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Family-friendly holiday rentals in Windley Key

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Top-rated family-friendly rentals in Windley Key

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

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Top guest favourite
The eco-friendly two-story River Queen vessel is anchored in a calm harbor, showcasing a modern design. The structure features large windows and a rooftop terrace, with a wind turbine on the left. The surrounding landscape includes lush greenery, complementing the serene water view.
Boat in Tavernier

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.

4.92 out of 5 average rating, 401 reviews
Guest favourite
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

Sunrise Escape - Ocean Front Villa - Sleeps 10

Wake up to the sunrise over the ocean and unwind with sunset views from your private jetty. This marina-front, ocean-view townhouse in Kawama Yacht Club puts you steps from kayaking, snorkeling, and the best of the Keys. Spacious, stylish, and designed for unforgettable family and friend getaways. Breathtaking sunrises from one of two private terraces, coffee in hand, overlooking the marina and the Atlantic Ocean. Located in an exclusive, quiet section of Kawama Yacht Club, this beautifully po

4.87 out of 5 average rating, 181 reviews
Top guest favourite
Home in Islamorada

OceanView 2/2.5 w Beach Pool & Marina Islamorada

Everything you need for your Islamorada vacation is here including 2 gorgeous private beaches, kayaks, paddle boards, heated resort style pool, porch seating with ocean view, and 2 balconies. Located in the middle row of Anglers Reef, this home accommodates up to 6. Boat slip can be reserved for additional fee, if available. REELaxation is our only vacation rental and with an extensive background in customer service, extraordinary guest service and helping to make lifetime memories are our goal.

5.0 out of 5 average rating, 21 reviews
Guest favourite
Houseboat in Islamorada Tavernier

Baycation Houseboat • Florida Keys Waterfront Stay

Escape to the laid-back luxury of the Florida Keys aboard your own floating oasis. This fully equipped houseboat offers the perfect blend of comfort, adventure and true waterfront living. Wake up to breathtaking sunrises, sip your morning coffee as the marine life glide by, and fall asleep to the gentle sway of the water. Whether you’re celebrating something special or simply craving a one-of-a-kind getaway, this houseboat is the ideal home base for both keys adventures and peaceful retreats 💫

4.9 out of 5 average rating, 278 reviews
Top guest favourite
A serene waterfront view captures the modern multi-story building surrounded by lush greenery. The calm water reflects the clear blue sky, while a private wooden dock extends into the water, providing an inviting entrance to the property.
Townhouse in Islamorada

NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom

🌊Welcome to The Seascape🌊 Experience waterfront living at its finest at The Seascape, a modern, newly constructed retreat nestled directly on the ocean where every morning begins in color, and every evening ends in calm. Here, the ocean isn’t just a view. It’s a presence. Come make memories at Islamorada's famous sandbar, legendary fishery, or gather on sunlit shores to relax and revel in life’s simplest joys with stunning views, direct water access, and a stylish escape from the everyday.

4.97 out of 5 average rating, 35 reviews
Top guest favourite
Townhouse in Islamorada

Closest Oceanfront Home - 3 Stories and Boat Dock

Welcome to Paradise Palms, the crown jewel of oceanfront living in Islamorada. This gated, three-story retreat is one of the closest homes to the water, offering unobstructed panoramic views, rare third-floor balcony access, and boat dockage. Thoughtfully designed with modern coastal elegance, enjoy two oceanfront balconies, luxury amenities, and unforgettable sunrises and sunsets. Your comfort and satisfaction are our top priorities. Let us help you turn your vacation dreams into reality.

5.0 out of 5 average rating, 23 reviews
Top guest favourite
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

My Little Oasis2 Waterfront Retreat, Key Largo

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.

4.97 out of 5 average rating, 231 reviews
Top guest favourite
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

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.

4.97 out of 5 average rating, 219 reviews
Superhost
A bright living area features a comfortable gray sofa, decorative chairs, and a coffee table on a patterned rug. Natural light floods the space through large windows, creating a relaxed atmosphere. A wall-mounted TV and a small desk can also be seen, along with coastal decor.
Flat in Tavernier

When Paradise is Key: Tropical Oceanfront Condo

🚨*PRICE YOU SEE IS ALL IN! Includes Airbnb fees and taxes!*🚨 🚨09.09.26 - 10.14.26 Elevator will be out of service due to installation of a new elevator 🚨 ☀️ Discover the ultimate beachfront getaway in our top floor, two-bedroom, two-bathroom condo, perfectly designed to offer an unforgettable escape. Nestled right on the oceanfront, this retreat comfortably accommodates up to six guests, making it ideal for families, friends, or couples seeking a serene coastal experience. ⛱️

4.88 out of 5 average rating, 101 reviews
Top guest favourite
A solar and wind powered houseboat is moored on calm waters, featuring bright yellow shutters and a roof deck. Wind turbines and an American flag adorn the top, contrasting with the soothing blue sky and fluffy clouds in the background.
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.

4.93 out of 5 average rating, 391 reviews
Superhost
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

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!

4.86 out of 5 average rating, 609 reviews
Guest favourite
Townhouse in Islamorada

Fishing Getaway | Dock, Pool & Sunrise

Wake up to breathtaking oceanfront sunrises in the Sportfishing Capital of the World. This luxury 3BR, 3BA townhome in Islamorada features a private dock, waterfront resort-style pool, and a quiet gated community just minutes from the Keys’ best fishing, marinas, restaurants, and attractions. Pet-friendly and fully equipped, it’s the perfect escape for anglers, families, couples, and extended stays.

5.0 out of 5 average rating, 13 reviews

Popular amenities for Windley Key family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Guest favourite
Flat in Tavernier

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

4.96 out of 5 average rating, 295 reviews
Top guest favourite
Apartment in Tavernier

Turtles Nest 2 Beach, Pool, Restaurant 2bed 2bath

4.94 out of 5 average rating, 158 reviews
Top guest favourite
A light-filled living space features a turquoise sofa with yellow accent pillows, paired with a round glass dining table. Rattan chairs complement the decor, which includes a vibrant tropical wall mural and a circular mirror. Modern appliances are visible in the kitchen area.
Apartment in Tavernier

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

4.96 out of 5 average rating, 251 reviews
Guest favourite
A private beach area is revealed, featuring rows of blue lounge chairs set on soft, sandy ground. Lush greenery borders the beach, while a wooden pier extends into the calm, turquoise water. A thatched gazebo provides shade, and scattered palm trees complete the coastal scene.
Apartment in Tavernier

Your Happy Place - Oceanfront

4.95 out of 5 average rating, 151 reviews
Top guest favourite
A clear view of the ocean is captured from the balcony, showcasing the shimmering water beneath a bright blue sky. Lush greenery lines the foreground, while a dock extends into the sea. The scene conveys a serene coastal atmosphere.
Apartment in Tavernier

Ocean Views at Ocean Pointe

4.99 out of 5 average rating, 224 reviews
Guest favourite
A private beach area is visible, featuring soft white sand and arranged lounge chairs facing the calm ocean. Lush greenery lines the shore, with a small tree providing shade. In the background, a wooden pier extends into the water under a partly cloudy sky.
Apartment in Tavernier

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!

4.9 out of 5 average rating, 337 reviews
Superhost
Villa in Key Largo

Oceanfront Resort W/Indoor Pickleball - Speakeasy!

4.82 out of 5 average rating, 126 reviews
Guest favourite
A cozy living area features a tropical-themed sofa with blue accent pillows and vibrant wall art. Large glass doors open to a balcony with ocean views, while potted plants add a touch of greenery. Natural light enhances the warm wood flooring.
Apartment in Tavernier

Sunshine Paradise Key Largo Ocean Pointe 4402

4.94 out of 5 average rating, 111 reviews

Family- and pet-friendly home rentals

Guest favourite
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.
Apartment in Key Largo

Gorgeous lagoon-front 2BR Townhouse with 2 pools

4.91 out of 5 average rating, 170 reviews
Guest favourite
A sandy beach area is framed by smooth rocks leading to clear blue waters. Two kayaks, one yellow and one green, are positioned along the shoreline. In the distance, several boats are visible on the water, under a partly cloudy blue sky.
Home in Key Largo

Banana Cabana

4.85 out of 5 average rating, 133 reviews
Guest favourite
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

Tiny Home on Waterfront | Bay Views | Deck | Pool

4.91 out of 5 average rating, 205 reviews
Guest favourite
Tiny home in Key Largo

Modern beach tiny house/Tiki hut/ boat dock 20ft

4.89 out of 5 average rating, 219 reviews
Guest favourite
The tranquil canal is illuminated by soft lights reflecting off the crystal-clear waters. Lush palm trees line the banks, and tiki huts with ambient lighting add to the serene atmosphere. The scene captures a peaceful nighttime setting with boats moored along the dock.
Cottage in Key Largo

2 bedroom & 25' Boat Dock Waterfront Atlantic Side

4.93 out of 5 average rating, 104 reviews
Top guest favourite
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

Waterfront House with 37 ft Dock & Cabana Club

4.98 out of 5 average rating, 129 reviews
Top guest favourite
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

Waterfront Oceanside, 60 Ft Dock, As seen on HGTV

5.0 out of 5 average rating, 126 reviews
Top guest favourite
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

TheSandbar: Partial Ocean view,Pool,Free Dockage

5.0 out of 5 average rating, 26 reviews

Family-friendly home rentals with a pool

Guest favourite
A comfortable living area is highlighted by a light-colored sofa with textured cushions, accompanied by a woven coffee table. Natural light enters through multiple windows, revealing touches of coastal decor and a glimpse of a bedroom in the adjacent space.
Cottage in Islamorada

Islamorada bungalow 2 bed & pool

4.95 out of 5 average rating, 105 reviews
Guest favourite
A serene pool area is surrounded by lush tropical landscaping and palm trees. Lounge chairs are positioned around the pool, along with blue umbrellas providing shade. The clear water sparkles under the bright sun, creating an inviting space for relaxation.
Cottage in Islamorada

Charming 2BR cottage in prime keys location w/pool

4.96 out of 5 average rating, 151 reviews
Top guest favourite
Townhouse in Key Largo

Key Largo Luxury Townhome | Pools & Marina

4.97 out of 5 average rating, 117 reviews
Guest favourite
A serene sunset casts warm orange and purple hues across the calm water, reflecting the fading light. Silhouetted trees and land are visible along the horizon, enhancing the tranquil ambiance of the tropical surroundings.
Townhouse in Key Largo

Key Largo House

4.89 out of 5 average rating, 159 reviews
Top guest favourite
Aerial view of the resort-style community featuring a central heated pool surrounded by lush landscaping. Palm trees and outdoor seating areas are visible. The property borders a marina with docks for boats, highlighting the connection to the water.
Home in Islamorada

Exceptional vaca in Angler's Reef Islamorada

5.0 out of 5 average rating, 28 reviews
Superhost
Home in Marathon

Marathon Oceanfront 4BR Private Pool 60’ Boat Dock

5.0 out of 5 average rating, 4 reviews
Superhost
Home in Islamorada

Islamorada Bungalow # 5

4.81 out of 5 average rating, 42 reviews
Guest favourite
A spacious fishing pier extends into clear turquoise waters under a bright blue sky. The sandy beach surrounding the pier invites relaxation, while lush greenery can be seen in the distance. Minimal benches are positioned along the pier for enjoying the scenery.
Home in Islamorada

Marlin House @ Tarpon Point

5.0 out of 5 average rating, 7 reviews

Destinations to explore