
Family-friendly holiday rentals in Florida Keys
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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, 182 reviews
Cottage By The Sea
Cottage By The Sea...! If you love turtles.This is the spot for you.I have a 150 pound giant sulcata tortoise in the front yard.And then I have four other little turtles that live in an enclosement , also in the front yard and a giant snapping turtle in my koi pond Our 2 bedroom Guest House is located on the Oceanside of Key Largo in a quaint and quiet neighborhood, with a huge yard surrounded by exotic flowers and trees. It is walking distance to a famous local's Tiki Bar and Restaurant
4.9 out of 5 average rating, 422 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
Oceanfront Lookout Point w/two Kayaks & Deck
Lookout Point is Wide open breathtaking Water View , Amazing Sunrises with a cup of Morning coffee, Refreshing breeze, Sound of water and Rustle of palm trees will start your day… Fishing right from the property, Kayaking. Taking sunbath on Chaise lounges or Reading books or just sitting under Tiki having a nice conversations and enjoying beautiful scenery of the view. You will see fishes jumping out of water, seagulls trying to catch up it , you might see manatee swimming by or dolphins.
4.96 out of 5 average rating, 213 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, 237 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
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!
4.86 out of 5 average rating, 619 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
Angler's Eden
Amazing get-away in the beautiful Florida Keys! This property (constructed in 2018) is a haven for families seeking to escape to paradise year-round. Situated on a deep water canal with ocean access and enough dock space to park your boat for the week. A floating dock is also provided with kayaks. Enjoy the large pool or ping pong table, or lounging in the sun! Beautiful Sombrero Beach is within walking distance (approx 1.5 miles) via a paved bike path.
4.97 out of 5 average rating, 114 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

Ocean Pointe Condo | Beach, Pool, Hot Tub & Tennis
5.0 out of 5 average rating, 103 reviews
Casa Solaris | Key Largo home with Private Pool!
4.95 out of 5 average rating, 117 reviews
Florida Keys Resort-Style Home w/ Pool & Dock 5/3
4.95 out of 5 average rating, 152 reviews
Palm Breezes! Room for Everyone on the Ocean.
4.83 out of 5 average rating, 112 reviews
When Paradise is Key: Tropical Oceanfront Condo
4.88 out of 5 average rating, 102 reviews
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
Gorgeous Ocean View in Paradise, Close to Key West
4.99 out of 5 average rating, 141 reviewsFamily- and pet-friendly home rentals

Waterfront Cozy Cottage with Boat Ramp & Dock
4.89 out of 5 average rating, 185 reviews
Flakey's
4.97 out of 5 average rating, 220 reviews
Cottage 30 min from Key West, free parking, pool
4.88 out of 5 average rating, 133 reviews
Tiny Home on Waterfront | Bay Views | Deck | Pool
4.91 out of 5 average rating, 208 reviews
The Miracle Cottage & Pool on Acre Miami Florida
4.97 out of 5 average rating, 430 reviews
South Miami Gem • Mini Golf, Pool table • Pool_BBQ
4.85 out of 5 average rating, 163 reviews
Resort Style Pool House 5 Bed Mini-Golf Pool Table
4.8 out of 5 average rating, 173 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
Luxury Oasis, Pool, Kayaks, Dock, Near Beach
5.0 out of 5 average rating, 18 reviews
Tropical Keys Retreat | Pool | Hot Tub | Cinema
5.0 out of 5 average rating, 81 reviews
Waterfront Pool Home w/ Private Dock, Tiki Hut & B
5.0 out of 5 average rating, 5 reviews
Serenity Oasis~Pool!~Putt-Putt!~Kayaks~Bikes~Spa
5.0 out of 5 average rating, 52 reviews
🏝Beautiful🏖 Water🏊♀️ View🌅 Pool Gym🏋️ Room, Private⛵️ Dock⚓️
4.96 out of 5 average rating, 56 reviews
Beach House, Private Pool, Dock, Gulf View Sunsets
4.93 out of 5 average rating, 82 reviews
Kampground Paradise w/Kayaks, Heated Pool & Marina
4.95 out of 5 average rating, 80 reviewsDestinations to explore
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