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.

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Guest favorite

Home in Clearwater Beach

4.97 out of 5 average rating, 108 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.

Superhost

Home in Clearwater Beach

4.97 out of 5 average rating, 206 reviews

Clearwater Beach Townhome w/Game Room & Boat Slip!

PLEASE ASK ABOUT OUR OTHER 2 WATERFRONT PROPERTIES ON CLEARWATER BEACH IF YOUR DATES ARE NOT AVIALABLE!! Welcome to Brightwater Blue, our newer vacation Town Home in Clearwater Beach! 3 floors of fun, elegance & relaxation await you. Custom interior decorated with Restoration Hardware & other high end furnishings. Located on Clearwater Bay & within easy walking distance to Clearwater Beach, Beach Walk, restaurants, shopping & everything Clearwater Beach has to offer! Why book 3 hotel rooms when

Guest favorite

Guesthouse in Largo

4.99 out of 5 average rating, 316 reviews

Paradise Cottage Largo high ground Safe - Beaches

We are PARADISE COTTAGE, and the standards of super host are status quo! We're ready for you! Although only 2 miles from the Gulf, we're on high ground! We are on a Priority One Energy Grid. With over 300 huge potted plants, many trees, etc we live in a lush tropical "Paradise". Our guests' highest praises include private, quiet, serene, safe and secluded; attributes we're fortunate to claim We have no neighbors while being so close to so much. Read the next section "The Space" to learn more.

Superhost

Townhouse in Clearwater

4.89 out of 5 average rating, 101 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.

Guest favorite

Townhouse in Clearwater

5 out of 5 average rating, 108 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!

Guest favorite

Guest suite in Largo

4.97 out of 5 average rating, 343 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

Condo in Clearwater

4.95 out of 5 average rating, 112 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

Rental unit in Dunedin

4.98 out of 5 average rating, 227 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

Guest favorite

Townhouse in Clearwater

4.85 out of 5 average rating, 159 reviews

Luxurious, Family Beach Condo w/Rooftop Terrace-#4

This spacious, well appointed & continuously updated vacation home is located (1) block from the beach & is absolutely perfect for a family vacation. Highlighted with a stunning rooftop terrace that includes a hot tub, outdoor furniture, grill & views of the beach & bay. Undeniably as good as it gets when it comes to "beach life" in Clearwater Beach! The layout allows for amazing comfortability with a group.

Guest favorite

Rental unit in Clearwater

4.94 out of 5 average rating, 200 reviews

Your own apartment, private with patio & driveway.

This Triplex apartment is centrally located in Clearwater near US Hwy 19 and Gulf to Bay Blvd (Rt 60). Clearwater Beach is a straight drive ahead (about 4 miles). This is a large 1 bedroom apartment that is perfect for two, but can also sleep four with the sleeper-sofa. There is a full sized, fully stocked kitchen, and a screened in patio in the back where smoking is allowed.

Guest favorite

Bungalow in Clearwater

4.89 out of 5 average rating, 222 reviews

King-1 BR, waterfront villa, 2 min walk to beach

1 Bedroom, 1 Bathroom, 1 queen sofa sleeper in living room, Located in a four villa complex and just 3 Blocks to white sandy gorgeous Clearwater Beach! Quaint and casual is our motto. Villa equipped with Cable TV, WI FI. Full kitchen and dining area. Seperate bedroom, now with a King bed! We now have washer and dryer on site for guest use, no fee.

Guest favorite

Home in Clearwater

4.96 out of 5 average rating, 357 reviews

Coastal Cottage E - 1318 - Bikes and Beach items!

This guest house has been fully remodeled with brand new mini split-air conditioners. It shares a parking lot, grill, and laundry with other units. Included with this unit are 4 beach cruiser bikes, beach chairs, beach towels, umbrellas, coolers beach bag, bag of sand toys, beach cart, and more! Note: sorry no animals 💕🙏