
Condo holiday rentals in Caladesi Island
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Top-rated condo rentals in Caladesi Island
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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.
4.99 out of 5 average rating, 243 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!
4.95 out of 5 average rating, 128 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.
4.98 out of 5 average rating, 182 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.
4.91 out of 5 average rating, 488 reviews
Modern, Luxurious Beach Condo -Steps To The Beach!
Come enjoy your piece of paradise on this luxurious, newly renovated beach condo, just 40 steps from the beach! The condo has two bedrooms with two private baths, and a living space with an extra half bathroom. The recently updated kitchen has new stainless steel appliances, granite countertops, and a spacious breakfast bar. The living room has a 51 inch TV and 2 leather pull-out couches. Free private parking for two cars. Beach chairs, umbrellas, towels and 2 bicycles are included!
4.87 out of 5 average rating, 403 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.
4.9 out of 5 average rating, 444 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!
4.95 out of 5 average rating, 107 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.
4.72 out of 5 average rating, 548 reviews
Beachfront Condo | Gulf Views & Stunning Sunsets
Wake up to the sound of the waves and breathtaking Gulf views from this beautifully updated beachfront condo on the sugar-white sands of Indian Rocks Beach. This inviting 2-bedroom, 2-bath retreat features renovated bathrooms, unobstructed ocean views, and a private balcony perfect for morning coffee or unforgettable sunsets. Steps from the beach, it's the perfect escape for couples, families, and friends seeking the ultimate Florida Gulf Coast getaway.
4.82 out of 5 average rating, 104 reviews
On Private Beach! Full Kitchen, Ground Level Unit5
Fully remodeled in 2025! We are back and better than ever! On the Private Beach! Breathtaking Gulf views! 2 bedroom 1 bath unit +bunkbeds & patio leading to private beach, full kitchen 2 queen beds plus twin bunkbed. Sleeps 6 guests. We furnish linens, towels, toiletries, beach towels, beach chairs. 1 Free parking space included. See our 1 bedroom units, same location, Gulf Dreams unit 6 & Tide Vibes unit 7.
4.91 out of 5 average rating, 121 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...
4.98 out of 5 average rating, 170 reviews
Panoramic Gulf View Beachfront Condo
Escape to our 7th-floor beachfront condo at Sand Castle II in Indian Shores! This spacious 3-bedroom, 2-bath sanctuary comfortably sleeps 8. Enjoy panoramic Gulf views from your private balcony, perfect for watching dolphins. With direct beach access, a heated pool, and a hot tub, this is the ultimate coastal getaway. Walk to Caddy's for dinner and live music!
4.93 out of 5 average rating, 152 reviewsPopular amenities for Caladesi Island condo rentals
Weekly condo rentals

Work Remote & Stay Beachfront
5.0 out of 5 average rating, 122 reviews
Relax in a Newly Renovated Beach Front Paradise
4.98 out of 5 average rating, 139 reviews
Indian Rocks Beach hidden gem 3/2 modern condo
4.95 out of 5 average rating, 103 reviews
Studio King Sunset at Beso Del Sol (Pool/Hot Tub)
4.95 out of 5 average rating, 56 reviews
Quiet Locale King Beds 1 Mile To Honeymoon Island
4.94 out of 5 average rating, 31 reviews
Beachfront Belleair Beach Condo Est. rental 2016
4.97 out of 5 average rating, 33 reviews
Beachfront Condo | Pool + Direct Beach Access
5.0 out of 5 average rating, 3 reviews
Oceanfront Condo with Beach Access
4.96 out of 5 average rating, 76 reviewsPet-friendly condo rentals

Beachfront Condo in Exclusive Resort
4.86 out of 5 average rating, 671 reviews
Penthouse Condo on Water Steps to Beach+Johns Pass
4.97 out of 5 average rating, 103 reviews
Innisbrook Condo 1st Floor next to Island Course
5.0 out of 5 average rating, 119 reviews
Steps 2 beach! Beachy and Luxurious! Easy Living!
4.95 out of 5 average rating, 346 reviews
2 Story Penthouse | Pool | Balcony | Gulf View 602
4.89 out of 5 average rating, 160 reviews
SolMate 2/2, kayaks, beach, views, boat slip
4.93 out of 5 average rating, 147 reviews
BBC216 - Gulf Breezes & Beachfront Vibes!
4.84 out of 5 average rating, 111 reviews
Luxury Seashell Oceanfront Condo with Pool
4.9 out of 5 average rating, 119 reviewsCondo rentals with a pool

Waterfront, Harbourside, Water Park, Beach, #5516
4.89 out of 5 average rating, 126 reviews
Glorious Sunsets - Beachfront 2BR Condo
5.0 out of 5 average rating, 102 reviews
Spectacular beach to bay views from this resort.
4.99 out of 5 average rating, 231 reviews
End Unit Remodeled 3/2- We Are Open For Business!
4.92 out of 5 average rating, 146 reviews
The Seascape Premier Beachfront Cottage-Gulf View
4.98 out of 5 average rating, 163 reviews
Island Escape • Pool • Jacuzzi • Minutes to Beach!
4.93 out of 5 average rating, 111 reviews
Double the Views, Double the Fun at Ocean Side
5.0 out of 5 average rating, 8 reviews
Location! 30-Steps Beach Access
4.94 out of 5 average rating, 86 reviewsDestinations to explore
- Miami Holiday rentals
- Four Corners Holiday rentals
- Miami Beach Holiday rentals
- Orlando Holiday rentals
- Fort Lauderdale Holiday rentals
- Panama City Beach Holiday rentals
- Tampa Holiday rentals
- Destin Holiday rentals
- Hollywood Holiday rentals
- Savannah Holiday rentals
- Jacksonville Holiday rentals
- Kissimmee Holiday rentals
- Anna Maria Island
- Weeki Wachee Springs
- Anna Maria Island Beach
- Raymond James Stadium
- Busch Gardens Tampa Bay
- Coquina Beach
- Bean Point Beach
- Amalie Arena
- Hard Rock Casino
- University of South Florida
- Vinoy Park
- Dunedin Beach
- Epperson Lagoon
- John's Pass
- Tropicana Field
- MidFlorida Credit Union Amphitheatre
- Sand Key Beach
- Weeki Wachee Springs State Park
- Img Academy
- Anna Maria Public Beach
- River Strand Golf and Country Club
- Cortez Beach
- Busch Gardens
- Fort De Soto Park





