Holiday houses in Caladesi Island

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Top-rated holiday rentals in Caladesi Island

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
The exterior of a charming blue beach house is surrounded by lush palm trees and vibrant landscaping. A spacious front yard features a green lawn and neatly trimmed bushes, while a driveway accommodates parked vehicles. Sunlight filters down, creating a warm atmosphere.
Home in Clearwater Beach
4.98 out of 5 average rating, 140 reviews

THE HOUSE - 32 Steps to the Beach - Beautiful Clea

House sleeps 6 - Private patio and Hot Tub, Wifi, Grill . '32 Steps to the Beach' is a charming and cozy Clearwater Beach retreat in a TOP LOCATION. The pristine Gulf Beach is just across the street! We also have a Cottage at the same address and they can be rented separately or together. Covid-19 UPDATE - See below. To book the House & Cottage or the Cottage on its own please see the links to their descriptions at the right of this page. THE HOUSE is a tastefully decorated, upscale

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
4.97 out of 5 average rating, 183 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
Home in Dunedin
4.98 out of 5 average rating, 339 reviews

Barefoot Parrot /Walk DT & Waterfront/Sleeps 8

Steps from Main Street Dunedin, a short walk to the waterfront and an easy drive to award-winning beaches, Honeymoon Island & Clearwater Beach. Experience the charm of the Barefoot Parrot House, a private pet friendly house with designer decor and abundant outdoor space. Walk, bike, or cart to stunning sunsets, shops, dining, breweries, and Pinellas Trail. Great for families, couples, groups. Loaded with beach gear, kids's items & pup supplies. Treat yourself to this beloved Dunedin favorite!

Top Guest favourite
An aerial view showcases a modern two-story house surrounded by water and greenery. A private boat dock is positioned in the foreground, along with a manicured lawn featuring a putting green and colorful kayaks. Solar panels are visible on the rooftop.
Apartment in Tarpon Springs
5 out of 5 average rating, 102 reviews

Waterfront studio w/Hot Tub and Putting Green

Studio Apartment on ground level. Direct access to Gulf of Mexico w/short boat/kayak ride. Queen-size bed and pullout sofa. Microwave, coffee maker, stove top, refrigerator/freezer, 62" Smart TV, gas BBQ. Hot tub (only available from Oct 1st-May 31st) Enjoy the sun, beautiful nature of Anclote River with 3 kayaks and 3 paddle boards. Daily sightings of dolphins, manatees and many species of birds passing by. Fish right off the sea wall. Beach is a short 2-miles away. Overnight boat docking.

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, 260 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
Home in Oldsmar
4.97 out of 5 average rating, 39 reviews

Modern Private Estate | Central to Tampa & Beaches

Experience a private 1-acre modern home designed for space, calm, and everyday comfort. Surrounded by mature oaks and palms, this serene property offers rare privacy just minutes from Tampa Airport, Clearwater Beach, Safety Harbor, St. Pete, and top attractions. Enjoy a chef’s kitchen with modern appliances, spacious living areas, and peaceful outdoor spaces with a patio, electric grill, and koi pond. Ideal for families, longer stays, and guests who value quiet and thoughtful design!

Top Guest favourite
Home in Largo
5 out of 5 average rating, 7 reviews

Lux Spa Retreat•Pool•Hot Tub•Sauna•10 min to Beach

You asked, we delivered. Inspired by our Top 1% listing and consistent 5⭐ stays at “The Tiny Oasis”, Haus De Noir is a moody, boutique 3BR/3BA retreat with Plunge Pool, Hot Tub, Sauna, Outdoor Cinema and More! Slip into the Midnight Kafana, your own after-hours Hideaway Bar with Karaoke, Lights, and Late-Night energy. Fully stocked with everything you need and then some! Family-Owned and Managed! We don’t just host we LOVE what we do! Just 10 mins to Indian Rocks & Madeira Beach🏝️.

Superhost
A bright living area is featured, with light streaming through white-blinded windows. A soft, cream-colored sofa is positioned next to a cozy armchair, complemented by a patterned area rug. A small potted plant and a woven pouf add natural elements to the space.
Home in Palm Harbor
4.96 out of 5 average rating, 28 reviews

Crystal Beach Cottage

Take a break and unwind at this peaceful oasis in Crystal Beach. Walking distance to the waterfront park where you’ll see the most beautiful sunsets and can go for a stroll on the waterfront walking trail. The Pinellas Trail is also steps away where you can rent or bring your own bike and enjoy the local breweries and restaurants. Crystal Beach is centrally located to several beaches and less than an hour from beautiful fresh water springs and everything Tampa has to offer.

Top Guest favourite
The living area showcases a spacious layout with a modern sectional sofa adorned with soft pillows. A stylish coffee table sits in the center, surrounded by inviting armchairs. A striking staircase with a metal railing leads to an upper level, illuminated by contemporary light fixtures.
Home in Tampa
5 out of 5 average rating, 107 reviews

New Prime location Riverwalk Luxe 3BR 3BA

Tampa's newest 3BR 3BA gem: Aster Haus, just 4-streets over from the Riverwalk & Armature Works. Primary King en-suite bedroom boasts private balcony for two; living area, a grand 25ft ceiling. Outdoors, a lush courtyard with covered porch, pergola & relaxing fountain beckon. Private parking for 2 cars. Modern amenities seamlessly blend with timeless bungalow charm, in this new build. Enjoy the prime walkable Tampa Heights location to access the Tampa’s finest.

Top Guest favourite
A tranquil lagoon pool is surrounded by lush tropical foliage and colorful flowers. A shaded seating area is visible, along with a light-colored house in the background. Multiple palm trees contribute to the serene atmosphere of this private oasis.
Apartment in Dunedin
4.99 out of 5 average rating, 267 reviews

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

Top Guest favourite
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, 123 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 favourite
Home in Palm Harbor
5 out of 5 average rating, 8 reviews

Gulf View on Bay: Newly Renovated

Your cozy getaway awaits in Palm Harbor at this enchanting house. Great view of the Gulf from the living room, back porch and upstairs bedroom. Nice relaxing front deck with rocking chairs. With two spacious bedrooms featuring king beds and a living room that includes a twin bed pullout, guests have plenty of room to relax. The two bathrooms offer both a soothing bathtub and a refreshing shower, perfect for unwinding after a day of adventure.

Popular amenities for Caladesi Island holiday rentals

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