
Family-friendly holiday 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.

Sunrise Escape - Ocean Front Villa - Sleeps 10
Wake up to the sunrise over the ocean and unwind with sunset views from your private jetty. This marina-front, ocean-view townhouse in Kawama Yacht Club puts you steps from kayaking, snorkeling, and the best of the Keys. Spacious, stylish, and designed for unforgettable family and friend getaways. Breathtaking sunrises from one of two private terraces, coffee in hand, overlooking the marina and the Atlantic Ocean. Located in an exclusive, quiet section of Kawama Yacht Club, this beautifully po
4.87 out of 5 average rating, 181 reviews
Captain’s Quarters Ahoy Mateys! Florida, Keys
This is located at the Florida Keys in Key Colony, Marathon. It is a spacious two bedroom, two bathroom duplex surrounded by water. It is a renovated beauty and close to the best restaurants and the tranquility of this city. It is the perfect getaway where you can recharge your exhausted batteries. Captain’s Quarters is a clean and spacious base camp location for the many adventures that await you in this amazing location. Water views and the accessibility to the best fishing in the world.
4.93 out of 5 average rating, 154 reviews
My Little Oasis2 Waterfront Retreat, Key Largo
Million Dollar view at a fraction of the price! This property is on the water with amazing bay views. It includes one kayak for 2 people, paddle board, fishing rod, washer and dryer, kitchen with all cooking utensils. Note: The upstairs room is not comfortable for seniors or adults, the ceiling height is 4 feet (an adult has to walk on his knees). The property is located on a residential island, restaurants, bars, stores and grocery stores are within a 15 minute drive from the property.
4.97 out of 5 average rating, 236 reviews
Cozy Cottage
Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with 250 foot dock, ramp, and basin for your boat. It's a must-see rustic outdoor environment and fishery experience, very typical in the Keys! The property lot is almost an acre with a work section and still very spacious. Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the dock and enjoy the underwater scenery!
4.89 out of 5 average rating, 185 reviews
When Paradise is Key: Tropical Oceanfront Condo
🚨*PRICE YOU SEE IS ALL IN! Includes Airbnb fees and taxes!*🚨 🚨09.09.26 - 10.14.26 Elevator will be out of service due to installation of a new elevator 🚨 ☀️ Discover the ultimate beachfront getaway in our top floor, two-bedroom, two-bathroom condo, perfectly designed to offer an unforgettable escape. Nestled right on the oceanfront, this retreat comfortably accommodates up to six guests, making it ideal for families, friends, or couples seeking a serene coastal experience. ⛱️
4.88 out of 5 average rating, 102 reviews
360 DEGREE WATERVIEW HOUSEBOAT
IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.
4.93 out of 5 average rating, 394 reviews
The Lighthouse - Beach Houses Key West
If you’re reading this, you’re already one step closer to paradise. Thank you for considering us for your getaway. Our charming Lighthouse Bungalow is a 2-bedroom, 1-bath loft-style retreat located just steps from our private beach. The master bedroom loft, accessed by a spiral staircase, offers a stunning bird’s-eye view of the Atlantic Ocean. The nautical-inspired living area opens to an exterior deck overlooking the beach—an ideal spot for peaceful mornings and ocean breezes.
4.93 out of 5 average rating, 134 reviews
Cudjoe Key Home with a View
We are so excited to share our little piece of paradise with you! Our unit is located a short walk away from all the amenities the Venture Out community has to offer such as a pool, hot tub, lagoon, bocce ball, tennis courts, playground and boat marina. On the property we have a 2-person hybrid kayak for your enjoyment. We also provide table games (we love a game night) as well as the equipment to play bocce ball and darts which can be played in the recreation center.
4.96 out of 5 average rating, 213 reviews
Gorgeous Ocean View Home!
Beautiful family friendly ocean view home centrally located in the heart of Marathon (only 10min from Sombrero Beach) were you’ll be able to do many things like snorkeling, fishing, boating, Scuba, museums, visit the aquarium, and/or the dolphin research center, and even dine on the water with many restaurants selections near by. This property does NOT have dock space for a boat or trailer parking. Licensed and inspected by the city of Marathon Lic.# VACA-23-144
4.84 out of 5 average rating, 100 reviews
Palm Breezes! Room for Everyone on the Ocean.
This 5 bedroom 3 bath house with pool on Ocean front property on Highway 1.. This lovely home has its own huge pool area with full lounge chairs all the way around pool area, the pool is heated. Grill, Jacuzzi. Full WiFi. TVs in every bedroom! Travel down our private dock way to the beautiful Cudjoe Bay, hop one of the many kayaks and take a healthy paddle with your friends/family or just enjoy the breathtaking ocean view while you sit on the porch.
4.83 out of 5 average rating, 112 reviews
Florida Keys Resort-Style Home w/ Pool & Dock 5/3
Perfect for families, couples, groups, or solo travelers, this spacious home offers 5 bedrooms, 3 bathrooms, an open living room, and a fully stocked kitchen. Easy to reach and simple to access, it’s set in a peaceful neighborhood close to island fun and water adventures. Just a short walk to Sweet Savannah’s Ice Cream & Sweets Parlor, this retreat is ideal for relaxing or exploring. We look forward to hosting you!
4.95 out of 5 average rating, 152 reviews
70ft Dock, Bikes, Beach, Spacious, VACA23-16
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.
4.94 out of 5 average rating, 206 reviewsPopular amenities for Florida Keys family-friendly rentals
Family-friendly home rentals with a hot tub

Largo Getaway: 3 King Suites + In-Law Space
4.93 out of 5 average rating, 100 reviews
Oceanfront Resort W/Indoor Pickleball - Speakeasy!
4.82 out of 5 average rating, 126 reviews
Ocean Pointe Condo | Beach, Pool, Hot Tub & Tennis
5.0 out of 5 average rating, 103 reviews
Private Paradise between Miami & the Keys
4.93 out of 5 average rating, 456 reviews
Casa Solaris | Key Largo home with Private Pool!
4.95 out of 5 average rating, 116 reviews
4BR 3B, Heated Pool & Spa, 60' Dock
4.95 out of 5 average rating, 108 reviews
ATLANTIS...Ocean Front Cottage Retreat!
4.89 out of 5 average rating, 178 reviews
Miami Luxury Escape w/Heated Pool/Jacuzzi & BBQ
4.9 out of 5 average rating, 182 reviewsFamily- and pet-friendly home rentals

New Aqua Lodge 2Beds 1 Bath with Full Kitchens
4.86 out of 5 average rating, 619 reviews
South Miami Gem • Mini Golf, Pool table • Pool_BBQ
4.85 out of 5 average rating, 163 reviews
Flakey's
4.97 out of 5 average rating, 220 reviews
Tiny Home on Waterfront | Bay Views | Deck | Pool
4.91 out of 5 average rating, 207 reviews
Cottage 30 min from Key West, free parking, pool
4.88 out of 5 average rating, 133 reviews
The Miracle Cottage & Pool on Acre Miami Florida
4.97 out of 5 average rating, 430 reviews
Resort Style Pool House 5 Bed Mini-Golf Pool Table
4.8 out of 5 average rating, 172 reviews
Marathon Oceanfront 4BR Private Pool 60’ Boat Dock
5.0 out of 5 average rating, 6 reviewsFamily-friendly home rentals with a pool

Private Pool Tropical Oasis - Centrally Located
5.0 out of 5 average rating, 120 reviews
Angler's Eden
4.97 out of 5 average rating, 114 reviews
Your Key Colony Beach Paradise Awaits!
4.96 out of 5 average rating, 184 reviews
Oceanfront Lookout Point w/two Kayaks & Deck
4.96 out of 5 average rating, 213 reviews
The Paradise 2
4.9 out of 5 average rating, 174 reviews
Luxury Oasis, Pool, Kayaks, Dock, Near Beach
5.0 out of 5 average rating, 18 reviews
Pescayo Paradise-Luxurious Waterfront-75 ft Dock
5.0 out of 5 average rating, 15 reviews
Tropical Keys Retreat | Pool | Hot Tub | Cinema
5.0 out of 5 average rating, 81 reviewsDestinations to explore
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