
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.
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

Tootsie’s Beachside Retreat

Heated Pool, 10 min to Beach, Close to Restaurants

Private Pool 2BR/2B 3.5 mi Tarpon & Beaches

Beautiful Tampa Bay Pool Home Near Gulf Beaches

Lakefront home near beaches w/ waterview, pets ok

Piece of paradise in Indian Rocks Beach.

Tropical Pool Retreat in Tarpon Springs

The Oasis | Heated Pool - Arcades - Mini Golf
Caladesi Island beach vacation rentals

Cozy Coastal Casita

Tiki Bungalow | Gorgeous Htd Pool | Steps to Beach

Pool Private Adult only Paradise “The Blue Room”

Dock of the Bay, Coastal Elegance | Walk to Beach!

Cozy condo at Belleview Gulf

Ocean Front Beach Condo Summer Sale

Beach, dolphin/manatee sightings, fishing, sunset

~Shore Thing~ Coastal Exquisite Waterfront Condo
Beach house rentals in Caladesi Island

4/2 Fenced- Giant HotTub-Kayak-SUP-Golf Cart-Bikes

Fun Beach Escape: Pool Bar, Mini-Golf, Pong, Games

Beach access! Private Pool! Whole house 2 Kitchens

Gameroom & Bikes! Near Beaches, Downtown & Trail!

Beach Retreat Ocean View Steps To Beach

Playa Vista Villa

Stunning views! Spot dolphins from the pool!

Luxe BeachHouseA Heated Pool, 2 min walk to Beach
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- Anna Maria Island
- Anna Maria Public Beach
- Weeki Wachee Springs
- Dunedin Beach
- John's Pass
- Bean Point Beach
- Raymond James Stadium
- Busch Gardens Tampa Bay
- Cortez Beach
- Amalie Arena
- Coquina Beach
- Gulfport Beach Recreation Area
- Fort De Soto Park
- Vinoy Park
- North Beach
- Jannus Live
- ZooTampa at Lowry Park
- Curtis Hixon Waterfront Park
- Adventure Island
- Splash Harbour Water Park
- Tampa Palms Golf & Country Club
- Honeymoon Island Beach
- North Beach At Fort DeSoto Park
- Ben T Davis Beach