Family-friendly holiday rentals in Clearwater Beach Island

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Top-rated family-friendly rentals in Clearwater Beach Island

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

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Top guest favourite
The exterior of a charming blue beach house is surrounded by lush palm trees and vibrant landscaping. A spacious front yard features a green lawn and neatly trimmed bushes, while a driveway accommodates parked vehicles. Sunlight filters down, creating a warm atmosphere.
Home in Clearwater Beach
4.98 out of 5 average rating, 142 reviews

THE HOUSE - 32 Steps to the Beach - Beautiful Clea

House sleeps 6 - Private patio and Hot Tub, Wifi, Grill . '32 Steps to the Beach' is a charming and cozy Clearwater Beach retreat in a TOP LOCATION. The pristine Gulf Beach is just across the street! We also have a Cottage at the same address and they can be rented separately or together. Covid-19 UPDATE - See below. To book the House & Cottage or the Cottage on its own please see the links to their descriptions at the right of this page. THE HOUSE is a tastefully decorated, upscale

Guest favourite
The exterior view of a charming blue cottage is presented, featuring white accents and shutters. Two light-colored lounge chairs are positioned on the paved front area. Lush greenery surrounds the property, enhancing the inviting beach house vibe.
Cottage in Clearwater
4.79 out of 5 average rating, 174 reviews

Corner Cottage Sleeps 5, Steps to Beach, Pets OK.

1925 beach house just steps to the beach. . All shops and resturaunts just a few blocks walk. Beach is 120 steps away. Part of Clearwater Cottages, a group of historic beach houses. This is an entire small house that will sleep 5 Guests Restored antique kitchen. Just cute as a button. Families with pets welcome shared commercial hot tub in recreation area. has queen size bed in private master bedroom and pull out sofa bed in living room . as well as an additional twin bed in the living room

Top guest favourite
Gentle waves lapping against a sandy shore create a serene coastal scene. The sky is filled with wispy clouds and varying shades of blue, reflecting the tranquil atmosphere of the beach. The shoreline reveals patterns in the wet sand as the water recedes.
Apartment in Clearwater
4.95 out of 5 average rating, 333 reviews

Steps 2 beach! Beachy and Luxurious! Easy Living!

Easy Living is a beachy newly renovated condo with 2 bedrooms & 2 full bathrooms, nestled between the intercoastal water and the magnificent Clearwater beach! Located a very short walk to the beach (less than 2 blocks) and across the street from a park. The Clearwater Beach Rec Pool is another short two minute walk from the condo! The condominium is quiet area yet, it is within walking distance to practically everything in town, including the beach, many restaurants, bars, Pier 60, & the marina!

Guest favourite
A modern kitchen area is presented with white cabinetry and a backsplash featuring blue and gray mosaic tiles. Two wooden bar stools are positioned at a countertop, while an adjacent open area displays a console table with decorative items. Natural light brightens the space.
Flat in Clearwater
4.91 out of 5 average rating, 110 reviews

Newly Remodeled 2 Bedroom Condo

Prime Clearwater Beach location with exceptional walkability. Located in a quiet area just north of Pier 60, within walking distance to restaurants & bars. A public playground & pickleball courts are immediately next door. The beach is 1.5 blocks away (5-min walk), & the pool shown in photos is on the next block (2-min walk). Fully equipped for beach days, w/ a beach wagon, chairs, towels & toysโ€”so you can enjoy full days on the sand. First floor condo w/ washer & dryer & free onsite parking.

Top guest favourite
A screened-in lanai features a heated saltwater pool surrounded by colorful outdoor furniture. Childrenโ€™s toys and pool floats are placed nearby, alongside a small bike. The serene space is perfect for relaxation and play, with trees visible beyond the enclosure.
Home in Palm Harbor
5 out of 5 average rating, 159 reviews

Coastal Escape: Kid-Friendly Pool & Playground

โ˜… Family-friendly Palm Harbor retreat near beautiful beaches - Honeymoon Island: 6 miles away - Clearwater Beach: 15 miles away โ˜… Heated saltwater pool โ˜… Screened-in lanai โ˜… BBQ grill โ˜… Large fenced backyard with playground โ˜… Outdoor dining area โ˜… 3 bedrooms with new mattresses - California king size bed - Queen size bed - Kid-friendly room w/ 2 bunk beds โ˜… Renovated kitchen and bathrooms โ˜… Open living space for family gatherings and movie nights โ˜… Toys, games and kid-friendly extras

Guest favourite
A modern dining area features a round glass table set for six, surrounded by white chairs. A unique blue chandelier hangs above, while large windows offer a view of the water. The kitchen area is equipped with white cabinetry and stainless steel appliances.
Flat in Clearwater
4.89 out of 5 average rating, 259 reviews

Waterfront 2BR Escape Walk to Beach Pool Sleeps 6

๐ŸŒด Your Clearwater Beach Escape Starts Here Wake up to peaceful water views, sip coffee on your private patio, and end your day watching the sunset just minutes away on the beach. This spacious 2BR/2BA condo perfect for families, couples, or small groups looking for a relaxing getaway.Quiet location while still being close to everything Waterfront patio with serene views (yes, dolphins are often spotted ๐Ÿฌ) Walk to Clearwater Beach, restaurants, and shops Pool for relaxing after the beach

Top guest favourite
A cozy living area showcases a modular blue sofa, adorned with soft pillows and a warm throw. A light wooden coffee table rests in the center, complemented by decorative items. Natural light enters through a window, creating a bright and welcoming atmosphere.
Cottage in Dunedin
4.99 out of 5 average rating, 367 reviews

Walk to Downtown and Waterfront - Private Yard

Steps to Main Street and minutes to beaches, yet tucked away on a quaint street. Private yard with grill in a prime location. Walk to restaurants, breweries, shops, and live music. Walk to Dunedin's stunning sunsets or drive minutes to award-winning beaches such as Honeymoon Island, Caladesi Island & Clearwater Beach. Sleeps 6. Two king bed suites and a luxury couch that sleeps 2 more. Fully loaded for kids, pets and beach days. Treat yourself and book this Dunedin favorite today.

Superhost
A sandy pathway leads through beach grass and wildflowers, with palm trees framing the scene. The azure ocean and clear blue sky serve as a backdrop, inviting guests to enjoy the nearby beach.
Cottage in Clearwater
4.85 out of 5 average rating, 158 reviews

Mermaid Cottage

Located in a three unit 'Olde Florida Style Complex' and just 45 steps to Clearwater Beach! The Mermaid Cottage is located on the 1st floor at the back of the complex. This Florida style unit is adorned wood floors and charming island decor. Open to an outdoor patio with furniture. The cottage has two bedrooms, two full baths and an outdoor shower! Living room has a queen pull-out bed. The patio area is completely fenced for private use. Nice, park like charcoal grill.

Top guest favourite
The image captures a spacious townhouse community, featuring white architectural designs. A clear view of the intercoastal waterway is presented, with boats visible in the distance. A community pool is seen among vibrant greenery, inviting leisure and relaxation.
Townhouse in Clearwater
4.99 out of 5 average rating, 136 reviews

3 Bedroom Waterfront Paradise Sleeps 8

Welcome to Brightwater Blue, our newer vacation Town Home in Clearwater Beach on the intercostal! The 3 floors of custom interior decoration and high end furnishings await you. Located on Clearwater Bay with an easy stroll (5-10 min) to Clearwater Beach, Beach Walk, Pier 60, restaurants, and shopping. You are centrally located to everything in Clearwater with luxury accommodations ! !! You have a 2 car garage, community pool, hot tub, grill steps from your back door.

Top guest favourite
A balcony view features two cushioned chairs adorned with pink pillows, overlooking a quiet street leading to the beach. Palm trees and lush greenery frame the scene, while the ocean is visible in the distance. Bright blue skies enhance the coastal atmosphere.
Apartment in Clearwater
4.99 out of 5 average rating, 186 reviews

Newly Reno Luxury Condo 30 Steps to Paradise

Welcome to our serene top-floor beach condo. This is a two-bedroom, two-bathroom condo in the heart of Clearwater Beach. This ocean-side condo is steps from the country's #1-rated beach and less than a five-minute walk from top restaurants and shopping. Clearwater Beach is renowned for its award-winning beaches, incredible restaurants, and lively nightlife. We have made every effort to make this condo a home away from home! We hope you enjoy our piece of paradise.

Guest favourite
A cozy bedroom features a spacious bed with crisp white linens, accompanied by decorative pillows. A ceiling fan is installed above, enhancing comfort. Natural light fills the room through the window, which is adorned with greenery and blinds. Nightstands with lamps provide additional lighting.
Flat in Clearwater
4.85 out of 5 average rating, 172 reviews

Waterfront Coastal Condo 2 Blocks to Beach

๐ŸŒŠ Ultimate Waterfront Escape โ€“ Adventure Awaits! ๐Ÿšดโ€โ™‚๏ธ๐Ÿ„โ€โ™‚๏ธ Welcome to your dream beach getaway! This stunning waterfront rental puts you right on the water with breathtaking views and endless adventure. Paddle on a kayak or stand-up paddleboard, then cruise around town on our complimentary beach bikes. Jet ski island tours, parasailing, and moreโ€”all available right from the property! This is the perfect spot to make unforgettable beach memories! ๐ŸŒ…๐Ÿ๏ธ๐Ÿšค

Top guest favourite
A stone fire pit is surrounded by two blue chairs, positioned on a grassy area by the waterfront. Trees provide shade, and a dock is visible across the lake, complementing the serene outdoor setting.
Home in Odessa
4.96 out of 5 average rating, 123 reviews

A perfect Lake House get away

Make some memories at this unique and family-friendly slice of paradise. Located on 100-acre Lake Anne. 20 minutes from beautiful Gulf of Mexico beaches. Enjoy breathtaking sunsets around the fire pit. Kayak, paddle board (included) or fish from the dock. Or sit and relax on the screened patio with your favorite beverage at the outdoor bar. Or venture to beautiful downtown Tampa and enjoy the Buccaneers, Tampa Bay Lightning, or the Rays baseball team

Popular amenities for Clearwater Beach Island family-friendly rentals

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Pinellas County
  5. Clearwater
  6. Clearwater Beach Island
  7. Family-friendly rentals