Holiday houses in Caladesi Island

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Top-rated holiday rentals in Caladesi Island

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Top Guest favourite
A small outdoor patio is surrounded by lush tropical plants. A round table with white metal chairs is shaded by a teal umbrella, providing a cozy spot for relaxation. The entrance to the cottage, with a glass door, is visible in the background.
Home in Clearwater Beach
4.94 out of 5 average rating, 191 reviews

The Cottage - 32 Steps to the Beach - Sleeps 2, drive to your door, Wifi, Grill. Just Steps from the beach.

Our tastefully decorated and cozy Cottage offers everything you need for a romantic get-away and a relaxing stay in sunny Clearwater Beach. The Cottage is part of our vacation property '32 Steps to the Beach' which consists of a 3 bedroom house and a separate 1 bedroom cottage. The Cottage can be booked separately or together with the House. To book The House or House & Cottage together please see the listings at the side of this page. Covid-19 UPDATE - See below. The Cottage is located in a quiet and idyllic residential neighbourhood of Clearwater North Beach. The beautiful, award-winning and pristine Gulf Beach is just steps away from the house. If you prefer to have a calm beach day away from the crowds this is where you want to stay. Clearwater Beach with its vibrant public beach life and diverse restaurants is just a mile away. The Cottage offers a spacious, elegant room with a queen bed, a sitting area with a sofa sleeper and a remodeled bathroom. The new kitchenette gives you the opportunity to prepare meals and enjoy them in the small dining area or outside on the secluded patio. Savour a cup of coffee in the morning, a glass of wine after a relaxing day on the beach or enjoy a BBQ in the backyard. Clearwater North Beach is an upscale, safe residential neighborhood that welcomes families and couples. It is not suitable for 'spring breakers' or any group that wants an environment that allows loud parties. The area of Clearwater offers an astonishing diversity of leisure activities. If you enjoy sports you might want to try out the numerous jogging, skating, biking, golfing, hiking, swimming, surfing, tennis or fitness opportunities. In Florida's state parks and on the breathtaking beaches you will experience the beauty and serenity of nature. Several theme parks guarantee fun for the whole family and the diversity of the many restaurants in the area will surprise you. From casual to upscale dining, from local and national to international cuisine - you will find it all! Please also visit our website for more information about our Clearwater Beach homes, Clearwater Beach and the area: www.clearwater-beach-vacations.net Check-in is 4:00pm or later; check-out is promptly at 10:00am to leave time for cleaning crew. We will be happy to answer all of your questions. When using the 'Book it Now' button please include information on the ages and number of people in your party to help us make a quick decision on your request. IMPORTANT: We do not advertise on Craigslist! Be safe and only deal with the owner. COVID-19 Pinellas County is open for short term vacation rentals with guidelines that we are following in full. We take the safety of our guest and cleaning staff extremely seriously. Our cleaning crews are using sanitizer and disinfectant on all surfaces before your arrival and as cleaning is taking longer than previously it is unlikely that we can offer early check-ins or late checkouts. Our houses have well equipped kitchens and we believe that separate units are the best option for vacationing in the time of Covid-19. Florida is seeing an increase in cases at the moment and we stress the importance of guests taking travel insurance that would cover them in the event that they no longer want to travel to Florida. In the event that the administration halts vacation rentals we would of course refund guests as we could no longer accept them. We have to stress that after two months of cancellations and re-bookings we will not be able to offer refunds if Clearwater Beach remains open for vacation rentals but guests decide not to travel.

Top Guest favourite
Gentle waves lapping against a sandy shore create a serene coastal scene. The sky is filled with wispy clouds and varying shades of blue, reflecting the tranquil atmosphere of the beach. The shoreline reveals patterns in the wet sand as the water recedes.
Condo in Clearwater
4.95 out of 5 average rating, 309 reviews

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!

Top Guest favourite
The exterior of a coastal cottage is shown, featuring a gravel driveway and tropical landscaping with palm trees. Two wicker chairs are positioned under a covered porch, inviting relaxation. Large windows allow natural light to brighten the welcoming facade.
Cottage in Dunedin
4.97 out of 5 average rating, 357 reviews

Walk Downtown and to Waterfront, Mins to Beaches

Steps to Main Street ! Experience modern coastal luxury in this stylish, spacious upstairs 2-bedroom cottage. Professionally designed and fully stocked. Walk to Main Street Dunedin or take the short stroll to stunning sunsets at the waterfront. Quick drive to award winning beaches--Honeymoon Island & Clearwater Beach. Walk to restaurants, shops, & breweries. Pet-friendly w/ 2 king beds, a sleeper sectional, & lovely treetop views. Treat yourself today and escape to the Barefoot Parrot Cottages.

Top Guest favourite
A private outdoor space features lush greenery framing a stone pathway leading to a wooden seating area. The area is adorned with tropical plants, creating a serene ambiance. A small bar-height table with stools is visible in the background.
Bungalow in Oldsmar
4.99 out of 5 average rating, 160 reviews

salt living at its best

- Resort Style Water front - Stand alone - Hot tub - Sunrise / sunset views on dock - free Kayaks - Internet / YouTube cable - 65” smart TV - Spacious Bedroom with king size bed, walk in closet and flat TV - Washer and Dryer in unit - Designated work space -Pet friendly - Fenced private patio - Free 2 cars / Boat Parking. - Central location ( beaches, restaurants, Tampa, St Pete’s, safety Harbor, Dunedin - 11 minutes from Ruth Eckerd event Hall - Pristine clean - Coffee station - Dining area

Top Guest favourite
A spacious sleeping area features a large bed with a white comforter and decorative throw. A modern lamp illuminates a side table. Soft blue walls complement the artwork depicting a beach scene, while a cozy chair adds a comfortable seating option.
Guest suite in Dunedin
4.92 out of 5 average rating, 282 reviews

Downtown Coastal Studio, close to great beaches!

The studio has a bright and airy atmosphere, clean and cozy, it is the perfect place to rest and relax. Located in the heart of downtown Dunedin in walking distance to the Pinellas Trail and Main St. Simply park your car and enjoy town on foot or rent a bike and cruise around. We are close to Honeymoon Island and Clearwater Beach. Beach towels, chairs, cooler, and umbrella are provided. There is also a park across the street with a nice path to stroll along the water or take in the sunset.

Top Guest favourite
A spacious living area is presented with a modern sofa adorned with decorative pillows. Two comfortable armchairs complement a circular coffee table. Natural light floods the space through sliding glass doors, leading to an outdoor patio with water views. Soft, neutral tones and contrasting textures are visible.
Apartment in Clearwater Beach
4.91 out of 5 average rating, 148 reviews

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.

Top Guest favourite
Two wooden Adirondack chairs are positioned on a deck overlooking a serene lake. A floating dock extends into the water, featuring two red lounge cushions. The clear blue sky enhances the tranquil atmosphere, with greenery visible along the shoreline.
Cottage in Tampa
4.98 out of 5 average rating, 241 reviews

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. Dogs okay, sorry no cats, pet fee $50.

Top Guest favourite
A sandy path leads through lush greenery towards the beach, framed by overhanging branches. The ocean is visible in the distance, with light reflecting off the water. Shadows create a peaceful atmosphere as the sun casts a warm glow.
Cottage in Indian Shores
4.96 out of 5 average rating, 180 reviews

Beautiful Beachfront Cottage on the Water

Renovated, romantic 1937 beach front cottage. Last of its kind in the quiet family setting of Indian Shores Florida, halfway between Clearwater Beach and Treasure Island/John's Pass. Truly an "Old Florida" experience with original pine floors, Florida room and covered porches, as well as updated kitchen and bathroom. This house, uniquely built near ground level, allows it to be waterfront on the beach while shaded by huge pine trees. You won't find a more tranquil setting on the beach.

Guest favourite
A charming farmhouse exterior is showcased under large trees, with a welcoming front porch featuring red seating and decorative plants. A spacious gravel parking area is visible, complemented by a green landscape in the background, enhancing the tranquil setting.
Home in Palm Harbor
4.92 out of 5 average rating, 143 reviews

Peaceful Pet friendly 2 BR cottage with hot tub.

Wellcome to our tranquil 2-bedroom, 1-bathroom farmhouse, nestled in the peaceful countryside of Palm Harbor. Whether you're seeking relaxation or adventure, this fully remodeled country cottage provides a serene and comfortable retreat. Whether you're relaxing with a movie, soaking in the hot tub, or exploring the nearby attractions, our farmhouse offers a serene and comfortable home away from home. Book your stay today and experience the tranquility of country living!

Top Guest favourite
The image captures a spacious townhouse community, featuring white architectural designs. A clear view of the intercoastal waterway is presented, with boats visible in the distance. A community pool is seen among vibrant greenery, inviting leisure and relaxation.
Townhouse in Clearwater
4.99 out of 5 average rating, 119 reviews

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.

Top Guest favourite
A modern kitchen features white cabinetry and sleek stainless steel appliances. A central island with two wooden stools invites gatherings. Natural light spills through a nearby doorway, illuminating decorative greenery and tasteful textures along the walls.
Condo in Clearwater
4.99 out of 5 average rating, 146 reviews

Seasalt Breeze - Easy pool access, Free parking.

The Avalon at Clearwater is a gated community with a nice size heated pool and community gym. Parking space is not assigned and it’s free of charge. Location is central with short distance to nearby beaches, attractions and other nearby towns. Unit is approximately 500 square feet with a living room-kitchen open concept and One bedroom - bathroom open concept. Great access from Tampa Airport 20 minutes and 1.5/hours drive from Orlando airport

Guest favourite
Condo in Indian Shores
5 out of 5 average rating, 5 reviews

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.

Popular amenities for Caladesi Island holiday rentals

  1. Airbnb
  2. United States
  3. Florida
  4. Pinellas County
  5. Dunedin
  6. Caladesi Island