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, 112 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, 161 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!

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

4.94 out of 5 average rating, 127 reviews

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.

Apartment in Dunedin

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 cozy patio area features four matching armchairs surrounding a glass-top table. Overhead, a ceiling fan provides comfort, while palm trees frame the view of the waterfront beyond the railing. Light streams in through two large windows, enhancing the inviting atmosphere.

4.93 out of 5 average rating, 73 reviews

Waterfront Gorgeously Updated Condo 2 Bed/2 Bah

Relax in this renovated waterfront apartment. Unwind after your day at the beach on the patio overlooking the sun setting over the water. This fresh space has everything you need for your stay; a full kitchen stocked with cooking supplies, two full bedrooms & bathrooms, a large living area with ocean views to name a few highlights. Only 5 miles to the #1 rated Clearwater Beach, 1.3 miles to the fun Downtown Dunedin, a block to the Pinellas Trail, & 1 mile to the Blue Jay’s stadium!

4.9 out of 5 average rating, 185 reviews

The Breezeway #2 only a 2 min walk to the Beach!

Our studio has a King Bed, as well as a microwave, mid-size fridge, regular coffeemaker and toaster. We do not provide kitchen utensils, paper towels etc. but you’ll find tons of amazing local restaurants just a short walk away. We offer a heated Pool and free parking for our guests on site. We have a brand-new Pickle ball court and Playground on one side and a public pool and tennis court on the other. We are just short stroll to historic Pier 60 and vibrant beach nightlife.

4.92 out of 5 average rating, 26 reviews

Waterfront, Coastal Escape #4, 2 BR, 2 Bath

Enjoy your stay in this charming 2-bedroom, 2nd-floor Airbnb just a few blocks from the beach! Located along the scenic Intracoastal Waterway, this unit is within walking distance to shops, restaurants, and local attractions. Relax outside with water views, take a stroll to the beach, or explore the vibrant neighborhood. Perfect for couples, families, or small groups looking for comfort and convenience near the beach. NOTE This unit does not have a view of the water.

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

A welcoming living area is presented with a round dining table and four wooden chairs, positioned near large windows offering views of the waterfront. A ceiling fan adds comfort, while a cozy armchair and side table complete the space, enhancing the serene ambiance.

4.85 out of 5 average rating, 151 reviews

Direct Waterfront "The Lily Pad" Walk 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. We are pet friendly! Pet fee is $150 for the first dog, $100 for the second dog.

4.98 out of 5 average rating, 264 reviews

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.

Apartment in Dunedin

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

Superhost

The modern kitchen features sleek white cabinetry and a tiled backsplash. An island bar with three chrome stools is positioned in front of a cooktop. Stainless steel appliances, including a refrigerator and a microwave, are visible, along with various kitchen essentials.