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Family-friendly vacation rentals in Florida Keys

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Florida Keys

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Home in Key Largo

4.84 out of 5 average rating, 426 reviews

WATER VIEWS ON J. PENNEKAMP Free Kayaks

Ocean views on Largo Sound, totally renovated home with large TV’s, spacious living area, 2 Large Balconies including roof top great for star gazing, all the amenities of home. Free use of kayaks at the house, Kayak John pennekamp state park steps away from front door. 27 foot boat available 4 all water activities Which I captain.Quiet private street close to all keys activities and restaurants. There is a downstairs space that on a very rare occasion is occupied by myself or family member

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!

Townhouse in Duck Key

4.98 out of 5 average rating, 155 reviews

3Bd 3Ba Cottage/Village at Hawks Cay/Ocean Views

Our Cottage is located between Islamorada and Marathon Key on Duck Key at the Village of Hawks Cay; one of the most desirable locations in the Florida Keys. This is at Mile Marker 61. With ocean views, high end finishes, comfy beds and plenty to do in the surrounding areas, the Cottage offers something for everyone. The outdoor green space overlooking the water is gorgeous. Sunsets are amazing right off the screened in lanai. We hope to host you as our guest in the beautiful Florida Keys.

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 Islamorada

4.97 out of 5 average rating, 176 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.

Rental unit in Key Largo

4.83 out of 5 average rating, 317 reviews

Escape to the Keys!

Charming Keys Home located in a quiet residential neighborhood on the bay side. The house is on the 2nd floor with a large breeze balcony, great space to relax with a cup of coffee, tea or wine. Large fenced yard for sunbathing or for kids to run and play. Close to restaurants, shopping center, major hospital, beaches, parks and water sport activities. Perfectly located between Key Largo and Islamorada.

Boat in Miami

4.98 out of 5 average rating, 726 reviews

Hunter 26 Sailboat

A one-of-a-kind experience for those who want to enjoy Miami from a different perspective. Can accommodate up to two people, includes a basic toilet and freshwater. The boat is anchored in Biscayne Bay, which allows you to view the Miami skyline from a distance. You'll be in the famous Coconut Grove area. I will be taking you from the dinghy dock to the boat. Two kayaks are included for guests.

Guest suite in Homestead

4.99 out of 5 average rating, 271 reviews

beautiful private king studio on nearly 5 acres

Close to Everglades National Park, Biscayne National Park, FL Keys, located in the Redland tropical agricultural area. This is a gated property with secure parking for campers, boats, trailers, etc. The studio is totally renovated with the highest quality of materials. Fruit is available to guests when in season and there is usually something in season during the year.

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).

Vacation rentals for every style

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Villas

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Popular amenities for Florida Keys family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Rental unit in Coconut Grove

4.95 out of 5 average rating, 165 reviews

Stunning Corner Water/City View Free Pkg/Pool

Home in Homestead

4.93 out of 5 average rating, 375 reviews

Private Paradise between Miami & the Keys

Rental unit in Marco Island

4.93 out of 5 average rating, 242 reviews

Best JW Marriott Alternative Prime~ Location~Pool

Condo in Tavernier

4.83 out of 5 average rating, 141 reviews

Bright & Sunny Suite w/ Magnificent Ocean Views

Guest suite in Miami

4.87 out of 5 average rating, 474 reviews

Studio Apartment Dino's Place

Rental unit in Tavernier

4.83 out of 5 average rating, 257 reviews

Breathtaking Oceanfront Views at Tropical Daze

Rental unit in Miami Beach

4.91 out of 5 average rating, 184 reviews

Ocean View Sorrento Fontainebleau Miami Beach Unit

Condo in Miami

4.95 out of 5 average rating, 546 reviews

Marriott Villas and Doral 2BD sleeps 8

Family- and pet-friendly home rentals

Home in Miami

4.92 out of 5 average rating, 167 reviews

Private Pool and Tropical Garden Oasis

Condo in Miami Beach

4.86 out of 5 average rating, 170 reviews

FontaineBleau|1BR Ocean View w/ Balcony

Guesthouse in Miami

4.94 out of 5 average rating, 547 reviews

Brand NEW Cottage with Gorgeous Patio! 5 mi Beach!

Guesthouse in Miami

4.89 out of 5 average rating, 344 reviews

Charming private cottage for two.

Townhouse in Key West

4.92 out of 5 average rating, 197 reviews

Spotlessly clean 3 bedroom/3 bathroom family home

Rental unit in Oakland Park

4.96 out of 5 average rating, 165 reviews

Renovated cozy private small one bedroom apt

Guesthouse in South Miami

4.97 out of 5 average rating, 232 reviews

Cozy Cane Cottage close to UM

Serviced apartment in Miami Beach

4.87 out of 5 average rating, 279 reviews

1 Hotel 1BR/1.5BA Beachfront Residence w/ Balcony

Family-friendly home rentals with a pool

Townhouse in Key Largo

4.84 out of 5 average rating, 116 reviews

LIC. MGR. - 2/2 VILLA - OCEANFRONT BEACH RESORT!

Condo in Hollywood

4.98 out of 5 average rating, 120 reviews

Oceanfront condo with amazing views

Hotel room in Miami Beach

4.89 out of 5 average rating, 253 reviews

OCEAN AND BAY VIEW LUXURY 1BR MONTE CARLO PARKING!

Rental unit in Miami Beach

4.78 out of 5 average rating, 121 reviews

Special 1BR Apartment Daily Cleaning Include

Rental unit in Key Biscayne

4.93 out of 5 average rating, 186 reviews

Key Biscayne Unit 1/2 block from the beach

Home in Marco Island

4.98 out of 5 average rating, 294 reviews

⭐ Rare Waterfront Western Exposure Vacation Home

Townhouse in Key Largo

4.94 out of 5 average rating, 139 reviews

Your island home away from home!

Condo in Marco Island

4.99 out of 5 average rating, 117 reviews

Incredible Waterfront Views, Dock, Pool & Fishing!

Destinations to explore