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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, 339 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, 474 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 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.

Home in Key Largo

4.9 out of 5 average rating, 374 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.

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, 124 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

4.97 out of 5 average rating, 258 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, 377 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

Villas

Luxurious estates for the ultimate escape

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Key West family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a pool

Home in Key Colony Beach

5 out of 5 average rating, 39 reviews

Florida Keys Retreat with Cabana Club.

Home in Marathon

4.89 out of 5 average rating, 37 reviews

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

Home in Marathon

4.98 out of 5 average rating, 82 reviews

4BR 3B, Heated Pool & Spa, 60' Dock

Condo in Key West

4.82 out of 5 average rating, 44 reviews

Casa Arosa

Condo in Key West

4.87 out of 5 average rating, 93 reviews

Key Wes't Best- Upgraded condo 5 mins to Smathers

Townhouse in Key Largo

4.94 out of 5 average rating, 139 reviews

Your island home away from home!

Condo in Key West

5 out of 5 average rating, 22 reviews

Saltwater Harmony @ The Annex - Charming Condo

Home in Cudjoe Key

4.8 out of 5 average rating, 86 reviews

Palm Breezes! Room for Everyone on the Ocean.

Family-friendly home rentals with air conditioning

Townhouse in Marathon

4.83 out of 5 average rating, 47 reviews

Beautiful Coral Lagoon #12 in #1 Resort - Marathon

Home in Marathon

4.83 out of 5 average rating, 41 reviews

Waves of the Sea, Ocean View Home with Dock, Priva

Rental unit in Key Largo

5 out of 5 average rating, 49 reviews

Key Largo, Florida - Gem by the Sea

Tiny home in Key Largo

4.81 out of 5 average rating, 192 reviews

Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

Home in Marathon

5 out of 5 average rating, 25 reviews

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

Home in Key West

5 out of 5 average rating, 7 reviews

Incredible townhouse in Key West

Home in Key Largo

4.91 out of 5 average rating, 98 reviews

Sunsets In Palms Paradise

Condo in Key West

4.82 out of 5 average rating, 34 reviews

Henry's Piece of Paradise On The Ocean In Key West

Family-friendly home rentals with Wifi

Townhouse in Key Largo

4.97 out of 5 average rating, 67 reviews

Keys LaniKai Retreat.

Rental unit in Key West

4.79 out of 5 average rating, 222 reviews

The Green House ❀ Cool Shade

Home in Key West

4.85 out of 5 average rating, 145 reviews

Coral Hammock Poolside Home 3 bdrm 3 bath10 minute

Condo in Key Largo

4.89 out of 5 average rating, 84 reviews

Penthouse with Ocean View

Villa in Marathon

4.87 out of 5 average rating, 55 reviews

New Paradise On Sombrero Beach

Rental unit in Key Largo

4.83 out of 5 average rating, 319 reviews

Escape to the Keys!

Home in Key West

4.95 out of 5 average rating, 198 reviews

Lennon's Lodge, Luxury Accommodations for up to 6!

Home in Key West

4.91 out of 5 average rating, 138 reviews

A Royal Escape in Key West

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