Condo holiday rentals in Caladesi Island

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Top-rated condo rentals in Caladesi Island

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Top Guest favourite
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!

Top Guest favourite
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, 181 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.

Top Guest favourite
An aerial view captures a stretch of beach alongside a series of buildings, including two-story structures and green spaces. The coastline meets the turquoise waters, while a street lined with parked cars runs parallel to the beach, showcasing the proximity of the community to the shore.
Condo in Indian Rocks Beach
4.95 out of 5 average rating, 103 reviews

Indian Rocks Beach hidden gem 3/2 modern condo

Welcome to your beach getaway at Ship-A-Hoey in Indian Rocks Beach, Florida. It is nestled between the attractions of Clearwater Beach and John's Pass Boardwalk in Madeira Beach. The building is located on the west side (beach side with no direct view of the beach)of Gulf Blvd and comes with 2 parking spaces. There is a row of buildings between this condo and the beach. The condo is situated on the top floor ( 2 flights of stairs with NO ELEVATOR) of a quaint four unit complex on stilts.

Guest favourite
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.

Guest favourite
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, 443 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.

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.

Guest favourite
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, 546 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.

Top Guest favourite
A bright and airy living area features a large flat-screen TV mounted above a stone fireplace. A sliding glass door provides direct views of the beach, while comfortable seating is arranged around a cozy coffee table adorned with decorative sea-themed accents.
Condo in Clearwater Beach
4.95 out of 5 average rating, 102 reviews

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

Newly painted & refreshed beachfront condo, located directly on beautiful North Clearwater Beach! Unit is located on the 3rd floor with gorgeous views of the Gulf of Mexico. 2 Bedrooms, 2 bathrooms with a private balcony overlooking the beach. Sleeps 6 with the futon & an 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.

Top Guest favourite
A spacious living room features a large sectional sofa adorned with decorative cushions, providing a comfortable seating area. A coffee table with a natural wood finish is central to the room. Sliding glass doors open to a balcony, revealing views of the beach and ocean.
Condo in Indian Rocks Beach
5.0 out of 5 average rating, 121 reviews

Work Remote & Stay Beachfront

Beachfront & Beautiful Gulf Views - EVERY Room ★Gorgeously updated ★Stunning views from balcony & interior ★ Private beach access ★Hotel Like Amenities: TVs in all rooms, Toiletries, Coffee provided, Pickle Ball & Tennis ★ Walkable to restaurants, stores & Trolley stop ★ Beach equipment provided ★ Fully-stocked kitchen & Laundry in-unit ★ High-speed internet & workspace ★ Kid & Dog-friendly ★ New landscaping, pool deck & court resurfacing

Guest favourite
A bright living area features a modern, light-colored sectional sofa and a round coffee table. A comfortable armchair is placed nearby. Large glass doors lead to a private balcony, enhancing views of the waterfront. A ceiling fan and wall-mounted TV are also visible.
Condo in Belleair Beach
4.84 out of 5 average rating, 111 reviews

BBC216 - Gulf Breezes & Beachfront Vibes!

🌊 Gulf-Front Condo w/ Balcony | Beach Access | Pool | Sleeps 6 🌴 ✨ Relax on Your Private Balcony with Stunning Views of Belleair Beach! ✨ Unwind in this beautifully updated boutique beachfront condo located at the exclusive Belleair Beach Club—just minutes from the white sands of Clearwater Beach. Whether you're here for a romantic getaway or a family vacation, this coastal gem offers the perfect mix of comfort, style, and location.

Top Guest favourite
An expansive view captures the beach's soft white sand and gentle turquoise waves, with resorts lining the coastline. A backdrop of clear skies complements the vibrant atmosphere, while people enjoy the beach area. The shoreline curves into the distance, inviting exploration.
Condo in Clearwater Beach
4.87 out of 5 average rating, 148 reviews

Newly Reno Condo! Spot Dolphins from Your Balcony!

Welcome to this peaceful and spacious 4th-floor beach condo. A three-bedroom, two-bathroom condominium located in the heart of South Clearwater Beach. This beach condo is just a 5-minute walk to the #1 rated beach in the country and various restaurants and shopping. Clearwater Beach is known for its award-winning beaches, great restaurants, and lively nightlife. We have made every effort to make this apartment a home away from home!

Top Guest favourite
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, 169 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...

Popular amenities for Caladesi Island condo rentals