
Family-friendly holiday rentals in Islamorada
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Islamorada
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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

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.

Renovated Anglers Reef 2BR + Sleeper + Ocean Views
Welcome to Anglers Reef, a bright coastal cottage in Islamorada, FL, with access to resort-style amenities. Enjoy a private boat slip, tropical pool, sandy beach, and walkable marina. Inside, relax in open living spaces, a fully equipped kitchen, and serene bedrooms. Unwind on breezy porches or explore nearby snorkeling, fishing, dining, and Keys adventures. Ideal for families, couples, and boaters seeking laid-back luxury. Thoughtfully designed for comfort, privacy, and effortless island life.

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.

Florida Keys Houseboat, unique 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 💫

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.

Turtle-By-The-Sea: the Best Deal in KCB!
A perfect get-away for couples or budget travelers, Turtle-by-the-Sea is the best priced vacation rental or hotel room in the middle-keys. Together with its prime location and amenities there simply isn’t a better deal to be had! Bursting with Keys charm, this cozy retreat is the perfect place to relax & escape. Owners Mallory & Steve infused their love of the Keys & its surrounding ocean into every aspect of their waterside home. Shoot us a message & start planning your dream Keyscation!

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.

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.

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.

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!

Great key Largo home with water front and pool
we have a dog clean fee , always ask the before booking Fantastic canal front home located in Key Largo. Bring your own boat and enjoy it all! The home is minutes away from Gilbert resort, best seafood in the world at any number of local restaurants, Souvenir stores and the best fishing and diving spots. The home has 2 bedrooms and 2 bathrooms, fully furnished, spacious living room with large TV, Full kitchen with all appliances and amenities and a beautiful deck
Popular amenities for Islamorada family-friendly rentals
Family-friendly home rentals with a hot tub

Reel Large END Unit in Ocean Point Suites

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

Your Happy Place - Oceanfront

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!

Casa Solaris | Key Largo home with Private Pool!

Mariners 212 Great Location with Marina Views

4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina

New Listing! Tropical Oasis at the Mariners Club!
Family- and pet-friendly home rentals

Tiny Home on Waterfront | Bay Views | Deck | Pool

Waterfront Cottage Walk to World Famous Lorelei

Gorgeous lagoon-front 2BR Townhouse with 2 pools

Florida Keys Resort-Style Home w/ Pool & Dock 5/3

Large Waterfront Home, w/Efficiency, Pool, Kayaks

Boater’s Paradise 3br/2.5ba at Coral Lagoon

Waterfront House with 37 ft Dock & Cabana Club

Waterfront Oceanside, 60 Ft Dock, As seen on HGTV
Family-friendly home rentals with a pool

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

Luxury condo with boat slip overlooking the bay

Heated&Cooled PrivatePool/CabanaClub/Bikes/PaddleB

Beach House, Private Pool, Dock, Gulf View Sunsets

Castillo Del Mar- Ocean access from your backyard

NEW! Private Pool, 50’ Dock, Kayaks, Waterfront

Condo in Tavernier

Tequila Sunrise
When is the best time to visit Islamorada?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $456 SGD | $511 SGD | $535 SGD | $468 SGD | $518 SGD | $454 SGD | $454 SGD | $447 SGD | $447 SGD | $416 SGD | $463 SGD | $479 SGD |
| Avg. temp | 20°C | 22°C | 23°C | 25°C | 27°C | 28°C | 29°C | 29°C | 28°C | 27°C | 24°C | 22°C |
Quick stats about holiday rentals that are family-friendly in Islamorada

Total holiday rentals
Explore 530 holiday rentals in Islamorada

Nightly prices starting at
Islamorada holiday rentals start at $115 SGD per night before taxes and fees

Verified guest reviews
Over 5,170 verified reviews to help you choose

Pet-friendly holiday rentals
Find 260 rentals that welcome pets

Holiday rentals with a pool
420 properties feature pools

Rentals with dedicated workspaces
290 properties have a dedicated workspace

Wifi availability
520 of Islamorada holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Islamorada rentals

4.8 Average rating
Islamorada stays are highly rated by guests – averaging 4.8 out of 5!
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- Everglades National Park
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- Zoo Miami
- John Pennekamp Coral Reef State Park
- Biscayne National Park
- Long Beach
- Coral Castle
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- Homestead-Miami Speedway
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