
Condo vacation rentals in Caladesi Island
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Top-rated condo rentals in Caladesi Island
Guests agree: these condos are highly rated for location, cleanliness, and more.
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Popular amenities for Caladesi Island condo rentals
Weekly condo rentals

Wonderful Condo at Avalon - Fully Renovated
Jeremy never fails to impress. I have stayed at other properties and he always exceeds expectations. The place is fabulous and he is the perfect host. I try to stay at one of his spots whenever I'm in Clearwater.

"Haven at the Shores" 2/2 Beachfront
This place is an oasis on the beach. We felt comfortable and relaxed daily here. This place has everything you need- literally! Just bring your toiletries although there’s shampoo, conditioner and lotion. The view is beautiful and peaceful. The sound of waves provides a tranquil atmosphere. Thank you Deborah for being and amazing host! 5 stars in every way! The home was clean and well maintained. Deborah answered all the questions we had and provided tips on things to do nearby. We will be back!

Welcome to Sun Haven~Newly Remodeled! Waterfront!
We cannot say enough good things about this rental. It was beautiful inside and truly felt like a home away from home. The beds and couches were comfortable, and they provided plenty of bathroom towels. They even thought of things like phone charging outlets near the beds and nightlights in the bathrooms. There were plenty of beach chairs, toys and towels and even a wagon to take everything down to the beach. The location was also fabulous. Within walking distance to great restaurants, gelato, & markets and a short distance to the beach. We even enjoyed watching dolphins from the back patio in the evenings. The owners were wonderful to work with, and we would recommend this rental and will definitely stay here again.

AWESOME PENTHOUSE CONDO ON GULF OF MEXICO
This is our second time staying here in one year and both times were fantastic. Perfect location and beautiful condo. We will definitely stay again!! David & Robin

Cozy Renovated 1 BR w/ Pool view & King size bed!
We had such a wonderful stay at Nick’s place! The house was spotless, the kitchen had everything we needed, and he even provided beach chairs, umbrellas, and toys, which made our beach days so easy and fun. The location was great, just a short drive to the beach. Nick was super helpful with parking tips and local restaurant recommendations. We were so happy with our stay and would definitely love to come back. Highly recommend!

Chambre 303-Great Beachfront Condo!
Amazing place right on the beach and walking distance to John’s Pass. Everything was just as advertised. Plenty of space and awesome view of the ocean from the balcony (the high Adirondack chairs on the balcony added a good touch and made for easy viewing). Easy beach access. Clean, Furnished nicely, and bed was comfortable. Has everything you’ll need for a fun relaxing vacation. We’ll be back!

Beachfront Condo in Indian Shores
We had a great stay at this condo! We have visited this area numerous times but this was our first time in that condominium. It was absolutely gorgeous! You get a beautiful view right out the window and the condo was well decorated and clean. The owner was also very responsive. We would definitely stay here again.

NEW! Direct Beach-front with Old Florida charm!
We had an AMAZING time during our stay! The location and property were perfect!! We cannot wait to go back!!
Pet-friendly condo rentals

Seasalt Breeze private cozy unit
Beautiful, very clean condo, very clean pool. Great location only a short drive to Clearwater beach. Margaret was very responsive to our questions and was an excellent host. Would highly recommend staying at this location.

Tropical Getaway #2 Studio Close to Downtown
Both the hosts were great. We will definitely stay again.

Waterside Studio in the heart of TI, walk to beach
My husband and I needed a little staycation after a stressful few months. The little apartment at the beach was perfect. The location was beautiful despite the fact that the area is still recovering from a few hurricanes last year. The host was also very helpful and gave some great recommendations. The only negative thing that I can say is that my stay was too short. I look forward to staying there again.

Heron's Hideaway- Studio by the bay!
Alison went above and beyond to make this trip everything and more. she was responsive, personable and kind. would stay here again and recommend to family/friends. five stars!

Beach Chill Inn #3 - Studio
This studio was a perfect and cozy little spot for my fiancée and I. Literal steps to the beach, ice cold AC, super clean, and very close to tons of shopping/eating/drinking spots. I would absolutely book this rental again for another weekend getaway!

Penthouse Water View, Steps to Sandy Beach
Great location with easy access to beach and short walk to restaurants at boardwalk. About 30 minutes to a rays game or Airport (Pie).

Florida Breeze
loved the area and condo. We had a nice view of the pool, lagoon and Gulf. Condo had everything we needed. We saw dolphins and manatees. All restaurants we tried were great. Mike was a wonderful host and we would love to come again.

5 *Waterfront Condo,3 BDR.2 Baths, Pool, HOT-TUB.
The condo was beautiful. Clean and spacious. Lots of amenities. Close to the public beach, restaurants, bars, and shops. Plus David ordered a perfect week of weather for us! Wonderful.
Condo rentals with a pool

Oceanfront View, Spacious Townhouse, Heated Pool
Excellent place to stay. Great pool and beach access! Incredible sunset ocean views. We would absolutely stay here again.

Beach Front Penthouse with Views
We just loved this place ! Beach chairs and towels were so nice to have. The view from the balcony is amazing . This condo is beautifully decorated and super clean ! The tiki bar was a fun addition too. Everyone was very friendly. We can’t wait to go back !

Relax in a Newly Renovated Beach Front Paradise
The pictures are amazing, but still don’t do the condo justice. The views are amazing from the balcony, and the interior is so clean and well kept. Also, the beds are the most comfortable I’ve slept in away from home. Matt, the host, is very accommodating and responsive. He checked in on us throughout our stay to make sure everything was great. His instructions for check in and check out were very clear and easy to understand. He even provided recommendations for local food, the best grocery stores, etc. The beach was never overly busy even on the weekend and there are so many things to do close by. Any time my family and I travel back to the clearwater area we’ll be booking with Matt for sure.

INCREDIBLE SUNSET BEACH OCEANFRONT TOP FLOOR CONDO
Beautiful view of the Gulf of America to watch dolphins, shipping carriers and cruise ships coming and going. The beach area is mostly crushed shells until you get to the water. Nice seeing the beach was patrolled by police regularly even in a gated area. Was able to see Manatee in the canal and watch fishing boats coming and going. Parking was easy. Condo is very clean and well decorated with that comfortable relaxing feeling - we enjoyed the balcony for awesome sunsets and star gazing or our morning coffee. The restaurant/bars are not within walking distance but were only a short drive (all of them had good food). You pay by card for parking at most locations. We would definitely stay at this beautiful location again - one of my most relaxing trips.

Sonrisa 1 - | Beachfront Condo in Belleair Beach
Had a great wonderful relaxing time away from work. It was a Mother/daughter get away. Location. location.Location Images on line were point on but in person it is so much more. Steps from putting your feet in the sand. Feet from the pool. The most beautiful sunsets from your front row seat on your own patio. Close to stores and restaurants. Cafe for coffee/tea. Home made ice cream and local shops all conveniently located. Rental management always available And checking in. Will be planning on returning next year. Donna

Beachside Mini-Condo on North Redington Beach!
Great little crash pad with easy access to the beach. Well kept pool. Easy walking

712 Beach Trail
We adored this place! We have been coming to IRB for several years, and this is the best location on the beach in my opinion. Walkable to restaurants, coffee, our favorite ice cream shop, etc. The unit was fully stocked with several pantry staples, condiments, etc. which also saved us from purchasing and throwing away after a week. The other 3 families in the building were kind and friendly. We can't wait to come back!

Beachfront Belleair Beach Condo Est. rental 2016
We enjoyed our stay here so much. The hosts are extremely responsive and helpful. We are a family of five and the space was perfect for us. The beach is beautiful and not crowded at all. It felt like we had our own private beach! The pool was also very nice. The house had everything we needed to stay comfortably. We used the beach chairs, umbrella, and sand toys daily! We will be dreaming about those amazing sunsets from the deck for months to come!
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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