Condo holiday rentals in Caladesi Island

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Popular amenities for Caladesi Island condo rentals

Weekly condo rentals

Superhost
Condo in Dunedin
4.84 out of 5 average rating, 81 reviews

Nautical Landings West-Honeymoon Island!

JenRating, 5 starstoday
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.
Guest favourite
Condo in Indian Shores
5 out of 5 average rating, 11 reviews

Modern Luxury Ocean & Pool View Condo!

EdRating, 5 stars2 weeks ago
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.
Guest favourite
Condo in Clearwater
4.8 out of 5 average rating, 45 reviews

Beach vibes

JoshRating, 5 stars1 week ago
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!
Guest favourite
Condo in Clearwater
4.93 out of 5 average rating, 71 reviews

#2- SALE! Beautiful 2/2 Condo-ON the Sand!

JasonRating, 5 stars1 month ago
We absolutely loved our stay at Kristen’s 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.
Superhost
Condo in Clearwater
5 out of 5 average rating, 3 reviews

Welcome to Sun Haven~Newly Remodeled! Waterfront!

KariRating, 5 stars3 weeks ago
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.
Guest favourite
Condo in Redington Shores
4.96 out of 5 average rating, 50 reviews

Sunny Retreat on Pristine Beach | Redington Shores

LinRating, 5 stars2 weeks ago
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 — they absolutely loved the place! Thank you for helping make our trip so special.
Guest favourite
Condo in Madeira Beach
4.92 out of 5 average rating, 13 reviews

Chambre 303-Great Beachfront Condo!

JosephRating, 5 stars3 weeks ago
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!
Top Guest favourite
Condo in Clearwater
4.93 out of 5 average rating, 40 reviews

Cozy Renovated 1 BR w/ Pool view & King size bed!

MajidehRating, 5 stars1 month ago
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!

Pet-friendly condo rentals

Superhost
Condo in St. Petersburg
4.81 out of 5 average rating, 129 reviews

Breathtaking Waterview Condo!

JeffRating, 5 stars1 month ago
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
Superhost
Condo in St. Petersburg
4.81 out of 5 average rating, 243 reviews

Tropical Getaway #1 Studio Close to Downtown

PaulRating, 5 starstoday
Great location. Perfect for a couple or solo traveler.
Guest favourite
Condo in Treasure Island
4.9 out of 5 average rating, 126 reviews

Waterside Studio in the heart of TI, walk to beach

FrancineRating, 5 stars5 days ago
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.
Guest favourite
Condo in St. Petersburg
4.92 out of 5 average rating, 157 reviews

Heron's Hideaway- Studio by the bay!

TylerRating, 5 stars3 weeks ago
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!
Guest favourite
Condo in Madeira Beach
4.75 out of 5 average rating, 449 reviews

Beach Chill Inn #3 - Studio

RjRating, 5 stars5 days ago
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!
Top Guest favourite
Condo in Seminole
4.97 out of 5 average rating, 149 reviews

SUNNY DELIGHT! HEATED POOL 2 miles to the beach🐶

LaquitaRating, 5 stars1 week ago
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.
Guest favourite
Condo in Clearwater
4.93 out of 5 average rating, 146 reviews

5 *Waterfront Condo,3 BDR.2 Baths, Pool, HOT-TUB.

RobertRating, 5 stars1 month ago
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.
Guest favourite
Condo in Clearwater
4.94 out of 5 average rating, 282 reviews

Steps 2 beach! Beachy and Luxurious! Easy Living!

StylianosRating, 5 stars2 weeks ago
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

Top Guest favourite
Condo in Indian Shores
5 out of 5 average rating, 25 reviews

"Haven at the Shores" 2/2 Beachfront

DonnaRating, 5 stars3 days ago
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!
Guest favourite
Condo in Indian Shores
4.94 out of 5 average rating, 99 reviews

Beachfront Condo, Heated Pool and SPA!

AmyRating, 5 stars4 days ago
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
Top Guest favourite
Condo in Clearwater
4.97 out of 5 average rating, 78 reviews

Lovely Condo minutes from beach & King bed

SamanthaRating, 5 stars2 days ago
I would recommend this place to anyone!! There was 4 of us, plus our fur baby. I know it’s not right on the ocean, but it’s 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 didn’t use. But, if you forget anything it’s nice that’s it’s 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 Damian’s condo. Thank you for such an excellent stay.
Superhost
Condo in Treasure Island
4.92 out of 5 average rating, 48 reviews

INCREDIBLE SUNSET BEACH OCEANFRONT TOP FLOOR CONDO

MaryRating, 5 stars1 month ago
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.
Top Guest favourite
Condo in Indian Rocks Beach
5 out of 5 average rating, 93 reviews

Beachfront w/ views! Heated Pool+Tennis +GymPass

KimRating, 5 stars2 weeks ago
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!
Superhost
Condo in Treasure Island
4.85 out of 5 average rating, 149 reviews

King Oceanfront Suite! Kitchenette + Balcony!

JeremyRating, 5 stars6 days ago
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
Top Guest favourite
Condo in Indian Shores
4.99 out of 5 average rating, 96 reviews

Five Star Beachfront Condo Newly Renovated

TrishRating, 5 stars5 days ago
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!!!
Top Guest favourite
Condo in Indian Rocks Beach
5 out of 5 average rating, 28 reviews

Beachfront Bliss! Directly on Gulf with pool!

KelseyRating, 5 stars1 month ago
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 isn’t 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.

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Pinellas County
  5. Dunedin
  6. Caladesi Island
  7. Condo rentals