Holiday rentals in Clearwater Beach Island

Steps 2 beach! Beachy and Luxurious! Easy Living!

Easy Living is a beachy newly renovated condo with 2 bedrooms & 2 full bathrooms, nestled between the intercoastal water and the magnificent Clearwater beach! Located a very short walk to the beach (less than 2 blocks) and across the street from a park. The Clearwater Beach Rec Pool is another short two minute walk from the condo! The condominium is quiet area yet, it is within walking distance to practically everything in town, including the beach, many restaurants, bars, Pier 60, & the marina!

Wonderful Condo at Avalon - Fully Renovated

Ground Floor Completely RENOVATED!!! Amazing & Very cozy and it has a a 60” Fireplace. 1 king size bed and a queen pullout couch new style, 1 bathroom with the best water pressure including a rain shower and a hand held unit. This unit is very well equipped with everything you need and have at your home. The condo is great for a couple’s getaway or a nice family vacation. YOUR HOME AWAY FROM HOME!!! Steps to the POOL, beach chairs, Floaties, wagon, cooler, etc. The Beach is a 10 minutes!!

Waterfront Industrial Chic #2 Clearwater Beach

This prime location is on the bay just steps away from the beach and the main strip offering a complete home experience. This spacious apartment is equipped with a full kitchen, washer/dryer, two full bathrooms, a large family room, dining area, access to the pool and two assigned parking spaces. A split floor plan ensures privacy, accommodating guests on either side of the apartment. The private patio overlooks the bay, offering stunning views of the sunrise and the occasional dolphin.

Beach Haven in South Clearwater Beach

This unique two-story vacation rental with a loft is perfect for a large family or two. It has large panoramic windows with incredible views of the harbor from every bedroom and living space. The Dockside Condos are centrally located in South Clearwater Beach close to all the action of Shephard's nightclub, restaurants, sports bars, miniature golf and more, as well as being only two blocks to the beach. Come and enjoy this condo just one block from the white sands of Clearwater Beach.

Gorgeous and Updated Waterfront Condo 2 Bed/2 Bath

Relax in this renovated waterfront apartment. Unwind after your day at the beach on the patio overlooking the sun setting over the water. This fresh space has everything you need for your stay; a full kitchen stocked with cooking supplies, two full bedrooms & bathrooms, a large living area with ocean views to name a few highlights. Only 5 miles to the #1 rated Clearwater Beach, 1.3 miles to the fun Downtown Dunedin, a block to the Pinellas Trail, & 1 mile to the Blue Jay’s stadium!

New private guesthouse walk to downtown Dunedin

This new construction (July, 2024) unique and tranquil unit is perfect for your weekend getaway or a longer stay. Light, bright and neutral, 10 foot ceilings make property feel more spacious. Very quiet and private, concrete block construction provides solid insulation. Close to Clearwater and Honeymoon Island beaches, walking distance to TD Ballpark .6 miles, downtown Dunedin 1.2 miles to shops and restaurants, Pinellas Trail is across the street, easy transit to airport.

Beachfront Getaway with Patio – Perfect For 6

Welcome to the piece of paradise you’ve been dreaming of!! This charming seaside townhouse is located just 70 STEPS from the beautiful white sand of Clearwater Beach. Enjoy the convince of it's prime location, cook great seafood at the grill, and truly live the Florida beach lifestyle. Walking distance from bars, restaurants, and stores. This house has been entirely renovated and furnished so it can offer an outstanding beach experience. Don't delay and enjoy Florida!

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.

Waterfront Courtyard 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. We are pet friendly! Pet fee is $150 for the first dog, $100 for the second dog.

Oceanview Seaside Cottage | Walkout Beach Access

Wake up to the sound of the waves at this charming oceanfront cottage! Enjoy coffee on your ocean-view balcony or step right onto the sand with walk-out beach access. Inside, relax in the king bedroom or on the pullout sofa with inflatable topper. Smart TVs, an updated kitchen, and coastal décor add comfort and charm. Outside, unwind on the patio with chairs and a picnic table. Beach essentials included for a stress-free stay.

1/1 located at JW Marriott on Clearwater Beach,914

JUST LISTED! Beach front, water and beach view! Relax and unwind at this luxurious condo located at the JW Marriott Resort and Spa on Clearwater Beach! This privately owned 1-bedroom, 1-bathroom residence features stunning views of the Gulf of Mexico from your 9th floor private balcony, which is accessible from both bedrooms and the living room. The unit sleeps up to 4.

Coastal Retreat in Downtown Dunedin w/ Yard+Grill

These luxury townhomes were thoughtfully built as vacation havens in the heart of Downtown Dunedin, a place we proudly call home. Designed with privacy in mind, each home features professionally built lockout units between floors and neighboring townhomes, allowing guests to book individual spaces or entire homes - while always maintaining complete privacy and comfort.