
Family-friendly vacation 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

2 Bedroom 2 Bath Condo, 3 min walk to Beach
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 & toys—so you can enjoy full days on the sand. Second floor condo w/ washer & dryer & free onsite parking.

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!

Beach 1BR Suite w/full kitchen on Clearwater Beach
🐬 The Porpoise Inn & Suites is a charming boutique motel located right on world-famous Clearwater Beach. Just steps from the sand, shops, restaurants, attractions, and even a recreation pool, it’s the perfect spot for your next Florida getaway. Newly renovated suites feature the stylish touches of coastal living you’ll love, creating a cozy and welcoming space couples, Come for the location, stay for the charm 🏖️✨ (4 Max. Guest/Strictly Enforced & No Pets Strictly Enforced!)

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.

Ocean Breeze • Easy - Heated Pool Access
The Avalon at Clearwater is a gated community with a nice size heated pool and community gym. Parking space is not assigned and it’s free of charge. Location is central with short distance to nearby beaches, attractions and other nearby towns. Unit is approximately 500 square feet with a living room-kitchen open concept and One bedroom - bathroom open concept. Great access from Tampa Airport 20 minutes and 1.5/hours drive from Orlando airport

Waterfront Courtyard Condo 2 Blocks to Beach
🌊 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. We are pet friendly! Pet fee is $150 for the first dog, $100 for the second dog.

CWB Retreats at Bayside Villas - Studio 1
Kick back in this first floor space only 5 minute walk to the beach. This charming studio is perfect for a single traveler or a couple. Prepare your snacks and meals in the kitchenette or grill local seafood on the patio bayside. Enjoy water views and dolphins from our bay front dock. This unit has access to the newly completed pool located between 617 & 611 Bay Esplanade buildings. There is a washer and dryer next door.

Pink Gulfside Cottage, Steps to Beach, Pets OK
100 steps from beach restored 1925 house duplex with modern amenities. Sleeps 5 Guests have enjoyed this group of cottages since 1925. Fun, funky Key West style back yard is great for kids to run around, parents to relax in shade are, old growth tropical plants. Amenities include offers use of hot tub, beach chairs, fishing poles Full time Cottage Counselors here to insure you have a great beach vacation

Resort living in paradise
1-bedroom, 1-1/2 bath modern chic condo hotel suite can accommodate 5 people. It features a King bed, with a Nectar memory foam mattress and a full bathroom in the master bedroom, a den area with a twin sofa bed that can accommodate an additional 2 people on the full-sized sofa bed. Enjoy people-watching from three to four stories above the activity. You can even catch a glimpse of the beach to the west.

CBC 2-19F: Gulf Front Paradise Awaits!
🌸Get away from the hustle and bustle of Clearwater Beach and opt for a tranquil experience on the peaceful shores of Sand Key Beach. Looking for a quiet, tranquil beach vacation away in a secluded beachfront paradise? Look no further than CBC 2-19F located at Sand Key Beach in Clearwater, FL! This fully updated 19th-floor condo has a spacious open floor plan with jaw-dropping water views!!!
Popular amenities for Clearwater Beach Island family-friendly rentals
Family-friendly home rentals with a hot tub

La Casita, 1 of 4 rentals on-site. Heated Pool!

The Jungalow SOHO - Pool/Hot Tub

Waterfront Condo | Steps to Clearwater Beach 2King

Gulfview Retreat, Clearwater Beach, Florida

Tiki Hut Cottage

Pet‑Friendly Beach Home w/ Heated Pool & Spa

4 BR Clearwater Beach Townhome•Rooftop Lounge

Luxurious Beach House, Private Rootop, & Hot Tub!
Family- and pet-friendly home rentals

Little Manatee River Cottage

Seascape! Studio Apt near the Beach• Pets Welcome

Insta Worthy Retreat -Arcade Room- Htd Pool- Golf

Lovely Condo minutes from beach & King bed

Renovated 2025 - Retro Beach Oasis with Color Pop

Beach Cottage in Garden, semi-Private area Pets Ok

Tropical Oasis Retreat w/ Heated Pool

Walk Downtown and to Waterfront, Mins to Beaches
Family-friendly home rentals with a pool

Beautiful Clearwater Beach House, Steps to Beach

Clearwater Mediterranean Retreat • Pool & Fire Pit

Seaside Cottage

The Palm Haus • Heated Pool • Near Beach • Games

Custom Waterfront 3BR Paradise/Salt WaterPool-Spa

The Breezeway #2 only a 2 min walk to the Beach!

Clearwater w Pickleball Court, Cinema, Heated Pool

Luxury on water & Steps to beach
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- Anna Maria Island
- Raymond James Stadium
- Busch Gardens Tampa Bay
- John's Pass
- Weeki Wachee Springs
- Coquina Beach
- Vinoy Park
- Lido Key Beach
- Dunedin Beach
- Amalie Arena
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