
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 Cottage - 32 Steps to the Beach - Sleeps 2, drive to your door, Wifi, Grill. Just Steps from the beach.
Our tastefully decorated and cozy Cottage offers everything you need for a romantic get-away and a relaxing stay in sunny Clearwater Beach. The Cottage is part of our vacation property '32 Steps to the Beach' which consists of a 3 bedroom house and a separate 1 bedroom cottage. The Cottage can be booked separately or together with the House. To book The House or House & Cottage together please see the listings at the side of this page. Covid-19 UPDATE - See below. The Cottage is located in a quiet and idyllic residential neighbourhood of Clearwater North Beach. The beautiful, award-winning and pristine Gulf Beach is just steps away from the house. If you prefer to have a calm beach day away from the crowds this is where you want to stay. Clearwater Beach with its vibrant public beach life and diverse restaurants is just a mile away. The Cottage offers a spacious, elegant room with a queen bed, a sitting area with a sofa sleeper and a remodeled bathroom. The new kitchenette gives you the opportunity to prepare meals and enjoy them in the small dining area or outside on the secluded patio. Savour a cup of coffee in the morning, a glass of wine after a relaxing day on the beach or enjoy a BBQ in the backyard. Clearwater North Beach is an upscale, safe residential neighborhood that welcomes families and couples. It is not suitable for 'spring breakers' or any group that wants an environment that allows loud parties. The area of Clearwater offers an astonishing diversity of leisure activities. If you enjoy sports you might want to try out the numerous jogging, skating, biking, golfing, hiking, swimming, surfing, tennis or fitness opportunities. In Florida's state parks and on the breathtaking beaches you will experience the beauty and serenity of nature. Several theme parks guarantee fun for the whole family and the diversity of the many restaurants in the area will surprise you. From casual to upscale dining, from local and national to international cuisine - you will find it all! Please also visit our website for more information about our Clearwater Beach homes, Clearwater Beach and the area: www.clearwater-beach-vacations.net Check-in is 4:00pm or later; check-out is promptly at 10:00am to leave time for cleaning crew. We will be happy to answer all of your questions. When using the 'Book it Now' button please include information on the ages and number of people in your party to help us make a quick decision on your request. IMPORTANT: We do not advertise on Craigslist! Be safe and only deal with the owner. COVID-19 Pinellas County is open for short term vacation rentals with guidelines that we are following in full. We take the safety of our guest and cleaning staff extremely seriously. Our cleaning crews are using sanitizer and disinfectant on all surfaces before your arrival and as cleaning is taking longer than previously it is unlikely that we can offer early check-ins or late checkouts. Our houses have well equipped kitchens and we believe that separate units are the best option for vacationing in the time of Covid-19. Florida is seeing an increase in cases at the moment and we stress the importance of guests taking travel insurance that would cover them in the event that they no longer want to travel to Florida. In the event that the administration halts vacation rentals we would of course refund guests as we could no longer accept them. We have to stress that after two months of cancellations and re-bookings we will not be able to offer refunds if Clearwater Beach remains open for vacation rentals but guests decide not to travel.

Coastal Escape: heated saltwater pool & playground
★ Close to beaches - Honeymoon Island: just 6 miles away. - Clearwater Beach: 15 miles away - crowned the nation's #1 beach Trip Advisor in 2018 ★ Heated saltwater pool ★ Screened-in lanai ★ BBQ grill ★ Large backyard w/ playground ★ Outdoor dining area ★ 3 bedrooms New Mattresses - California king size bed - Queen size bed - Kid-friendly room w/ two bunk beds ★ Renovated kitchen and bathrooms ★ Open living space - great for family gatherings, movie nights ★ Children toys and games

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!

salt living at its best
- Resort Style Water front - Stand alone - Hot tub - Sunrise / sunset views on dock - free Kayaks - Internet / YouTube cable - 65” smart TV - Spacious Bedroom with king size bed, walk in closet and flat TV - Washer and Dryer in unit - Designated work space -Pet friendly - Fenced private patio - Free 2 cars / Boat Parking. - Central location ( beaches, restaurants, Tampa, St Pete’s, safety Harbor, Dunedin - 11 minutes from Ruth Eckerd event Hall - Pristine clean - Coffee station - Dining area

Renovated 2025 - Retro Beach Oasis with Color Pop
Book with confidence—our property is in great shape and ready to host your Clearwater Beach getaway! -No hidden fees -No chores Just a breezy, beachy stay with: -2-minute walk to the beach -Beach Chairs -Free parking -Heated pool -Cold AC -Easy self check-in -Pet friendly (One Pet max -$150 fee) We provide essentials (linens, towels, toilet paper, soap etc.) to get you started. For longer stays, we recommend buying additional supplies. 📍648 Poinsettia Ave, Clearwater Beach, FL 33767

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. Come for the location, stay for the charm 🏖️✨ (4 Max. Guest/Strictly Enforced & No Pets Strictly Enforced!)

Beachfront Getaway with Patio – Perfect For 6
Welcome to the piece of paradise you’ve been dreaming of!! This charming seaside townhouse is located just 70 STEPS from the beautiful white sand of Clearwater Beach. Enjoy the convince of it's prime location, cook great seafood at the grill, and truly live the Florida beach lifestyle. Walking distance from bars, restaurants, and stores. This house has been entirely renovated and furnished so it can offer an outstanding beach experience. Don't delay and enjoy Florida!

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.

Coastal Cottage C Bikes, Beach Items, Adventure!
This cottage is my favorite one and hope will be yours too! It’s a small space but designed to make you feel right at home! Please see pictures with the couch pulled out for reference. Sorry no animals/pets. Very quiet and peaceful. Free beach items included especially the beach bikes! The bedroom has a closet and a queen bed allows for suitcases to easily slide underneath….the couch is also a queen pull out bed for more sleeping options

Lemon Cottage Steps from Beach
1925 beach cottage with king size mattress, new kitchen with granite countertops LG stainless steel double over, just 130 steps to the sand with no streets to cross. Great location with Frenchy s Rockaway Grill and Palm just 2 blocks away with the Pier 50 five blocks walk Enjoy a commercial size hot tub right out your back door with large wood party deck tin roof gazebo and massive Ficus Tree private patio overlooks Mandalay Ave

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.

Waterfront Coastal 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 in 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 per pet.
Popular amenities for Clearwater Beach Island family-friendly rentals
Family-friendly home rentals with a hot tub

Cozy AF Tiny-House Oasis

The Jungalow SOHO - Pool/Hot Tub

Gulfview Retreat, Clearwater Beach, Florida

[Top Pick] Family Fun Getaway | Heated Pool

Tiki Hut Cottage

Heart of Safety Harbor | Hot Tub | Luxe Comfort

Waterfront Coastal Bliss at Brightwater w/ Heated

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

Sabal Palm Steps to Clearwater Beach

Insta Worthy Retreat -Arcade Room- Htd Pool- Golf

Beautiful Beachfront Cottage on the Water

Walk to Downtown and Waterfront - Private Yard

Sunset Bungalows Big Blue: Heated Pool, near Beach

Spacious, private bungalow - gorgeous water views

Clearwater Gameroom- Pool/Mini golf/Home Theatre

Watch the Sunrise at Sunrise! @ Clearwater home.
Family-friendly home rentals with a pool

Wonderful Condo at Avalon - Fully Renovated!

5BR Pool Villa | Game Room | Near Clearwater Beach

Heated POOL- 99 Steps 2 BEACH- Coastal Lower Unit

Beachfront Condo with Centerline Sunsets

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

Luxury Tiny Home 2 Bed 1 Bath Unit A "Sunny"

Clearwater w Pickleball Court, Cinema, Heated Pool

Heated Pool Home | Close to Clearwater Beach
Destinations to explore
- Seminole Holiday rentals
- Central Florida Holiday rentals
- Miami Holiday rentals
- St Johns River Holiday rentals
- Orlando Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Tampa Holiday rentals
- Four Corners Holiday rentals
- Kissimmee Holiday rentals
- Key West Holiday rentals
- Beach apartment rentals Clearwater Beach Island
- Boutique hotels Clearwater Beach Island
- Flat rentals Clearwater Beach Island
- Rentals with beach access Clearwater Beach Island
- Pet-friendly rentals Clearwater Beach Island
- Rentals with a fireplace Clearwater Beach Island
- Rentals with pools Clearwater Beach Island
- Rentals with an EV charger Clearwater Beach Island
- Apartment rentals Clearwater Beach Island
- Rentals with breakfast Clearwater Beach Island
- Luxury rentals Clearwater Beach Island
- House rentals Clearwater Beach Island
- Waterfront rentals Clearwater Beach Island
- Rentals with a kayak Clearwater Beach Island
- Rentals with a hot tub Clearwater Beach Island
- Aparthotel rentals Clearwater Beach Island
- Hotel rooms Clearwater Beach Island
- Rentals with a washing machine and dryer Clearwater Beach Island
- Fitness-friendly rentals Clearwater Beach Island
- Rentals with a patio Clearwater Beach Island
- Beachfront rentals Clearwater Beach Island
- Rentals with lake access Clearwater Beach Island
- Rentals with outdoor seating Clearwater Beach Island
- Rentals with a firepit Clearwater Beach Island
- Family-friendly rentals Clearwater
- Family-friendly rentals Pinellas County
- Family-friendly rentals Florida
- Family-friendly rentals United States
- Anna Maria Island
- Raymond James Stadium
- Busch Gardens Tampa Bay
- John's Pass
- Weeki Wachee Springs
- Coquina Beach
- Vinoy Park
- Lido Key Beach
- Amalie Arena
- Dunedin Beach
- Cortez Beach
- Bean Point Beach
- Anna Maria Public Beach
- Jannus Live
- ZooTampa at Lowry Park
- Tampa Palms Golf & Country Club
- Hard Rock Casino
- River Strand Golf and Country Club
- North Beach At Fort DeSoto Park
- Tampa Convention Center
- Busch Gardens
- Splash Harbour Water Park
- Adventure Island
- Lakewood National Golf Club




