Kid-friendly vacation rentals in Islamorada

Find and book unique kid-friendly rentals on Airbnb

Top-rated kid-friendly rentals in Islamorada

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

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Superhost

Home in Key Largo

4.94 out of 5 average rating, 127 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!

Guest favorite

Vacation home in Key Largo

4.94 out of 5 average rating, 115 reviews

Ocean Shores Villa 3 with pool and boat slip

This centrally located boater's paradise is the perfect place to relax. Walk to restaurants, cook in kitchen or grill downstairs. With only 4 units in the building the guests have half an acre of waterfront entertainment (boat slip, Kayaks, Bikes, Hammock and Pool). 32ft Dock Slip and Trailer Parking are included in the rental. Relaxing Balcony that looks down the Ocean Canal is the perfect place to have your morning coffee. Conveniently located near Sandbars, State parks and many attractions.

Superhost

Home in Key Largo

4.91 out of 5 average rating, 100 reviews

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

No hidden fees! Casa Azul blends luxury and laid-back island vibes in the heart of Key Largo. With Superhost status and hundreds of 5-star reviews, a perfect escape. Voted the #1 Vacation Rental in Key Largo, it’s ideal for families, couples, and groups alike. Enjoy a free golf cart, fast Wi-Fi, 2 pools, private beach, saltwater lagoon, kayaks, tennis and pickleball courts with gear, marina access, boat ramp, trailer parking, and optional slip rentals. Salt Life meets luxury - this is the one.

Top guest favorite

Cottage in Key Largo

4.96 out of 5 average rating, 173 reviews

Charming Key Largo Cottage on the Water w/Kayaks!

Charming "Tiny House" Cottage on a main canal just two units from open water. Amazing location for boaters, fisherman and alike. This is a quaint and close knit RV park where you can keep to yourself or wander around and enjoy happy hour with new local friends. Bar none the best kayak, paddle board and fishing area. Two Tandem (each kayak accommodates two people) Kayaks and two paddle boards included in rental. Great outdoor space to dock your boat, fish off of or enjoy a few cocktails!

Guest favorite

Vacation home in Marathon

4.97 out of 5 average rating, 67 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 favorite

Apartment in Key Largo

4.93 out of 5 average rating, 153 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

Guest favorite

Condo in Tavernier

4.99 out of 5 average rating, 106 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.

Guest favorite

Condo in Key Colony Beach

4.96 out of 5 average rating, 253 reviews

Amazing Ocean Front Views Key Colony Beach

Ocean front Florida Keys Studio Condo in Key Colony Beach with private balcony, heated pool and sandy beach. Continental Inn Unit #40 is a studio condo with a tropical interior featuring 2 queen beds and kitchen stocked with everything needed to cook a complete meal (stove, oven, toaster, microwave, blender, fridge, etc). Relax on the back balcony and enjoy sunsets from Sunset Park right next door. Private beach with lounge chairs, patio tables, tiki's and BBQ grills for guest use.

Top guest favorite

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 favorite

Condo in Key Largo

4.96 out of 5 average rating, 164 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

Apartment 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.

Superhost

Home in Key Largo

4.86 out of 5 average rating, 100 reviews

Cary’s Oceanside

Oceanside Canal front House Walking Distance to Ocean, Family and pet friendly. Bottom floor of a 2 story house, 2 Bedrooms, 1 1/2 Bath, Sleeps 4-6. Private pool (heated during winter months) and an outdoor shower for guests, Pergola with a Charcoal Grill/Smoker and a Blackstone Gas Griddle. Convenience of accessing your boat right from the backyard with easy access in and out to the ocean.

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What guests are saying

Huge Swim Spa~ Incredible Special Fall Pricing

5 out of 5 average rating, 5 reviews1 month ago

We really enjoyed our stay. The host, Sherry, gave timely information and quickly responded to messages. We were pleasantly surprised by the number of amenities that were available to us at the house. The Cabana Club was a real hit with my teenage daughters. It had reasonably priced drinks and lunch type meals. They enjoyed just laying by the pool or beach and sun tanning. We saw manatees one of the evenings right in the backyard of the home.

Home in Key Colony Beach

What guests are saying

Waterfront Escape -VACA-23-408

5 out of 5 average rating, 33 reviews1 week ago

We loved staying at this home in Marathon. My family of 5 (three young kids; 9, 6 & 1) plus 4 other adults all stayed here comfortably and thoroughly enjoyed ourselves. We all felt right at home! The home was spotless and kept very clean. The location was great and we LOVED the backyard with everything it offered. The kids especially loved the yard. There are numerous marinas right by the home, which made renting a boat very convenient. Highly recommend doing so! We loved having the extra amenities like the kayak and paddle boards as well! Whenever I needed to get in touch with the host Carmen, she was very communicative and responded right away. Would definitely stay here again and highly recommend! Thank you again!

Home in Marathon

What guests are saying

Sunset Catch Gulf Front, Pool, Dock, Kayaks, Fish

4.89 out of 5 average rating, 37 reviews7 months ago

We booked this home last minute and now have our go-to vacation spot in Marathon! Alida is a friendly host with great communication. The home is very clean. Beds are very comfortable. Kitchen is well stocked with pots, pans, etc. The kayaks and paddle board made our vacation even more special! The steet is very quiet and peaceful. The setting in the back yard is very private, as is the long dock. We had a 23' rental boat for our stay. The view is amazing and the sunsets are a special treat each evening. I very much appreciated the ample, comfortable seating everywhere - inside and outside of the home. Thank you Alida. We made great family memories here!

Home in Marathon

What guests are saying

Yellow Home Free Pontoon Rental! See details

4.83 out of 5 average rating, 30 reviews2 months ago

This place was perfect! To have your own pool to relax in without other guests was amazing. Such a peaceful space. Views are amazing! Mitch and Lu were so quick with answers. Did have a small problem finding it. GPS had me going a weird way and some construction going on. Mitch was quick to help me find his place! I miss it already!

Home in Cudjoe Key

What guests are saying

Catch n' Relax Canalfront Cottage in Marathon

4.97 out of 5 average rating, 32 reviews1 month ago

We stayed for 11 nights at Wendy's beautiful home. We had everything we needed for our entire stay. The area is very quiet and peaceful. It was so lovely walking up on the water and enjoying breakfast outside. Extra touches like having bikes and kayaks to use were also sooo nice! Wendy was very helpful with local spots to check out as well. We will definitely be back!

Cottage in Marathon

What guests are saying

146 RV Vacation Rental n Key Largo Kampground, FL

4.92 out of 5 average rating, 26 reviews2 weeks ago

Julie’s place was great as a snowbird escape! The weather in Key Largo is fantastic and her location is great! The pool was heated and had plenty of deck chairs. The sandy beaches at the campground made it super easy to launch our kayaks and get to the mangrove kayak trails super fast. There are so many restaurants in town to try, and Publix grocery store is super close (walkable if needed). Her outside patio is super relaxing and has an outside tv (where we watched the Super Bowl). The bikes at her site were a great amenity too! We loved our time at Julie’s place!!!

Camper/RV in Key Largo

What guests are saying

VOTED TRIPADVISOR'S #1 DESTINATION, POOL, TENNIS

4.84 out of 5 average rating, 69 reviews1 month ago

Pedro was extremely helpful and very responsive with communication. We had a few hiccups but Pedro was able to help sort it out. Beautiful house! Beautiful neighborhood! Very relaxing and accommodating for all ages and families! We had our 3 year old and 7 month old with their grandma and we all had a blast. Would definitely return!

Townhouse in Key Largo

What guests are saying

A motorhome in paradise

4.78 out of 5 average rating, 18 reviews2 weeks ago

We stayed here over spring break 2025- and it was very fun. It has such close proximity to John Pennekamp State Park.. so if you are an avid snorkeler, this is the place for you. My kids loved the pool, and went for night swims every night. It's very safe, and the neighborhood can be a little loud at night, but if you close the windows it's so peaceful. We weren't here often ( out doing adventures on the Florida Keys) but it was a nice place to come back to after a long day. The hammocks are very very nice and the marina has a gorgeous view. Thank you!

Camper/RV in Key Largo

What guests are saying

Key Largo Village getaway

4.94 out of 5 average rating, 16 reviews2 weeks ago

If you are looking for a place to stay in the Keys, look no further. To start things off, Jenn is the best host you can ask for!! She was extremely responsive and incredibly sweet throughout the whole stay. She would always check in on us at the perfect times and really helped us feel right at home. Best experience I have ever had with a host!! As for the AirBnB itself, it was absolutely perfect for what we were looking for. It is tucked in a private family-friendly neighborhood that does a good job of drowning out any noise from the roads. It was exceptionally clean when we arrived and the amenities were fantastic. Really felt like a home away from home. The location was also very convenient and made our day trips to Miami and Key West a cinch. It is also near lots of amazing local beaches, snorkeling and kayaking spots, and restaurants. We will definitely be staying with Jenn again anytime we are in the area!!

Home in Key Largo

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