Pet-friendly holiday rentals in Clearwater Beach Island

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.

NEW! Luxurious King Bed! 10 Steps to the Beach!

AMAZING LOCATION! This vacation rental is located within crawling distance of the beach. As soon as you open the front gate you can see the beach entrance. Locate 1 house from the sugary white sands of the world famous Clearwater Beach! Also located within walking distance of practically everything including many great restaurants, bars, shops, Pier 60, the marina and much more, yet still located on a quiet street. Once you park your car in your reserved spot, you probably won't need it again!

Modern design in tropical paradise

This beautiful 6-person modern chic condo hotel suite has views of the Gulf of Mexico across the sandy white beach from your private balcony. Your 2 bedrooms include 2 King beds, 2 full large bathrooms and a half bathroom in the hallway. With the use of the full-sized sofa bed, this suite will accommodate 6 people looking for a relaxing get-away. Enjoy watching the sunset into the Gulf of Mexico while enjoying a pre-dinner drink or look for dolphins who love to frolic in the early morning surf.

Best Location in Clw! Near Beach & Saltwater Pool!

PRIME LOCATION NEAR BEACH! Welcome to our newly renovated vacation home in beautiful Clearwater, FL. Located in the heart of downtown Clearwater within walking distance to several restaurants and shops and just a few mins drive to Clearwater Beach. This coastal styled home comes with a heated pool (at no extra charge), putting green, and a fun little game room for kids! The entire home is yours to enjoy and comes fully stocked with everything you need for a relaxing beach getaway vacation.

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!

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

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.

Quiet Beachfront Bungalow on Florida’s Gulf Coast

Welcome to The Sunset Beach Bungalow! This top-floor luxury water-front home located in Indian Shores, FL has been completely remodeled. Our serene getaway is situated on the Gulfs Coast. The large deck looks out over the water, providing a calming sanctuary to which you can retreat any time of day or night. Our home is over 1000 sq. ft and is newly furnished with plenty of room to relax during your stay. Our beach is private so there aren’t large crowds!

Cottage on Pinellas Bike Trail

This cottage on the trail is a gem. It is an easy one mile bicycle ride to downtown Dunedin and a quick stroll to waterfront Edgewater Park to watch sunsets or see the lights of Clearwater Beach across the intracoastal waterway. Circular driveway with a carport for off street parking. The cottage is equipped with a Keurig, microwave, mini fridge, as well as beach amenities and wifi. There's a fenced back patio for you to enjoy our beautiful weather!