Holiday rentals 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, 147 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 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, 127 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 the beautiful Gulf of Mexico beaches. Enjoy breathtaking sunsets around the fire pit. 3 Kayaks and 1 paddle board (included) or fish from the dock. Or sit and relax on the screened patio with your favorite beverage at the outdoor bar, by the fire pit, or on the dock. Or venture to beautiful downtown Tampa and enjoy the Buccaneers, Tampa Bay Lightning, or the Rays baseball team

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.
Guest house in Tampa
4.97 out of 5 average rating, 165 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, 193 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, 352 reviews

Barefoot Parrot /Walk Downtown & Water/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 gorgeous 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
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.
Flat in Tarpon Springs
5 out of 5 average rating, 104 reviews

Waterfront studio great for Pasco scallop season!

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
The charming guest house exterior is framed by a lush green lawn. A walkway leads to a welcoming front door, with two comfortable chairs positioned by the entrance. Large windows allow natural light into the space, complemented by a well-maintained garden area.
Guest house in Palm Harbor
4.98 out of 5 average rating, 102 reviews

New Guesthouse with Pool in Palm Harbor

This Brand new Beautiful Guest house was completed in August 2024 and is located in the back corner of a 1/2 acre lot with all the amenities for a short stay or longer stay. From private access to the house and use of the shared pool and patio this house has it all! Full Kitchen, Dining Area, Living room, Washer and Dryer. Stunning Master Bedroom, Master Bath with Dual Vanity, Jacuzzi and walk in shower and spacious master closet. This Gem includes all the amenities for a Luxurious Stay!

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, 265 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 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.
Flat in Dunedin
4.99 out of 5 average rating, 270 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 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, 276 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 favourite
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, 167 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 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.
Apartment in Indian Rocks Beach
4.98 out of 5 average rating, 165 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

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