy the fishing/sunrise/sunset at the jetty/pier, a 3-acre salt-water lagoon for swimming, snorkeling, kayaking, paddle boarding, 2 tennis/pickle ball courts and a children's playground. Primary Bedroom - Queen Bed (2 people) 2nd Bedroom - Queen Bed (2 people) 2 Full bathrooms WIFI Basic Cable TV BBQ Grill Pack N Play Ideal for 4 Adults

Popular amenities for Windley Key pet-friendly home rentals

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Islamorada
  6. Windley Key
  7. Pet-friendly rentals