Family-friendly vacation rentals in Clearwater Beach Island

5 out of 5 average rating, 132 reviews

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

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

Gentle waves lapping against a sandy shore create a serene coastal scene. The sky is filled with wispy clouds and varying shades of blue, reflecting the tranquil atmosphere of the beach. The shoreline reveals patterns in the wet sand as the water recedes.

4.95 out of 5 average rating, 308 reviews

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!

4.97 out of 5 average rating, 134 reviews

2 BR/2 BA Key West Retreat, A+Pool, 3mi to Beach

🌴 😎 Stunning Key West Style Retreat featuring: - Memory foam Queen bed - Covered porch for unwinding - Hotel linens, towels and many creature comforts Enjoy the beach 🏄‍♂️ vibes decor & accents in this spacious two bed two bath property. Located less than three miles from the white, sugar sand of Clearwater Beach 😎 (rated #1 beach in the US by Trip Advisor). Relax by the oversized resort style pool and clubhouse. Convenient walking distance to nearby restaurants and grocery stores.

4.96 out of 5 average rating, 151 reviews

A spacious living area is furnished with a large, L-shaped gray sofa, providing comfort for relaxation. A flat-screen television is mounted on the wall opposite the sofa, while natural light enters through two windows, dressed with light curtains. A decorative rug and a console table add to the inviting ambiance.

Place to stay in Dunedin

The Zen Den Studio

Welcome to our home away from home, where you can relax and take it easy or enjoy all the excitement close by. Our Seaside Studio sleeps 2 guests comfortably, one queen size bed, one queen sofa bed, 1 full bath, and a fully stocked kitchen. Our studio provides all the amenities of a home with an extraordinary location close to all of your vacation needs. You can take a walk to the Blue Jays Stadium, you are 1 Mile to Downtown Dunedin where restaurants and shops awaiting to please your palate.

An inviting living space features a large sectional sofa adorned with cushions in soft blue tones. A decorative rug adds texture to the wood floor. A television is mounted on the wall, and a dining area with a wooden table and chairs is visible in the background.

4.86 out of 5 average rating, 284 reviews

2 Bedroom 2 Bath Condo, 3 min walk to Beach

Are you looking for something clean and spacious? A three minute walk to the beach? Central AC? A full kitchen with cooking tools? A king bed for a comfortable nights sleep? A cute & cozy beach apartment? 2 bedrooms & 2 full bathrooms. Fully equipped kitchen. Pull out sofa bed for extra guests. Kick back and relax during your beach vacation in this cozy condo with all the beach supplies you’ll need including beach umbrella, chairs, towels, wagon, toys and much more. Free on-site parking.

4.78 out of 5 average rating, 165 reviews

Cottage in Clearwater

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 4 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

Superhost

A set of two white wicker chairs and a small table are positioned on a balcony, providing views of the Gulf of Mexico. The ocean and sandy beach stretch into the distance, with clear blue skies overhead.

4.9 out of 5 average rating, 403 reviews

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.

Superhost

A cozy bedroom features a king-sized bed with soft linens, alongside a nightstand illuminated by a gentle lamp. A window allows natural light to enter, framing a view of palm trees outside. Walls are painted in a warm tone, creating a relaxed atmosphere.

Apartment in Clearwater

4.79 out of 5 average rating, 182 reviews

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

Superhost

An outdoor seating area is sheltered by a wooden pergola adorned with string lights. A cozy couch is positioned on a decorative area rug, complemented by a small table. Lush greenery surrounds the space, providing a tranquil environment for relaxation.

Guesthouse in Dunedin

4.82 out of 5 average rating, 134 reviews

Guest House in prime location!

This special place is close to everything, making it easy to plan your visit. Less than 30 minutes to TPA Airport, 13 miles to Clearwater Beach, 2.2 Miles to Honeymoon Island, 1.0 miles to US-19 to easily get to surrounding areas, and 3.5 miles to downtown Dunedin. Guest house located on property with friendly host. There is one parking space provided for guests onsite. Happy to provide recommendations for a local experience during your stay! Beach necessities available upon request.

Hotel room in Clearwater Beach

A well-equipped living space is displayed, featuring a sofa and a coffee table. A flat-screen television is mounted on a decorative wall. The kitchen includes modern appliances, with light cabinetry complemented by wooden accents, creating a bright and inviting environment.

4.88 out of 5 average rating, 371 reviews

Beach 1BR Suite w/Kit on Famous 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!)

4.94 out of 5 average rating, 105 reviews

Apartment in Clearwater

The Breezeway #6 only a 2 min walk to the Beach!

Our studio has a King Bed, as well as a microwave, mid-size fridge, regular coffeemaker and toaster. We do not provide kitchen utensils, paper towels etc. but you’ll find tons of amazing local restaurants just a short walk away. We offer a heated Pool and free parking for our guests on site. We have a brand-new Pickle ball court and Playground on one side and a public pool and tennis court on the other. We are just short stroll to historic Pier 60 and vibrant beach nightlife.