Holiday houses in Caladesi Island

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Caladesi Island

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

1 of 1 pages1 / 1
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, 151 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
Home in Tarpon Springs
5 out of 5 average rating, 24 reviews

Reel Retreat | Lakefront Home with Hot Tub

Reel Retreat is a stylish mid-century lakefront escape on Lake Tarpon, perfect for a relaxing getaway. This spacious 3-bedroom, 2-bath home features an open layout, game area, and thoughtfully designed spaces. Take in breathtaking lake views, unwind on the wraparound deck, soak in the hot tub, or gather by the fire pit. With a hammock, grill, and dock access, it’s the perfect spot for peaceful mornings and stunning sunsets. 2 kayaks on property for the lake.Come stay with us for a reel retreat!

Guest favourite
A serene outdoor space features a sparkling pool framed by lush tropical landscaping. A relaxing spa is integrated into the pool area, accompanied by comfortable lounge chairs. A shaded cabana and grilling station are visible in the background, enhancing the inviting ambiance.
Home in Tampa
4.93 out of 5 average rating, 136 reviews

The Jungalow SOHO - Pool/Hot Tub

The Jungalow is the ultimate urban oasis. Enjoy the luxuries of the home or venture out to local attractions like the iconic Bayshore Boulevard, Historic Hyde Park, SOHO, Downtown and more. This home was designed with comfort and convenience in mind. Fully equipped with a smart tv, high-speed WIFI, pool and hot tub - this place is paradise. Central to the action - walk to unique rooftop bars, restaurants and shops or Uber to local attractions like Water Street, Amalie Arena, and the Riverwalk.

Top Guest favourite
A private outdoor area features a golf putting green with a textured surface, a jacuzzi with soft blue hues, and a wooden pergola. Near the pergola, a grill is provided alongside comfortable seating. Vibrant green walls and string lights enhance the inviting atmosphere.
Guesthouse in Tampa
4.97 out of 5 average rating, 173 reviews

"Luxury Casita/Jacuzzi/Bush Gardens/USF/Casino"

Private townhouse style unit with its own entrance, parking, patio, and outdoor amenities. Attached to another Airbnb unit but completely separate with its own entrance and outdoor space. Enjoy this modern Tampa getaway with jacuzzi, pergola and putting green. Minutes from Busch Gardens, USF, and Seminole Hard Rock Casino. Features a modern kitchen, Smart TVs, Wi-Fi, and outdoor space. No parties, events, gatherings, or loud music permitted. Please respect quiet hours and neighboring guests.

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
4.95 out of 5 average rating, 198 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 two-story beach-style house is depicted, featuring a covered porch with white railings and blue shutters on the windows. Potted plants adorn the porch, complementing the light exterior. Lush greenery is visible in the background, providing a tropical ambiance.
Home in Dunedin
4.98 out of 5 average rating, 357 reviews

Steps to Downtown, Mins. to 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. Perfect for families, couples, groups. Loaded with beach gear, kids's items & pup supplies. Treat yourself to this Dunedin favorite today !

Top Guest favourite
A wooden dock extends over the calm waters of Lake Tarpon, surrounded by lush greenery. The expansive blue sky and gentle waves create a serene ambiance, ideal for enjoying nature. The space offers direct access to the lake, enhancing the outdoor experience.
Home in Palm Harbor
4.93 out of 5 average rating, 129 reviews

Lakefront home near beaches w/ waterview, pets ok

Imagine yourself waking up to a million-dollar view on Tampa Bay's largest lake - lake Tarpon. Close your eyes, relax and lose yourself to the sound of wind chimes, the caws and squeals of the birds, lapping of waves against the dock and fresh lake breeze. Watch an Osprey catch fish and other wildlife as you sip your morning coffee sitting on the dock. This is a quintessential lake house that one always desires in their dreams. Well that dream is attainable when you make this home your abode!

Guest favourite
Villa in Indian Rocks Beach
4.92 out of 5 average rating, 103 reviews

The Emerald Villa, Eco-Luxury by the Sea

Eco-friendly, earth conscious seaside villa. Located just steps from the soft sands of the Gulf of Mexico beach, this exquisitely designed family home offers a luxurious yet sustainable escape. Encased in natural light, 4 bedrooms and 3 baths, the villa sleeps dynamic families and small groups in uncompromising comfort and style and provides all the zen essentials. In-house health suite with gym, infrared sauna and red light therapy available upon request at small additional daily fee.

Guest favourite
Home in Palm Harbor
5 out of 5 average rating, 45 reviews

Waterfront Villa w/Hot Tub• Game Room•Kayaks•Bikes

Welcome to Seaside Sanctuary 🌊🌅 – Your Ultimate Waterfront Escape Nestled in charming Crystal Beach, this spacious 4-bedroom, 2.5-bath retreat perfectly blends luxury, comfort, and coastal fun. Go kayaking from your direct Intracoastal access, soak in unobstructed sunsets, relax in the hot tub, challenge friends in the game room, or grill a delicious meal on the patio 🥙. Perfect for family reunions, bestie getaways, wedding weekends—or simply because you deserve a seaside escape!

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, 274 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
Home in Palm Harbor
5 out of 5 average rating, 11 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.

Top Guest favourite
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
4.98 out of 5 average rating, 167 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...

Popular amenities for Caladesi Island holiday rentals