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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Guest favourite
A bright studio space features a cozy seating area with a soft blue love seat and a spacious bed adorned with white linens. Natural light filters through sheer curtains, illuminating the wood furnishings and decorative accents throughout the room.
Guest suite in Largo
4.91 out of 5 average rating, 324 reviews

"Twilight Sands Stud" Prvt Ent,Pool,Pk,Keyless Ent

Welcome to our cozy guest suite—where comfort is personal over perfect, and full of charm you won’t find at a hotel. Guests love the thoughtful touches, eclectic decor, cloud-like bed, and the irreplaceable feeling of being at home when you’re far from home. Our home uses one central AC unit. Because Florida is warm and humid year-round, we keep the thermostat at 70°F by day and 67°F at night for proper cooling and comfort. If you prefer more warmth, two space heaters are in the suite closet.

Guest favourite
A serene view of the bay is captured at sunset, with calm water reflecting the soft colors of the sky. A wooden dock extends into the water, leading to a covered area, surrounded by lush greenery and distant waterfront homes.
Apartment in Clearwater Beach
4.95 out of 5 average rating, 66 reviews

Fantastic Island Living on the Bay with Dock

Best of both worlds! Waterfront location on the bay with the beach just a few blocks away. Private entrance to a newly remodeled, spacious 2nd floor one-bedroom apartment with a full kitchen and view of the bay. Enjoy the beauty of living on the bay side of the island with a dock for water access, fishing, swimming and kayaking and just a short walk to miles of uncrowded pristine beaches. Shared use of the outdoor patio dining area, picnic table and lounge chairs on the dock and outdoor shower.

Top Guest favourite
A spacious living area is furnished with a large, L-shaped gray sofa, providing comfort for relaxation. A flat-screen television is mounted on the wall opposite the sofa, while natural light enters through two windows, dressed with light curtains. A decorative rug and a console table add to the inviting ambiance.
Place to stay in Dunedin
4.96 out of 5 average rating, 150 reviews

The Zen Den Studio

Welcome to our home away from home, where you can relax and take it easy or enjoy all the excitement close by. Our Seaside Studio sleeps 2 guests comfortably, one queen size bed, one queen sofa bed, 1 full bath, and a fully stocked kitchen. Our studio provides all the amenities of a home with an extraordinary location close to all of your vacation needs. You can take a walk to the Blue Jays Stadium, you are 1 Mile to Downtown Dunedin where restaurants and shops awaiting to please your palate.

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, 156 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

Guest favourite
Apartment in Largo
4.83 out of 5 average rating, 283 reviews

Cozy Largo Studio

Fantastic studio consisting of a comfortable queen bed, and small kitchenette, perfect for a long term stay or weekend get away. Parking on premises. Unit was newly renovated and is impeccably kept. Minutes away from popular Indian Rocks beach / Belleair beach and clear water beach. Easy hassle free check in. (This is a one room studio with 1 queen bed as shown) this is a private apartment with its own front door. Not a shared space. Close to the Largo hospital, medical students welcome

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, 88 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.

Guest favourite
An outdoor seating area is sheltered by a wooden pergola adorned with string lights. A cozy couch is positioned on a decorative area rug, complemented by a small table. Lush greenery surrounds the space, providing a tranquil environment for relaxation.
Guesthouse in Dunedin
4.85 out of 5 average rating, 132 reviews

Guest House in prime location!

This special place is close to everything, making it easy to plan your visit. Less than 30 minutes to TPA Airport, 13 miles to Clearwater Beach, 2.2 Miles to Honeymoon Island, 1.0 miles to US-19 to easily get to surrounding areas, and 3.5 miles to downtown Dunedin. Guest house located on property with friendly host. There is one parking space provided for guests onsite. Happy to provide recommendations for a local experience during your stay! Beach necessities available upon request.

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
4.97 out of 5 average rating, 239 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
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, 352 reviews

Walk Downtown and to Waterfront, Mins to Beaches

Experience modern coastal luxury in this stylish, spacious upstairs 2-bedroom cottage. Professionally designed and fully stocked. Steps from Main Street Dunedin, 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. Book your getaway at the Barefoot Parrot Cottages.

Guest favourite
A modern bedroom features a spacious bed with a unique wooden slatted frame. Light-coloured walls and grey curtains frame a window, while a large piece of wall art adds a touch of nature. Air conditioning is provided for comfort.
Guest suite in Tampa
4.96 out of 5 average rating, 239 reviews

"Chic/cozy Petite Studio •"Spa-Inspired Shower”P2

Welcome to your serene hideaway in Citrus Park, where modern comfort meets thoughtful design. Just 11 minutes from Tampa International Airport, this stylish and private studio is the perfect spot for couples, solo travelers, or business guests seeking a peaceful and rejuvenating stay. Located in a quiet, safe, and central neighborhood, you’ll enjoy a private entrance, free on-site parking, and easy access to restaurants, grocery stores, and major Tampa attractions.

Top Guest favourite
A compact kitchen area includes a white refrigerator, an oven, and a microwave, all arranged neatly against light cabinetry. A circular clock in red and black adorns the wall, while a small black dining table with two chairs is positioned in front. Glassware and kitchen accessories are displayed on open shelving.
Apartment in Dunedin
4.96 out of 5 average rating, 199 reviews

Cozy Apartment Overlooking Downtown Dunedin

Historic Home in the heart of Downtown Dunedin, known by locals as the Yellow House. Second floor 1 bedroom apartment is totally renovated. Walk just a few steps to restaurants, bars, shops, and the Pinellas Trail. Home overlooks Pioneer Park where you can enjoy the local farmers market on weekends, concerts, movies, art festivals and much more. Sit on the front porch and see all Dunedin has to offer.

Top Guest favourite
An open-concept kitchen and living area showcases modern design elements. A large island with a sink and sleek countertop is highlighted, accompanied by elegant pendant lighting. Expansive windows bring in natural light, while a comfortable seating area and dining space are visible in the background.
Townhouse in Dunedin
5 out of 5 average rating, 38 reviews

Rooftop+Balcony- Luxury Stay in Downtown Dunedin

***NEW AIRBNB PRICING STRUCTURE: Airbnb now displays all-in pricing to guests, which includes a 15.5% service fee charged directly by Airbnb (we have no control over), the $180 cleaning fee, & pet fees if applicable. Comfort meets elegant, modern luxury in this stunning brand new 2 bedroom, 2 bath second story townhome unit in the heart of Downtown Dunedin!

Popular amenities for Caladesi Island holiday rentals

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