Family-friendly holiday rentals in Windley Key

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Top-rated family-friendly rentals in Windley Key

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

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Guest favourite

Townhouse in Key Largo

4.86 out of 5 average rating, 105 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

Guest favourite

Apartment in Key Largo

4.96 out of 5 average rating, 112 reviews

Kawama Suntastic @ Key Largo

Beautiful Lagoon front Condo in Beachfront community. Why dream when you can actually be in a tropical island paradise!? Steps away from a swim in the salt water lagoon (lake) or one of 2 amazing pools. Short walk to the beach for swimming and to watch both sunrises and sunsets! Amenities include a playground, tennis/pickleboard court, walking path, & more! REST ASSURED YOU ARE RENTING A 100% LEGAL RENTAL! State of Florida License#CND5403670 Monroe Country Vacation Rental Exception #18-14

Guest favourite

Townhouse in Duck Key

4.98 out of 5 average rating, 143 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.

Guest favourite

Home in Key Largo

4.96 out of 5 average rating, 136 reviews

Key Largo Waterfront Home with Tiki & Boat Dock

Oceanside Keys delight- minimum stay 4 days. Your own private TIKI/ BOAT DOCK & swim ladder at the door; HOA boat launch. Bring or rent a boat up to 25' [ no jet skis] Snorkel in clear water in front of the house. The coral reef and sand bar are just offshore. One mile from the land base of Pennekamp State Park. Paddling, boating, fishing, snorkeling and diving are glorious in Pennekamp Park waters. Launch the PROVIDED tandem kayak from our beach down the street. No indoor smoking. No pets.

Guest favourite

Flat in Tavernier

4.83 out of 5 average rating, 255 reviews

Breathtaking Oceanfront Views at Tropical Daze

Deluxe 2/2 right on the ocean, offering spectacular views of the purple and aquamarine waters of Tavernier Key. Jr Olympic Pool with hot tub. Resort community has a beach, iconic pier, marina, tennis & pickle ball (we provide pickleball & tennis rackets in condo), café, and a fun pool bar. Gated entry with 24 hour security! Perfect location with popular waterfront restaurants, and the best fishing, snorkeling, kayaking, paddle boarding and diving the world has to offer at your footsteps.

Guest favourite

Townhouse in Key Largo

4.9 out of 5 average rating, 270 reviews

Casa Fish LLC

Vacation in paradise. Beautiful sunsets. Swim and snorkel in the salt water lagoon. The lagoon is fed from the bottom of the ocean, you will know when it is low tide and high tide. The community offers two pools. The north pool is just steps from our condo. The south pool is within walking distance of our condo. Our condo is fully equipped for your stay. It is 2 bedrooms and 2 full baths, living/dining room. Front porch with gas BBQ. Back porch overlooks salt water lagoon. Two stories.

Guest favourite

Home in Islamorada

4.97 out of 5 average rating, 167 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

Apartment in Tavernier

4.83 out of 5 average rating, 180 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 favourite

Townhouse in Key Largo

4.88 out of 5 average rating, 127 reviews

Key Largo House

Casa Key Largo has contemporary elegance in a tropical paradise, a laid back island vibe with all the amenities. We have stocked the home with everything you need and more. Restaurants, boating, fishing, swimming, snorkeling, scuba diving, shopping, and John Pennekamp Coral Reef State Park are all within minutes. It is a great central location for day trips to Key West, Marathon, Miami Beach, and the Everglades.

Guest favourite

Home in Marathon

4.93 out of 5 average rating, 169 reviews

Beach, 70ft Dock, Entire Home, VACA-23-16

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 favourite

Home in Key Largo

4.89 out of 5 average rating, 351 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.

Superhost

Apartment in Tavernier

4.88 out of 5 average rating, 113 reviews

Resort Getaway : Condo, Pool, Beach, Location

Your perfect location to enjoy all of the Florida Keys, offering the amenities of a high end resort get-a-way AND the comforts of home with views of the turquoise ocean. Olympic size pool, hot tub, beautiful beach, marina, outdoor grills, tennis courts, pickleball, playground and more. All of this in a value pricing leaving you more to spend on experiencing more of what the Keys have to offer.