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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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Home in Key Largo

4.95 out of 5 average rating, 115 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 favourite

Apartment in Tavernier

4.86 out of 5 average rating, 273 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 Key Largo

4.95 out of 5 average rating, 102 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.

Guest favourite

Cottage in Key Largo

4.96 out of 5 average rating, 160 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 favourite

Holiday home in Marathon

4.96 out of 5 average rating, 55 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

4.92 out of 5 average rating, 140 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

Home in Key Largo

4.9 out of 5 average rating, 105 reviews

NEW CASA PALMA VOTED BEST AIRBNB RENTAL! GOLF CART

NO HIDDEN FESS! CASA PALMA IS A LICENSED AND LEGAL VACATION RENTAL WITH HUNDREDS OF 5 STAR REVIEWS AND SUPER HOST STATUS ON ALL VACATION RENTAL SITES. VOTED #1 KEY LARGO VACATION RENTAL! LOCATED IN THE HEART OF KEY LARGO! IT'S THE PERFECT HOME BASE TO EXPLORE THE KEYS! 2 POOLS, BEACH, FREE GOLF CART, FAST WIFI, KAYAKS, TENNIS/PICKELBALL, MARINA WITH BOAT RAMP AND TRAILER PARKING! SLIP RENTAL AVAILABLE! SWIMMING LAGOON! 2 KING BEDS! PLAYGROUND! FREE PARKING! PACK AND PLAY AND BOOSTER SEAT!

Guest favourite

Apartment in Key Colony Beach

4.96 out of 5 average rating, 248 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.

Guest favourite

Home in Marathon

5 out of 5 average rating, 22 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, 184 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, 160 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.

Guest favourite

Apartment in Key Largo

4.9 out of 5 average rating, 86 reviews

Penthouse with Ocean View

Relax and enjoy! Fifth floor penthouse with spectacular views of the ocean and wetlands. Gated community only steps from the Atlantic Ocean. Newly renovated condo with open balcony overlooking ocean. Two bedrooms, two bathrooms plus sleeper sofa with upgraded mattress. Family friendly with portable crib/playpen and booster seat w/tray for dining chair. Pool, Playground, tennis courts and saltwater swimming lagoon. Min age of primary renter: 25

Holiday rentals for every style

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Popular amenities for Islamorada family-friendly rentals

Free parking on premises

Air conditioning

Kid-friendly house rentals

Home in Key Largo

4.74 out of 5 average rating, 19 reviews

Brand new beautiful and modern waterfront home

Guest favourite

Home in Marathon

4.94 out of 5 average rating, 182 reviews

Avail. Now! 70ft Dock, Close to Beach VACA23-16,

Guest favourite

Home in Marathon

4.94 out of 5 average rating, 126 reviews

Paradise - Pool, Hot tub, Mini Golf, Dockage, Fish

Guest favourite

Home in Marathon

5 out of 5 average rating, 12 reviews

Waterfront Oasis w/Private Pool-Dockage-Beach

Guest favourite

Home in Key Colony Beach

4.94 out of 5 average rating, 106 reviews

Waterfront Home 37.5-ft dock, Cabana Club Included

Guest favourite

Home in Key Largo

5 out of 5 average rating, 12 reviews

Island Breeze

Guest favourite

Home in Marathon

4.96 out of 5 average rating, 51 reviews

Paradise Ocean Front 4/3Home Heated Pool

Home in Key Colony Beach

4.73 out of 5 average rating, 133 reviews

NEW PET FRIENDLY Waterfront Single Home-Pool,Beach

Family-friendly apartment rentals

Flat in Key Colony Beach

4.84 out of 5 average rating, 104 reviews

Beachside Unit 22 - Private Beach on Atlantic

Guest favourite

Flat in Key Largo

4.99 out of 5 average rating, 142 reviews

Kawama Lagoon, 3D corner chickee 2bdr , 2 baths

Guest favourite

Flat in Islamorada

4.82 out of 5 average rating, 11 reviews

The House HMH

Flat in Key Largo

4.92 out of 5 average rating, 256 reviews

Waterfront Studio 2| Couples Oasis | Kayaks | Pool

Flat in Key Largo

4.82 out of 5 average rating, 38 reviews

Best Place to see the sunset

Flat in Key Largo

4.83 out of 5 average rating, 328 reviews

Escape to the Keys!

Guest favourite

Flat in Marathon

4.97 out of 5 average rating, 101 reviews

Beachfront Condo w/ Ocean Views in Marathon

Guest favourite

Flat in Tavernier

4.89 out of 5 average rating, 466 reviews

Capt Craigs Apartment

Family-friendly apartment rentals

Apartment in Tavernier

4.9 out of 5 average rating, 153 reviews

2BR - Key Largo Sunshine Getaway

Guest favourite

Apartment in Key Largo

4.87 out of 5 average rating, 116 reviews

Kawama Breeze

Guest favourite

Apartment in Key Largo

5 out of 5 average rating, 8 reviews

Key Lime Breeze Ocean Retreat | Waterfront Oasis

Guest favourite

Apartment in Key Largo

4.89 out of 5 average rating, 74 reviews

Island Palms~Overlooking Tennis Courts

Apartment in Key Largo

4.87 out of 5 average rating, 119 reviews

Waterfront Spacious Condo Key Largo #4, 10% Off 7+

Guest favourite

Apartment in Tavernier

4.89 out of 5 average rating, 112 reviews

Luxurious Suite+Open Ocean Views+Pool & Cabana Bar

Guest favourite

Apartment in Tavernier

5 out of 5 average rating, 34 reviews

Key Largo Sunrise Resort Style Ocean Pointe 5315

Guest favourite

Apartment in Key Largo

4.96 out of 5 average rating, 122 reviews

Kawama Suntastic @ Key Largo

Quick stats about holiday rentals that are kid-friendly in Islamorada

Total rentals
60 properties
Nightly prices starting at
₹6,894 before taxes and fees
Total number of reviews
1.3K reviews
Family-friendly rentals
60 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
40 properties have a pool

Destinations to explore