Apartment holiday rentals in Clearwater Beach Island

A modern living area features a comfortable sofa and two white chairs on a patterned rug. Natural light fills the space from nearby windows, with a view of the kitchen area in the background. A doorway leads to a private bedroom, creating a cozy ambiance.

4.98 out of 5 average rating, 99 reviews

1BR NEW Coastal Boutique Cottage Closest to Beach!

The one you've been dreaming of! Bright, modern, adorable cottage in the quieter North section of Clearwater Beach, just 50 steps from curb to the sand. Walk to all attractions, restaurants, shops & Pier 60. Modern kitchen w/ full-size appliances, wood-grained ceramic tile floors, calming colors throughout. Private BR w/Queen-size Casper cooling mattress. Queen sleeper sofa in living area. Sleeps up to 4. Outdoors a shared landscaped courtyard, BBQ and Treehouse Deck w/gulf views. Shared W/D.

A modern kitchen area is presented with white cabinetry and a backsplash featuring blue and gray mosaic tiles. Two wooden bar stools are positioned at a countertop, while an adjacent open area displays a console table with decorative items. Natural light brightens the space.

4.91 out of 5 average rating, 113 reviews

Newly Remodeled 2 Bedroom Condo

Prime Clearwater Beach location with exceptional walkability. Located in a quiet area just north of Pier 60, within walking distance to restaurants & bars. A public playground & pickleball courts are immediately next door. The beach is 1.5 blocks away (5-min walk), & the pool shown in photos is on the next block (2-min walk). Fully equipped for beach days, w/ a beach wagon, chairs, towels & toys—so you can enjoy full days on the sand. First floor condo w/ washer & dryer & free onsite parking.

An open living area features a blue couch and two bar stools at a kitchen counter. A green bed is visible in the background, with a light-colored dresser against the wall. Soft lighting brightens the space, which has light blue walls and patterned flooring.

4.93 out of 5 average rating, 162 reviews

NEW! High End King Mattress! 10 Steps to the beach

AMAZING LOCATION! Located within crawling distance of the sugary white sands of the world famous Clearwater Beach! Equipped with a Premium King Casper Wave Hybrid Snow Mattress which retails at $4,000, to ensure an amazing nights sleep. Located in a small building with just 6 units, only 1 house from the beach. Walking distance to practically everything in town including many great restaurants, bars, shops, Pier 60, the marina & more, yet still located on a quiet street. No car is necessary!

Guest favourite

A modern dining area features a round glass table set for six, surrounded by white chairs. A unique blue chandelier hangs above, while large windows offer a view of the water. The kitchen area is equipped with white cabinetry and stainless steel appliances.

4.89 out of 5 average rating, 260 reviews

Waterfront 2BR Escape Walk to Beach Pool Sleeps 6

🌴 Your Clearwater Beach Escape Starts Here Wake up to peaceful water views, sip coffee on your private patio, and end your day watching the sunset just minutes away on the beach. This spacious 2BR/2BA condo perfect for families, couples, or small groups looking for a relaxing getaway.Quiet location while still being close to everything Waterfront patio with serene views (yes, dolphins are often spotted 🐬) Walk to Clearwater Beach, restaurants, and shops Pool for relaxing after the beach

A serene outdoor seating area features white adirondack chairs positioned on a natural stone patio, surrounded by lush green foliage and tropical plants. A glimpse of a swimming pool can be seen in the background, framed by additional seating and vibrant landscaping.

4.94 out of 5 average rating, 127 reviews

Island Oak

This private vacation rental is a Second floor 1 bedroom apartment is newly furnished, professionally decorated and equipped with all the conveniences of home. Island Oak joins 4 other popular vacation rentals within the Grove Keeper Collective compound. This upper unit has a balcony off the bedroom which looks into a 175 year old oak that provides a tree house effect. We hope you come and enjoy this new addition to Grove Keeper Collective. All our units are non smoking and vaping.

A spacious bedroom is adorned with modern decor. A large bed with textured pillows is positioned across from two stylish chairs and small side tables. Natural light filters through three windows, creating a bright and airy atmosphere.

4.96 out of 5 average rating, 286 reviews

Private Balcony Apt Overlooking Dunedins Main St

This newly updated studio apartment is located in downtown Dunedin on Main Street. The large private balcony is the real gem. Inside you’ll find quality furnishings and attention to detail throughout. We are centrally located to both Tampa and St. Pete. Our award winning white sandy beaches are a short drive from the unit. Steps from your door you’ll find shopping breweries and dining options to please just about all. This unit is above a Pub/Bar, noise may be an issue.

Guest favourite

A bright living area features a navy blue sofa paired with a circular wooden side table and a lamp. Wall art includes framed phrases and decorative elements, while light wood flooring enhances the openness. A kitchenette is visible in the background, adding to the functional design.

4.92 out of 5 average rating, 138 reviews

Coastal Waterfront Condo 2 blocks to Beach

🌊 Ultimate Waterfront Escape – Adventure Awaits! 🚴‍♂️🏄‍♂️ Welcome to your dream beach getaway! This stunning waterfront rental puts you right on the water with breathtaking views and endless adventure. Paddle on a kayak or stand-up paddleboard, then cruise around town on our complimentary beach bikes. Jet ski island tours, parasailing, and more—all available right from the property! This is the perfect spot to make unforgettable beach memories! 🌅🏝️🚤

Guest favourite

4.79 out of 5 average rating, 179 reviews

Renovated 2025 - Retro Beach Oasis with Color Pop

Book with confidence—our property is in great shape and ready to host your Clearwater Beach getaway! -No hidden fees -No chores Just a breezy, beachy stay with: -2-minute walk to the beach -Beach Chairs -Free parking -Heated pool -Cold AC -Easy self check-in We provide essentials (linens, towels, toilet paper, soap etc.) to get you started. For longer stays, we recommend buying additional supplies. 📍648 Poinsettia Ave, Clearwater Beach, FL 33767

Superhost

4.77 out of 5 average rating, 13 reviews

Clearwater Beach Retreat - 2 blocks to beach

Charming 1 Bedroom, 1 Bath just steps from the white sands of Clearwater Beach! Perfect for a romantic getaway, weekend retreat of relaxation, beach walking, shell collecting and the most stunning sunsets in the world! Prime location in the heart of Clearwater beach close to the best restaurants, bars, and shops. Just a few blocks away is a children's playground and pickle ball courts! Everything you need for your next beach escape!

4.91 out of 5 average rating, 23 reviews

Waterfront, Coastal Escape #2, 2 BR, 2 Bath,

Newly renovated 2BR getaway on the Intracoastal Waterway, just a few blocks from the beach! Enjoy modern comforts, a fully equipped kitchen, and a bright, coastal-inspired living space. Relax by the water with peaceful water views or take a short walk to the sand, shops, and restaurants. Perfect for couples, families, or friends looking for a stylish stay in a prime location. NOTE This unit does not have a view of the water.

The kitchen features white cabinetry with modern appliances, including a black refrigerator and microwave. A dining table with plush chairs is positioned under a chandelier. Natural light filters through a nearby window, creating a bright, inviting space for meals and gatherings.

4.98 out of 5 average rating, 264 reviews

My Favorite Place 🍊downtown & city approved

LEGAL, CITY APPROVED 1 bedroom apartment w full kitchen, living , dining & separate bedroom located on the red brick streets of downtown Dunedin. Private entrance. BIKES Super clean Private driveway free parking Two great bikes Great for couples Tastefully decorated. Comfortable Queen bed. Luxurious bedding. Super clean. Shampoo, conditioner, body wash, coffee, tea, drinking water provided. SUPER CLEAN No pets

A cozy living area features a blue sofa adorned with light-colored pillows, positioned beside a round wooden coffee table. A stylish light fixture hangs from the ceiling, illuminating the space. A framed artwork of a cow is displayed on the wall, adding a charming touch.