Family-friendly holiday rentals in Islamorada

4.87 out of 5 average rating, 181 reviews

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

4.95 out of 5 average rating, 105 reviews

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

Welcome to paradise! Completely remodeled and immaculately maintained, Bungalow Blue is nestled away in the quiet quaint Shady Palms community of 7 cottages in Islamorada, MM 76. Ideally situated next to the community heated pool, down the street from private boat ramp. If you're looking to relax and unwind while also being close to all that Islamorada has to offer, this is the place for you. Enjoy the FL Keys lifestyle in your private backyard, take a bike ride to World Famous Robbie's Marina

4.96 out of 5 average rating, 151 reviews

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

Your slice of Islamorada awaits at Key Lime Cottage! Step inside this 2-bedroom retreat and you’ll instantly feel at home. Tucked in a quiet neighborhood yet right in the heart of the Florida Keys, it’s the perfect blend of relaxation and convenience. Enjoy a full kitchen, access to a beautiful pool shared with just six homes, outdoor seating with a grill and fire pit and paddle boards. Whether you’re here to unwind, explore, or fish, everything you need for a perfect Keys getaway is right here.

5.0 out of 5 average rating, 21 reviews

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.

4.97 out of 5 average rating, 35 reviews

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.

4.79 out of 5 average rating, 67 reviews

A floating home is anchored in clear waters, surrounded by lush greenery. The structure is highlighted by solar panels on the roof and a spacious white deck, featuring railings that outline the edges. Bright blue skies and distant mangroves create a serene backdrop.

Houseboat in Islamorada

Perfect escape to the ocean

Enjoy the sounds of nature when you stay in this unique place. What awaits you is fun filled days living and exploring out on the fabulous florida keys waters in your own private floating paradise that is completely solar powered and all the amenities run 24/7! This fabulous floating home was build in 2025 and very nice, update and comfortable, it is 100% solar powered and eco friendly All the amenities run off batteries and solar power so you'll be able to enjoy cold ac, fridge, tv , 24/7

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.

4.97 out of 5 average rating, 219 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.

4.88 out of 5 average rating, 101 reviews

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.

Apartment 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. ⛱️

4.93 out of 5 average rating, 391 reviews

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.

4.92 out of 5 average rating, 12 reviews

Private Beach | Heated Pool | Mahi Key

Relish ocean serenity in this residence set directly on a secluded beach, where an open-concept design seamlessly merges the living area and gourmet kitchen with a grand terrace, all framed by uninterrupted ocean views. Bask in the heated pool, unwind on the covered patio, or step onto your private dock for a true waterfront escape. With a pristine stretch of sand and loungers reserved just for you, this is coastal living at its finest. Enhanced cleaning practices implemented.

4.86 out of 5 average rating, 609 reviews

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!

4.8 out of 5 average rating, 41 reviews

Islamorada Bungalow # 5

Bring the whole family to this great place with lots of room for fun.Escape to our charming 2-bedroom, 1-bathroom bungalow in Islamorada, FL, where luxury and convenience await! Relax on the spacious patio and take a refreshing dip in the pool, perfect for unwinding after a day of exploring nearby attractions. You're just moments away from pristine beaches, world-class fishing. Whether you seek adventure or relaxation. Secure your stay now for an unforgettable experience!

Popular amenities for Islamorada family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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.

4.95 out of 5 average rating, 151 reviews

Your Happy Place - Oceanfront

5.0 out of 5 average rating, 107 reviews

The open-plan living area features a vibrant blue sofa with colorful cushions, complemented by two orange chairs. A round wooden coffee table sits atop a large, patterned rug. A green wall with decorative foliage and a neon sign adds a lively touch, with windows providing natural light and views of the outside.

Apartment in Tavernier

Island Time at Ocean Pointe Luxe 2 King Spa BR/BA

4.96 out of 5 average rating, 295 reviews

Apartment in Tavernier

4.82 out of 5 average rating, 126 reviews

Villa in Key Largo

Oceanfront Resort W/Indoor Pickleball - Speakeasy!

A bright living space features a comfortable gray sofa and a recliner, complemented by a white coffee table adorned with decorative items. The dining area, with a white table and several chairs, extends into the modern kitchen equipped with stainless steel appliances and a breakfast bar with stools.

4.88 out of 5 average rating, 186 reviews

Reel Large END Unit in Ocean Point Suites

A spacious living room features a light color palette with a large flat-screen television mounted on the wall. Comfortable seating is arranged around a coffee table, and large windows provide a view of the ocean and natural light. Coastal decor enhances the atmosphere.

4.91 out of 5 average rating, 166 reviews

Lux Suite Open Ocean Views- 2 Balconies+Pool & Bar

4.95 out of 5 average rating, 108 reviews

4BR 3B, Heated Pool & Spa, 60' Dock

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.

4.99 out of 5 average rating, 224 reviews

Ocean Views at Ocean Pointe

Family- and pet-friendly home rentals

4.97 out of 5 average rating, 231 reviews

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

4.98 out of 5 average rating, 129 reviews

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

A vibrant sunset casts a warm glow over the outdoor area featuring a sheltered gazebo, surrounded by lush greenery and reflective water. Nearby, a modern living room is furnished with comfortable seating and a large screen, creating an inviting space for relaxation.

4.94 out of 5 average rating, 122 reviews

Coco Plum Waterfront Hideaway Home in Marathon

4.85 out of 5 average rating, 132 reviews

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

4.81 out of 5 average rating, 235 reviews

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

Vibrant Beachfront Villa

4.91 out of 5 average rating, 169 reviews

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

Gorgeous lagoon-front 2BR Townhouse with 2 pools

Houseboat in Islamorada Tavernier

4.9 out of 5 average rating, 278 reviews

Baycation Houseboat • Florida Keys Waterfront Stay

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.

5.0 out of 5 average rating, 126 reviews

Waterfront Oceanside, 60 Ft Dock, As seen on HGTV

Family-friendly home rentals with a pool

5.0 out of 5 average rating, 23 reviews

Townhouse in Islamorada

Closest Oceanfront Home - 3 Stories, Views & Dock

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.

5.0 out of 5 average rating, 26 reviews

TheSandbar: Partial Ocean view,Pool,Free Dockage

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.

5.0 out of 5 average rating, 7 reviews

Marlin House @ Tarpon Point

4.97 out of 5 average rating, 58 reviews

A relaxing outdoor area features a sparkling pool surrounded by lounge chairs and vibrant blankets draped over the edge. Lush greenery and palm trees provide natural shade, creating an inviting space for leisure and family gatherings.

Apartment in Islamorada

The HMH House

An outdoor patio space is revealed, featuring comfortable seating with decorative pillows and a coffee table. A vibrant blue lounge chair is positioned alongside a heated plunge pool surrounded by lush palm trees. A grill is visible on the side, enhancing the outdoor living experience.

4.97 out of 5 average rating, 36 reviews

Heart of Islamorada ~ Private Boat Dockage

5.0 out of 5 average rating, 51 reviews

Serenity Oasis~Pool!~Putt-Putt!~Kayaks~Bikes~Spa

4.96 out of 5 average rating, 53 reviews

Condo in Tavernier

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.