
Holiday rentals in Caladesi Island
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Caladesi Island
Guests agree: these stays are highly rated for location, cleanliness and more.
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Popular amenities for Caladesi Island holiday rentals
Other great holiday rentals in Caladesi Island
Top guest favourite

Cottage in Dunedin
4.96 out of 5 average rating, 90 reviewsAdorable Villa 1 min to Downtown Dunedin
JamieRating, 5 stars3 weeks ago
Amazing location & SUPER clean!! Quiet area, perfect for relaxing, biking, walking, restaurants & enjoying the cute town of Dunedin. Highly recommend & would book again next time we are in the area. Absolutely perfect!
Superhost

Houseboat in Clearwater
4.86 out of 5 average rating, 98 reviewsBreathtaking Beachy Houseboat on Clearwater Island
AdamRating, 5 stars1 week ago
My girlfriend and I just spent 4 of the most amazing days here. Andrew and his team were the most attentive hosts I've ever had on vacation. The boathouse was so cute and the view while sitting on the back patio was so peaceful and serene. We went jetskiing which was located only a few feet away from all the units and Remy, our tour guide, was fantastic. I can't say enough about the way he assisted my girlfriend while she rode by herself for the first time. It was so much fun. We also went parasailing and the guides there, Zack and Jessie, were also awesome. They took our pictures using the photo package which came great. They gave us great recommendations about the things to do nearby, and played such good music on the boat. The view while up in the air was breathtaking, and also took pictures while riding and their photo package gave us great memories from the boat view. Andrew had beach chairs, towels, and golf cart that we used to get around the island. The main strip, where we
Guest favourite

Private room in Largo
4.95 out of 5 average rating, 127 reviewsRoom chiquito for one guest, shared bathroom
JohnRating, 5 stars2 days ago
awesome spot...peaceful lil comfy home...definitely recommend...great for the price as well..comfortable beds which is a rare thing for some airbnbs...well definitely stay again if in town!
Guest favourite

Bungalow in Clearwater
4.93 out of 5 average rating, 94 reviewsPermaculture Homestead
ErinRating, 5 stars2 weeks ago
Vanessa has a lovely rental and is a resposive host.

Apartment in Madeira Beach
5 out of 5 average rating, 4 reviewsMadeira Beach Retreat. Views, Pool, Location!
KennethRating, 5 stars4 weeks ago
Such an amazing condo!! It’s even better in person, we will definitely be staying here again! The condo has everything you need, host was always responsive if you had any questions, the view to the beach was so beautiful! Overall a 10/10 experience and I will recommend this condo to everyone I know!
Top guest favourite

Cottage in Dunedin
4.95 out of 5 average rating, 129 reviewsBeachBunkies Cottage 2. Four miles to the beach!
LindaRating, 5 stars2 days ago
Wow, this place was absolutely amazing! We loved our time here and cannot wait to come back ♥️
Top guest favourite

Guest house in Clearwater
5 out of 5 average rating, 11 reviewsGuesthouse near the Beach
KaylaRating, 5 stars1 week ago
Nice place close to everything we needed we enjoyed our stay here
Guest favourite

Home in Indian Rocks Beach
4.98 out of 5 average rating, 132 reviewsBeachfront Bungalow w/ Pool & Hot Tub in IRB
AmyRating, 5 stars3 weeks ago
Amazing house right on the beach!!! Beautiful & private pool enjoyed daily by our family! House was perfect size for our family of 4. We plan to return in the near future!
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- Anna Maria Island
- Weeki Wachee Springs
- Dunedin Beach
- Anna Maria Public Beach
- John's Pass
- Bean Point Beach
- Busch Gardens Tampa Bay
- Raymond James Stadium
- Cortez Beach
- Amalie Arena
- Coquina Beach
- Gulfport Beach Recreation Area
- Vinoy Park
- North Beach
- Fort De Soto Park
- Tampa Theatre
- Jannus Live
- Curtis Hixon Waterfront Park
- ZooTampa at Lowry Park
- Splash Harbour Water Park
- Adventure Island
- River Strand Golf and Country Club
- North Beach At Fort DeSoto Park
- Ben T Davis Beach