
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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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!

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!

3Br GULF FRONT, Best Views, POOL and Hot tub! BC
š 5-Star Review for Ellenās Beachfront Retreat š We had an unforgettable stay at this beach getaway! From the moment we arrived, the property exceeded our expectations. š” Accommodation: The home was spotless and beautifully decorated, offering a perfect blend of comfort and style. The spacious living areas and cozy bedrooms made it feel like a true home away from home. š Location: Just steps from the beach, we enjoyed breathtaking sunsets and easy access to the ocean. The neighborhood was peaceful, yet close to local shops and restaurants. šļø Host: Ellen was a gracious and attentive host. She provided thoughtful touches like beach towels, chairs, and beach toys long with local recommendations. Her communication was prompt, and she ensured we had everything we needed for a relaxing stay. š“ Overall Experience: This getaway was the perfect blend of relaxation and adventure for my daughterās 16th birthday. We left feeling content & rejuvenated and already planning our next visit

Walk to Beach, Bars, and Restaurants Nearby
We love the location. Very walkable to the beach and local restaurants. Host is always very responsive. We have stayed here twice and will likely stay again.

Golf Cart, 2 bed 2 Bath, Heated Pool
My 4 sisters and I booked this for a girlās trip, and our stay at the Chunky Mermaid was everything we hoped it would be! Caleb was very responsive, helpful, and overall a great host. There was not anything lacking in the airbnb, and we found it very easy to settle in. There is a great living room space with a nice TV and comfy couch for the rainy days or when we got a little too much sun. We were at the beach most of the time, so didnāt get to enjoy the pool but it looked beautiful and clean. The golf carts are an absolute must! Definitely worth the small extra fee to be able to drive right up to the beach walk, coffee shops, and restraints near by. The beach feels very close, definitely an easy walk. You share the duplex with another renter, and occasionally we could hear them above us, but nothing disturbing, and you definitely still feel like your space is separate. Aside from maybe crossing paths in the stairwell or garage if youāre there at the same time, you donāt even have to

Literally: 15 steps to the Pool, GroundFloor Condo
Carmenās apartment truly exceeded our expectations, not only because of everything it offered, but also thanks to its fantastic location. It was easy to find, and just minutes from some amazing beaches. We had a wonderful time. Carmen herself was exceptional: proactive, thoughtful, and always ready to help. Sheās simply a fantastic host.

Beach Front Casa De Playa, Unit 212
The location was perfect, right on the beach with gorgeous views from the balcony and lounge with walkable eating places. The accommodation had everything we needed and was comfortable. We really enjoyed our time there.
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
Both the hosts were great. We will definitely stay again.

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.

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!

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.
Condo rentals with a pool

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 canāt wait to go back !

Relax in a Newly Renovated Beach Front Paradise
The pictures are amazing, but still donāt 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 Iāve 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 weāll be booking with Matt for sure.

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.

"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!

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.

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

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!

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!
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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