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Kid-friendly holiday rentals in Islamorada

Find and book unique family-friendly rentals on Airbnb

Top-rated family-friendly rentals in Islamorada

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

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Holiday home in Key Largo

4.84 out of 5 average rating, 254 reviews

Charming Waterside Cabana in Key Largo | Cabana 4

Enjoy water front living in Key Largo! Watch the boats go by with fresh catch served daily at the local restaurants. See manatees, nurse sharks and fish swim by the canal all day. Dock your boat at the Pilot House Marina just down the street. Our unit is Modern, Spacious and Spotless with Private Parking, Fast Wifi, Netflix, Cold AC, Plush Pillows and a Cozy bed. We are on a main canal to open ocean. Near Rodriguez Key, Mosquito Bank, Christ of the Abyss and many sunken shipwrecks for exploring.

18–25 Jul

$254 SGD per night

Guest favourite

Flat in Tavernier

4.89 out of 5 average rating, 434 reviews

Capt Craigs 1 Bedroom /1 Bath Apartment

Capt. Craig’s Guest Quarters The Starfish is a luxurious retreat located in Islamorada. Only 1 ½ hours from Miami International Airport, we are located in the heart of the fishing and diving areas of the Florida Keys. From watersports, to eco tours, to parasail, to museums, shopping and beaches, allow us to be your base for all of your Florida Keys activities. Freshly remodeled with the traveler in mind, enjoy our little piece of paradise...minutes from all that the Upper Keys has to offer.

14–21 Jul

$272 SGD per night

Guest favourite

Guest suite in Marathon

4.98 out of 5 average rating, 185 reviews

Casa Mariposa: Easy walk to Sombrero Beach

Book your relaxing getaway now at Casa Mariposa in the heart of the Florida Keys! See why we were rated a top 15 cozy retreat in the Keys, 1 0f 24 amazing AirBNB rentals in the Keys, and, in 2023, 1 of 23 Amazing Airbnbs In Florida Keys. Step out from your private suite to our 50' lap pool surrounded with tropical foliage, large patio, and tropical gardens. Avoid beach parking fees with a short walk from your suite at Casa Mariposa! Contact us if you are interested in other lengths of stay.

12–19 Oct

$302 SGD per night

Guest favourite

Apartment in Tavernier

4.95 out of 5 average rating, 108 reviews

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

Welcome to our remodeled costal 1BR 1 Bath condo nestled in the premier oceanfront complex in Tavernier, FL. Escape to paradise and enjoy the wonderful Ocean views from the private balcony while just a few steps away from the sunny private beach, marina, minutes away from restaurants, shops, and attractions. ✔ Comfortable Queen BR ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Balcony ✔ Smart TVs/WI FI ✔ Complex Amenities (Pool, Hot Tub, Marina, BBQ, Sports, Free Parking) Learn more below!

30 Aug – 6 Sep

$372 SGD per night

Guest favourite

Flat in Key Largo

4.94 out of 5 average rating, 248 reviews

Waterfront Studio 1| Kayaks | Pool |Bay View |Wifi

Escape to Northern Key Largo for a relaxing vacation! Discover great restaurants, beautiful state parks, and marine life. This bright, modern studio boasts excellent views of Manatee Bay, free kayaks and paddle boards, and a full kitchen. With access to a swimming pool and docks, there’s always something to do. 10 Min Drive to the Gilbert’s Resort 15 Min Drive to John Pennekamp Coral Reef State Park 22 Min Drive to African Queen Canal Cruise Experience Key Largo With Us & Learn More Below!

28 Oct – 4 Nov

$246 SGD per night

Guest favourite

Cottage in Key Largo

4.96 out of 5 average rating, 146 reviews

Charming Key Largo Cottage on the Water w/Kayaks!

Charming "Tiny House" Cottage on a main canal just two units from open water. Amazing location for boaters, fisherman and alike. This is a quaint and close knit RV park where you can keep to yourself or wander around and enjoy happy hour with new local friends. Bar none the best kayak, paddle board and fishing area. Two Tandem (each kayak accommodates two people) Kayaks and two paddle boards included in rental. Great outdoor space to dock your boat, fish off of or enjoy a few cocktails!

2–9 Oct

$497 SGD per night

Guest favourite

Holiday home in Key Largo

4.99 out of 5 average rating, 145 reviews

Waterfront, GROUND LEVEL, Awesome Sunsets!!!

This ground level unique location is close to everything. Walk to some of the most iconic restaurants and bars Key Largo has to offer for fresh seafood and awesome drinks! We Do Not allow fishing on our Property! Dockage Available for additional fee! Enjoy the amazing sunsets over the water from your private porch and dock. John Pennekamp Coral Reef State Park close by. Walk to dolphin research center!! 28 day rental I am a licensed charter boat captain and offer discounts for all guests

19–26 Sep

$281 SGD per night

Guest favourite

Boat in Islamorada

4.9 out of 5 average rating, 171 reviews

HOUSEBOAT 2BD, PRIVATE KEYS COTTAGE LOGGERHEAD

Tucked away in the vibrant Florida Keys, is our pristine paradise. We are located in the heart of Islamorada, where the weather is always gorgeous, the fishing never disappoints, and the sunsets are mesmerizing. If you are seeking a relaxing get away, look no further. On site, you will have the luxury of renting your own private boat. Boat rentals are 20% off for guests! Unfortunately, we do not have spare slips for private boats at this time. A 5% lodging tax will be charged on arrival.

11–18 Sep

$241 SGD per night

Guest favourite

Home in Islamorada

4.97 out of 5 average rating, 166 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.

30 Nov – 7 Dec

$366 SGD per night

Guest favourite

Boat in Islamorada

4.92 out of 5 average rating, 327 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.

8–15 Apr

$260 SGD per night

Guest favourite

Guest house in Key Largo

4.91 out of 5 average rating, 192 reviews

Oceanside, 1 bedroom, Bungalow in Key Largo

Canal front bungalow with beautiful views of the ocean. Private water front and pergola with steamer chairs and hammock. BBQ your fresh catch while lounging on the back porch, relaxing in the tropical landscape. One bedroom with Queen bed. Queen size pull-out couch in the living-room. Full kitchen boasting high-end appliances. One Car Parking by unit. Centrally located between shopping centers and destination activities.

5–12 Oct

$281 SGD per night

Guest favourite

Home in Key Largo

4.9 out of 5 average rating, 348 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.

28 Sep – 5 Oct

$253 SGD per night

Holiday rentals for every style

Get the amount of space that is right for you

Villas

Luxurious estates for the ultimate escape

Cottages

Quaint homes, peaceful surroundings

Houses

A space that's all yours, with room for everyone

Popular amenities for Islamorada family-friendly rentals

Free parking on premises

Air conditioning

Kid-friendly house rentals

Guest favourite

Home in Marathon

4.99 out of 5 average rating, 106 reviews

Sea Ray Cove , 75’ boat dock, 1 block from beach!

24–31 Aug

$566 SGD per night

Guest favourite

Home in Marathon

4.96 out of 5 average rating, 125 reviews

Oceanfront Tiny Villa in the Heart of the FL Keys

28 Jul – 4 Aug

$689 SGD per night

Guest favourite

Home in Islamorada

4.98 out of 5 average rating, 140 reviews

Porter’s Corner

10–17 Jun

$646 SGD per night

Guest favourite

Home in Marathon

4.91 out of 5 average rating, 159 reviews

Beachfront Villa - Florida Keys

28 Nov – 5 Dec

$609 SGD per night

Guest favourite

Home in Tavernier

4.87 out of 5 average rating, 208 reviews

Clean Houseboat w/ Great Wi-Fi,Luxury on the water

19–26 Oct

$567 SGD per night

Guest favourite

Home in Marathon

4.97 out of 5 average rating, 118 reviews

Marathon one-level home on the Marina - with slip!

23–30 Mar

$889 SGD per night

Guest favourite

Home in Key Largo

4.96 out of 5 average rating, 135 reviews

Key Largo Waterfront Home with Tiki & Boat Dock

26 Sep – 3 Oct

$399 SGD per night

Guest favourite

Home in Key Largo

4.88 out of 5 average rating, 163 reviews

Outdoor Paradise - Beach, Boats, Snorkeling & Sun!

3–10 Aug

$275 SGD per night

Family-friendly apartment rentals

Guest favourite

Flat in Tavernier

4.95 out of 5 average rating, 149 reviews

Capt Craigs 1 Bedroom /1 Bath Apartment

14–21 Nov

$291 SGD per night

Guest favourite

Flat in Tavernier

4.95 out of 5 average rating, 147 reviews

Boho FL Keys Condo

11–18 Apr

$573 SGD per night

Guest favourite

Flat in Key Largo

4.98 out of 5 average rating, 125 reviews

Key Largo Kawama Lagoon Free Cancel Deutsch Spain

29 Jul – 5 Aug

$432 SGD per night

Guest favourite

Flat in Tavernier

4.83 out of 5 average rating, 255 reviews

Breathtaking Oceanfront Views at Tropical Daze

3–10 Apr

$415 SGD per night

Guest favourite

Flat in Tavernier

5.0 out of 5 average rating, 15 reviews

Beautiful condo with a balcony

20–27 Jun

$297 SGD per night

Guest favourite

Flat in Key Largo

5.0 out of 5 average rating, 21 reviews

Studio apartment in Calusa Resort & Campgrounds

12–19 Nov

$225 SGD per night

Guest favourite

Flat in Tavernier

4.96 out of 5 average rating, 25 reviews

2 Bed 2 Bath Remodeled Condo!

9–16 Jul

$424 SGD per night

Guest favourite

Flat in Tavernier

5.0 out of 5 average rating, 13 reviews

Turtles Nest 2 Ocean Point condo

10–17 Jan

$474 SGD per night

Family-friendly apartment rentals

Guest favourite

Apartment in Tavernier

4.88 out of 5 average rating, 228 reviews

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!

27 Aug – 3 Sep

$341 SGD per night

Guest favourite

Apartment in Key Colony Beach

4.9 out of 5 average rating, 249 reviews

Coastal Key Colony Beach Condo, Oceanfront Complex

19–26 Oct

$335 SGD per night

Guest favourite

Apartment in Key Colony Beach

4.91 out of 5 average rating, 112 reviews

Beachside Unit 39 Tiki Huts, Private Beach & Pool

22–29 Aug

$323 SGD per night

Guest favourite

Apartment in Tavernier

4.96 out of 5 average rating, 159 reviews

Best View Ocean Pointe Pool Beach King Bed, Gated

11–18 Dec

$580 SGD per night

Guest favourite

Apartment in Tavernier

4.93 out of 5 average rating, 133 reviews

It's Tiki Time! Top Floor SeaView Mid-Mod 1 Br/1Ba

14–21 Feb

$584 SGD per night

Guest favourite

Apartment in Tavernier

4.98 out of 5 average rating, 142 reviews

Ocean Views at Ocean Pointe

8–15 Nov

$499 SGD per night

Apartment in Tavernier

4.88 out of 5 average rating, 112 reviews

Resort Getaway : Condo, Pool, Beach, Location

20–27 Sep

$306 SGD per night

Guest favourite

Apartment in Tavernier

4.91 out of 5 average rating, 111 reviews

500 Burton Drive Tavernier, Key Largo

19–26 Jan

$423 SGD per night

Quick stats about holiday rentals that are kid-friendly in Islamorada

Total rentals
60 properties
Rentals with a pool
40 properties have a pool
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
60 properties are a good fit for families
Total number of reviews
870 reviews
Nightly prices starting at
$122 SGD before taxes and fees

Destinations to explore