Holiday rentals in Sand Key, Clearwater

Walk Downtown & to Waterfront Designer Home for 8

Experience the charm of the Barefoot Parrot House, a private home with beautiful designer coastal decor and abundant outdoor space. Steps from Main Street Dunedin, a short walk to the waterfront and an easy drive to award-winning beaches - Honeymoon Island and Clearwater Beach. Walk, bike, or cart to gorgeous sunsets, restaurants, breweries, shops, and the Pinellas Trail. Perfect for families, couples, small groups. Loaded with beach gear, kids's items and games. Treat yourself and book today!

Luxury Beach Bungalow | Walk to Dining & Sunset

Escape to paradise at Sunshine Escapes! Welcome to #CocoPalmsIRB, nestled in the heart of Indian Rocks Beach. IRB is a hidden gem that radiates a whimsical, small-town charm, evoking nostalgic memories of carefree childhood summers by the shore. The Gulf of Mexico beckons just two blocks away, offering pristine fluffy sands and unforgettable sunsets. As the sister cottage of Mango, #CocoPalmsIRB invites you to immerse yourself in the laid-back beachy vibes of IRB. Your perfect getaway awaits!

Direct Ocean View Top Floor Renovated. 2BR, 2 Bath

The Marquise 204 is a Beautiful 1300sq ft DIRECT beachfront unit! Direct Gulf front views! Top floor corner unit. Small and quiet 10-unit building. Tremendous location for getaways with family and friends. After arriving you can literally leave your car behind and walk to over 10 local restaurants, bars and shops! Enjoy some of the best sunsets you will see in all of Florida from your private balcony! NO PETS. Renter MUST be at least 25 years old. NOTE: TWO flights of stairs NO elevator.

One step to the Beach! Ocean views from 3 decks!

Welcome to "Beach Blues" where you'll only have the "Blues" when you are leaving! Newly renovated decks and beach level travertine patio allows you full ocean view from 3 levels and direct beach access in one step! Professionally and comfortably decorated inside too! No more lugging your beach items as we provide chairs, umbrella, sand toys, and beach towels. Perfectly located close to restaurants, groceries and activities. Few miles from Clearwater, Dunedin and the new St Pete Pier.

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.

Private Ocean View Beach Retreat with Balcony

Only steps from the beach, this newly updated and perfectly located beach condo is your luxury getaway. The large bedroom, lofty living area and modern open kitchen, as well as the generous balcony with direct view of the Gulf will make you never want to leave again. This condo is better equipped than your average vacation rental and comes with your private daily sunset spectacle. Continue to read for more...

CBC 2-18F: Beach Front Escape, Book Now!

🌊Indulge in the epitome of tranquility at CBC 2-18F, a hidden gem nestled along the shores of Sand Key Beach in Clearwater, FL. Escape to the 18th floor of this spacious condo, where an open floor plan unveils jaw-dropping water views, setting the stage for a perfect beachfront vacation. This 2-bedroom, 2-bath haven is adorned with tasteful coastal decor, offering a stylish yet comfortable ambiance.

𖤓Updated Stilt home: just steps to the beach!𖤓

Experience a stylish and relaxing beach vacation at our vacation retreat! We are a very popular spot for Honeymooners and anniversaries! As a 4-year Superhost, we offer a charmingly renovated home just steps away from the beach and local restaurants. Explore Indian Rocks Beach with our provided bikes and unwind in the bubbly spa. Escape the everyday and find paradise here! BTR #2292

Luxe Waterfront Villa: Pool, Hot Tub, Golf Cart

Soothe your soul at this ultra-private luxe waterfront villa. Perched on the shores of the Intracoastal Waterway (not on a canal directly facing other homes), this hidden gem offers exceptional seclusion and extraordinary views.