
Apartment holiday rentals in Caladesi Island
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Top-rated apartment rentals in Caladesi Island
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Steps 2 beach! Beachy and Luxurious! Easy Living!
Easy Living is a beachy newly renovated condo with 2 bedrooms & 2 full bathrooms, nestled between the intercoastal water and the magnificent Clearwater beach! Located a very short walk to the beach (less than 2 blocks) and across the street from a park. The Clearwater Beach Rec Pool is another short two minute walk from the condo! The condominium is quiet area yet, it is within walking distance to practically everything in town, including the beach, many restaurants, bars, Pier 60, & the marina!
4.95 out of 5 average rating, 346 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, 129 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, 183 reviews
BBC216 - Gulf Breezes & Beachfront Vibes!
🌊 Gulf-Front Condo w/ Balcony | Beach Access | Pool | Sleeps 6 🌴 ~ Managed by Sandy Feet Vacation Rentals ~ ✨ 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.
4.84 out of 5 average rating, 111 reviews
Waterfront, Harbourside, Water Park, Beach, #8819
Welcome! This newer 2-bedroom, 2-bath condo is located at the 'Harborside@Marker 33' and 'Splash Harbour Water Park' complex. Your 8th-floor penthouse unit has a balcony that offers the best views of the Intracoastal Waterway both day and night. Enjoy watching the dolphins and boats as they pass by. Unit 8819 comes with 4 free daily Splash Harbour Water Park passes. That's a $ 100-a-day value. 6 additional passes are offered at a discounted rate. Washer/dryer in unit.
4.87 out of 5 average rating, 195 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, 108 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
New! Condo in exclusive Avalon Club
This 3-bedroom, 2-1/2-bathroom modern chic condo hotel suite offers stunning views of the Bay, Honeymoon Island, and Dunedin. It has room for 8 with one King bed, 2 Queen beds, plus a full-sized sofa bed. The private balcony provides the perfect place for people watching in the street below and south, down Mandalay Ave., or to enjoy watching the sun rise over Mandalay Bay. Please note that one of the queen bedrooms does not have a window.
4.91 out of 5 average rating, 185 reviews
Waterfront, Harbourside, Water Park, Beach, #6620
4 FREE daily water park passes and parking for one car are included! 3/5 minute walk to the BEACH! This 2/2 condo is located at the 'Harborside@Marker 33' and 'Splash Harbour Water Park' complex. This 6th-floor "end" unit has a balcony that overlooks the Intracoastal and another that overlooks the Water Park! Come stay in this rare unit. There is a fully stocked kitchen that even includes a stackable washer and dryer.
4.87 out of 5 average rating, 263 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, 122 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, 171 reviewsPopular amenities for Caladesi Island apartment rentals
Weekly apartment rentals

Modern, Luxurious Beach Condo -Steps To The Beach!
4.87 out of 5 average rating, 403 reviews
Panoramic Gulf View Beachfront Condo
4.93 out of 5 average rating, 153 reviews
Golf Cart, 2 bed 2 Bath, Heated Pool
4.9 out of 5 average rating, 148 reviews
Beachfront corner condo 3 bedroom, 2 bathroom.
4.82 out of 5 average rating, 127 reviews
Work Remote & Stay Beachfront
5.0 out of 5 average rating, 123 reviews
Quiet Locale King Beds 1 Mile To Honeymoon Island
4.94 out of 5 average rating, 31 reviews
Studio King Sunset at Beso Del Sol (Pool/Hot Tub)
4.95 out of 5 average rating, 56 reviews
September Deals! Beach Front Penthouse!
4.88 out of 5 average rating, 50 reviewsPet-friendly apartment rentals

Beachfront Condo Resort on Treasure Island
4.89 out of 5 average rating, 215 reviews
2 Story Penthouse | Pool | Balcony | Gulf View 602
4.89 out of 5 average rating, 160 reviews
Innisbrook Condo 1st Floor next to Island Course
5.0 out of 5 average rating, 119 reviews
Walk to Beach, Bars, and Restaurants Nearby
4.85 out of 5 average rating, 125 reviews
Lovely Condo minutes from beach & King bed
4.98 out of 5 average rating, 121 reviews
Beach Retreat I
4.92 out of 5 average rating, 198 reviews
Luxury Seashell Oceanfront Condo with Pool
4.9 out of 5 average rating, 120 reviews
SolMate 2/2, kayaks, beach, views, boat slip
4.93 out of 5 average rating, 147 reviewsApartment rentals with a pool

Newly Reno Luxury Condo 30 Steps to Paradise
4.98 out of 5 average rating, 197 reviews
Spectacular beach to bay views from this resort.
4.99 out of 5 average rating, 231 reviews
Rincón Divino MB 2 Balconies, Ocean & Marina Views
4.99 out of 5 average rating, 243 reviews
The Shack at IRB
4.93 out of 5 average rating, 112 reviews
Modern Waterfront Condo - Captivating Sunset Views
4.95 out of 5 average rating, 386 reviews
Beachfront Belleair Beach Condo Est. rental 2016
4.97 out of 5 average rating, 34 reviews
Beachfront Oasis / Pool, Beach Access & Ocean View
4.93 out of 5 average rating, 86 reviews
Wonderful Condo at Avalon - Fully Renovated
5.0 out of 5 average rating, 73 reviewsDestinations to explore
- Miami Holiday rentals
- Four Corners Holiday rentals
- Orlando Holiday rentals
- Kissimmee Holiday rentals
- Miami Beach Holiday rentals
- Panama City Beach Holiday rentals
- Tampa Holiday rentals
- Fort Lauderdale Holiday rentals
- Destin Holiday rentals
- Savannah Holiday rentals
- Hollywood Holiday rentals
- Jacksonville Holiday rentals
- Anna Maria Island
- Weeki Wachee Springs
- Raymond James Stadium
- Anna Maria Island Beach
- 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
- Busch Gardens
- Cortez Beach
- Splash Harbour Water Park





