
Family-friendly holiday rentals in Big Pine Key
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Big Pine Key
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 Big Pine Key family-friendly rentals
Family-friendly home rentals with a hot tub

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

Sweet Retreat! 4 bedroom 2.5 Baths Sombrero Beach

Affordable Beachfront Luxury Condo Sleeps 6

Bright & Sunny Suite w/ Magnificent Ocean Views

Palm Breezes! Room for Everyone on the Ocean.

Plunge Pool Villa on Blue Water Lagoon

Darling of Duval at Old Town

Casablanca Too ~Chicly updated home with hot tub
Family- and pet-friendly home rentals

Last Minute Discount! 48' Yacht & Beautiful Resort

Sunset - The Best Downtown Locations in Key West

Waterfront luxury Villa (14) with sunset views and boat slip

Ocean Front Home in Great Location

Coral Quay-III Canal waterfront,access BEACH club!

Fish Camp, Fun, Keysy Oasis, with Tiki, pool, dock

Pier Pressure~ Waterfront Pool Home, 100' Dock

New Paradise On Sombrero Beach
Family-friendly home rentals with a pool

Anglers Reef Islamorada

Historic Key West - Cigar House - Sleeps 4

Waterfront, dock, easy ocean access, heated pool!

Anglers Reef is Oceanfront, Yellowtail Hse. 2/2.5

Family Retreat

Beautiful open plan remodeled home in Key Colony

Sunrise Townie - Maison Matecumbe Islamorada, FL

Keys Elegance. Pool, Hot Tub, Dock Summer Specials
Quick stats about holiday rentals that are family-friendly in Big Pine Key
Total rentals
190 properties
Nightly prices starting at
$163 NZD before taxes and fees
Total number of reviews
2.8K reviews
Pet-friendly rentals
100 properties allow pets
Rentals with a pool
80 properties have a pool
Rentals with dedicated workspaces
80 properties have a dedicated workspace
Destinations to explore
- Key West Holiday rentals
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- Rentals with outdoor seating Big Pine Key
- Rentals with beach access Big Pine Key
- Rentals with a washing machine and dryer Big Pine Key
- Fitness-friendly rentals Big Pine Key
- Beachfront rentals Big Pine Key
- Pet-friendly rentals Big Pine Key
- Waterfront rentals Big Pine Key
- House rentals Big Pine Key
- Rentals with pools Big Pine Key
- Rentals with a hot tub Big Pine Key
- Kid-friendly rentals Big Pine Key
- Rentals with a fire pit Big Pine Key
- Villa rentals Big Pine Key
- Rentals with a patio Big Pine Key
- Cottage rentals Big Pine Key
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