
Family-friendly holiday rentals in Key West
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Key West
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Key West family-friendly rentals
Family-friendly home rentals with a hot tub

Key West Beachside 1400sf, 2 Bedroom Condo

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

Tropical Escape at Sunrise

Affordable Beachfront Luxury Condo Sleeps 6

OCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!

Fully renovated 2/2 bath condo w/ shared pool!

Waterfront Sanctuary in the Keys!

Villa in Paradise. Plunge pool. Middle of the Keys
Family- and pet-friendly home rentals

La Dolce Vita, Old Town Steps to Duval! 3 blks bch

Cottage 30 min from Key West, free parking, pool

Comfortable, clean,beautiful home Summer Special

Waterfront Cozy Cottage with Boat Ramp & Dock!

Flakey's

Houseboat Getaway In Marathon

The Snapper House 3/2.5 45' dock sleeps 8+ pets OK

Paradise found
Family-friendly home rentals with a pool

Easy Livin' by AvantStay | Mins to the Ocean!

Movie Theater | HotTub | Pool | Boat/RV/EV Parking

The Palms

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

Bohemian Beach Bungalow

Having fun in the lower Keys

Exceptional Water View With Boat Dock!

Charming 1BD Cottage in Old Town Key West w/ Pool
Quick stats about holiday rentals that are family-friendly in Key West
Total rentals
1.3K properties
Nightly prices starting at
€ 8 before taxes and fees
Total number of reviews
30K reviews
Pet-friendly rentals
430 properties allow pets
Rentals with a pool
1.1K properties have a pool
Rentals with dedicated workspaces
770 properties have a dedicated workspace
Destinations to explore
- Seminole Holiday rentals
- Central Florida Holiday rentals
- Miami Holiday rentals
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- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
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- Fort Lauderdale Holiday rentals
- Tampa Holiday rentals
- Kissimmee Holiday rentals
- Four Corners Holiday rentals
- Tampa Bay Holiday rentals
- Rentals with a firepit Key West
- Rentals with a washing machine and dryer Key West
- Cottage rentals Key West
- Rentals with outdoor seating Key West
- Rentals with a hot tub Key West
- Rentals with an accessible-height toilet Key West
- Rentals with an EV charger Key West
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- Hotel rentals Key West
- Rentals with pools Key West
- Mansion rentals Key West
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- Pet-friendly rentals Key West
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- Boutique hotel rentals Key West
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- Apartment rentals Key West
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- Family-friendly rentals Monroe County
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- Family-friendly rentals United States
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- Things to do United States
- Sports activities United States
- Art and culture United States
- Sightseeing United States
- Nature and outdoors United States
- Entertainment United States
- Tours United States
- Food and drink United States
- Wellness United States