Family-friendly vacation rentals in Islamorada

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Top-rated family-friendly rentals in Islamorada

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

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Superhost

An aerial view captures the scenic landscape of Key Largo, showcasing a coastline that merges crystal-clear water with lush greenery. Modern buildings line the marina, with boats gently moored along the waterfront, emphasizing the tranquil atmosphere of this resort area.

Townhouse in Key Largo

4.85 out of 5 average rating, 132 reviews

LIC. MGR. - 2/2 VILLA - OCEANFRONT BEACH RESORT!

If you want to experience the true meaning of a Key Largo Island Vacation, then look no further than our spacious Villa on the ocean side of the world famous Key Largo, Florida... ..The Dive Capital of the World! This Villa is located inside Kawama Yacht Club, a beautiful Hawaiian Island style resort that is situated along the southern border of John Pennekamp National Underwater Park. This is the only resort in Key Largo with a Saltwater Lagoon and Oceanfront Swimming Beach/Tiki Huts and Palms

Top guest favorite

A private heated pool is surrounded by a spacious patio with laid brick flooring. Palm trees frame the scene, while a vibrant sunset casts warm colors across the sky. Lounge chairs are positioned by the pool, inviting relaxation by the serene water view.

Villa in Marathon

4.95 out of 5 average rating, 143 reviews

Private 4/3 Pool Heater/Dock/Kayaks/Bikes,etc

Wake up to breathtaking water views at our 4-bedroom, 3-bathroom villa. Enjoy the 1800 sq ft layout, fully equipped kitchen w/stainless steel appliances, and granite countertops. Sleeps 10 with memory foam beds. Outside, relax by your private heated pool (winter) and tiki-shaded area. Fish from the 32' dock or use the BBQ gas grill. Includes 2 kayaks, 2 paddleboards, and 4 adult bikes for a 5-minute ride to Sombrero Beach. Exterior cameras for security. Vacation License #VACA-22-40. Book now!

Guest favorite

The charming cottage displays a pastel-colored exterior with a triangular roof and white trim. A small front porch is set above the entrance, flanked by two sets of French doors. Lush greenery and a white picket fence enhance the welcoming entryway.

Townhouse in Duck Key

4.98 out of 5 average rating, 177 reviews

3Bd 3Ba Cottage/Village at Hawks Cay/Ocean Views

Our Cottage is located between Islamorada and Marathon Key on Duck Key at the Village of Hawks Cay; one of the most desirable locations in the Florida Keys. This is at Mile Marker 61. With ocean views, high end finishes, comfy beds and plenty to do in the surrounding areas, the Cottage offers something for everyone. The outdoor green space overlooking the water is gorgeous. Sunsets are amazing right off the screened in lanai. We hope to host you as our guest in the beautiful Florida Keys.

Top guest favorite

The living area features a comfortable light blue sofa and a glass-top coffee table, complemented by tropical-themed decor. A ceiling fan circulates air above, while a kitchen bar with high chairs is visible in the background. Natural light enters through multiple windows, enhancing the welcoming atmosphere.

Home in Islamorada

4.97 out of 5 average rating, 195 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.

Superhost

A thatched-roof gazebo provides a sheltered seating area with wooden adirondack chairs. The serene ocean glimmers in the distance, while green navigation markers are visible on the water's surface. The structure features a wooden railing surrounding the space, enhancing the coastal atmosphere.

Condo in Tavernier

4.84 out of 5 average rating, 226 reviews

Toes in the Sand - 2 Bedroom Condo Sleeps 4

2-bedrooms, 2 full baths located on the 4th floor with ocean views. This condo has a beach, viewing pier, rentable boat slips, & boat trailer storage, café and a very large heated pool with a bar and gated entry with 24 hour security! Perfectly located between Key Largo and Islamorada, close to Pennekamp State Park, Harry Harris State Park, popular restaurants on the water, and the best fishing, snorkeling, kayaking, paddle boarding and diving the world has to offer at your footsteps.

Guest favorite

A waterfront view is captured, featuring a wooden table surrounded by several chairs under the shade of palm trees. The serene water reflects the clear blue sky, and a dock is visible in the background, enhancing the tropical atmosphere.

Home in Key Largo

4.91 out of 5 average rating, 109 reviews

Sunsets In Palms Paradise

Vacation Rental Permit #19300755 Enjoy one acre of privacy and coconut palms galore! Features include spectacular sunsets & dolphins for neighbors! While relaxing by the waterfront, you can watch pelicans, herons, wild dolphins, manatees and Ibis gliding by. Fish, kayak, & swim from the dock & basin. Bring a boat to access the Keys by water. Sunsets in Palms’ Paradise is a waterfront Keys home where you can spend quality time with your family/friends.

Top guest favorite

A serene canal view is framed by a tiki hut, with seashell decorations hanging gently. Clear water reflects the blue sky, while surrounding palm trees and thatched roofs add a tropical touch, creating a peaceful atmosphere. A boat dock is visible along the waterway.

Home in Key Largo

4.97 out of 5 average rating, 161 reviews

Key Largo Waterfront Home with Tiki & Boat Dock

WATERFRONT Oceanside Key Largo. Private 29 footTIKI/ BOAT DOCK & staircase swim ladder at the door; HOA boat launch & boat trailer parking. Bring or rent a boat up to 25' [ no jet skis] Snorkel in front of the house. Launch the PROVIDED tandem kayak from the beach down the street. 1 mile from the land base of Pennekamp State Park. Paddling, boating, fishing, snorkeling and diving are glorious in Pennekamp Park waters. No indoor smoking. No pets.

Guest favorite

A collage highlights an inviting outdoor space featuring a heated pool, hot tub, and two putting greens on lush lawn. The open living area showcases comfortable seating, light-colored furnishings, and ocean-themed decor. Exterior views reveal spacious patios and well-maintained landscaping under a colorful sunset.

Home in Marathon

4.95 out of 5 average rating, 137 reviews

Paradise - Pool, Hot tub, Mini Golf, Dockage, Fish

House suits multiple families with kids, groups of couples, small and large families, or solos. Home is easy to get to, easy to get inside and the neighborhood is very peaceful. Plenty to do around the island or on the water. 5 large bedrooms and 3 large bathrooms with an open living room and a fully stocked kitchen. We look forward to hosting you. Very Short Walking distance to Sweet Savannah's Ice Cream and Sweets Parlor

Top guest favorite

The entrance to the home is framed by lush greenery and colorful plants. A welcoming pathway leads to the front door, which features intricate wooden detailing. Bright flowers and palm trees enhance the tropical ambiance of the exterior.

Home in Marathon

4.94 out of 5 average rating, 190 reviews

May availability 70ft Dock, Near Beach 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.

Guest favorite

A wooden dock extends over the turquoise waters, supported by sturdy wooden posts capped with white tops. The clear sky above complements the tranquil scene, with hints of distant land visible along the horizon.

Home in Key Largo

4.9 out of 5 average rating, 410 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.

Guest favorite

A light-filled living room features a blue sofa, a comfortable chair, and a glass coffee table. Large sliding doors open to a balcony with ocean views. A soft area rug lies on the tiled floor, adding warmth to the space, while sunlight illuminates the room.

Apartment in Marathon

4.97 out of 5 average rating, 105 reviews

Beachfront Condo w/ Ocean Views in Marathon

Beautifully decorated 2nd floor end unit with stunning panoramic ocean views from the balcony, living room and master bedroom. Two bedrooms / two full bathrooms and washer and drier in unit. Full kitchen. Directly on the beach! Beach chairs, umbrellas and towels provided for you. Guests have access to the heated swimming pool, tennis court and beach. Master bedroom king-size memory foam mattress

Superhost

A bright living area showcases a gray sofa and an armchair with a patterned design. A high-top table for four is positioned near sliding glass doors, offering views of the ocean and lush greenery beyond. Soft natural light fills the space.

Condo in Tavernier

4.85 out of 5 average rating, 101 reviews

Top Floor Suite Near Local Dive & Snorkeling Shops

Relax & Recharge at our Quiescent Condo with Stunning Views of the Blue Green Colors of the Atlantic all Nestled on 60 Secluded Acres. Situated in Tavernier, the property is centrally located between Key Largo and Islamorada, with restaurants, shops, attractions, charter & dive boats and more nearby. SEAS THE DAY - OR JUST RELAX - YOU'RE ON ISLAND TIME