
Holiday houses 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

Apartment in Palm Harbor
5 out of 5 average rating, 9 reviewsWe cross 102
GraceRating, 5 stars3 weeks ago
Our stay with Lynn was fantastic! She was such a great host and gave us great recommendations on what to do during our stay. She made our vacation so much better and she is so sweet!
Superhost

Bungalow in Gulfport
4.9 out of 5 average rating, 42 reviewsGulfPort Paradise, Bali-like Oasis with Pool
McKennaRating, 5 stars20 months ago
Absolutely loved our stay here- can’t wait to be back! It was so easy to feel right at home, and had everything we needed and more! (Thanks to the beautiful pool) This was our favorite trip to Florida we’ve had yet, and we’ve been coming for many years. Thanks Megan and Ang 😊
Guest favourite

Home in Indian Rocks Beach
4.98 out of 5 average rating, 133 reviewsBeachfront Bungalow w/ Pool & Hot Tub in IRB
CalanRating, 5 stars2 weeks ago
We had an amazing stay at the Beachfront Bungalow. The location was great with easy access to the beach. We used the pool and hot tub daily. It’s hard to imagine a better place to stay at Indian Rocks Beach. The host was communicative and helped resolve the few minor issues we had. We hope to come back in the near future!
Guest favourite

Home in Clearwater
5 out of 5 average rating, 6 reviewsFamily-Friendly Oasis~Sports Court~Heated Pool~Spa
WendyRating, 5 stars5 days ago
I am so glad we found this property. It has so much to do, especially with the pool and pickle ball. The beach is fairly near by as well. There were so many other amenities. The description of the place is very accurate. We found everything very nice and clean. Jason was great in communicating with us and answered all my questions in a timely manner. My husband had open heart surgery a month and a half ago and as a family, we really needed this relaxing time. We are definitely coming back soon.
Top Guest favourite

Home in Clearwater
5 out of 5 average rating, 12 reviewsIdeal home to relax"
KatieRating, 5 stars4 days ago
We had 9 perfect days at this house. There were many beaches within 20 minutes. The house was clean and had what was needed. The pool was absolutely perfect and well kept. The host was extremely responsive to any outreach and available to answer questions. We would definitely stay here again.
Top Guest favourite

Guest suite in Port Richey
5 out of 5 average rating, 19 reviewsCozy & Stylish Studio Getaway
LindseyRating, 5 stars1 week ago
Very nice, clean studio. Everything was spotless and smelled really good and clean. Will definitely stay again if I’m in the area and it’s available!!
Top Guest favourite

Condo in Clearwater
4.99 out of 5 average rating, 93 reviewsLiterally: 15 steps to the Pool, GroundFloor Condo
CrystalRating, 5 stars1 week ago
I loved everything about our stay. We had everything we needed from kitchen items to beach needs. Carmen was so helpful with suggestions for restaurants and clear instructions for checking in. I would definitely stay again.
Top Guest favourite

Guest suite in Largo
5 out of 5 average rating, 20 reviewsTiny Oasis|Big Vibes|Pool&Beach|Top 1% of Homes!
MelissaRating, 5 stars3 days ago
We had a wonderful stay at Tiny Oasis. I don't think I've ever stayed at an Airbnb with more accurate photos and descriptions. The space, while tiny, is perfectly laid out and the amenities were far beyond what we've experienced before. Ana, Admir, and Priscilla have thought of everything. From instructions for all appliances, remotes, tvs, and the pool, to a well-stocked, "Oops, I forgot it" basket, they also left amazing snacks and an ample supply of coffee & tea. If you're looking to be near all the things to do but still want a place to have some peace & quite then I'd highly recommend Tiny Oasis.
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- Anna Maria Island
- Weeki Wachee Springs
- Anna Maria Public Beach
- 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
- North Beach
- Fort De Soto Park
- Vinoy Park
- Jannus Live
- Tampa Theatre
- ZooTampa at Lowry Park
- Curtis Hixon Waterfront Park
- Adventure Island
- Splash Harbour Water Park
- Tampa Palms Golf & Country Club
- North Beach At Fort DeSoto Park
- Ben T Davis Beach