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Condo vacation rentals in Caladesi Island

Find and book unique condos on Airbnb

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Popular amenities for Caladesi Island condo rentals

Weekly condo rentals

Superhost
Condo in Clearwater
4.81 out of 5 average rating, 144 reviews

Luxury condo at Avalon Club

HopeRating, 5 stars1 month ago
Clean, open space. Was plenty of room for 3 people and a dog. Convenient parking and beach access. Walking distance to many shops and dinner spots. Park across the street to take dog out. Pool was nice and warm even at night.
Superhost
Condo in Clearwater
5 out of 5 average rating, 3 reviews

Two Bedroom Deluxe, Clearwater Beach (A442)

ElizabethRating, 5 stars1 month ago
We had a great stay at William’s property. He was greet work with! Will book again for one next stay.
Top guest favorite
Condo in Indian Shores
4.85 out of 5 average rating, 41 reviews

BEAUTIFUL Condo w/Balcony ON THE BEACH

ZoeRating, 5 stars1 month ago
My family and I stayed here recently and absolutely loved the place and the location. We had to book it last minute after our other Airbnb cancelled 2 days before the trip. Joyce was very helpful and kind which was a relief after booking it such short notice. It’s right on the beach and the condo was super spacious, clean, and homey. We had easy access through her thorough and well communicated instructions. Absolutely no complaints. We hope to come back to the area and would stay with Joyce again! Very
Guest favorite
Condo in Madeira Beach
4.84 out of 5 average rating, 83 reviews

Special July 2025 - All Rooms Direct Beach Front

CatherineRating, 5 stars3 weeks ago
Despite the fact that the condo building is still recovering from Hurricane Helene (the elevator and pool needed repairs and was not available to us); we still had a wonderful vacation at Samuel's condo! Large and spacious place, very clean, all the comforts of home. The location was perfect...the beach was steps away; restaurants and stores- a short drive. We absolutely loved our stay!
Top guest favorite
Condo in Clearwater
4.93 out of 5 average rating, 145 reviews

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

RobertRating, 5 stars2 weeks 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.
Superhost
Condo in St. Petersburg
5 out of 5 average rating, 6 reviews

Corner unit with patio. Pools, hot tub, pickleball

LeeRating, 5 stars19 months ago
Well, where to start! Firstly, it’s not very often that the pictures and description of a property don’t do it justice. A true pice of paradise. We even survived our first hurricane!! But it wasn’t without the help of hosts, being extremely responsive, helpful and going the extra mile. Thank you for an amazing stay.
Guest favorite
Condo in Clearwater Beach
4.9 out of 5 average rating, 50 reviews

April Availability |Bay Front| FREE Parking

ErinRating, 5 stars1 week ago
Gorgeous place! We loved our stay!
Superhost
Condo in Bradenton
4.88 out of 5 average rating, 26 reviews

Luxury Condo in River Strand Golf & Country Club

JayRating, 5 stars5 months ago
Loved this place! Exactly how it was advertised. It was easy to find and access was a breeze. It worked out great for us. It is only a few miles from our kids and grandkids. Restaurants and shopping is unlimited in this area. Close to everything that you could want. Hope to come here again a few times a year.

Pet-friendly condo rentals

Top guest favorite
Condo in Indian Shores
5 out of 5 average rating, 16 reviews

Stylish Beachfront Condo, Stunning Views

MadelynRating, 5 stars1 week ago
We had an amazing stay at this beach place. The view is amazing with great sunsets right from the balcony. The fully stocked beach closet is so helpful, especially when going to and from the beach with kids. The space is beautifully decorated and all the bedrooms were even larger than we expected. We will definitely return to this place and would highly recommend to anyone looking for a quiet beach retreat! Max was also very helpful and responsive!
Guest favorite
Condo in Madeira Beach
4.88 out of 5 average rating, 140 reviews

John's Pass/ Madeira Beach -2Bed / 2Bath

AshleyRating, 5 stars1 week ago
The condo was excellent and was exactly as described. Loved how close it was to the beach and walkable to shopping, restaurants and activities. Can’t wait to come back!
Guest favorite
Condo in Lutz
4.92 out of 5 average rating, 25 reviews

Little Retreat Studio, clothing optional N9S

RickRating, 5 stars2 weeks ago
2nd stay,was very relaxing,jim is very helpful with everything,will be back again
Top guest favorite
Condo in Tampa
4.95 out of 5 average rating, 19 reviews

MJ’s Condo Minutes from TPA and Busch Gardens

JebRating, 5 stars4 months ago
What a delightful find - Mallory is an excellent host and her condo was clean, comfortable, conveniently located, and well stocked with coffee and toiletries.
Guest favorite
Condo in St. Petersburg
4.95 out of 5 average rating, 189 reviews

Sea La Vie- Studio by the bay!

MarieRating, 5 stars2 weeks ago
I was impressed as soon as I opened the door to Alison’s unit at Boca Ciega Resort. The studio condo was beautifully decorated, impeccably clean, and updated throughout. The view from the condo was outstanding, overlooking the stunning Boca Ciega Bay. The sunsets from the balcony were breathtaking. Alison responded promptly when I encountered a minor issue entering the unit. I highly recommend Alison's place and will definitely return.
Guest favorite
Condo in St. Petersburg
4.97 out of 5 average rating, 87 reviews

Updated Condo-Heated Pool-Private Balcony

KathiRating, 5 stars1 week ago
We really enjoyed staying at Tamas’s place. It was so pleasant and being on the balcony every morning watching the dolphins was so relaxing. We used the pool and hot tub and drove to beaches around the St.Pete area. Tamas took care of any issues we had immediately. We appreciated the vacation time there and would recommend it as the perfect size for one couple.
Top guest favorite
Condo in Seminole
4.97 out of 5 average rating, 146 reviews

SUNNY DELIGHT! HEATED POOL 2 miles to the beach🐶

RomanRating, 5 stars2 days ago
Sandra is an amazing host. Super responsive and accommodating! Place is nice and cozy with all the little details carefully thought through. Great location close to everything. Highly recommend!
Top guest favorite
Condo in North Redington Beach
5 out of 5 average rating, 18 reviews

Entire Beach Condo (pool,WiFi,Gym)

PeterRating, 5 stars2 weeks ago
This place was furnished perfectly ,easy access to the beach, walking distance to great restaurants and fabulous fish market. Nice quiet location. Neighbors are friendly and accommodating. You could not ask for anything more.

Condo rentals with a pool

Guest favorite
Condo in Madeira Beach
4.88 out of 5 average rating, 80 reviews

Lovely-2 bedroom condo with 2 pools, Madeira beach

JenniferRating, 5 stars1 week ago
Great vacation in a great condo. Matthew was a very responsive host with clear check-in instructions and good communication throughout our stay. Location was perfect for our family - easily walked to the beach in the morning and enjoyed the pool in the afternoon. Car rental made it easy to visit local attractions. It is worth noting that the hurricane wrecked all of the bottom units in the complex and all of the central AC units. Matthew had portable AC in the condo, which was listed in the amenities section, but I must have missed when booking so we were surprised to find them. Other than the constant low hum of the units, the air was cool enough and did not have an effect on our enjoyment. Others should note that Madeira Beach is not 100% back from the hurricane but still was a great location for our vacation.
Guest favorite
Condo in Madeira Beach
4.86 out of 5 average rating, 50 reviews

Walk to Beach,Extra Clean,WiFi, 2 Pools Staycation

RickRating, 5 stars8 months ago
This was our second stay with Tina and we were very pleased that we were able to go back. The condo is ideally situated and has all of the amenities you need. We had a great stay and hope to go back in the near future.
Top guest favorite
Condo in Clearwater
4.96 out of 5 average rating, 81 reviews

Welcome to your vacation home

BrookeRating, 5 stars1 week ago
Our stay here was so clean and comfortable! I really didn’t want to leave! We would absolutely stay here again
Top guest favorite
Condo in Tampa
4.97 out of 5 average rating, 149 reviews

Tiki Themed Waterfront Condo on Tampa Bay

CindyRating, 5 stars1 week ago
The tiki themed suite is absolutely magical! Walking in was such an awesome experience for my family! We loved the decor, sounds, smells and views but we especially loved Chief the parrot! Chris explains everything you need to know with great detail, no questions go unexplained! We really enjoyed the onsite restaurant & bar too! The sunset should not be missed! We can’t wait to go back!
Guest favorite
Condo in St. Petersburg
4.9 out of 5 average rating, 58 reviews

2 bedroom condo with a pool on Boca Ciega Bay

GeraldRating, 5 stars5 months ago
The number one thing is that this has a beautiful view of the water out of the living room sliding glass door/window. The living room is large and comfortable. The beds are comfortable. The kitchen is functional to take care of yourself. The washer/dryer work well and have good capacity. Probably the only complaints are the parking is somewhat limited especially for a large SUV. The TV is not a "Smart" TV so I had to go out and buy a Roku to be able to watch shows. I never figured out how the cable worked. One can hear the road noise from the causeway, but surprisingly, it didn't keep anyone awake. Richard is easy to work with and responded fast to our numerous questions. I look forward to staying there again.
Guest favorite
Condo in Clearwater
4.93 out of 5 average rating, 117 reviews

POOL VIEW IN A MODERN CONDO - Feel at Home

SusanRating, 5 stars3 months ago
The condo was great. Impeccably clean and provided everything you might need during your stay. It was excellent value for the rate. It was also a very short and simple drive to get to Clearwater beach. I would definitely go back.
Guest favorite
Condo in Hudson
4.94 out of 5 average rating, 16 reviews

Tropical Resort

Shane/JackieRating, 5 stars2 months ago
This was a perfect getaway. Fantastic views of the Gulf of Mexico, lots of wildlife, amazing heated pool, and the space was relaxing and chill. We even got in a few games of tennis,
Guest favorite
Condo in Indian Shores
4.88 out of 5 average rating, 52 reviews

Intracoastal | Indian Shores | Beach across street

LizRating, 5 stars3 weeks ago
The bnb was in the perfect location close to restaurants and shops as well as stocked with beach chairs, a cooler and more to complete our beach experience. Scott was super accommodating to our travel needs! Highly recommend and will be back!

Destinations to explore

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