Vacation rentals in Caladesi Island

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Top-rated vacation rentals in Caladesi Island

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

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Guest favourite

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

$148 CAD per night

Guest favourite

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.

Jan. 28 – Feb. 4

$187 CAD per night

Guest favourite

Guest suite in Dunedin

4.94 out of 5 average rating, 202 reviews

Downtown Coastal Studio

Our Downtown Coastal Studio was recently renovated. The studio has a bright and airy atmosphere. Both clean and cozy, it is the perfect place to rest and relax. Located in the heart of downtown Dunedin and two blocks to the Pinellas Trail. Simply park your car and enjoy downtown on foot or rent a bike and cruise around. We are close to two major beaches, the marina, and John G. Hubbard Park, which is just across the street with a nice path to stroll along the water or take in the sunset.

Aug. 20 – 27

$163 CAD per night

Guest favourite

Condo in Redington Beach

4.97 out of 5 average rating, 457 reviews

AmazingBeachCondo/NoCleaningFee/AwesomeAmenities

Welcome to our condo. We have provided you with just about everything you need to come and vacation at this amazing beach area. The condo is right by the heated pool and a 2-minute walk to the beach. The complex has high-speed internet throughout and a laundry facility. Shopping/Grocery/Pharmacy are all close by. Restaurants/bars very close by. This is an amazing area of Florida, with so many things to see and do. You will love it here. We have also provided bikes for your use to get around.

Sep. 10 – 17

$158 CAD per night

Guest favourite

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.

Aug. 26 – Sep. 2

$254 CAD per night

Guest favourite

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!

Aug. 18 – 25

$182 CAD per night

Guest favourite

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.

Jun. 25 – Jul. 2

$183 CAD per night

Guest favourite

Townhouse in Palm Harbor

4.95 out of 5 average rating, 109 reviews

Walk to beach & trail-bikes, beach gear, porch

* Walk/bike to Crystal Beach Pier * 10min to Honeymoon & Caladesi Island * Fenced yard w/grill, a dock out to the pond, a fire pit * Screened patio w/fan for enjoying our weather & beautiful sunsets * 1/2 block to the Pinellas trail: a 55 mile loop * 2 adult bikes provided * Fully stocked kitchen w/ all amenities * Beach chairs, towels and beach toys provided- even some fishing poles for the dock! * WiFi/TV/streaming apps

Nov. 14 – 21

$257 CAD per night

Superhost

Hotel room in Dunedin

4.78 out of 5 average rating, 160 reviews

Seaside Artisan Apartment 3

This Airbnb offers a unique experience to stay at a mom and pop style retro motel. 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.

Sep. 17 – 24

$106 CAD per night

Guest favourite

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

$168 CAD per night

Guest favourite

Apartment in Dunedin

4.98 out of 5 average rating, 208 reviews

My Favorite Place 🍊downtown & city approved

LEGAL, CITY APPROVED 1 bedroom apartment w full kitchen, living , dining & separate bedroom located on the red brick streets of downtown Dunedin. Private entrance. BIKES Super clean Private driveway free parking Two great bikes Great for couples Tastefully decorated. Comfortable Queen bed. Luxurious bedding. Super clean. Shampoo, conditioner, body wash, coffee, tea, drinking water provided. SUPER CLEAN No pets

Oct. 8 – 15

$234 CAD per night

Guest favourite

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!

May 26 – Jun. 2

$214 CAD per night