
Condo holiday rentals in Caladesi Island
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Top-rated condo rentals in Caladesi Island
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Popular amenities for Caladesi Island condo rentals
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Nautical Landings West-Honeymoon Island!
Nice area. Little bit from downtown, but right on the causeway to beautiful Honeymoon beach. They left us a state park pass which was Awesome. Publix, restaurants and gas station close. The little dock area is across the street and so cute and relaxing.

Modern Luxury Ocean & Pool View Condo!
This space was as close to perfect as I can imagine. location, amenities, ease of access, view, i could go on and on. it's like we had the VIP treatment. each sunset was custom delivered to just us. we had a great time and will be back for sure.

Beach vibes
Super friendly host, very quick responses. The place was exactly as described and was a perfect fit for our overnight. Would easily stay there again if need be!

#2- SALE! Beautiful 2/2 Condo-ON the Sand!
We absolutely loved our stay at Kristenās beachside condo. The view is unbeatable, location just as good. The place does have stairs, but very private and a great space. We would highly recommend and would definitely stay here again.

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.

Sunny Retreat on Pristine Beach | Redington Shores
We had a wonderful stay! We truly enjoyed the days we spent in the condo. It was comfortable, clean, and had everything we needed. My kids were especially excited ā they absolutely loved the place! Thank you for helping make our trip so special.

Chambre 303-Great Beachfront Condo!
Amazing place right on the beach and walking distance to Johnās 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 youāll need for a fun relaxing vacation. Weāll be back!

Cozy Renovated 1 BR w/ Pool view & King size bed!
We had such a wonderful stay at Nickās 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!
Pet-friendly condo rentals

Breathtaking Waterview Condo!
We really enjoyed our stay at this condo. It was a very clean condo with beautiful views from the patio. Saw dolphins almost every morning and at dusk. Close to many restaurants. Close to the beach also had a very nice and clean pool with plenty of chairs for seating. When we were there, the pool was not crowded at all. There were also beach towels, beach chairs, and beach umbrellas available to use. Well stocked kitchen with good pans for cooking and two grills that were available to use at no additional cost Overall it was a great stay and we will definitely be back

Tropical Getaway #1 Studio Close to Downtown
Great location. Perfect for a couple or solo traveler.

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 fiancƩe 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!

SUNNY DELIGHT! HEATED POOL 2 miles to the beachš¶
Sandra was very kind and very responsive. She even set out a bottle of wine for us. The instructions for check out were clear and seamless. We loved the stay and were close to the beach.

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.

Steps 2 beach! Beachy and Luxurious! Easy Living!
The apartment was amazing. The location is very close to restaurants and bars, not to mention how close it is from the beach. We also had our fur babies with us, and the dog beach was also in a walking distance. The parking was absolutely a plus. It will be our choice every time we visit Clearwater for sure ! Thank you Mike and Alex!
Condo rentals with a pool

"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 thereās 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!

Beachfront Condo, Heated Pool and SPA!
Rafal was super responsive; this was my first experience, choosing Airbnb over our standard hotel accommodations and it completely exceeded our expectations!!!!! Probably will be the only way we travel from now on

Lovely Condo minutes from beach & King bed
I would recommend this place to anyone!! There was 4 of us, plus our fur baby. I know itās not right on the ocean, but itās just a short 15 minute drive to the beaches! Damian was an excellent host, responded right away. I had no issues whatsoever! The place was loaded with beach stuff, which we didnāt use. But, if you forget anything itās nice thatās itās available. Also had plenty of dishes if you want to make your own meals. He also sent a bunch of recommendations which was nice. The condo was very clean and homie feeling. The pool was nice, though we only used it once. We had a really quiet stay. I would most definitely come back to Damianās condo. Thank you for such an excellent stay.

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.

Beachfront w/ views! Heated Pool+Tennis +GymPass
This place was wonderful for our family. Since we flew down we were nervous we would not have all the things we usually take to the beach. We were shock at how well the beach supplies were stocked. This might seem trivial to some but I even appreciated the extra mile on toilet paper! Plenty for the week and not one ply! The access to the beach is amazing with a very short two minute walk. The place was very clean. Refrigerator had condiments. So many little added touches. I would stay here again and I highly recommend this host/hostess!

King Oceanfront Suite! Kitchenette + Balcony!
Karen's place was an amazing clean spot with a great view. She was very friendly and helpful. I will definitely be back to stay here again. Can't beat tge location and all the fun stuff to do in the area

Five Star Beachfront Condo Newly Renovated
We spent almost a week at the condo and had a great time! Small extended family get together and the set up with bathrooms and bedrooms was great for us. We always look for a condo right on the beach, we were able to enjoy coffee every morning from our patio and then just a quick walk back and forth to enjoy the day at the beach!!!

Beachfront Bliss! Directly on Gulf with pool!
We had a great time with our 3 young children. Everything we needed was there- chairs, umbrella, toys, a wagon. Bliss was very accessible and responsive to all texts. The location of the condo, right on the beach, was so convinient which isnāt always the case when traveling with kids. The beds and pillows were so comfortable! We will definitely be back if we ever have the opportunity again.
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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