Vacation rentals in Caladesi Island

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Top-rated vacation rentals in Caladesi Island

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Top guest favorite
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, 195 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 favorite
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
4.98 out of 5 average rating, 174 reviews

salt living at its best

- Resort Style Water front - Stand alone - Hot tub - Sunrise / sunset views on dock - free Kayaks - Internet / YouTube cable - 65ā€ 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 favorite
The front exterior of Cooper Cottage features a welcoming porch with two black rocking chairs and potted plants. A pathway leads to the entrance, while large windows allow natural light to illuminate the space. Lush trees provide shade and a tranquil atmosphere.
Cottage in Tarpon Springs
4.99 out of 5 average rating, 179 reviews

Cooper Cottage: Cozy, Convenient and Comfortable

Cooper Cottage is for cyclists, boaters, beach goers or those who just want to relax! The Cottage is the front half of a duplex in downtown Tarpon with all the amenities including bikes and beach gear! Walk/bike to Restaurants, Churches, Museums and Parks in under 12 minutes or drive to Fred Howard Beach or Sunset Beach in 7 minutes! Due to allergies of visiting family & friends we do NOT ALLOW PETS OR COMPANION ANIMALS, so you can rest assured that animal allergens will NOT be an issue.

Top guest favorite
A well-equipped kitchenette features a granite countertop with three bar stools. Natural light enters through a window, illuminating the space, which is complemented by a small dining area and a comfortable seating arrangement. A wall-mounted TV and a lamp add to the cozy ambiance.
Farm stay in Odessa
4.96 out of 5 average rating, 110 reviews

Cabin 3 - Nasturtium Nest

Discover the peaceful retreat at Cahaba Cabins, a hidden gem nestled on a working microgreen farm in Odessa. The property offers a unique blend of charm and agricultural expertise. We offer three cozy cabins where you can unwind and reconnect with nature while still being close to everything the Tampa Bay area has to offer. Each cabin offers two queen beds, a private bathroom, and a kitchenette—providing all the essentials for a relaxing stay. We look forward to seeing you on the Farm!

Top guest favorite
A serene outdoor seating area features white adirondack chairs positioned on a natural stone patio, surrounded by lush green foliage and tropical plants. A glimpse of a swimming pool can be seen in the background, framed by additional seating and vibrant landscaping.
Apartment in Dunedin
4.94 out of 5 average rating, 124 reviews

Island Oak

This private vacation rental is a Second floor 1 bedroom apartment is newly furnished, professionally decorated and equipped with all the conveniences of home. Island Oak joins 4 other popular vacation rentals within the Grove Keeper Collective compound. This upper unit has a balcony off the bedroom which looks into a 175 year old oak that provides a tree house effect. We hope you come and enjoy this new addition to Grove Keeper Collective. All our units are non smoking and vaping.

Top guest favorite
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, 255 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 favorite
A stone fire pit is surrounded by two blue chairs, positioned on a grassy area by the waterfront. Trees provide shade, and a dock is visible across the lake, complementing the serene outdoor setting.
Home in Odessa
4.96 out of 5 average rating, 120 reviews

A perfect Lake House get away

Make some memories at this unique and family-friendly slice of paradise. Located on 100-acre Lake Anne. 20 minutes from beautiful Gulf of Mexico beaches. Enjoy breathtaking sunsets around the fire pit. Kayak, paddle board (included) or fish from the dock. Or sit and relax on the screened patio with your favorite beverage at the outdoor bar. Or venture to beautiful downtown Tampa and enjoy the Buccaneers, Tampa Bay Lightning, or the Rays baseball team

Top guest favorite
A serene sleeping area is defined by a wooden bed frame draped with sheer white fabric. The plush bedding features a subtle pattern. A vibrant green plant wall provides a backdrop, and a decorative neon sign reading 'Tiny Tulum' adds a modern touch.
Guest suite in Tampa
4.98 out of 5 average rating, 232 reviews

Tiny Tulum | Tropical Oasis in Tampa’s Heart!

Welcome to Our Romantic Tulum-Inspired Retreat! Escape to a tropical paradise at our enchanting Tulum-inspired oasis, designed with romance and relaxation in mind. Nestled in a serene neighborhood, our beautifully decorated retreat offers the perfect blend of luxury, comfort, and bohemian charm, creating an idyllic getaway for couples seeking a memorable experience. Why book a generic Airbnb when you can book a hand crafted Tropical Paradise?

Top guest favorite
The grotto-style pool area features natural rock formations with cascading waterfalls and lush tropical plants. A hot tub is integrated into the design, providing a relaxing space. The serene water reflects the clear blue sky, while views of the bay are visible in the background.
Home in Oldsmar
5 out of 5 average rating, 155 reviews

Bayside Retreat your tropical oasis

"Bayside Retreat" is a Charming Private 1~bedroom/1 bath with full living room suite, located right on the water of upper Tampa Bay. Spend a quiet day lounging in the grotto pool, kayaking the bay, or a lazy day reading in the hammock. Enjoy breath taking sunrise and sunsets from the dock. Your own Tropical Paradise away from the rest of the world....... Just 15min to Raymond James Stadium. Centrally located 15 miles from TPA Airport

Top guest favorite
The image captures a serene view of the canal with calm, reflective waters. Lush greenery lines the banks, while several boats are seen docked along the shore. Bright sunlight illuminates the scene, highlighting the tranquility of the waterfront setting.
Home in Palm Harbor
4.98 out of 5 average rating, 110 reviews

Tarpon Lake Escape LLC

Key West-inspired, newly furnished house on Lake Tarpon. Decorated in bright Key West style! 3 bedrooms, 2 bathrooms, 2 porches, and a ping pong table on a corner lot with over 190 feet of water property. One of the best properties on the lake! Innisbrook Golf Resort is 1/2 mile away Clearwater Beach 15 mi Tarpon Springs Sponge Docks 5 mi Downtown Dunedin 9.6mi Honeymoon Island 8.7mi TPA airport 20mi Raymond James Stadium 20mi

Guest favorite
A bright living area features a comfortable light-colored sofa and armchairs, complemented by a decorative round coffee table. Large glass doors provide an unobstructed view of the beach and palm trees outside, allowing natural light to fill the space.
Condo in Indian Rocks Beach
4.97 out of 5 average rating, 156 reviews

Private Ocean View Beach Retreat with Balcony

Only steps from the beach, this newly updated and perfectly located beach condo is your luxury getaway. The large bedroom, lofty living area and modern open kitchen, as well as the generous balcony with direct view of the Gulf will make you never want to leave again. This condo is better equipped than your average vacation rental and comes with your private daily sunset spectacle. Continue to read for more...

Top guest favorite
A modern living area showcases a sleek gray couch featuring soft tufting and a white decorative pillow. A circular wooden coffee table, supported by a geometric metal base, rests nearby, providing a casual yet stylish touch to the space.
Home in Palm Harbor
4.89 out of 5 average rating, 227 reviews

Cute Lil' House Near Historic Downtown Palm Harbor

They say that the best things come in small packages. Well that certainly rings true in this case. Our house may be small, but it is large on personality and full of elegant charm. Newly remodeled and filled with personal touches, this small package is ready to be your Florida retreat. Enjoy charming palm harbor on our golf cart for a small rental fee.

Popular amenities for Caladesi Island vacation rentals

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