
Family-friendly holiday rentals in Clearwater Beach Island
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Clearwater Beach Island
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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

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

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!

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 & toysโso you can enjoy full days on the sand. First floor condo w/ washer & dryer & free onsite parking.

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

Waterfront 2BR Escape Walk to Beach Pool Sleeps 6
๐ด 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 ๐ฌ) Walk to Clearwater Beach, restaurants, and shops Pool for relaxing after the beach

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.

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.

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.

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.

Waterfront Coastal Condo 2 Blocks to Beach
๐ Ultimate Waterfront Escape โ Adventure Awaits! ๐ดโโ๏ธ๐โโ๏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 moreโall available right from the property! This is the perfect spot to make unforgettable beach memories! ๐ ๐๏ธ๐ค

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
Family-friendly home rentals with a hot tub

Lush Harbor Oasis with Private Hot Tub

Cozy AF Tiny-House Oasis

Heated Pool and Spa | 5 min to beach

The Jungalow SOHO - Pool/Hot Tub

TIKI Bar+SAUNA+HOT Tub+Heated POOL! 2 KING beds!

Gulfview Retreat, Clearwater Beach, Florida

Clearwater Gem! XL-Pool | Courts & More!

[Kids Favourite] Family Fun Retreat | Heated Pool
Family- and pet-friendly home rentals

Lux Tiny Home | 1 Bed - 1 Bath Unit B "Sandy"

Beautiful Tampa Bay Pool Home Near Gulf Beaches

Luxury Beach Cottage | Walk to Dining & Sunset

Beachfront Getaway with Patio โ Perfect For 6

Renovated 2025 - Retro Beach Oasis with Color Pop

Beachcomber Beach House | Steps to The Sand!

New Upscale Retreat Downtown Dunedin w/ Balcony

Beach Retreat #24 โข Walk to Beach + Pool
Family-friendly home rentals with a pool

Best! Pickle ball * Karaoke* Arcade* Glam

Honeymoon Luxury Residence with Heated Pool &Sauna

Mandalay Sandcastle

Sunny Groove Oasis: Heated Pool, Playset @Clearwat

WOW! Dunedin Coastal POOL Home-beaches-eateries

Luxury Clearwater Home โข Heated Pool + Near Beach

Sleeps 10 - Game Room - Putt Putt - Movie Theater

Luxury on water & Steps to beach
Destinations to explore
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- Fitness-friendly rentalsย Clearwater Beach Island
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- Family-friendly rentalsย United States
- Anna Maria Island
- Raymond James Stadium
- Busch Gardens Tampa Bay
- John's Pass
- Anna Maria Island Beach
- Weeki Wachee Springs
- Bean Point Beach
- Coquina Beach
- Lido Key Beach
- Amalie Arena
- Vinoy Park
- Tampa Convention Center
- Dunedin Beach
- Sand Key Beach
- Cortez Beach
- Hard Rock Casino
- St Pete Beach
- Anna Maria Public Beach
- Jannus Live
- Tropicana Field
- River Strand Golf and Country Club
- University of South Florida
- ZooTampa at Lowry Park
- Busch Gardens





