Family-friendly holiday rentals in Islamorada

4. Cozy Waterfront Apartment in Key Largo!

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.

Paradise Casa Bayfront sunsets,pool,King bed ,dock

Welcome to Paradise Casa! Just five feet from the waterfront, you will think your on a cruise ship when you look out the windows. Breathtaking Unobstructed views of the sunset every night. This Glamping at its finest with an amazing pool. 2 bedrooms plus loft, with the main bedroom having a king size bed. Fireplace, fully stocked kitchen, massage chairs, 2 AC units for your comfort. 2 miles from John Pennekamp that has kayak rentals, glass bottom boats, create memories scuba diving/snorkeling

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

NEW luxury RV, Marina, 6 beds&1.5 baths, 2 pools!

This hidden gem is anything but ordinary!!! Come enjoy a piece of paradise in Key Largo while you relax in this spacious NEW luxury RV. It has a BOAT RAMP, indoor/outdoor kitchen with a TV, outdoor speakers, 2 hammock chairs, outdoor sofa, outdoor dining, separate bedrooms including a bunk room that can sleep 5-6, 1.5 baths, 2 heated pools, 2 beaches, volleyball court, playground, & shuffleboard. There are so many outdoor activities to enjoy right at the Kampground, you'll never want to leave!

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.

Escape to the Seaside!

Our 2-story ocean front home is a quite and tranquil oasis. Centrally located in south Key Largo, allows for easy travel to the lower Keys. Our home is decorated in a casual coastal style to provide a comfortable and relax setting. Upstairs is 3 bedroom 2 baths and spacious open concept living room, dining room and kitchen. It provides all the comforts of home. Equipped with flat screen TV, complimentary Wi-Fi and premium cable programming. Here, you’ll have everything you need.

Key Largo Waterfront: Tiki, Dock, Kayak & Pool

This waterfront retreat is perfect for couples, families, or boaters looking to explore the best of the Keys. Snorkel right from the dock, paddle through mangroves with the tandem kayak, or relax with a drink while the sun sets over the canal. Steps from two heated pools, a playground, and a sandy beach, plus only 0.3 miles from groceries and restaurants. Whether you’re fishing, diving famous reefs, or just unwinding under the tiki, this home puts paradise at your doorstep.

Oceanfront Tiny Villa in the Heart of the FL Keys

Welcome to your happy place in the beautiful Florida Keys! Our oceanfront villa is located on Duck Key right outside of Marathon and next to the world famous Hawks Cay Resort. Halfway between Key Largo and Key West, it’s the perfect location to explore all our island paradise has to offer. Enjoy world class fishing, diving and snorkeling or kick back with a cold beverage and enjoy a stunning sunset on one of our covered porches. And always remember…it’s 5 o’clock somewhere!!

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!

Coco Plum Waterfront Hideaway Home in Marathon

This Coco Plum home is the ultimate family getaway! With four bedrooms, two bathrooms, a modern living room with a 4K TV and surround sound, and an outdoor area that includes a fire pit, outdoor dining, and outdoor living space. The boat dock and breathtaking sunset views make this the perfect home for your fishing adventures. Beautiful Coco Plum beach is just a ten minute walk away. Make this home your next island adventure.