Caladesi Island vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Caladesi Island

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

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Guest favorite

Home in Dunedin

4.93 out of 5 average rating, 119 reviews

Everything you'll need, plus! Park Model RV

A relaxing and open space great for beach lovers, cyclists, and people who love the outdoors. This cozy setting provides all the necessities for daily living, plus more to make for a great get away! Accommodates up to four. Within 2 miles of Honeymoon Island State Park and Caladesi Island. Easy drive to Clearwater Beach, St. Pete's Airport and surrounding areas. Short walks to town, bike trails and beautiful Gulf coast sunsets make this a perfect getaway or home base for exploring the area.

Aug 23 – 30

$83 per night

Guest favorite

Guesthouse in Palm Harbor

4.97 out of 5 average rating, 203 reviews

Private Suite, 1 bedroom, 1 bathroom, pool, patio

Private suite located in Palm Harbor with king-size bed, Split unit A/C Amenities include: Large Bathroom with Jacuzzi, Walk-in Shower, Double sink Vanity. Access to Patio, Swimming Pool , Backyard and Sundeck. Room includes small refrigerator/freezer, Microwave, Coffee maker, Espresso, Iron and much more. Bistro set in room. Private entrances to room and patio/backyard. Cable TV, Netflix and Wi-Fi included. Centrally located to Restaurants and shopping. 10 mins. to the beach/Pinellas Trail.

Nov 9 – 16

$102 per night

Guest favorite

Guest suite in Dunedin

4.94 out of 5 average rating, 204 reviews

Downtown Coastal Studio, 10 min. to the beach!

The studio has a bright and airy atmosphere, clean and cozy, it is the perfect place to rest and relax. Located in the heart of downtown Dunedin in walking distance to the Pinellas Trail and Main St. Simply park your car and enjoy town on foot or rent a bike and cruise around. We are close to Honeymoon Island and Clearwater Beach (ranked in the top 15 white sand beaches in the world), the marina, a park just across the street with a nice path to stroll along the water or take in the sunset.

Aug 21 – 28

$85 per night

Guest favorite

Cottage in Palm Harbor

4.78 out of 5 average rating, 167 reviews

Crystal Beach Cottage #1

Original MCM bungalow located 1 blk from the Crystal Beach park. This property has original windows, AC window units, renovated bath and kitchen and every six month upgraded soft goods. It is appointed with all the travelers' needs for a quick get-away or a vacation. Located in a quaint neighborhood setting conveniently located by the Pinellas trail so cyclist, runners & walkers have immediate access. Close to local towns near by & Palm Harbor's Restaurant/bars, & 10 min all the best beaches.

Nov 16 – 23

$92 per night

Guest favorite

Guest suite in Tarpon Springs

4.95 out of 5 average rating, 108 reviews

Private suite in heart of Tarpon Springs!

House centrally located in a safe, residential area. Enjoy a clean, cozy & comfortable private suite with private entrance! Next to Downtown Tarpon, Tarpon Springs Sponge Docks, Sunset Beach, Safety Harbor, and many other attractions. Less than 5 minutes from the beach! Enjoy fast wifi, cable, and a cozy queen bed! Full kitchen. During your stay you’ll have access to bicycles, plenty of beach towels, hats, beach toys. Beach chairs, chairs umbrellas, small cooler and a variety of sunscreens

Nov 15 – 22

$73 per night

Guest favorite

Guest suite in Dunedin

4.87 out of 5 average rating, 175 reviews

Dunedin Suite West, 15 minutes to local beaches

Dunedin Suite West is modern and spacious with a full kitchen and private patio area out back. You will feel a sense of lightness, comfort, and style while staying at here. The suite is a 15 minute drive to Honeymoon Island and Clearwater Beach, ranked some of the nicest beaches in the world. Beach supplies are included. Or be adventurous and rent bikes and bike the Pinellas Trail. Blue Jays Stadium is in walking distance as well as Main St. with tons of restaurants, breweries, and shops.

Jun 21 – 28

$98 per night

Guest favorite

Hotel room in Dunedin

4.84 out of 5 average rating, 167 reviews

Seaside Artisan Apartment 9

This Airbnb offers a unique experience to stay at a mom and pop style retro motel. The property has total of 10 airbnb’s. There is no lobby for the guests, however we do list for rent the owner suit with front desk on airbnb as well. You can find it under “Seaside Artisan Motel Owner Suit”. This Airbnb is walking distance from the restaurants, shops and bars in Dunedin. It’s about 4 miles away from Honeymoon Island and about 6 miles from Clearwater Beach.

Oct 8 – 15

$54 per night

Guest favorite

Apartment in Dunedin

4.99 out of 5 average rating, 202 reviews

Tropical Paradise

Watch this video first to experience this wonderful Property https://vimeo.com/444390022 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 4- (2 adults and 2 children or 4 adults)

Apr 19 – 26

$162 per night

Guest favorite

Apartment in Dunedin

4.96 out of 5 average rating, 186 reviews

The Coastal Retreat

Studio apartment. Light airy Coastal Eclectic décor. Walk in closet, full size bath, Fully equipped kitchen . Key west style tropical courtyard with fish pond. Off street parking . Gas grill and outdoor dining area. One block off the Pinellas Bike trail, walking/biking to historic downtown Dunedin, Toronto Blue Jays spring training. Minutes to the 3 of the country's best beaches! Clearwater Beach, Honeymoon Island, and Caladesi Island.

Dec 12 – 19

$91 per night

Guest favorite

Bungalow in Dunedin

4.89 out of 5 average rating, 185 reviews

Cozy Park Model RV with Sun Room. No pets

A relaxing space great for beach lovers, cyclist , and people who love the outdoors. Close to beaches restaurants and historic Downtown Dunedin. Located in the Dunedin RV Resort . Honeymoon Island State Park is 3 miles, Clearwater Beach is about 9 miles. Jolly Trolley goes to Clearwater Beach St Petersburg , Tarpon Springs where the sponge docks are. Greek Food and pastries are amazing in Tarpon Springs. NO PETS

Aug 29 – Sep 5

$88 per night

Guest favorite

Apartment in Dunedin

4.94 out of 5 average rating, 111 reviews

Summer Sale! Nice Studio apt- Downtown Dunedin!

Come relax in this beautiful Studio apartment. Close to everything! One block off of The Historic Main Street of Downtown Dunedin. Tons of restaurants, shops, parks and activities super close-by. World Famous Beaches near-by. Whether your traveling for work or fun, there are Lots of fun things to keep you entertained! Great for traveling healthcare workers- ONE block away from the Mease Dunedin Hospital!

Jul 12 – 19

$117 per night

Guest favorite

Home in Palm Harbor

4.89 out of 5 average rating, 166 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.

Jan 8 – 15

$115 per night