Condo vacation rentals in Caladesi Island

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Top-rated condo rentals in Caladesi Island

Guests agree: these condos are highly rated for location, cleanliness, and more.

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Top guest favorite

The kitchen features navy blue cabinets, providing a stylish contrast to the stainless steel appliances. A spacious countertop holds essential kitchen gadgets, and a modern backsplash adds texture. Adequate storage is available with cabinets and drawers, contributing to a well-organized cooking space.

Condo in Madeira Beach

4.99 out of 5 average rating, 242 reviews

Rincón Divino MB 2 Balconies, Ocean & Marina Views

EXCLUSIVE: Saturday checkout is at 5pm. This condo features 2 private balconies, w/ spectacular ocean & marina views. It's stylish decor, meticulously picked quality & comfortable furnishing/accessories are sure to please. It’s conveniently located just across the street from the pristine white sands and sunsets of the Gulf of Mexico. It is adjacent to the #1 tourist destination in the county, John's Pass Village. The property offers a heated swimming pool, hot tub, fitness room & event center.

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Top guest favorite

An inviting living area showcases a comfortable blue couch with a colorful throw blanket. A wooden dining table is positioned nearby, and natural light flows through expansive glass doors leading to a balcony with a glimpse of trees and water outside.

Condo in Indian Rocks Beach

4.95 out of 5 average rating, 127 reviews

Beachside, Lux, 3 Minute Walk, Views Fam.-Friendly

Completely remodeled luxury beachside condo with balcony. Water/beach view- balcony and living room. Short walk down to beach. Saatva Luxury mattress in Master. 2nd Bed- has double over double bunk bed with twin trundle. Couch -pullout bed that sleeps two more. Kid-friendly! Pack n play with memory foam mattress and diaper genie. Toys, child-proofing, kid utensils etc in unit. Beach supplies, towels, wagon, chairs, toys umbrellas.. below in storage. Paddleboard and bike rental available nearby!

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Top guest favorite

An aerial view captures a multi-story condominium overlooking a beach. Lush palm trees surround a heated pool area, with docks lining the waterfront. The expansive coastline is visible in the background, highlighting the scenic proximity of beach and bay.

Condo in Treasure Island

4.99 out of 5 average rating, 231 reviews

Spectacular beach to bay views from this resort.

Our condo has spectacular water views from the Bay to the Beach. We have a large one of a kind kitchen that is unique to our resort, with granite counter tops, hardwood cabinets, and all stainless steel appliances. Everything you need to prepare a meal is provided along with basic spices and condiments, Coffee, creamer, and sugar. The master bedroom has a new king size bed and walk in closet with all beach gear also available for your use. We have 2 - 50" flat screen TV's with cable as well.

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Top guest favorite

A doorway opens to a view of the coastal pathway, leading to a sandy beach area. Bright skies and a seating area are visible in the distance, framed by the entrance's surroundings and greenery at the base of the walls.

Condo in Indian Shores

4.97 out of 5 average rating, 140 reviews

Beachfront Steps to Sand - New Remodeled Bathroom

Escape to our cozy 1-bed, 1-bath gulfside condo for ultimate relaxation. We have a newly renovated bathroom with a walk-in shower. Unwind on the front porch or walk to the beach just moments away. Nestled in a peaceful coastal area, discover nearby restaurants within a 10-min walk. Short term or long term stays (ask for SNOWBIRD deals). NO Pets are allowed. Check local swim advisories. The community shower is located near the beach & round picnic tables. These tables are for the community.

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Top guest favorite

A scenic view of a fishing pier extends into the water, framed by gentle waves and a sandy beach. The sky is filled with colorful clouds, reflecting hues of orange and blue as the sun sets on the horizon.

Condo in Clearwater Beach

4.98 out of 5 average rating, 182 reviews

Upgraded 3 Bed, 3 Bath Corner Water Front Condo!

Stylish & Sunny Corner Unit On Dolphin Faved Inlet Across The Street From Florida's #1 Beach. This all-inclusive unit allows you to walk everywhere and enjoy all Clearwater Beach has to offer from sand & sun to restaurants & shopping. Updated & upgraded 3 bedroom, all with connected bathrooms offers amazing space, a chef's kitchen as well as bright & beautiful dining & living rooms. Private balcony to relax & watch the sunset. Beach concessions include sea kayaks, jet ski's, boating & more.

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Guest favorite

A set of two white wicker chairs and a small table are positioned on a balcony, providing views of the Gulf of Mexico. The ocean and sandy beach stretch into the distance, with clear blue skies overhead.

Condo in Clearwater Beach

4.91 out of 5 average rating, 486 reviews

Amazing views on beachfront

This spacious upper-floor, 3-bedroom condo hotel suite offers views of the Gulf of Mexico from your private balconies. While preparing your morning coffee on the spacious kitchen island, you can see the water of the Gulf of Mexico. Each suite can accommodate 10 people, with 3 bedrooms, 2 of them with a King bed in each bedroom and the third with 2 Queen beds, each of them with their own ensuite bathroom, in total 3 1/2 bathrooms, also a comfortable full-sized sofa bed in the living room.

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Guest favorite

The image shows a view of the beach, with smooth, sandy shores leading to a row of modern condo buildings in the background. The condos are designed with balconies, featuring multiple stories and large windows, under a clear blue sky.

Condo in Indian Shores

4.9 out of 5 average rating, 444 reviews

Indian Shores Gulf Front Rental

Beautiful 2 bed 1 bath luxury condo on the Gulf of Mexico. We are steps from the beach. Unit has partial water view. Beautiful state of the art kitchen and luxurious furnishings. Everything you need for your perfect vacation. Totally non-smoking unit. Come and stay with us. This is a second floor walk up condo. There are 27 steps. May not be suitable for the elderly or small children. Check in 3pm. Check out 10am Our maximum occupancy is 4 people including children.

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Top guest favorite

A balcony space is shown with two white lounge chairs positioned facing the ocean. The beach and turquoise waters are visible in the background, complemented by a clear blue sky. The glass door provides seamless access to the indoor area.

Condo in Indian Shores

4.98 out of 5 average rating, 139 reviews

Relax in a Newly Renovated Beach Front Paradise

Immerse yourself in the stunning beauty of the Gulf Coast at this hidden gem, perfectly nestled in the charming Indian Shores. This property exudes a coastal ambiance, providing a tranquil sanctuary to bask in the sugar-white sands and sparkling turquoise waters. Beach chairs & towels are thoughtfully provided. All you need to bring is a swimsuit & toothbrush. Exciting updates include new furniture & bedding added in '25 as well as a beautifully renovated walk-in shower in '24.

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Superhost

The exterior of the Ocean Club building is showcased, featuring a modern design with a white façade and large balconies. Palm trees line the front, enhancing the tropical setting. A welcoming entrance is visible, set against a backdrop of a bright sky with soft clouds.

Condo in Treasure Island

4.86 out of 5 average rating, 670 reviews

Beachfront Condo in Exclusive Resort

The most stunning views from this brand new condo directly on Treasure Island Beach. This lovely unit is on the 4th, 5th, or 6th floor and provides sweeping views of the ocean. This units has 2 bedrooms and 2 full bathrooms. The inviting open concept living area has one of the best views of the ocean, especially when the retractable sliding doors are opened. The dining table on your private balcony provides a perfect dining area, with the ocean providing a beautiful backdrop.

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Top guest favorite

A spacious bed is positioned in front of large windows offering views of the Gulf of Mexico. Soft blue accent pillows complement the bedding. Outside, two chairs on the balcony overlook the sandy beach, creating a serene coastal ambiance.

Condo in Clearwater Beach

4.95 out of 5 average rating, 107 reviews

#1- SALE! Nice 2/2 Condo-Directly on the sand!

Kick back and relax in this calm & quiet beachfront condo, located directly on beautiful North Clearwater Beach! Unit is located on the 2nd floor with gorgeous views of the Gulf of Mexico. 2 Bedrooms, 2 bathrooms with a private balcony overlooking the beach. Sleeps 6 with the air mattress. WiFi included, Smart TV's, beach chairs, towels, toys, etc. Just bring yourselves and you are ready to go! Fully equipped full-sized kitchen with enough supplies to get you started!

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Guest favorite

A balcony view that captures the tranquil beach scene, featuring soft pastel hues in the sky. A round table with intricate design sits next to two woven chairs. Below, umbrellas dot the sandy beach, while gentle waves touch the shore.

Condo in Belleair Beach

4.72 out of 5 average rating, 547 reviews

BEACHFRONT Condo - Belleair Beach Club - RENOVATED

RECENTLY RENOVATED. This cozy 1 bedroom condo with a kitchen in Belleair Beach just steps from the sugar-white sand and crystal clear waters that are consistently ranked among America's most beautiful beaches! It has a lovely pool area that overlooks the gulf with a patio, chairs and grills. You’ll love the beachfront views and quiet ambiance. 3rd Floor, balcony with DIRECT BEACH/GULF VIEW. Minutes away from Clearwater Beach. Perfect for couples! ONE parking spot.

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Top guest favorite

A bright living area features a comfortable light-colored sofa and armchairs, complemented by a decorative round coffee table. Large glass doors provide an unobstructed view of the beach and palm trees outside, allowing natural light to fill the space.

Condo in Indian Rocks Beach

4.98 out of 5 average rating, 170 reviews

Private Ocean View Beach Retreat with Balcony

Only steps from the beach, this newly updated and perfectly located beach condo is your luxury getaway. The large bedroom, lofty living area and modern open kitchen, as well as the generous balcony with direct view of the Gulf will make you never want to leave again. This condo is better equipped than your average vacation rental and comes with your private daily sunset spectacle. Continue to read for more...

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