
Family-friendly holiday rentals in Islamorada
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Islamorada
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!
Enjoy a Top Floor condo with stunning ocean views from your living room and balcony. This condo features a King bed in the bedroom, updated kitchen, a queen pull out sofa and a new washer and dryer. Enjoy the wonderful amenities the property offers to include a Large pool/ spa area or relax on the private beach with lounge chairs provided. There are lighted tennis courts, areas to grill out and a small playground. This property sits on 68 acres and one side is surrounded by a nature preserve.

Turtle-By-The-Sea: the Best Deal in KCB!
A perfect get-away for couples or budget travelers, Turtle-by-the-Sea is the best priced vacation rental or hotel room in the middle-keys. Together with its prime location and amenities there simply isn’t a better deal to be had! Bursting with Keys charm, this cozy retreat is the perfect place to relax & escape. Owners Mallory & Steve infused their love of the Keys & its surrounding ocean into every aspect of their waterside home. Shoot us a message & start planning your dream Keyscation!

Waterfront Sunsets, Great Price, Relaxing Spot!!!
Beautiful Waterfront, Modern Coastal Décor, Spacious !! Enjoy your vacation in this beautiful recently renovated home. Views from almost every window and door of the harbor. Walk to many local restaurants and bars for fresh local seafood and a cold draft beer!! Enjoy the sunsets from your private porch. Easy access to Atlantic Ocean. We Do Not Allow Fishing on our Property! 28 day I am a licensed charter captain and offer discounts to guests! Fishing, Sandbar or a Sunset Cruise!!!

🏝 Oceanfront Paradise Awaits You
Bring your boat to next vacation in tropical paradise surrounded by mangrove forest, coconut trees and the pristine turquoise Fl. Keys waters. Welcome to the most visited resort in the beautiful Florida Keys. Ocean Pointe is one of the most luxurious resorts in Tavernier, Florida Keys. The resort offers a private sandy beach, heated swimming pool, jacuzzi, tennis courts, oceanfront marina with boat ramp and dockage, boat & trailer storage, and more - all situated on 60 lush tropical acres.

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.

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.

Blue Haven Key Largo | Ocean Pointe 1315
Tastefully decorated and newly renovated 2 Bedroom & 2 Bathroom Condo with a wonderful view of Florida Keys Nature. Relax and escape to this beautiful getaway in the heart of Tavernier, ideally located between Key Largo & Islamorada. The property itself has amenities galore: sparkling pool with hot tub and newly re opened POOL BAR, boat ramp and marina, tennis courts which convert into pickle ball courts, beach with pier, free parking and charcoal grills to cook your catch!

Ocean views at “Sangria Sunrise” 10% off Charters
Welcome to Sangria Sunrise at Ocean Pointe Suites in the beautiful Tavernier Key Florida. Relax and enjoy all of the options offered such as Jr. Olympic sized pool, beach, marina, kayak rentals, tennis courts, and so much more! We invite you to come stay at this cozy and updated one bedroom and one bathroom top floor condo with the most amazing ocean views. We offer a very comfortable queen sized bed and also a queen sleeper sofa that's equally as comfortable.

2br/1ba w heated pool, 1 mile to robbies marina
Your slice of Islamorada awaits at the Key Lime Cottage! Step inside this charming 2 bedroom cottage and you will instantly feel at home. Located in the heart of the Florida Keys yet nestled in a serene neighborhood, it offers the perfect blend of comfort and relaxation. With a full kitchen, access to a gorgeous pool shared with only 6 other homes, outside seating with grill and a fire pit, beach chairs and key lime treats - there is something for everyone!

BEAUTIFULLY DESIGNED OCEANFRONT CONDO
Enjoy a Tavernier adventure on a private 60-acre oceanfront sanctuary. The condo was recently renovated & is beautifully designed with comfortable, beach chic decor. It offers an abundance of natural light surrounded by windows overlooking lush landscaping and the Atlantic Ocean. Ocean Pointe Suites offers a private sandy beach, a junior Olympic sized pool, a 14-person spa, a boardwalk, a pickleball court, deep-water marina, gazebo, 2 tennis courts & more!

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.

Key Largo! Tavernier! Welcome to Paradise!
A perfect tropical getaway! Life is good today! Bright, airy, 500 plus sq ft., canal front studio, close to the bay. From the dock you can KAYAK to mangrove tunnels, fish, or just relax. Cold drink in your hand, life is good today! You are going to have an awesome vacation!! ( NOTE: THE POOL MAY BE SHARED ON OCCASION, WITH OUR FAMILY. A SIGNED LIABILITY RELEASE IS REQUIRED AT CHECK IN )
Popular amenities for Islamorada family-friendly rentals
Family-friendly home rentals with a hot tub

Luxury Top Floor Suite W/ Unobstructed Ocean View

1BR - Key Largo Sun & Sand Hideaway

Your Happy Place - Oceanfront

Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s

New Tinyhouse RV, Kayak, Beach, Fish, Marina, Pool

Ocean Pointe Condo | Beach, Pool, Hot Tub & Tennis

Oceanview | Jacuzzi | Private Beach | Marina | BBQ

Villa in Paradise. Plunge pool. Middle of the Keys
Family- and pet-friendly home rentals

Private Home,Hot Tub,BBQ.Boat & RV Parking FL Keys

The Nest Villa & Marina in the heart of Islamorada

Waterfront Key Largo Escape | Boat Slip Included

Gorgeous lagoon-front 2BR Townhouse with 2 pools

Waterfront Studio 2| Couples Oasis | Kayaks | Pool

NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom

Paradise in Key Largo, FL

Key Largo downstairs guest house
Family-friendly home rentals with a pool

Islamorada bungalow 2 bed & pool

The Paradise 2

Islamorada house with best location. Lic # 24-0055

Oceanfront 3‑Stories of Bliss • Dockage & Gameroom

Condo in Tavernier

Bayview Beautiful townhouse in Islamorada, FL KEYS

Tequila Sunrise

Gone Coastal @ Ocean Pointe
When is the best time to visit Islamorada?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $529 AUD | $592 AUD | $620 AUD | $543 AUD | $601 AUD | $527 AUD | $527 AUD | $518 AUD | $518 AUD | $486 AUD | $511 AUD | $570 AUD |
| Avg. temp | 20°C | 22°C | 23°C | 25°C | 27°C | 28°C | 29°C | 29°C | 28°C | 27°C | 24°C | 22°C |
Quick stats about holiday rentals that are family-friendly in Islamorada

Total holiday rentals
Explore 570 holiday rentals in Islamorada

Nightly prices starting at
Islamorada holiday rentals start at $133 AUD per night before taxes and fees

Verified guest reviews
Over 5,150 verified reviews to help you choose

Pet-friendly accommodation
Find 260 rentals that welcome pets

Holiday rentals with a pool
420 properties feature pools

Rentals with dedicated workspaces
310 properties have a dedicated workspace

Wi-Fi availability
560 of Islamorada holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Islamorada rentals

4.8 Average rating
Islamorada stays are highly rated by guests—averaging 4.8 out of 5!
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