
Family-friendly vacation 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.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Islamorada family-friendly rentals
Family-friendly home rentals with a hot tub

1BR - Key Largo Sun & Sand Hideaway

Reel Large END Unit in Ocean Point Suites

Your Happy Place - Oceanfront

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

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

Sunsets In Palms Paradise

Condo in the Keys, Peaceful ocean view retreat!

Boho FL Keys Condo
Family- and pet-friendly home rentals

Waterfront Cozy Cottage with Boat Ramp & Dock!

Seaside Vista - Ocean Front 2/1 with dockage

Waterfront Duck Key Villa - Sleeps 8 (7058)

Houseboat Getaway In Marathon

Private 4/3 Pool Heater/Dock/Kayaks/Bikes,etc

Waterfront Home 37.5-ft dock, Cabana Club Included

Beachfront Villa - Florida Keys

Waterfront House with 37 ft Dock & Cabana Club
Family-friendly home rentals with a pool

Anglers Reef Islamorada

Cancellation Deal; Sept 27 thru Oct 04; Save now!

Oceanfront with Pool near Sombrero Beach

When Paradise is Key: Tropical Oceanfront Condo

CASA AZUL Golf Cart, Kayaks, Pools, Beach, 2 Kings

Ocean Shores Villa 2 with pool and boat slip

Beachside Unit 33-Private Tropical Beach Plus Pool

Coastal Key Colony Beach Condo, Oceanfront Complex
Quick stats about vacation rentals that are family-friendly in Islamorada
Total rentals
590 properties
Nightly prices starting at
$110 CAD before taxes and fees
Total number of reviews
4.9K reviews
Pet-friendly rentals
260 properties allow pets
Rentals with a pool
440 properties have a pool
Rentals with dedicated workspaces
310 properties have a dedicated workspace
Destinations to explore
- Seminole Vacation rentals
- Central Florida Vacation rentals
- Miami Vacation rentals
- Saint Johns River Vacation rentals
- Orlando Vacation rentals
- Gold Coast Vacation rentals
- Miami Beach Vacation rentals
- Havana Vacation rentals
- Fort Lauderdale Vacation rentals
- Tampa Vacation rentals
- Kissimmee Vacation rentals
- Four Corners Vacation rentals
- Luxury rentals Islamorada
- Fitness-friendly rentals Islamorada
- Beachfront rentals Islamorada
- Beach house rentals Islamorada
- Villa rentals Islamorada
- Rentals with a patio Islamorada
- Rentals with a washer and dryer Islamorada
- Condo rentals Islamorada
- Rentals with a kayak Islamorada
- Rentals with a fireplace Islamorada
- Rentals with a hot tub Islamorada
- Rentals with a firepit Islamorada
- Townhouse rentals Islamorada
- Rentals with outdoor seating Islamorada
- House rentals Islamorada
- Rentals with pools Islamorada
- Resort rentals Islamorada
- Waterfront rentals Islamorada
- Pet-friendly rentals Islamorada
- Rentals with breakfast Islamorada
- Rentals with beach access Islamorada
- Apartment rentals Islamorada
- Rentals with an EV charger Islamorada
- Family-friendly rentals Monroe County
- Family-friendly rentals Florida
- Family-friendly rentals United States
- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Cannon Beach
- Coral Castle
- Biscayne National Park
- Calusa Beach & Loggerhead Beach
- Cocoa Plum Beach
- Theater of the Sea
- Conch Key
- Everglades Alligator Farm
- Far Beach
- Monkey Jungle
- Horseshoe Beach
- Sea Oats Beach
- Long Key State Park
- EAA Air Museum
- Windley Key Fossil Reef Geological State Park
- Keys' Meads
- Long Beach
- Bahia Honda State Park
- Sandspur Beach
- Schnebly Redland's Winery & Brewery