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Vacation rentals in Caladesi Island

Vacation rentals in Caladesi Island

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Caladesi Island

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

Sunrise, Sunshine, Sunset...Repeat!
SUPERHOSTEntire condominium · 4 guests · 2 beds · 2 baths
Sunrise, Sunshine, Sunset...Repeat!

Indulge in sunshine and relaxation at this full studio plus one full bed and bath. Sleeps 4, two full baths! Enjoy your morning coffee on the lanai with a view of the St. Joseph Sound. Get your vitamin D fix out on the pool patio while enjoying drinks from the on-site Tiki bar. Great residents and staff in this building! Tons to do in the area! Walk or bike the Pinellas Trail, eat, shop, enjoy the parks and splash pad, or check out the gorgeous Honeymoon Island state park.

What guests are saying:

“Beckys place was so cute and well put together. The tiki bar is just a minute walk outside and offers a pier to walk out to to fish or just hang out, as well as two pools to swim as you drink. They even have live music there sometimes which is always great! Renting a car was a bit too expensive for us, which ended up being okay as Becky offers two bikes to rent that makes getting around much easier (and allows you to exercise during vacay which makes eating poorly doable ;) ). Becky was very responsive and understanding when we had questions about the area. Highly recommend this place!”

Adorable Coral Cottage in downtown Dunedin
SUPERHOSTEntire cottage · 5 guests · 3 beds · 1 bath
Adorable Coral Cottage in downtown Dunedin

Adorable dog-friendly cottage right in the middle of quaint Dunedin- just three blocks from the water and downtown, two blocks from the Pinellas Trail, the library and the Blue Jays' stadium. This renovated 1920's bungalow is surrounded by tropical greenery and a private outdoor space for you and your dog. The sunny kitchen, the spacious living room/dining room, and the comfy beds make the cottage a wonderful stay. The neighborhood is great, with shops, restaurants, and sunset walks by the sea.

What guests are saying:

“This is a sweet 2-bedroom cottage within walking distance to Dunedin's town center, biking paths, and the ball park. Trisha and Waverly provided so many nice amenities -- thick towels, beach chairs/umbrella, soaps and shampoos, snacks, etc. We thoroughly enjoyed walking everywhere and being able to come back to such a nice, clean, quiet little house. I would definitely stay here again.”

Dunedin Suite East
SUPERHOSTEntire guest suite · 4 guests · 3 beds · 1 bath
Dunedin Suite East

Dunedin Suite East is modern and spacious. The suite has been recently upgraded throughout and includes a full kitchen. You will feel a sense of lightness, comfort, and style while staying at our Dunedin Suite East. We are legally zoned/inspected to operate short term rentals here in Dunedin. *We are leaving twice the recommended amount of time between guests that Airbnb recommends during this pandemic. At this time we are not accepting guests that need to self quarantine for 14 days.*

What guests are saying:

“This was a wonderful stay. You can expect an incredibly clean updated space in an adorable small town. With Steve living next door you have a friendly face to give insight on fun things to do around the area. Not only that, but they also have a booklet waiting for you upon your arrival with many brochures on various events/food/things to do within the area. They also provided extra items including an umbrella, beach towels, mats, and a cooler. This made our beach days even more comfortable and relaxing. We used this vacation as a couples getaway, but this is also fit for a fun family vacation spot. I would highly recommend this stay.”

Vacation rentals for every style

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Popular amenities for Caladesi Island vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Caladesi Island

Barefoot Parrot House- Walk Downtown & to Water
SUPERHOSTEntire house
Barefoot Parrot House- Walk Downtown & to Water
Price:ﺩ.ﺇ882 / night
Cozy Apartment
SUPERHOSTEntire guest suite
Cozy Apartment
Price:ﺩ.ﺇ217 / night
Dunedin Causeway Getaway
SUPERHOSTEntire townhouse
Dunedin Causeway Getaway
Price:ﺩ.ﺇ459 / night
Downtown Coastal Studio
Entire guest suite
Downtown Coastal Studio
Price:ﺩ.ﺇ214 / night
Overlooking Downtown Dunedin Two Bedroom apartment
SUPERHOSTEntire apartment
Overlooking Downtown Dunedin Two Bedroom apartment
Price:ﺩ.ﺇ290 / night
FLOH - delightful days in Dunedin!
SUPERHOSTEntire house
FLOH - delightful days in Dunedin!
Price:ﺩ.ﺇ331 / night
Downtown Dunedin on Main St w/  Balcony Unit 201
SUPERHOSTEntire apartment
Downtown Dunedin on Main St w/ Balcony Unit 201
Price:ﺩ.ﺇ328 / night
Quintessential II Downtown Dunedin Spacious Apt
Entire apartment
Quintessential II Downtown Dunedin Spacious Apt
Price:ﺩ.ﺇ275 / night
Brick Streets Dunedin House
Entire house
Brick Streets Dunedin House
Price:ﺩ.ﺇ735 / night
Downtown Keylime Cottages 3
SUPERHOSTEntire cottage
Downtown Keylime Cottages 3
Price:ﺩ.ﺇ430 / night
Pandion Point-Hawk's Nest Apartment
SUPERHOSTEntire apartment
Pandion Point-Hawk's Nest Apartment
Price:ﺩ.ﺇ331 / night
Quirky Apt steps from Downtown Dunedin & Beaches
SUPERHOSTEntire guest suite
Quirky Apt steps from Downtown Dunedin & Beaches
Price:ﺩ.ﺇ220 / night
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