Caladesi Island vacation rentals
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Top-rated vacation rentals in Caladesi Island
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Caladesi Island vacation rentals
Caladesi Island house rentals
Home in Clearwater Beach
4.93 out of 5 average rating, 162 reviewsThe Cottage - 32 Steps to the Beach - Sleeps 2, drive to your door, Wifi, Grill. Just Steps from the beach.
Home in Tampa
4.78 out of 5 average rating, 231 reviews*Waterfront* Kayaks & Bikes - Papa’s Rustic Cabin
Home in Tarpon Springs
4.96 out of 5 average rating, 183 reviewsTree House Treasure
Home in Indian Rocks Beach
4.95 out of 5 average rating, 119 reviewsBig 1/1 Beach house w/ Sunset Balcony
Home in Tampa
4.96 out of 5 average rating, 121 reviewsDowntown Tampa Pool House! Walk to Armature Works!
Home in Palm Harbor
4.87 out of 5 average rating, 170 reviewsCute Lil' House Near Historic Downtown Palm Harbor
Home in Palm Harbor
4.94 out of 5 average rating, 188 reviewsWell Appointed 100% Private Suite/Lake View
Home in Dunedin
4.97 out of 5 average rating, 112 reviewsDowntown Dunedin! Bikes,golf cart,marina, brewery
Caladesi Island beach vacation rentals
Cottage in Palm Harbor
4.78 out of 5 average rating, 170 reviewsCrystal Beach Cottage #1
Condo in Dunedin
4.84 out of 5 average rating, 109 reviewsFully stocked Condo next to Honeymoon Island
Tiny home in Oldsmar
4.96 out of 5 average rating, 252 reviewsLouisa's Cottage
Cottage in Indian Rocks Beach
4.99 out of 5 average rating, 157 reviewsCottage w/ Private Patio | 3 Min Walk to the Beach
Guest suite in Largo
4.97 out of 5 average rating, 321 reviewsPrivate Pool, Jacuzzi, Walk to Beach.
Guest suite in Safety Harbor
4.99 out of 5 average rating, 207 reviewsSuite Outlook-Upstairs unit with Spectacular views
Apartment in Tarpon Springs
4.91 out of 5 average rating, 129 reviewsBeaches Sunset/Free Bikes
Cottage in Dunedin
4.92 out of 5 average rating, 172 reviewsDowntown Keylime Cottages 3
Beach house rentals in Caladesi Island
Home in Gulfport
4.99 out of 5 average rating, 112 reviewsThe Boho - 2BR Gulfport Waterfront District House
Home in Indian Rocks Beach
4.98 out of 5 average rating, 107 reviewsBeachfront Bungalow w/ Pool & Hot Tub in IRB
Home in Indian Rocks Beach
4.86 out of 5 average rating, 309 reviewsStunning views! Spot dolphins from the pool!
Home in Clearwater
5.0 out of 5 average rating, 118 reviewsBeach House
Home in Tarpon Springs
4.96 out of 5 average rating, 324 reviewsTarpon Fun'n Sun-Pool, Beaches + Backyard Chickens
Home in Largo
4.97 out of 5 average rating, 102 reviewsBeautiful kid friendly renovated home near beaches
Home in Belleair Beach
4.96 out of 5 average rating, 172 reviewsBungalow in Private Beach ClearwaterBelleair Beach
Home in Indian Rocks Beach
4.83 out of 5 average rating, 147 reviewsNEWLY REMODELED POOL HOME - SHORT WALK TO BEACH
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