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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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Rental unit in Key West

4.78 out of 5 average rating, 338 reviews

Key West - Sunrise ❀ The Green House

Unique and beautifully renewed apartment in the heart of Key West. Spacious bedroom with King Size bed and Walk-in Closet, large living room with pull-out sofa bed and kitchen. Take advantage of our unbeatable price and enjoy! ♡ Best location for exploring Key West, in the epicenter of Old-Town and all attractions. One corner from world-famous Sloppy Joe's (Hemingway's favorite place) and Duval Loop, the free local ride. Check out the map and see all attractions right around The Green House!

Rental unit in Key West

4.98 out of 5 average rating, 470 reviews

Bella Vita: 1B/1B Condo for 2 Just Steps off Duval

1B/1B condo located in Old Town less than 1/2 block from Duval St. & a couple blocks from the Southernmost Point, Hemingway House & many other Key West attractions. Bella Vita accommodates 2 adults only and features a large porch with chairs & table, living room with leather sofa, galley kitchen with bar seating, king-size bed with Tempurpedic mattress, desk area, bathroom with large walk-in shower, wi-fi, sound machine, 2 Smart TVs, DVD players & BlueTooth stereo system with CD player & radio.

Villa in Marathon

4.95 out of 5 average rating, 123 reviews

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

Wake up to breathtaking water views at our 4-bedroom, 3-bathroom villa. Enjoy the 1800 sq ft layout, fully equipped kitchen w/stainless steel appliances, and granite countertops. Sleeps 10 with memory foam beds. Outside, relax by your private heated pool (winter) and tiki-shaded area. Fish from the 32' dock or use the BBQ gas grill. Includes 2 kayaks, 2 paddleboards, and 4 adult bikes for a 5-minute ride to Sombrero Beach. Exterior cameras for security. Vacation License #VACA-22-40. Book now!

Home in Cudjoe Key

4.9 out of 5 average rating, 105 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.

Home in Key West

4.97 out of 5 average rating, 234 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.

Rental unit in Key West

4.92 out of 5 average rating, 178 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

Home in Marathon

4.95 out of 5 average rating, 123 reviews

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

House suits multiple families with kids, groups of couples, small and large families, or solos. Home is easy to get to, easy to get inside and the neighborhood is very peaceful. Plenty to do around the island or on the water. 5 large bedrooms and 3 large bathrooms with an open living room and a fully stocked kitchen. We look forward to hosting you.

Rental unit in Key West

4.96 out of 5 average rating, 256 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).

Townhouse in Key West

4.92 out of 5 average rating, 197 reviews

Spotlessly clean 3 bedroom/3 bathroom family home

Great family home in the gated community of Coral Hammock, located just 10 minutes from the center of Key West. It boasts a saltwater pool just steps away from the property. Perfect for families or groups of mature adults. All renters must be 25 or over or with a parent/guardian.

Condo in Key West

4.86 out of 5 average rating, 115 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.

Rental unit in Key West

4.94 out of 5 average rating, 376 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.

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Cottages

Quaint homes, peaceful surroundings

Villas

Luxurious estates for the ultimate escape

Popular amenities for Key West family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Condo in Key West

4.77 out of 5 average rating, 276 reviews

Affordable Beachfront Luxury Condo Sleeps 6

Villa in Marathon

4.87 out of 5 average rating, 119 reviews

Duck Key 4 BR Villa Dock Behind & Cabana Club

Condo in Key West

4.78 out of 5 average rating, 63 reviews

Casa Papa Del Mar on the Atlantic Spectacular view

Condo in Key West

4.66 out of 5 average rating, 187 reviews

Sunrise Suites Resort, Key West FL U #408 2bdr2bth

Condo in Tavernier

4.76 out of 5 average rating, 343 reviews

Florida Keys Getaway - Slps 4 - Ocean View

Condo in Tavernier

4.83 out of 5 average rating, 141 reviews

Bright & Sunny Suite w/ Magnificent Ocean Views

Townhouse in Marathon

4.81 out of 5 average rating, 133 reviews

Plunge Pool Villa on Blue Water Lagoon

Home in Key Colony Beach

4.82 out of 5 average rating, 145 reviews

Waterview from three sides, Cabana Club, 30' Docks

Family- and pet-friendly home rentals

Home in Key Largo

4.84 out of 5 average rating, 426 reviews

WATER VIEWS ON J. PENNEKAMP Free Kayaks

Home in Marathon

4.89 out of 5 average rating, 37 reviews

Sunset Catch Gulf Front, Pool, Dock, Kayaks, Fish

Home in Islamorada

4.97 out of 5 average rating, 176 reviews

Flakey's

Home in Cudjoe Key

4.61 out of 5 average rating, 158 reviews

Ocean Front Home in Great Location

Camper/RV in Key Largo

4.53 out of 5 average rating, 248 reviews

2 BR/2 BA Oasis w Kayak, Pool, Beach & Dock Rental

Villa in Marathon

4.87 out of 5 average rating, 55 reviews

New Paradise On Sombrero Beach

Home in Key Largo

4.91 out of 5 average rating, 98 reviews

Sunsets In Palms Paradise

Home in Key Colony Beach

4.72 out of 5 average rating, 47 reviews

2200 Sq Feet. 4 bedroom. 37 ft Dock & Pool Club!

Family-friendly home rentals with a pool

Townhouse in Marathon

4.96 out of 5 average rating, 76 reviews

Life in Paradise in #1 Resort - Coral Lagoon

Townhouse in Key Largo

4.97 out of 5 average rating, 67 reviews

Keys LaniKai Retreat.

Rental unit in Key Largo

5 out of 5 average rating, 48 reviews

Key Largo, Florida - Gem by the Sea

Home in Marathon

5 out of 5 average rating, 25 reviews

( #5)Beautiful 4 Bed 3 Bath Pool Home w Free Dock

Condo in Key Largo

4.89 out of 5 average rating, 84 reviews

Penthouse with Ocean View

Home in Key West

5 out of 5 average rating, 7 reviews

Incredible townhouse in Key West

Villa in Key Largo

4.96 out of 5 average rating, 57 reviews

Oceanfront/Marina/Great views/Incredible kitchen

Rental unit in Marathon

4.97 out of 5 average rating, 97 reviews

Beachfront Condo w/ Ocean Views in Marathon

Quick stats about vacation rentals that are family-friendly in Key West

Total rentals
1.2K properties
Nightly prices starting at
$70 before taxes and fees
Total number of reviews
27K reviews
Pet-friendly rentals
330 properties allow pets
Rentals with a pool
930 properties have a pool
Rentals with dedicated workspaces
660 properties have a dedicated workspace

Destinations to explore