
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.

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!

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

Barefoot Parrot /Walk DT & Waterfront/Sleeps 8
Steps from Main Street Dunedin, a short walk to the waterfront and an easy drive to award-winning beaches, Honeymoon Island & Clearwater Beach. Experience the charm of the Barefoot Parrot House, a private pet friendly house with designer decor and abundant outdoor space. Walk, bike, or cart to stunning sunsets, shops, dining, breweries, and Pinellas Trail. Great for families, couples, groups. Loaded with beach gear, kids's items & pup supplies. Treat yourself to this beloved Dunedin favorite!

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

Amazing views on beachfront
This spacious upper-floor, 3-bedroom condo hotel suite offers views of the Gulf of Mexico from your private balconies. While preparing your morning coffee on the spacious kitchen island, you can see the water of the Gulf of Mexico. Each suite can accommodate 10 people, with 3 bedrooms, 2 of them with a King bed in each bedroom and the third with 2 Queen beds, each of them with their own ensuite bathroom, in total 3 1/2 bathrooms, also a comfortable full-sized sofa bed in the living room.

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.

Tropical Paradise
Please visit our website Grovekeeper collective for a video of the property Private vacation rental I know if you are coming to Delightful Dunedin you know how amazing this waterfront community is, from award winning restaurants , micro breweries, one of the #1 beaches in America, 40 miles of bike trails, waterfront parks. Just bring food and clothes, we have the rest covered! This rental is for a maximum of 5 guest all our units are non-smoking and vaping

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

Heated Pool and Spa | 5 min to beach

Cozy AF Tiny-House Oasis

The Jungalow SOHO - Pool/Hot Tub

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

Gulfview Retreat, Clearwater Beach, Florida

[Kids Favourite] Family Fun Getaway | Heated Pool

Best Celebration - Heated Pool - Hot Tub - Arcade

Clearwater Gem! XL-Pool | Courts & More!
Family- and pet-friendly home rentals

Beautiful Tampa Bay Pool Home Near Gulf Beaches

Renovated 2025 - Retro Beach Oasis with Color Pop

Luxury Beach Cottage | Walk to Dining & Sunset

Casa Flamingo - Private - Outdoor Bar+TV - Games

Beachfront Getaway with Patio โ Perfect For 6

Luxury Clearwater Home โข Heated Pool + Near Beach

Clearwater Beach Retreat - 2 blocks to beach

Beachcomber Beach House | Steps to The Sand!
Family-friendly home rentals with a pool

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

2/2 located at JW Marriott on Clearwater Beach 710

800 Ocean Club | Heated Pool, Theater, Basketball

Honeymoon Luxury Residence with Heated Pool &Sauna

Fun, Funky, Fire Pit, Pool! 4 miles to Beach

Sunny Groove Oasis: Heated Pool, Playset @Clearwat

Boaters Dream Clearwater Beach!

New Waterfront house pool hot tub golf cart kayaks
Destinations to explore
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- Rentals with beach accessย Clearwater Beach Island
- Rentals with a firepitย Clearwater Beach Island
- Aparthotel rentalsย Clearwater Beach Island
- Rentals with a hot tubย Clearwater Beach Island
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- Rentals with a kayakย Clearwater Beach Island
- Rentals with outdoor seatingย Clearwater Beach Island
- Pet-friendly rentalsย Clearwater Beach Island
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- Luxury rentalsย Clearwater Beach Island
- Rentals with a patioย Clearwater Beach Island
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- Boutique hotelsย Clearwater Beach Island
- Beach apartment rentalsย Clearwater Beach Island
- Rentals with lake accessย Clearwater Beach Island
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- Waterfront rentalsย Clearwater Beach Island
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- Family-friendly rentalsย Clearwater
- Family-friendly rentalsย Pinellas County
- Family-friendly rentalsย Florida
- 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
- Sand Key Beach
- Dunedin Beach
- Cortez Beach
- Hard Rock Casino
- Tropicana Field
- St Pete Beach
- Anna Maria Public Beach
- Jannus Live
- River Strand Golf and Country Club
- University of South Florida
- Busch Gardens
- ZooTampa at Lowry Park





