Cottage holiday rentals in Clearwater

Walk to Downtown and Waterfront - Private Yard

Steps from Main Street Dunedin & a short walk to stunning sunsets at the waterfront. Bright, beachy stylish modern décor & open floor plan. Concrete construction, a private yard, and a grill makes this cottage feel like your personal oasis. A quick drive to award-winning beaches like Honeymoon Island and Clearwater Beach. Enjoy stunning sunsets & easy access to restaurants, breweries, shops, live music. The perfect getaway in delightful Dunedin—come be our guest at the Barefoot Parrot Cottages.

Historic Heights Hideaway • Early Check-in

A perfect balance between suburban serenity & urban convenience in this historic Tampa neighborhood. Central air, Roku, strong Wi-Fi, coffee, tea, snacks. Easy self-check-in. The ideal home base for your Tampa adventures. Walk to Hillsborough River, Garden Center, & Florida Ave hotspots. 5 min to Zoo, 10 min drive to Amalie Arena, Busch Gardens, Ybor City, Ray Jay Stadium, Florida State Fairgrounds/Amphitheater, Riverwalk & Airport; 35 min to St Pete & nations best beaches, 70 min to Disney.

Flipper's @ Mad Beach Cottage

Flipper's at Mad beach is a few steps away from the sugary sands of Madeira Beach, and close by the famous John's Pass Village & Boardwark where shopping and entertainment is always great. Completely renovated with light porcelain tile, nice furniture, queen bed with memory Thempur-Pedic mattress, exquisite modern shower, tall kitchen cabinets with plenty of storage. Huge private paved fenced backyard with gazebo, great for entertainment and outdoor grilling. You will love the beach decor.

A little piece of Heaven

2 people max cozy cottage with all the amenities of home with a lakefront view. There's a firepit for those colder nights and kayaks & peddleboats for the more adventurous ones, or just sit back and take in some sun on our beautiful dock. Centrally located in between the Veterans Expressway and I 275, minutes from shopping, Lake Park, Adventure Island and Busch Gardens ...Lutz has something for everyone, don't let your friends and family stay in a hotel, we've got it all waiting right here!

Luxury Beach Bungalow | Walk to Dining & Sunset

Escape to paradise at Sunshine Escapes! Welcome to #MangoIRB, nestled in the heart of Indian Rocks Beach. IRB is a hidden gem radiating a whimsical, small-town charm that evokes nostalgic memories of carefree childhood summers by the shore. Just ✌🏽 blocks away, the Gulf of Mexico beckons, offering pristine fluffy sand and unforgettable sunsets. As the sister cottage of Coco, #MangoIRB invites you to immerse yourself in the laid-back beachy vibes of IRB. Your perfect beach getaway awaits!

Bay Lake Cottage

You’ll have the Entire 500sq ft Cottage & private entry, deck/dock, all to yourself. Located on a 37-acre private ski lake.Key-pad entry, private parking. 1 king bed, 1 bath, queen sofa bed, washer/dryer, WiFi, smart TV’s, blackout curtains,shampoo,conditioner,hairdryer,WiFi. Fully stocked kitchen, smokeless grill, wine fridge upon request, k-cup/drip coffee machine. The lake has bass, we provide fishing poles/tackle box. Rentable Kayaks & Canoe. Dog 30lb weight limit, no cats, fee $50.

Mermaid Cottage

Located in a three unit 'Olde Florida Style Complex' and just 45 steps to Clearwater Beach! The Mermaid Cottage is located on the 1st floor at the back of the complex. This Florida style unit is adorned wood floors and charming island decor. Open to an outdoor patio with furniture. The cottage has two bedrooms, two full baths and an outdoor shower! Living room has a queen pull-out bed. The patio area is completely fenced for private use. Nice, park like charcoal grill.

Modern Coastal Hideaway – Patio & Hammock by Beach

Sandy Toes Cottage is a fully renovated beach house just 2 minutes from the sand in Indian Rocks Beach, Florida. Enjoy new furnishings, a bright open kitchen, spa-style bathroom, free Wi-Fi, and a large backyard with a patio, fire pit, and hammock. Walk to restaurants, beach bars, and shops. This private, stylish retreat is perfect for couples, families, or friends seeking comfort, convenience, and coastal charm on Florida’s Gulf Coast.

Little Manatee River Cottage

This cottage is located on the Little Manatee River. Sun City Center 10 min Aquatic rentals walking distance. The cottage is updated. Abundant fishing charters, Little Harbor, manatee viewing center and Simmons Park all within minutes. Fully furnished, linens, kitchen utensils; bath towels; blankets pillows comfy furnishings. View sunsets out on the river, on the dock or at Little Harbor sipping your favorite drink.