
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

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: 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

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

The Jungalow SOHO - Pool/Hot Tub
The Jungalow is the ultimate urban oasis. Enjoy the luxuries of the home or venture out to local attractions like the iconic Bayshore Boulevard, Historic Hyde Park, SOHO, Downtown and more. This home was designed with comfort and convenience in mind. Fully equipped with a smart tv, high-speed WIFI, pool and hot tub - this place is paradise. Central to the action - walk to unique rooftop bars, restaurants and shops or Uber to local attractions like Water Street, Amalie Arena, and the Riverwalk.

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.

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

Waterfront Beach House Steps Away from #1 Beach!
Welcome to The Bombshell Beach House! This 3 story, 3 bedroom luxury water-front townhouse located in Clearwater Beach, FL has been a childhood dream come true for me as a Clearwater native! As avid travelers, my husband and I wanted to create a STAY-CATION spot that mixed in all of the comforts of HOME with all of the luxuries of a 5 star vacation & this beach house is JUST THAT! This listing is brand new and we are expecting dates to book extremely fast! Book now to secure your GETAWAY!

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.

#2- SALE! Beautiful 2/2 Condo-ON the Sand!
Newly painted & refreshed beachfront condo, located directly on beautiful North Clearwater Beach! Unit is located on the 3rd floor with gorgeous views of the Gulf of Mexico. 2 Bedrooms, 2 bathrooms with a private balcony overlooking the beach. Sleeps 6 with the futon & an air mattress. WiFi included, Smart TV's, beach chairs, towels, toys, etc. Just bring yourselves and you are ready to go! Fully equipped full-sized kitchen with enough supplies to get you started.
Popular amenities for Clearwater Beach Island family-friendly rentals
Family-friendly home rentals with a hot tub

Tropical Paradise

Gulfview Retreat, Clearwater Beach, Florida

Luxurious Beach House, Private Rootop, & Hot Tub!

Waterfront 4BR | Walk to Beach | Pool & Spa

Heated Pool and Spa | 5 min to beach

Luxury End-Unit w/ Rooftop Hot Tub & Beach Views

Hidden Oasis W Screened Heated Salt Pool / Hot Tub

Hot Tub, Heated Pool, Minutes to Clearwater Beach
Family- and pet-friendly home rentals

Coastal Waterfront Condo Steps to Beach

CWB Retreats at Bayside Villas - Studio 1

Renovated 2025 - Retro Beach Oasis with Color Pop

Insta Worthy Retreat -HTD Pool- Arcade Room- Golf

Clearwater Heated Pool Beach House | Games + Golf!

Ocean Dreaming: Waterfront Home with Heated Pool,

Private Beachfront 2BR BUNGALOW*POOL*PETS ok

Dream Retro, Pets Welcome-fenced, near beaches
Family-friendly home rentals with a pool

The Palm Haus • Heated Pool • Near Beach • Games

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

Heated Pool Home | Close to Clearwater Beach

4 Bedroom, 3 Bathroom House 1 Block From The Beach

4-Bed Beach Retreat: Steps to Sand + Private Pool

Coastal Breeze - Family Friendly Beach Pool Home!

Clearwater Beach Bungalow Beachfront w/Heated Pool

Providence Cove | Heated Salt Pool • Sleeps 12
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