Family-friendly vacation rentals in Clearwater Beach Island

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Top-rated family-friendly rentals in Clearwater Beach Island

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Top guest favorite

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

4.97 out of 5 average rating, 119 reviews

THE HOUSE - 32 Steps to the Beach - Beautiful Clearwater Beach Home just across from the Beach - Drive to your door.

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 and well-equipped beach home that has been completely remodeled. It sleeps 6 guests and offers 3 bedrooms, 2 bathrooms, an open kitchen and a cozy living/dining area with a sofa sleeper. You will love the secluded, tropical patio which offers a hot tub and a BBQ for relaxing moments. The property is located in a quiet and upscale, residential neighborhood of Clearwater North Beach, just across the street of the beautiful and pristine Gulf Beach. Clearwater Beach with its vibrant public beach life, various shopping opportunities and diverse restaurants is just a mile away. The House and Cottage can be BOOKED TOGETHER OR SEPARATELY and are the perfect place for families, family get togethers or romantic get-aways. It is NOT SUITABLE FOR SPRINGBREAKERS or any group that wants an environment that allows loud parties. THE AWARD-WINING GULF BEACH IS ONLY 32 STEPS AWAY! Grill, TVs, cable, WIFI, multiple driveways for parking, beautiful landscaping. Walk to shopping, dining or island attractions. Take the public trolley around the island or go as far south as Treasure Island! Check-in is 4:00pm or later; check-out is promptly at 10:00am to leave time for cleaning crew. 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.

Guest favorite

The modern kitchen features sleek stainless steel appliances, including a spacious refrigerator and a gas stove. An island with bar seating is highlighted in blue cabinetry, complemented by decorative pendant lighting. The inviting open-plan area connects to a cozy living space furnished with a comfortable sofa.

Cottage in Indian Rocks Beach

4.98 out of 5 average rating, 150 reviews

LUXURY beach house, Enjoy Sunsets, STEPS to Beach🏖

Sandy Feet Cottage is an exquisite vacation beach house, which has undergone a stunning remodel. This private haven is tastefully renovated and decorated, providing a luxurious retreat. With brand-new furniture, it features a bright open plan kitchen, living, dining space, spacious bedrooms, and a spa-like bathroom. The backyard, complete with a private patio, relaxing chairs, hammocks, and a fire pit, is just a 2-minute stroll from the beach, restaurants, bars, and stores. The perfect retreat!

Guest favorite

A spacious pool area features a large, inviting swimming pool surrounded by lounge chairs and palm trees. The pool is designed with a gradual slope, leading to a hot tub section. The well-maintained landscape adds to the relaxed atmosphere of the community.

Condo in Clearwater

4.73 out of 5 average rating, 108 reviews

Beautiful Cozy Condo 3 miles away Clearwater Beach

AVALON CONDO This gated community is located 3 miles away from Clearwater Beach (voted #1 beach in the US 2019 and 2020 Tripadvisor) ONE BEDROOM ONE BATH WALK IN SHOWER GRANITE KITCHEN ISLAND WITH SEATING FOR 3 GROUND FLOOR ( dont carry your luggages or beach supplies up the stairs) KING SIZE BED 1 SMART TV, INTERNET ACCESS, NETFLIX 2 FLAT SCREEN TV OVER 50 INCHES FULL SIZE WASHER AND DRYER BEACH SUPPLIES ( UMBRELLA, CHAIRS, COOLER, BEACH TOWELS) SLEEPING SOFA STEPS AWAY POOL FREE PARKING

Superhost

A balcony view that captures the tranquil beach scene, featuring soft pastel hues in the sky. A round table with intricate design sits next to two woven chairs. Below, umbrellas dot the sandy beach, while gentle waves touch the shore.

Apartment in Belleair Beach

4.7 out of 5 average rating, 460 reviews

BEACHFRONT Condo - Belleair Beach Club - RENOVATED

No impact from hurricanes! - RECENTLY RENOVATED. This cozy 1 bedroom condo with a kitchen in Belleair Beach just steps from the sugar-white sand and crystal clear waters that are consistently ranked among America's most beautiful beaches! It has a lovely pool area that overlooks the gulf with a patio, chairs and grills. You’ll love the beachfront views and quiet ambiance. 3rd Floor, balcony with DIRECT BEACH/GULF VIEW. Minutes away from Clearwater Beach. Perfect for couples! ONE parking spot.

Guest favorite

A spacious rooftop terrace is illuminated by string lights, showcasing a comfortable seating area with modern outdoor furniture. The view captures the surrounding buildings and a glimpse of the beach, framed by a warm sunset sky.

Townhouse in Clearwater

4.9 out of 5 average rating, 111 reviews

Amazing 5 story beach condo, views of everything

Minimal storm damage from Helene/Milton. We are 100% ready for guests Oct 20. Our home is easy walking distance to restaurants, bars, & shopping. The beach is a 3 minute walk from the front door. Our private 5th floor roof terrace has a hot tub, grill, TV and furniture and will give you 270 degree panoramic views of the beach to the intracoastal waterway. 4 bedrooms, 3.5 baths, gorgeously appointed kitchen/living area. You can take the stairs or your private elevator can take you up or down.

Top guest favorite

A modern kitchen showcases white cabinetry with marble countertops and stainless steel appliances. Natural light floods through large windows, highlighting decorative accents and elegant floral arrangements. A central island is surrounded by bar stools, complemented by stylish area rugs beneath.

Townhouse in Clearwater

5 out of 5 average rating, 121 reviews

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!

Top guest favorite

A clear blue pool is surrounded by lush greenery, including palms and other tropical plants. A red umbrella provides shade over a seating area nearby, while lounge chairs are positioned along the pool's edge, inviting relaxation in a serene outdoor setting.

Guest suite in Largo

4.97 out of 5 average rating, 372 reviews

Private Pool, Jacuzzi, Walk to Beach.

This Guest Suite is a large Studio Apt(360 sq ft) attached to our home. It has a private entrance, a large bath, large bedroom with pool view and private deck. Also includes a kitchenette with full size fridge, toaster, coffee maker and microwave. No Stove. Complimentary breakfast snacks including Coffee, tea and biscuits. Relax on the deck and watch the birds on the bird feeder or grab our bikes, beach chairs and head to the beach. Grill available. Please read house rules before booking.

Guest favorite

A cozy bedroom is illuminated by natural light streaming through large windows adorned with patterned curtains. A spacious bed is dressed with floral bedding, accompanied by decorative pillows. A bedside table holds a lamp, and a framed art piece enhances the calming atmosphere, with the pool view visible outside.

Condo in Clearwater

4.93 out of 5 average rating, 119 reviews

POOL VIEW IN A MODERN CONDO - Feel at Home

For your best vacation, welcome to stay in our newly renovated and tastefully decorated condo for having a relaxed vacation ! Family with kids, young retired or just couples who want to spend romantic moments, everybody is welcome.The condo is located in a beautiful gated community, 10 min. by car from Clearwater Beach, voted # 1 beach in U.S. in 2013 and 2018. You can enjoy a large, beautiful heated swimming pool with salt water, a barbecue area, fitness center and an elegant clubhouse.

Guest favorite

An outdoor lounging area is presented beside a saltwater pool, featuring comfortable seating around a central table. A bar with seating is visible in the background, surrounded by tropical plants, with soft lighting enhancing the atmosphere.

Home in Seminole

4.99 out of 5 average rating, 171 reviews

Resort Pool Home with Pool Cabana 🏝6 MIN to BEACH-

Discover this glamorous 3-bedroom, 2-bathroom home, a true showstopper! Enjoy a tropical backyard featuring a phenomenal (optional heated) pool and a resort-like cabana complete with a TV and beverage fridge. Just 6 minutes from stunning beaches and 4 minutes to Seminole Town Center, this location is unbeatable. Each room boasts a smart TV. Professionally decorated and immaculately cleaned, the interior design elevates your stay. Experience luxury and relaxation in one perfect package!

Top guest favorite

A tranquil lagoon pool is surrounded by lush tropical foliage and colorful flowers. A shaded seating area is visible, along with a light-colored house in the background. Multiple palm trees contribute to the serene atmosphere of this private oasis.

Apartment in Dunedin

4.99 out of 5 average rating, 243 reviews

Tropical Paradise

Please visit our website Grovekeeper collective for a video of the property Private vacation rental I know if you are coming to Delightful Dunedin you know how amazing this waterfront community is, from award winning restaurants , micro breweries, one of the #1 beaches in America, 40 miles of bike trails, waterfront parks. Just bring food and clothes, we have the rest covered! This rental is for a maximum of 5 guest all our units are non-smoking and vaping

Guest favorite

A cozy bedroom features a spacious bed with crisp white linens, accompanied by decorative pillows. A ceiling fan is installed above, enhancing comfort. Natural light fills the room through the window, which is adorned with greenery and blinds. Nightstands with lamps provide additional lighting.

Apartment in Clearwater

4.87 out of 5 average rating, 126 reviews

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 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! 🌅🏝️🚤

Top guest favorite

The kitchen features white cabinetry with modern appliances, including a black refrigerator and microwave. A dining table with plush chairs is positioned under a chandelier. Natural light filters through a nearby window, creating a bright, inviting space for meals and gatherings.

Apartment in Dunedin

4.98 out of 5 average rating, 241 reviews

My Favorite Place 🍊downtown & city approved

LEGAL, CITY APPROVED 1 bedroom apartment w full kitchen, living , dining & separate bedroom located on the red brick streets of downtown Dunedin. Private entrance. BIKES Super clean Private driveway free parking Two great bikes Great for couples Tastefully decorated. Comfortable Queen bed. Luxurious bedding. Super clean. Shampoo, conditioner, body wash, coffee, tea, drinking water provided. SUPER CLEAN No pets