Family-friendly vacation 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.

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Superhost

Home in Cudjoe Key

4.9 out of 5 average rating, 104 reviews

Sunrise Beach Escape

For your next vacation, come stay in this resort home, where you'll enjoy a cocktail at sunset alongside the Cudjoe bay overlooking the Atlantic Ocean. This beautiful and luxurious home is part of the Sunrise Beach Resort, an exclusive 11 home gated community overlooking the Atlantic Ocean & Cudjoe Bay. A community that is only 17 miles north of Key West. Make yourself at home in this tastefully decorated 1200 sq foot living space, which offers countless amenities such as kayaks and bikes.

Oct 10 – 17

$350 per night

Guest favorite

Home in Key West

4.97 out of 5 average rating, 205 reviews

Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!

Historic Harrison's Hideaway is in an 1880's Cigar Maker's cottage renovated in 2010. It features a K size Pottery Barn memory foam bed, custom made full sleeper sofa, newly renovated kitchen with granite counter tops, 2 burner stove, under counter fridge/freezer, dishwasher, microwave, tumbled marble 2 person shower, private front deck with seating for 4 and 2 person Solana spa. Perfect for a couple or a family with children. Freshly painted a Caribbean blue with plantation shutters.

Aug 26 – Sep 2

$398 per night

Guest favorite

Home in Islamorada

4.97 out of 5 average rating, 164 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.

Dec 7 – 14

$228 per night

Guest favorite

Home in Marathon

4.93 out of 5 average rating, 169 reviews

Beach, 70ft Dock, Entire Home, VACA-23-16

Enjoy the boutique decor of our large, spacious home. Our place is a short distance from Sombrero Beach, with bicycles available to ride there. Our property is on a wide and deep canal, with both ocean and gulf access. Our dock is 70 ft, so ideal place for large boats, or you can even bring 2 boats. Free parking, with space to park boat trailer. We include free passes to the Sea Turtle Hospital to guests.

Aug 19 – 26

$248 per night

Guest favorite

Home in Key Largo

4.9 out of 5 average rating, 346 reviews

Your Keys Getaway!

Beautiful two bedrooms, 1 bath Keys Home fully renovated interior in a quiet residential neighborhood. Large breeze veranda for open air meals and relaxation. Large fence yard for sunbathing or playing around. Close to restaurants, shopping center, major hospital, beaches, parks and water sport activities. Perfectly located between Key Largo and Islamorada. Once you've been here you will want to come back.

Mar 5 – 12

$157 per night

Guest favorite

Apartment in Key West

4.89 out of 5 average rating, 135 reviews

Key West Beachside 1400sf, 2 Bedroom Condo

Welcome to our Key West Condo. This spacious well appointed 2 bedroom, 2 bath condo sleeps 6 and is next to the best beach on Key West. This condo is the perfect alternative to staying in a hotel. It gives you a true island experience. Great for Couples and Families We have a Website specific to our Condo where we offer special pricing, discounts and additional pictures Search-keywestbeachsidecondo

Mar 9 – 16

$656 per night

Superhost

Apartment in Key West

4.92 out of 5 average rating, 174 reviews

KW Luxury 2/2 Beachfront resort Tropical Oasis

1357 s f Luxury beachfront resort condo w/ all the amenities - beachfront heated Olympic pool, 3 lighted tennis courts, 20 man hot tub, tropical gardens, beach, saunas, Gym, BBQ Grills everything to make your vacation spectacular! You must be at least 25 years old to rent this property. This is a no animal rental due to extreme allergies of the owner. Thank you for understanding

Mar 4 – 11

$613 per night

Guest favorite

Apartment in Key West

4.97 out of 5 average rating, 236 reviews

Poolside Truman Annex 2 Bed | Conch Life Condo

Cozy condo in the Truman Annex to fully experience the conch life. It is close to Fort Zachery Beach and State Park, Hemingway House, Mallory Square, and Duval Street. Location is perfect due to Island proximity to any event and occasion. My place is a great getaway for couples, solo adventurers, business travelers, and families (with kids).

Aug 12 – 19

$279 per night

Superhost

Condo in Key West

4.85 out of 5 average rating, 106 reviews

Moonlight Paradise Upgraded Family oasis Tropical

:Moonlight is a totally renovated condo that is located at 1800 Atlantic Blvd on the beach, with sunset views right from your own private balcony. Beautiful tropical decor. No attention to detail has been spared. Stainless Appliances & luxurious finishes.

Dec 1 – 8

$624 per night

Guest favorite

Apartment in Key West

4.94 out of 5 average rating, 358 reviews

Studio Blu - Key West, FL - Hip Studio in Old Town

Location, location, location! Situated in the heart of the Cuban district, steps from arguably the best 'con leche' in Key West, this Studio apartment is minutes from everything on the island. No cars are necessary, bikes & beach chairs are provided.

Aug 13 – 20

$222 per night

Superhost

Apartment in Key West

4.79 out of 5 average rating, 209 reviews

The Green House ❀ Cool Shade

Unique and beautifully renewed apartment in the heart of Key West. Spacious bedroom with one king size bed and Walk-in Closet, large living room with pull-out sofa bed and kitchen. Take advantage of our unbeatable reopening price and enjoy! ♡

Mar 12 – 19

$449 per night

Guest favorite

Townhouse in Key West

4.92 out of 5 average rating, 265 reviews

Sparkling clean. Newly Updated Family Friendly

Great family home in the gated community of Coral Hammock, located just 10 minutes from the center of Key West. It boasts a beautiful salt water pool just steps away from the property. Perfect for families or groups of mature adults.

Aug 30 – Sep 6

$604 per night