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.

Oct 24 – 31

G$18,459 GYD per night

Guest favorite

Guesthouse in Palm Harbor

4.97 out of 5 average rating, 199 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 26 – Dec 3

G$24,478 GYD per night

Guest favorite

Guest suite in Dunedin

4.94 out of 5 average rating, 202 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.

Sep 5 – 12

G$20,401 GYD 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.

Sep 10 – 17

G$22,094 GYD per night

Guest favorite

Guest suite in Largo

4.95 out of 5 average rating, 234 reviews

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

Welcome to your private Studio located 10 minutes from Indian Rocks Beach FL. Come stay with us and dip your toes in the warm white sugar sands of the Gulf of Mexico. Our beautiful cozy studio has private parking, entrance and keyless entry, cozy cal king bed, on suite bath/shower w/bidet, sweet retro kitchenette including mini fridge/freezer, microwave and Keurig coffee/tea express. Beat the crowd, book your stay, relax at the best beaches in the country or explore Tampa Bay or St.Pete!

Sep 15 – 22

G$18,307 GYD per night

Guest favorite

Guest suite in Dunedin

4.98 out of 5 average rating, 169 reviews

Dunedin Suite East, 15 minutes to local beaches

Dunedin Suite East 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.

Aug 18 – 25

G$25,044 GYD per night

Guest favorite

Home in Dunedin

4.99 out of 5 average rating, 102 reviews

Downtown Dunedin, Trail, Marina, Beach, Park

Welcome to our beautiful town of Dunedin. If you like to beach, walk, bike, eat, drink or shop, this is the place to vacation. Situated in the heart of Downtown Dunedin, we are across the street from the water and sunset pier and right on the Pinellas bike/walking trail. We are within walking distance to Main Street where you can see, eat lots of fresh seafood, try craft beers, enjoy an ice cream and more! We are a short drive to Honeymoon State park beach or Clearwater Beach.

Sep 5 – 12

G$30,381 GYD per night

Superhost

Hotel room in Dunedin

4.82 out of 5 average rating, 152 reviews

Seaside Artisan Apartment 6

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 16 – 23

G$13,062 GYD per night

Guest favorite

Guesthouse in Clearwater

4.9 out of 5 average rating, 182 reviews

Cottage on Pinellas Bike Trail

This cottage on the trail is a gem. It is an easy one mile bicycle ride to downtown Dunedin and a quick stroll to waterfront Edgewater Park to watch sunsets or see the lights of Clearwater Beach across the intracoastal waterway. Circular driveway with a carport for off street parking. The cottage is equipped with a Keurig, microwave, mini fridge, as well as beach amenities and wifi. There's a fenced back patio for you to enjoy our beautiful weather!

Nov 14 – 21

G$22,534 GYD 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)

Sep 30 – Oct 7

G$38,938 GYD per night

Guest favorite

Apartment in Dunedin

4.96 out of 5 average rating, 185 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.

Nov 11 – 18

G$22,367 GYD per night

Guest favorite

Bungalow in Dunedin

4.89 out of 5 average rating, 184 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 17 – 24

G$19,488 GYD per night