
Holiday houses in Caladesi Island
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Top-rated holiday rentals in Caladesi Island
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
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Popular amenities for Caladesi Island holiday rentals
Other great holiday rentals in Caladesi Island
Top Guest favourite

Home in Palm Harbor
5 out of 5 average rating, 21 reviewsCoastal 4 BR/3BA Home - Near Beach + Golf Cart
Top Guest favourite

Home in St. Petersburg
5 out of 5 average rating, 34 reviewsBoutique Stay Near the Bay | Walk to Downtown.
Guest favourite

Home in Palm Harbor
4.94 out of 5 average rating, 80 reviewsLuxe Private Waterfront Getaway with Pool in Ozona
Top Guest favourite

Home in Holiday
4.98 out of 5 average rating, 62 reviews*NEW* Riverside Retreat w/Pool
Top Guest favourite

Home in Palm Harbor
4.98 out of 5 average rating, 60 reviewsLuxury Waterfront w/ Private Heated Pool
Superhost

Home in St. Petersburg
5 out of 5 average rating, 4 reviewsWaterfront Luxury | Sunset Views
Top Guest favourite

Home in Dunedin
5 out of 5 average rating, 48 reviewsPerfectly located Palms Cottage Dunedin
Top Guest favourite

Home in Oldsmar
5 out of 5 average rating, 14 reviewsLuxury Modern Retreat I Spacious, Private & Serene
Destinations to explore
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- Anna Maria Island
- Weeki Wachee Springs
- Dunedin Beach
- John's Pass
- Raymond James Stadium
- Busch Gardens Tampa Bay
- Bean Point Beach
- Anna Maria Public Beach
- Amalie Arena
- Coquina Beach
- Cortez Beach
- Gulfport Beach Recreation Area
- Vinoy Park
- Jannus Live
- North Beach
- ZooTampa at Lowry Park
- Adventure Island
- Splash Harbour Water Park
- Tampa Palms Golf & Country Club
- River Strand Golf and Country Club
- Honeymoon Island Beach
- North Beach At Fort DeSoto Park
- Fred Howard Park
- Fort De Soto Park