
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.

Enjoy sunsets & sunrise in your home away home.
Keys largo best kept secret. Enjoy all that Florida keys have to offer. Superb location close to main land and best of all on the water. Enjoy sunset on your private dock. Don't worry about parking you have you very own private spot. Very close to miami if you wish to venture out off the Florida keys. Great beaches and great restaurants. Come and enjoy the best that Florida has to offer. Great location to relax. You can enjoy the pool, tennis and basketball. You can eat in the club on the water.

Charming 2BR cottage in prime keys location w/pool
Your slice of Islamorada awaits at Key Lime Cottage! Step inside this 2-bedroom retreat and you’ll instantly feel at home. Tucked in a quiet neighborhood yet right in the heart of the Florida Keys, it’s the perfect blend of relaxation and convenience. Enjoy a full kitchen, access to a beautiful pool shared with just six homes, outdoor seating with a grill and fire pit and paddle boards. Whether you’re here to unwind, explore, or fish, everything you need for a perfect Keys getaway is right here.

Toes in the Sand - 2 Bedroom Condo Sleeps 4
Two bedrooms and two full bathrooms on the 4th floor with ocean views. Amenities include a huge heated pool and hot tub with a bar, a beach cafe serving food and drinks, a private Key's beach, viewing pier, rentable boat slips & boat trailer storage, tennis, pickleball courts, basketball, children's swings, and BBQ areas, and gated entry with 24-hour security! Just remember that you're on "Island Time," mon, relax and enjoy! Perfectly located between Key Largo and Islamorada, close to Penneka

Large Waterfront Home, w/Efficiency, Pool, Kayaks
Large Waterfront home completely renovated in gated upscale community. 2/2 upstairs and complete 1/1 efficiency downstairs. Highest Airbnb Rating in the area. Only 12 houses away from the Bay and near many restaurants and attractions. BRAND NEW POOL along with new GAZEBO and BBQ area (Not shown it some pictures). Enjoy sunset cruises, island hopping and dock-side dining. 60' of waterfront, large dock and 2 kayaks available. pontoon rental available for Bayside only. Must be 25 or older.

Oasis2 in Key Largo With a million dollar view
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.

Luxury Heated Pool/Jacuzzi, Games & Nice Backyard.
✨Bring the whole family to this great located house with a nice pool with spa, combo game table and lots of room for fun, and enjoy the beach, restaurants and entertainments around the area. ✨5BRs with smart TVs and comfortable mattresses and pillows. 3BR upstairs/2BR downstairs. ✨3 bathrooms, 1BR downstairs/2BR upstairs. ✨2 kitchens fully equipped with everything you may need. ✨Nice and quite neighborhood. ✨Sunsets are amazing at The Florida Keys. ✨Guest are always our priority.

Tiki Time! Private Pool~Tiki Hut~Kayaks~Grill!
Tiki Time ~ your private paradise in beautiful Marathon, heart of the Florida Keys! This is the perfect place for a family vacation or relaxing getaway. Gorgeous 3BR home with your own private salt water pool, Tiki Hut, space to park a 30' boat/trailer, and ocean views from the balcony~Kayaks, grill, beach toys await you for your beautiful day in the Florida Keys! Less than 5 min to Sombrero Beach, Dining & Local Bars! Experience the Florida Keys like a local and book Tiki Time today!

Waterfront Home 37.5-ft dock, Cabana Club Included
Bright, Open Floor Plan with new floors & kitchen. East facing for sunny mornings and shady afternoons on the great screened porch. Two roomy bedrooms and 2 full baths. Plenty of parking on the paved driveway. Perfectly located with the boater and angler in mind on a 37. 5 ft concrete dock, on deep & wide canal. Here on Key Colony Beach you can walk or bike the entire city to the marina, Sunset Park, 3 restaurants, play golf, tennis, pickle ball, bocce ball, horseshoes & basketball.

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.

P88 - New on the rental market! 3 bedroom, 2 bath
Enjoy Marathon in this lovely 3 bedroom 2 bath canal home with private pool, located minutes from Sombrero Beach! Boasting a fully equipped kitchen with an open floor plan this home provides ample space for the perfect vacation! - Maximum Occupancy: 6 maximum (*children of any age, including infants, count toward occupancy) - No day guests or visitors allowed above the max advertised occupancy. - Parking: 3 vehicle max (*parking for 1 trailer only) - Deep Water Dock: 50 feet

New Aqua Lodge 2Beds 1 Bath with Full Kitchens
This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!

“Have Fun at Hacienda Paraíso” Suite 1 | pool |
Welcome to Room 1, the first addition at Hacienda Paraíso. This suite is conveniently located next to another Airbnb suite, providing flexibility for your stay. It features a private entrance, bathroom, kitchenette, and dining table, ensuring a comfortable and self-contained experience. Enjoy the convenience of hotel-like amenities paired with the added bonus of access to our stunning pool and lush yard, creating a truly relaxing retreat.
Popular amenities for Florida Keys family-friendly rentals
Family-friendly home rentals with a hot tub

Your Happy Place - Oceanfront

The Lighthouse - Beach Houses Key West

King MSTR, SS Quartz Kitchen, Bikes Kayaks, VIEWS!

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

Mariners 212 Great Location with Marina Views

Luxurious Suite+Open Ocean Views+Pool & Cabana Bar

Palm Breezes! Room for Everyone on the Ocean.

Waterfront Sanctuary in the Keys!
Family- and pet-friendly home rentals

Dream Catamaran

Coastal Oasis #44 Key Largo 4BR Villa | Partial

Everglades-Homestead. Tropical Retreat. Miami-Keys

Flakey's

Ultimate Heated Pool Escape:Midway to Keys & Miami

Waterfront Studio 2| Couples Oasis | Kayaks | Pool

Tropical Paradise Between Miami and the FL Keys

Premium Floating Bungalow by Stay Ombi
Family-friendly home rentals with a pool

Modern Casita

Ocean Escape 97

Seas the Keys Getaway with plunge pool/spa

Renovated Anglers Reef 2BR + Sleeper + Ocean Views

Special Spring Break Stay Home in Marco Island

Remodeled July 2025 2/2 Townhouse

Waterfront 6BR Luxury Retreat w/ Pool & Dock

Complimentary Breakfast & Daily Housekeeping!
Destinations to explore
- Seminole Holiday rentals
- Central Florida Holiday rentals
- Miami Holiday rentals
- St Johns River Holiday rentals
- Orlando Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Havana Holiday rentals
- Tampa Holiday rentals
- Four Corners Holiday rentals
- Kissimmee Holiday rentals
- Campsite rentals Florida Keys
- Ski-in/ski-out rentals Florida Keys
- Beach condo rentals Florida Keys
- Condo rentals Florida Keys
- Pet-friendly rentals Florida Keys
- Rentals with an EV charger Florida Keys
- Hotel rooms Florida Keys
- RV rentals Florida Keys
- Beachfront rentals Florida Keys
- Rentals with a home theatre Florida Keys
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- Rentals with a washing machine and dryer Florida Keys
- Rentals with an accessible height bed Florida Keys
- Villa rentals Florida Keys
- Rentals with outdoor seating Florida Keys
- Rentals with beach access Florida Keys
- Townhouse rentals Florida Keys
- Houseboat rentals Florida Keys
- Fitness-friendly rentals Florida Keys
- Rentals with a fire pit Florida Keys
- Rentals with an accessible height toilet Florida Keys
- Bungalow rentals Florida Keys
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- Boat rentals Florida Keys
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- Rentals with a hot tub Florida Keys
- Private suite rentals Florida Keys
- Holiday home rentals Florida Keys
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- Rentals with breakfast Florida Keys
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- Family-friendly rentals Florida
- Family-friendly rentals United States
- Bayfront Park
- Bayside Marketplace
- Kaseya Center
- Brickell City Centre
- Everglades National Park
- University of Miami
- Calle Ocho Plaza
- Sombrero Beach
- LoanDepot Park
- Dolphin Mall
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Florida International University
- Key Biscayne Beach
- Biscayne National Park
- CG Cosmetic Surgery
- Crandon Beach
- Biltmore Golf Course Miami
- Avana Plastic Surgery
- Phillip and Patricia Frost Museum of Science
- Coral Castle
- Fairchild Tropical Botanic Garden
- Schnebly Redland's Winery & Brewery
- Sea Oats Beach
- Things to do Florida Keys
- Food and drink Florida Keys
- Tours Florida Keys
- Nature and outdoors Florida Keys
- Art and culture Florida Keys
- Sightseeing Florida Keys
- Sports activities Florida Keys
- Things to do Florida
- Entertainment Florida
- Art and culture Florida
- Sightseeing Florida
- Tours Florida
- Food and drink Florida
- Nature and outdoors Florida
- Wellness Florida
- Sports activities Florida
- Things to do United States
- Wellness United States
- Food and drink United States
- Nature and outdoors United States
- Sports activities United States
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