Family-friendly holiday rentals in Clearwater Beach Island

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.

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!

Private Beachfront 4BR 2BA Bungalow*Pool*PETS OK

PRIVATE BEACH OPEN! Barrett Beach Bungalows preserves the traditional Florida beach endearments in style with 4 charming beach bungalows. Why spend your Florida beach vacation in a busy hotel ? Stay in your own private bungalow! No crowded halls, elevators, lobby areas. Enjoy a vacation the way Florida was before the development boom. No waiting for crowded elevators! Direct on sandy beach with sparkling pool! All bungalows have modern amenities, are extra clean & beautifully decorated

5 *Waterfront Condo,3 BDR.2 Baths, Pool, HOT-TUB.

PLEASE ENTER DATES for Accurate Pricing . AIRBNB SUPER HOST 5 * RATING . LUXURY 5 * WATERFRONT CONDO/3 BEDS/2 BATH/ POOL/HOT TUB. . AUG.THRU ALL OF 2025 -2026/ RATES DISCOUNTED. VIEW CALENDAR FOR ALL 2025-2026 Availability. We are located In THE Heart OF Clearwater BEACH, a 5 minute walk to the #1 Beach in the USA, Great Local Restaurants ,SHOPS, Entertainment Nearby, Enhanced cleaning procedures that followed CDC guidelines and recommendations are still in place to ensure safety .

Tropical Paradise

Please visit our website Grovekeeper collective for a video of the property Private vacation rental I know if you are coming to Delightful Dunedin you know how amazing this waterfront community is, from award winning restaurants , micro breweries, one of the #1 beaches in America, 40 miles of bike trails, waterfront parks. Just bring food and clothes, we have the rest covered! This rental is for a maximum of 5 guest all our units are non-smoking and vaping

Tiki Bungalow | Gorgeous Htd Pool | Steps to Beach

An original early 1900 Indian Rocks Beach bungalow, beautiful and bright with pool! Across Gulf Boulevard from 8th Ave beach access with all the comforts of home. Rest in the tropical garden pool, hang out in the private tiki hut out back , hop on the trolley to explore the area. Many shops and restaurants are within walking distance. Splash Harbour water park at the Holiday Inn is walking distance for a day of fun! Have an unforgettable stay! City tax#1479

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

Bay Apartment with Water View 6b

Our goal is to preserve the old Florida and to offer you the opportunity to experience a stay at a vintage themed motel. Our Airbnbs are all unique. Some include neon signs, some the original colorful subway tiles, and others terrazzo floors. You will be staying at the exact Airbnb as pictured on the listing. We seek to keep the properties original and authentic by implementing repairs instead of replacements.

Luxurious Beach House w/Rooftop Terrace & Hot Tub

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.