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, 151 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

FamilyIndoor spacesSleep quality

Top Guest favourite

A screened-in lanai features a heated saltwater pool surrounded by colorful outdoor furniture. Children’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

5.0 out of 5 average rating, 170 reviews

Coastal Escape: Heated Pool, Playground&Family fun

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

FamilyIndoor spacesComfort

Guest favourite

A spacious living area features soft gray couches, a coffee table, and a large television. Natural light filters through the partially transparent window coverings. A dining table with chairs is visible in the corner, complemented by light-colored hardwood flooring throughout the space.

Apartment in Clearwater Beach

4.9 out of 5 average rating, 213 reviews

NEW! Luxurious King Bed! 10 Steps to the Beach!

AMAZING LOCATION! This vacation rental is located within crawling distance of the beach. As soon as you open the front gate you can see the beach entrance. Locate 1 house from the sugary white sands of the world famous Clearwater Beach! Also located within walking distance of practically everything including many great restaurants, bars, shops, Pier 60, the marina and much more, yet still located on a quiet street. Once you park your car in your reserved spot, you probably won't need it again!

KitchenIndoor spacesWi-Fi

Guest favourite

A private balcony is seen featuring two white chairs and a table, offering uninterrupted views of the Gulf of Mexico. The calming blue sky meets the horizon, enhancing the serene beachfront experience.

Condo in Clearwater Beach

4.91 out of 5 average rating, 328 reviews

Beachfront in exclusive resort

This upper floor, 3-bedroom modern chic condo hotel suite offers sweeping views of the Gulf of Mexico from private balconies. While preparing your morning coffee on the spacious kitchen island, you can see the shrimp trawlers making their way out to sea. Enjoy a cocktail while watching the sunset over the open water of the Gulf of Mexico. This suite can sleep 8, with King or Queen-size beds in each of the three bedrooms, a comfortable full-sized sofa bed in the living room & 3-1/2 bathrooms.

Indoor spacesKitchenHot tub

Top Guest favourite

A scenic view of a fishing pier extends into the water, framed by gentle waves and a sandy beach. The sky is filled with colorful clouds, reflecting hues of orange and blue as the sun sets on the horizon.

Condo in Clearwater Beach

4.98 out of 5 average rating, 179 reviews

Upgraded 3 Bed, 3 Bath Corner Water Front Condo!

Stylish & Sunny Corner Unit On Dolphin Faved Inlet Across The Street From Florida's #1 Beach. This all-inclusive unit allows you to walk everywhere and enjoy all Clearwater Beach has to offer from sand & sun to restaurants & shopping. Updated & upgraded 3 bedroom, all with connected bathrooms offers amazing space, a chef's kitchen as well as bright & beautiful dining & living rooms. Private balcony to relax & watch the sunset. Beach concessions include sea kayaks, jet ski's, boating & more.

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Top Guest favourite

The exterior of a coastal cottage is shown, featuring a gravel driveway and tropical landscaping with palm trees. Two wicker chairs are positioned under a covered porch, inviting relaxation. Large windows allow natural light to brighten the welcoming facade.

Cottage in Dunedin

4.97 out of 5 average rating, 386 reviews

Walk Downtown and to Waterfront, Mins to Beaches

Just steps to Main Street Dunedin and minutes to Honeymoon Island and Clearwater Beach, this stylish upstairs 2-bedroom cottage blends modern coastal design with exceptional comfort. Tropical murals, treetop views, two king beds, and a sleeper sectional create a chic and indulgent stay. Fully stocked. Walk to dining, shops, breweries, and Dunedin’s stunning waterfront sunsets, then drive minutes to the beaches. Pet-friendly. Every detail beautifully done—reserve the Barefoot Parrot today.

FamilyIndoor spacesBeach

Superhost

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.

Apartment in Clearwater Beach

4.87 out of 5 average rating, 262 reviews

Waterfront 2BR Escape Walk to Beach Pool Sleeps 6

🌴 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 🐬) Walk to Clearwater Beach, restaurants, and shops Pool for relaxing after the beach

FamilyIndoor spacesWalkability

Top Guest favourite

Home in Clearwater

4.98 out of 5 average rating, 229 reviews

Specious home W/ Heated Pool ! ! ! Great Location.

Cozy, spacious home 🏡 w/ heated swimming 🏊‍♀️ pool, next to a golf ⛳️ course. Close to the famous beaches ⛱️, St.Pete and Tampa. This cozy open home has a large living room, big kitchen and pool deck patio. All 3 bedrooms have large TV's. The big back patio has a swimming 🏊‍♀️ pool, TV, fridge and BBQ for cook outs & R&R. Located in a quiet family-friendly neighborhood. Location! 15 min - Clearwater Beach, Dunedin, Safety Harbor 30 min from - St.Pete, TPA Airport, Tampa

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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 Beach

4.84 out of 5 average rating, 166 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.

KitchenFamilyDecor

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 Beach

4.99 out of 5 average rating, 143 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.

FamilyIndoor spacesView

Superhost

Large sliding glass doors open to waterfront views, revealing a sunlit space with a modern kitchenette. A small dining table with two chairs is set near the doors, and a flat-screen TV is mounted on the wall, complementing the serene aquatic surroundings.

Houseboat in Clearwater Beach

4.78 out of 5 average rating, 136 reviews

Breathtaking Beachy Houseboat on Clearwater Island

🌊 Ultimate Waterfront Escape – Adventure Awaits! 🚴‍♂️🏄‍♂️ 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 more—all available right from the property! This is the perfect spot to make unforgettable beach memories! 🌅🏝️🚤

KitchenFamilyShared spaces

Guest favourite

The exterior of the multi-story vacation home is shown, featuring light-colored walls with arched windows and balconies. Palm trees line the front, and a paved driveway leads to individual garages below. The rooftop terrace is visible, suggesting additional outdoor space and amenities.

Townhouse in Clearwater Beach

4.86 out of 5 average rating, 177 reviews

Luxurious Beach House, Private Rootop, & Hot Tub!

This spacious, well appointed & continuously updated vacation home is located 1 block from the beach & is absolutely perfect for a family vacation! Highlighted with a stunning rooftop terrace that includes a brand new hot tub, outdoor furniture, TV, & views of the beach & bay. Undeniably as good as it gets when it comes to "beach life" in Clearwater Beach! The layout allows for amazing comfortability with a group!

KitchenIndoor spacesHospitality