Family-friendly vacation rentals in Sugarloaf Key

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Top-rated family-friendly rentals in Sugarloaf Key

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

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Guest favorite

A well-appointed kitchen area features stainless steel appliances and granite countertops. A doorway leads to a light-filled hallway, which connects to two bedrooms. Decorative fishing-themed artwork and coastal colors create a refreshing atmosphere.

Villa in Marathon

4.95 out of 5 average rating, 136 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

A bright bathroom features a walk-in shower enclosed by a glass door. White tiles are complemented by decorative black accents. A window with blinds allows natural light to enter, while fresh towels are neatly displayed on a rack. Colorful artwork decorates the wall.

Home in Key West

4.92 out of 5 average rating, 283 reviews

Family House, 2 K BR's, Private Spa/Deck, 2 pools.

The Historic Family House is decorated in a light, Caribbean motif. It is a Cigar Maker's Cottage from 1880's. 2 K memory foam beds upstairs w/32” Smart TV's, Q sleeper sofa (memory foam mattress) in LR with 56” Smart TV. Bring your Netflix, Amazon or other UN and PW for your favorite programming. Bose blue tooth speakers and Alexa's. 1/2 bath up, full bath down plus an outdoor private shower. Full kitchen! Perfect for Families! Private rear deck with new 6 person Jacuzzi. 2 heated pools!

Superhost

A scenic pool area features colorful adirondack chairs overlooking the calm waters of the bay. A thatched-roof tiki hut provides shade, while a paved patio surrounds the pool, with the serene horizon merging with the sky in the background.

Home in Cudjoe Key

4.91 out of 5 average rating, 110 reviews

Sunrise Beach Escape

For your next vacation, come stay in this resort home, where you'll enjoy a cocktail at sunset alongside the Cudjoe bay overlooking the Atlantic Ocean. This beautiful and luxurious home is part of the Sunrise Beach Resort, an exclusive 11 home gated community overlooking the Atlantic Ocean & Cudjoe Bay. A community that is only 17 miles north of Key West. Make yourself at home in this tastefully decorated 1200 sq foot living space, which offers countless amenities such as kayaks and bikes.

Guest favorite

A serene beachfront area is presented with several white lounge chairs facing the tranquil blue waters. Rocky shoreline and greenery outline the space, creating a peaceful environment for relaxation.

Villa in Key Largo

4.92 out of 5 average rating, 113 reviews

Kawama Yacht Club and Molasses Reef Marine

Vacation in paradise. Beautiful sunsets. Swim at the salt water lagoon or at the beach plus two pools. Our villa is fully equipped, 3 bedrooms wish tv and 3 full baths First floor: garage, 1 bedroom, full bathroom, game room, pool table, bar, family room with TV, and terrace with barbecue and swing. Second floor 2 bedrooms and 2 full bathrooms, fully equipped kitchen and living a big TV, outside balcony with outdoor furniture . Tennis courts available. Optional 24' ft boat slip available.

Guest favorite

Condo in Tavernier

4.99 out of 5 average rating, 106 reviews

Modern and Coastal Ocean Pointe 2307

Are you looking for a Caribbean Vacation in a tropical resort without leaving the USA? Look no further than our Ocean view 2 bedroom and 2 bath condo at Ocean Pointe Suites! Our property offers: 24 hour front gate security, Heated Junior Olympic Pool with 15 person hot tub, tropical Beach, Marina, Tennis/Pickle ball courts. Enjoy our newly re opened ISLAND GRILL pool bar! We are located 60 miles from Miami International Airport and 90 miles from Fort Lauderdale International Airport.

Top guest favorite

A vibrant garden area is surrounded by tall palm trees, featuring colorful tables in yellow, red, and blue, arranged around a sunshade awning. Lush greenery creates a serene ambiance, with pathways and cozy seating inviting relaxation and social gatherings.

Home in Islamorada

4.97 out of 5 average rating, 189 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.

Guest favorite

Apartment in Tavernier

4.83 out of 5 average rating, 259 reviews

Breathtaking Oceanfront Views at Tropical Daze

New Island Grill Pool Bar & Marina Cafe now open! 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. 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.

Superhost

A spacious living area is highlighted by large windows, providing views of lush greenery. A sectional sofa adorned with patterned cushions complements a wooden coffee table in the center. Tropical ceiling fans enhance the airy atmosphere of this inviting space.

Townhouse in Key Largo

4.82 out of 5 average rating, 110 reviews

Oceanfront Resort W/Indoor Pickleball - Spacious!

An island paradise situated in the heart of Key Largo, adjacent to John Pennekamp Coral Reef State Park and Molasses Reef. This 3/3.5 villa is located in Key Largo's most upscale oceanfront resort. The area has the distinction of being Key Largos newest oceanfront gated destination, with some of the most unique amenities in all of the keys. It caters to those who simply desire the very best in luxury accommodations.

Guest favorite

Townhouse in Key Largo

4.88 out of 5 average rating, 140 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 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, 186 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 tennis court is visible behind a large tree, with a lush green lawn surrounding it. The court is enclosed with a fence, and additional trees and shrubs are present in the vicinity, contributing to a natural landscape.

Apartment in Marathon

4.97 out of 5 average rating, 103 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

The image captures a vibrant blue tennis court, featuring well-maintained lines on a green surface. Surrounding greenery and fencing provide a natural backdrop, with ample space for play and relaxation. The sky above is partly cloudy, enhancing the outdoor setting.

Condo in Tavernier

4.76 out of 5 average rating, 365 reviews

Florida Keys Getaway - Slps 4 - Ocean View

Check out this recently remodeled 1-bedroom condo with relaxing and tasteful beach decor - perfect for your Keys Getaway. Ideally located between Key Largo and Islamorada, it offers the best of both worlds! Ocean Pointe is an oceanfront condo property that's just steps away from all the Keys have to offer - the world's best fishing, diving, snorkeling, paddle boarding, and kayaking.