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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
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19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured Condo Rentals in Caladesi Island State Park

Westwinds Waterfront Resort
Aerial view

Westwinds Waterfront Resort

3.0 star property
9.0 out of 10, Wonderful, (677)
"Loved our stay!!! "
Westwinds Waterfront Resort
Provident Oceana Beachfront Suites
Sundeck

Provident Oceana Beachfront Suites

3.5 star property
9.4 out of 10, Exceptional, (587)
"Loved being able to walk across to the beach, the sunrises from the Bay were beautiful. Clean condo, super friendly staff, quiet location. "
The price is AU$321
includes taxes & fees
24 Aug - 25 Aug
Provident Oceana Beachfront Suites
Breathtaking Gulf Facing Condo Hotel Suite
Beach

Breathtaking Gulf Facing Condo Hotel Suite

10.0 out of 10, Exceptional, (261)
"The staff was very friendly and always ready to help out in any way. The property was very clean. The view from the balcony was awesome, the beach a few steps away. We would stay here again and would recommend the property to anyone traveling to this area."
The price is AU$978
includes taxes & fees
24 Aug - 25 Aug
Breathtaking Gulf Facing Condo Hotel Suite
New Beachfront Property in Exclusive Resort
Terrace/patio

New Beachfront Property in Exclusive Resort

9.6 out of 10, Exceptional, (215)
"Clean, lovely view matched photos"
The price is AU$732
includes taxes & fees
1 Sept - 2 Sept
New Beachfront Property in Exclusive Resort
Spectacular Oceanfront Condo with Sweeping Views! on the Gulf
Property grounds

Spectacular Oceanfront Condo with Sweeping Views! on the Gulf

9.8 out of 10, Exceptional, (205)
"We had a GREAT time for our 45 year anniversaryand look forward to coming back soon!"
Spectacular Oceanfront Condo with Sweeping Views! on the Gulf
Chic Modern Condo Hotel Suite on the Beach
Beach

Chic Modern Condo Hotel Suite on the Beach

9.8 out of 10, Exceptional, (157)
"Beautiful modern. Had everything."
The price is AU$725
includes taxes & fees
26 Aug - 27 Aug
Chic Modern Condo Hotel Suite on the Beach
ESCAPE to enjoy the most beautiful SUNSETS on the Gulf of Mexico!!!
A heated pool

ESCAPE to enjoy the most beautiful SUNSETS on the Gulf of Mexico!!!

9.6 out of 10, Exceptional, (261)
"Everything about this stay was as described in the listing. It was close to great food and drink. The beach was steps away and the pool area was great for relaxing."
ESCAPE to enjoy the most beautiful SUNSETS on the Gulf of Mexico!!!
New! Condo in exclusive Avalon Club
Beach

New! Condo in exclusive Avalon Club

9.6 out of 10, Exceptional, (143)
"Nice place, walk to beach, clean, friendly"
The price is AU$767
includes taxes & fees
24 Aug - 25 Aug
New! Condo in exclusive Avalon Club
Spacious Gulf View Condo Hotel Suite
Beach towels

Spacious Gulf View Condo Hotel Suite

10.0 out of 10, Exceptional, (102)
"The room was great. Plenty of room for our entire family of 9. Having access to beach chairs umbrellas and towels was very nice. Worth the money. Great access to beach and restaurants."
The price is AU$1,028
includes taxes & fees
25 Aug - 26 Aug
Spacious Gulf View Condo Hotel Suite
Welcome to Seaview #103, your perfect beach destination!
Property grounds

Welcome to Seaview #103, your perfect beach destination!

10.0 out of 10, Exceptional, (31)
"The condo was clean and beautifully decorated! The pool and hit tub were up and running and well cared for. The view was indescribably beautiful! We loved it!"
Welcome to Seaview #103, your perfect beach destination!
Modern Design Gulf Facing Condo on the Beach
Beach

Modern Design Gulf Facing Condo on the Beach

10.0 out of 10, Exceptional, (71)
"Our family enjoyed our stay"
The price is AU$827
includes taxes & fees
28 Aug - 29 Aug
Modern Design Gulf Facing Condo on the Beach
❤Waterfront View, Amazing Sunsets, Heated Pool 3mins to Airport ☀🐬🏖
Property grounds

❤Waterfront View, Amazing Sunsets, Heated Pool 3mins to Airport ☀🐬🏖

9.2 out of 10, Wonderful, (144)
"My daughter, granddaughter and I stayed for 3 nights after a cheerleading competition and greatly enjoyed the condo and chance to relax around the pool and in the sandy beach area with tiki torches and fire pit. The pool restaurant bar was also enjoyed!!"
The price is AU$370
includes taxes & fees
24 Aug - 25 Aug
❤Waterfront View, Amazing Sunsets, Heated Pool 3mins to Airport ☀🐬🏖
Top Floor Beachfront Studio Breathtaking Views. Heated Pool. Fantastic Location in Treasure Island!
On the beach

Top Floor Beachfront Studio Breathtaking Views. Heated Pool. Fantastic Location in Treasure Island!

9.2 out of 10, Wonderful, (171)
"We loved our stay! Very nice room with the perfect view!!!"
Top Floor Beachfront Studio Breathtaking Views. Heated Pool. Fantastic Location in Treasure Island!
2 BR 2 Bath Sandy Shores Condos Right Across the street from JohnsPass Village
A heated pool

2 BR 2 Bath Sandy Shores Condos Right Across the street from JohnsPass Village

9.2 out of 10, Wonderful, (227)
"10 out of 10. Would definitely stay again."
2 BR 2 Bath Sandy Shores Condos Right Across the street from JohnsPass Village
Gulf front 2 bed 2 bath, private elevator on 3rd floor
Outdoor pool, a heated pool

Gulf front 2 bed 2 bath, private elevator on 3rd floor

9.8 out of 10, Exceptional, (102)
"very comfortable lodging great parking near the private elevator to our balcony. ideal location to beach and warm pool. we decided to book again for 2026. Good experience.Gary and Deb. "
Gulf front 2 bed 2 bath, private elevator on 3rd floor
Spectacular 2br/2bth isld apartm
Property grounds

Spectacular 2br/2bth isld apartm

8.6 out of 10, Excellent, (20)
"Owner was very responsive and was open to ideas on improving stay. Look forward to going back again."
Spectacular 2br/2bth isld apartm
Unit 413 - Picture Perfect 4th Floor Beachfront Stateroom. Elegant Accommodations. Incredible View.
On the beach

Unit 413 - Picture Perfect 4th Floor Beachfront Stateroom. Elegant Accommodations. Incredible View.

9.2 out of 10, Wonderful, (186)
"Had a very pleasant weekend at this unit. The owner has done a great job of updating it, beautiful decor. The balcony has a fabulous view of the beach and all that was going on there. Plenty of restaurants close by. Would definitely like to return!"
Unit 413 - Picture Perfect 4th Floor Beachfront Stateroom. Elegant Accommodations. Incredible View.
South Beach Condo Hotel
On the beach

South Beach Condo Hotel

4.0 star property
8.6 out of 10, Excellent, (14)
"We always love staying at this location. It's always clean and so nice that it's right on the water"
South Beach Condo Hotel
Adorable Studio with Gulf Views and Easy Access to the Beach!
Beach nearby, sun-loungers, beach towels

Adorable Studio with Gulf Views and Easy Access to the Beach!

9.6 out of 10, Exceptional, (307)
"Clean and close to the beach"
Adorable Studio with Gulf Views and Easy Access to the Beach!
Luxurious Penthouse Oasis - Direct Beachfront/Oceanfront - 2 Parking Spots!!!
Outdoor pool, a heated pool

Luxurious Penthouse Oasis - Direct Beachfront/Oceanfront - 2 Parking Spots!!!

10.0 out of 10, Exceptional, (153)
"Easy check in and check out . Owners very thorough with directions and specs on property.Would recommend "
Luxurious Penthouse Oasis - Direct Beachfront/Oceanfront - 2 Parking Spots!!!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Caladesi Island State Park Hotel Reviews

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

10/10 Excellent
"We absolutely loved everything about our vacation. Another small pool would be our only suggestion. We’ll be back next summer no doubt! Thank you to all of you!! (Grand Deluxe King) gulf front. Take the sunset cruise! "
Michele B 4-night trip
Posted 5 hours ago
Wyndham Grand Clearwater Beach