Kid-friendly holiday rentals in Islamorada

Find and book unique family-friendly rentals on Airbnb

Top-rated family-friendly rentals in Islamorada

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

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Guest favourite

Home in Key Colony Beach

5 out of 5 average rating, 5 reviews

Huge Swim Spa~ Incredible Special Fall Pricing

3 Bedroom~ 2 Bath Duplex With Outdoor Solar Shower, on a Deep Water Canal in Key Colony Beach. Near The Vaca Cut Makes For Easy Access To The Gulf Of Mexico or Atlantic Ocean. Boat Dockage for up to a 34' Boat. Golf Course, Pickle Ball~Tennis Courts, and Great Playground. We have a Large Swim Spa in The Private Garden, Arcade Game Room~Ice Maker, Paddle Board, 2 Kayaks, 4 Fishing Rods & Bait, Margarita Machine, Outdoor Shower. Cabana Club Membership With Free Beach/ Ocean Access & Huge Pool.

Superhost

Home in Key Largo

4.94 out of 5 average rating, 126 reviews

Mariners Club Resort, Best in the Upper Keys

SPACIOUS AND STUNNING Family Friendly 4+ br home. One of the few to allow 10 guests! POOLS w/ hot tubs MARINA for direct access to reef; diving, snorkeling, fishing & sandbars KAYAKING Pennekemp DISCOUNT to swim with dolphins at DPMMR ACTIVITIES; tennis & pickleball courts, gym & game room. LOCATION: restaurants, bars, grocery and other conveniences PARKING for two cars on site WE ARE LOCALS who know the importance of family time so look no further than this special slice of paradise!

Superhost

Apartment in Tavernier

4.86 out of 5 average rating, 277 reviews

Condo in the Keys, Peaceful ocean view retreat!

Newly renovated ocean view condo in beautiful Tavernier, FL! Ideally situated in the Upper Keys, between Miami and Key West, this condo is close to state parks and coral reefs great for diving, fishing, and snorkeling. Relax on the private beach where kayak and paddle board rentals are available. Then enjoy a stroll on the pier to the gazebo. Splash around in the beautifully renovated heated pool and hot tub with mermaid bar! You can also enjoy food and beverages in the on-site cafe and bar

Guest favourite

Holiday home in Marathon

4.97 out of 5 average rating, 66 reviews

Perfect Paradise

Perfect paradise is located in the heart of marathon. Only 9 minutes away from sombrero beach. Restaurant, supermarkets, ice cream, aquarium, and much more less than 7 minutes away. Public boat ramp is 5 minutes away. The house has plenty of parking spaces in the front to park your boat and cars. The home is fully stocked with everything you will need during your stay. For specific dates please message me first before booking so I may accommodate you to the dates that you would like to book.

Guest favourite

Flat in Key Largo

4.93 out of 5 average rating, 152 reviews

2/1 Oceanfront Apartment 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

Superhost

Home in Homestead

4.88 out of 5 average rating, 8 reviews

Casa Génesis

Perfect Location, enjoy with your family in this peaceful and family friendly house. Ideally located to explore the beautiful Florida Keys and Everglades National Park, for world-class fishing, snorkeling, and more. High-speed internet, plentiful parking space for 6 cars, Just a short drive to the Homestead Miami Speed way. Easily access to Baptist Health, Homestead & Black Point Park and many attractions. After adventure-filled days, return home and relax at this comfortable property.

Guest favourite

Apartment in Tavernier

4.99 out of 5 average rating, 105 reviews

Modern and Coastal Ocean Pointe 2307

Are you looking for a Caribbean Vacation in a tropical resort without leaving the USA? Look no further than our Ocean view 2 bedroom and 2 bath condo at Ocean Pointe Suites! Our property offers: 24 hour front gate security, Heated Junior Olympic Pool with 15 person hot tub, tropical Beach, Marina, Tennis/Pickle ball courts. Enjoy our newly re opened ISLAND GRILL pool bar! We are located 60 miles from Miami International Airport and 90 miles from Fort Lauderdale International Airport.

Top guest favourite

Home in Marathon

5 out of 5 average rating, 30 reviews

Waterfront Escape -VACA-23-408

Come stay at this brand new home construction on a deep and wide canal leading to the ocean with pool and exotic decor. 75 foot dock with water and electric. Top of the line appliances with a fully stocked kitchen. Spa style showers with high end decor. Luxury at its best. Heated pool with sundeck and lots of seating around the edges. (Pool heater is an additional $100 per stay). Ground level cooking and dining for those beautiful days after boating or while laying around in the pool.

Guest favourite

Home in Islamorada

4.97 out of 5 average rating, 188 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.

Guest favourite

Apartment in Key Largo

4.96 out of 5 average rating, 162 reviews

KEYS BEACH RETREAT WITH CAPTIVATING WATERVIEW!

LICENSED 3/3 VACATION HOME ON THE OCEAN SIDE WITH LOTS OF OUTDOOR LIVING/DINING SPACE. TWO POOLS, FREE GOLF CART, FAST FREE WIFI, TWO ADULT KAYAKS, TWO KIDS KAYAKS, TWO BICYCLES, TWO TENNIS AND PICKLEBALL COURTS. MARINA FOR YOUR BOAT WITH FREE BOAT RAMP AND FREE PARKING WITH QUICK ACCESS TO THE ATLANTIC OCEAN. SLIP RENTAL AVAILABLE FROM THE DOCK MASTER. PIRATE SHIP PLAYGROUND! FREE PARKING! SANDY BEACH! SALTWATER SWIMMING LAGOON! PACK AND PLAY AVAILABLE AND A BOOSTER SEAT.

Superhost

Home in Key Largo

4.9 out of 5 average rating, 106 reviews

New Oceanside Casa Palma Voted #1! Golf Cart-Beach

No Hidden Fees! Casa Palma is a top-rated Key Largo vacation home with Superhost status and hundreds of 5-star reviews. Voted the #1 Vacation Rental in Key Largo, it’s ideal for families, couples, and groups alike. Enjoy 2 pools, a private beach, exclusive use of a free golf cart, fast Wi-Fi, kayaks, tennis and pickleball courts, a saltwater lagoon, and marina with boat ramp and trailer parking. Includes 2 king beds, playground, free parking, Pack and Play, and booster seat!

Superhost

Flat in Key Largo

4.82 out of 5 average rating, 108 reviews

MODERN OCEANFRONT CONDO! OCEAN VIEWS! 2 KING BEDS!

You have just discovered one of the most unique properties in the heart of Key Largo. This OCEAN FRONT condo is located inside Kawama Yacht Club, a beautiful Hawaiian Island style resort that is situated along the southern border to the most popular park in all of the Keys, John Pennekamp National Underwater Park. Everything you could ever imagine making your Florida Keys vacation complete can be found here.