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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

A spacious houseboat is illuminated at night, surrounded by gently swaying palm trees adorned with soft yellow lighting. The deck features a modern outdoor seating area, complemented by vibrant red umbrellas. Nearby boats are moored in the marina, contributing to the serene waterfront atmosphere.

Houseboat in Tavernier

4.89 out of 5 average rating, 237 reviews

Florida Keys Luxury Houseboat on the water WiFi

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

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

4.85 out of 5 average rating, 137 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

A bright and airy hallway features a set of modern drawers for convenient storage. Light wood flooring runs throughout the space, leading towards an open area with visible kitchen appliances. Natural light streams in from large windows at the end of the hall, enhancing the inviting ambiance.

Home in Key Largo

4.94 out of 5 average rating, 148 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!

Top guest favorite

The exterior of the cottage features a vibrant mural adorned with large floral designs, complemented by a light blue roof and shutters. Surrounded by lush greenery, the property sits on a textured gravel area under a clear blue sky.

Cottage in Islamorada

4.95 out of 5 average rating, 41 reviews

Waterfront Cottage Walk to World Famous Lorelei

Waterfront Conch Cottage with Dockage. Short walk to world famous Lorelei for sunset celebrations. Great location for kayaking & paddleboarding. Custom length of stays can be arranged if booking a sandbar/fishing charter with our family. The fishing cottage built in the 1940s is not fancy, as photos show, but in the heart of Islamorada! Dockage available for additional $50 per night fee not included in nightly rate. Free trailer storage on site. Pet friendly :) 1 pet under 20 lb $150 fee.

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

4.94 out of 5 average rating, 108 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.

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

4.88 out of 5 average rating, 281 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

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, 192 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.

A waterfront property is surrounded by lush palm trees, with a gravel area leading to a private dock. The home is painted in soft blue tones, reflecting a comfortable coastal vibe. The expansive water views offer shimmering reflections under the clear sky.

Cottage in Little Torch Key

4.9 out of 5 average rating, 167 reviews

Waterfront Cozy Cottage with Boat Ramp & Dock!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with 250 foot dock, ramp, and basin for your boat. It's a must-see rustic outdoor environment and fishery experience, very typical in the Keys! The property lot is almost an acre with a work section and still very spacious. Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the dock and enjoy the underwater scenery!

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, 116 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.

A shaded outdoor porch features four blue adirondack chairs arranged around a round table, overlooking tranquil water views. The surrounding area is adorned with lush greenery and distant views of a bridge, creating a serene space for relaxation.

Townhouse in Duck Key

4.84 out of 5 average rating, 176 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. ****

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

4.91 out of 5 average rating, 320 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!

A waterfront view is captured, featuring a wooden table surrounded by several chairs under the shade of palm trees. The serene water reflects the clear blue sky, and a dock is visible in the background, enhancing the tropical atmosphere.

Home in Key Largo

4.91 out of 5 average rating, 107 reviews

Sunsets In Palms Paradise

Vacation Rental Permit #19300755 Enjoy one acre of privacy and coconut palms galore! Features include spectacular sunsets & dolphins for neighbors! While relaxing by the waterfront, you can watch pelicans, herons, wild dolphins, manatees and Ibis gliding by. Fish, kayak, & swim from the dock & basin. Bring a boat to access the Keys by water. Sunsets in Palms’ Paradise is a waterfront Keys home where you can spend quality time with your family/friends.

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Popular amenities for Windley Key pet-friendly home rentals

Free parking on premises

Air conditioning

Pet-friendly house rentals

A bright living area showcases a comfortable leather sofa, paired with a circular coffee table. Natural light is welcomed through large glass doors that lead to an outdoor space. A television is mounted on the wall, enhancing the welcoming ambiance of the room.

Home in Key Largo

4.84 out of 5 average rating, 44 reviews

Casa Largo

The outdoor area features a heated pool surrounded by tropical landscaping, with a thatched-roof gazebo and a gentle curve in the pool's design. An American flag waves in the background, while the two-story residence is illuminated, highlighting the inviting atmosphere.

Home in Key Largo

4.93 out of 5 average rating, 29 reviews

Island Breeze

The image captures a sandy beach scene with clear turquoise waters. Sunbathers and beachgoers are seen enjoying the sun on the shore, while lush palm trees line the beach. A beachfront villa is visible in the background, enhancing the coastal setting.

Home in Marathon

4.91 out of 5 average rating, 179 reviews

Beachfront Villa - Florida Keys

A two-story home is set along a deep canal, featuring wooden decks that overlook the water. Lush palm trees and shrubbery frame the property, while a swimming pool and a boat can be seen nearby, enhancing the serene waterfront setting.

Home in Islamorada

4.86 out of 5 average rating, 7 reviews

Venetian Tropics private heated pool at 82 degrees

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, 105 reviews

Waterfront House with 37 ft Dock & Cabana Club

Two outdoor sun loungers are positioned on a concrete patio, facing a tranquil waterfront scene. A stunning sunset casts warm hues over the water, with boats visible in the distance. Wooden pilings line the dock, enhancing the idyllic setting.

Home in Key Colony Beach

4.94 out of 5 average rating, 33 reviews

Water, Water Everywhere! "The Wheel House"

A private wooden dock extends over calm waters, featuring a boat with a blue canopy and a small table with colorful umbrellas nearby. Palm trees line the waterfront, and a series of pastel-colored homes are visible across the canal, creating a serene setting.

Home in Marathon

5 out of 5 average rating, 114 reviews

Waterfront Oceanside, 60 Ft Dock, As seen on HGTV

A serene view of the lagoon reflecting the blue sky and clouds. Boats are docked along the wooden slips, with a glimpse of the townhome complex visible in the background. Palm trees gently sway along the water's edge, enhancing the tranquil setting.

Home in Key Largo

5 out of 5 average rating, 3 reviews

Beautiful Lagoon Front Townhome!

Pet-friendly home rentals with a pool

An aerial view reveals a modern house with a light blue exterior and a metal roof. A private pool is situated in the backyard, surrounded by lush greenery and lounge chairs. The property is enclosed with wooden fencing, providing a secluded outdoor space.

Home in Marathon

4.97 out of 5 average rating, 68 reviews

Sombrero beach oasis,great location,many amenities

Apartment in Key Largo

4.86 out of 5 average rating, 29 reviews

Overlooking Marina/Ocean view & FREE GOLF CART

Top guest favorite

A fenced outdoor area features a covered porch with seating options, including two teal chairs. The porch leads to a spacious, paved surface, with the home visible in the background. An American flag is proudly displayed, adding to the welcoming atmosphere.

Camper/RV in Key Largo

5 out of 5 average rating, 33 reviews

Anchor Inn (Calusa Campground Resort & Marina)

A sandy shoreline is bordered by swaying palm trees, providing a peaceful oceanfront view. A yellow kayak rests on the beach, while a hammock is visible nearby, adding to the tranquil setting. The distant jetty extends into the calm sea, enhancing the serene atmosphere.

Guesthouse in Marathon

4.95 out of 5 average rating, 21 reviews

The Pink Dolphin House.

Townhouse in Key Largo

4.91 out of 5 average rating, 90 reviews

5 O'clock Somewhere - Key Largo

Top guest favorite

A private heated pool is surrounded by a spacious patio with laid brick flooring. Palm trees frame the scene, while a vibrant sunset casts warm colors across the sky. Lounge chairs are positioned by the pool, inviting relaxation by the serene water view.

Villa in Marathon

4.95 out of 5 average rating, 139 reviews

Private 4/3 Pool Heater/Dock/Kayaks/Bikes,etc

Three colorful adirondack chairs—one red, one yellow, and one green—are positioned on a sandy beach under palm trees. The calm blue water extends towards the horizon, while a rocky wall forms a subtle boundary in the background.

Home in Marathon

4.9 out of 5 average rating, 31 reviews

Oasis in The Keys-Kayaks-Paddle Boards-Cabana Club

A private outdoor space features a heated pool surrounded by lounge chairs on a grassy area. Tropical palm trees provide shade, and the house displays large windows that allow natural light. An inviting patio area is visible, enhancing outdoor relaxation.

Home in Marathon

4.96 out of 5 average rating, 52 reviews

Waterfront Private Home w/Pool-Family&Pet Friendly

Private, pet-friendly home rentals

A serene waterfront scene is depicted, featuring paddle boards laid along a grassy area beside a concrete pathway. Palm trees and a sunset over the water contribute to the natural beauty, while boats are visible in a nearby dock.

Villa in Islamorada

5 out of 5 average rating, 3 reviews

The Nest Villa & Marina in the heart of Islamorada

An aerial view captures a curvilinear pool surrounded by palm trees and lounge chairs. The surrounding landscape features pathways and landscaped areas, enhancing the serene atmosphere of the resort. The pool area is complemented by a light-colored deck and nearby structures.

Villa in Key Largo

4.9 out of 5 average rating, 20 reviews

Lux Villa for Spring Break: Pool, Kayak & Marriott

A covered balcony offers ocean views and features a stylish, woven chair. Bright blue skies and calm waters add to the serene atmosphere, while white railings complement the coastal architecture.

Home in Islamorada

5 out of 5 average rating, 7 reviews

TheSandbar: Oceanfront,Pool,Free Dockage,Gameroom

The view from the patio showcases a vibrant sunset reflecting on the tranquil water. Lush palm trees frame the scene, with the illuminated pool area visible below. A distant pier extends into the water, enhancing the serene ambiance of the location.

Villa in Marathon

4.76 out of 5 average rating, 152 reviews

Sunset Villa in Duck Key

A modern living space is highlighted by large windows showcasing expansive ocean views. A gray sofa is positioned centrally, complemented by a patterned chair. A sleek coffee table decorated with seashells sits below a mounted television, while dining chairs are visible through the glass doors.

Home in Key Largo

5 out of 5 average rating, 20 reviews

Oceanside Paradise - Pool, HotTub, Kayaks, Pets OK

A modern living area features a light color palette and tasteful decor. Two woven armchairs are positioned around a circular coffee table, complemented by a dining area with a wooden table and chairs. A well-equipped kitchen is visible in the background, with stainless steel appliances.

Villa in Islamorada

4.67 out of 5 average rating, 51 reviews

Picturesque Villa Near History of Diving Museum

The kitchenette area is equipped with a modern sink, a compact microwave, and open shelving. The spacious room features two queen beds, a bedside table, and a television on a dresser. Light-colored wood flooring enhances the light, airy atmosphere.

Apartment in Islamorada

4.73 out of 5 average rating, 15 reviews

Private Beach Resort w/ Kayaking & Bicycle Rental

Top guest favorite

An outdoor terrace features a dining table surrounded by wicker chairs, providing a space for gatherings. A small area rug and potted plants are positioned near the entrance. Steps lead to a door that offers access to the interior, with a ceiling fan overhead for comfort.

Casa particular in Key Largo

5 out of 5 average rating, 5 reviews

Reef Heaven Vacation Home

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