Cottage vacation rentals in Clearwater

Walk to Downtown and Waterfront - Private Yard

Steps to Main Street and minutes to beaches, yet tucked away on a quaint prime downtown street. Private yard with grill in fantastic location. Walk to restaurants, breweries, shops, and live music. Stroll to Dunedin's gorgeous sunsets or drive minutes to award-winning beaches such as Honeymoon & Caladesi Island & Clearwater Beach. Sleeps 6. Two king bed suites and a luxury leather couch that sleeps 2 more. Loaded for kids, pets and beach days. Treat yourself and book this Dunedin favorite today!

Entire home and yard 2 /1 with two sleep sofas

This lovely beach bungalow has all the updates, including a walk-in shower, on-demand hot water, quartz and stainless steel appliances. Comfortable, clean, and cozy. Two queen beds and two full sofa sleepers! The beach is just a short walk across Gulf Blvd and views of million-dollar homes, piers, and sunsets to die for! Great shell collecting. Fantastic location with lots to walk to. Groceries, Dollar store, bars, restaurants, and coffee are all walkable. Just under two miles to John's Pass.

Beautiful Beachfront Cottage on the Water

NO BOOKING FEE! Renovated, romantic 1937 beach front cottage. Last of its kind in the quiet family setting of Indian Shores Florida, halfway between Clearwater Beach and Treasure Island/John's Pass. Truly an "Old Florida" experience with original pine floors, Florida room and covered porches with updated kitchen and bathroom. This house, uniquely built near ground level, allows it to be waterfront on the beach while shaded by huge pine trees. You won't find a more tranquil setting on the beach.

Clearwater Cottage Short Drive to Beach & Dunedin!

Perfectly nestled between the quaint town of Dunedin & Clearwater. Just a short drive across the bridge & you’ll be Sinking your toes into the beautiful white sandy beaches of Honeymoon Island State Park or Clearwater Beach. Enjoy Honeymoon Island natural beauty or exciting tourist attractions of Clearwater beach! Take a cruise on the dinner boats to watch the beautiful sunset. Walk or rent a bike & explore the Pinellas trail. Kayak or jet ski the Gulf. Max 5 Adult guests with government ID.

Florida Guest House

Seminole Oaks House...Beautifully appointed new construction 2-story Guesthouse located in a very quiet setting 10 minutes from Indian Rocks Beach. Walking/biking distance from Walsingham Park and Lake and the Pinellas Trail. Enjoy your morning coffee or evening glass of wine on the balcony..or tree shaded rear Patio w/BBQ grill..Great location for exploring all Pinellas has to offer including the Beaches, Downtown St. Pete,and open air Markets..dedicated parking..very peaceful and private ..

Kooky Coconut Cottage, Indian Rocks Beach

Coconut Cottage only steps away from the beautiful beaches of Indian Rocks Beach. 2 bedroom,1 bath. The entire cottage has been renovated. Next door to the local famous Kooky Coconut Cafe. Perfect for couple, friends or small families. ONLY 3 GUESTS ALLOWED. NO sleeping on the sofa ALLOWED. If you bring more then 3 guests you will be charged $100.00 surcharge per night per extra guest. Due to cleaning restriction we DO NOT allow cooking with CURRY or FISH OIL in the cottage.

#5 Cottage on the beach-*Water View* -Indian Rocks

LOCATION, location! OLD SCHOOL BUNGALOW - Closest beach cottage to the water at Indian Rocks beach, view of the water from your porch & easy access to grass for pets. Perfect couples' getaway. Enjoy some of Florida’s best beaches. Minimalistic living. Shared gazebo right outside. Shared Washer & dryer takes quarters. WALKING DISTANCE to local restaurants and bars. Minutes away from Clearwater beach, tourist attractions and mini golf. Property located next to public access.

Charming Newly Reno 1 min to Downtown Dunedin

Welcome to our cottage-style home, which is minutes from Downtown Dunedin. Only a short walk to Main Street and a 12 min drive to Honeymoon/Caladesi Island! Walk to the Pinellas Trail, breweries, eateries, waterfront marina, and Blue Jay baseball stadium. Enjoy award-winning cuisine, live entertainment, and breathtaking sunsets before returning to the peace and quiet of your own private area. Dunedin is a gulf cart friend city with local rental available to cruise around town.

Mermaid Cottage

Located in a three unit 'Olde Florida Style Complex' and just 45 steps to Clearwater Beach! The Mermaid Cottage is located on the 1st floor at the back of the complex. This Florida style unit is adorned wood floors and charming island decor. Open to an outdoor patio with furniture. The cottage has two bedrooms, two full baths and an outdoor shower! Living room has a queen pull-out bed. The patio area is completely fenced for private use. Nice, park like charcoal grill.

Beach Cottage | Pool | Walk to Dining & Sunset

Welcome to Coco Cottage! Your coastal cottage retreat in Indian Rocks Beach cottage just a 3-minute walk from the Gulf! Spend your mornings on the sand, afternoons lounging in the heated saltwater pool, and evenings strolling to local coffee shops, restaurants & cocktails. Inside, enjoy a king bedroom, thoughtfully stocked kitchen and relaxed coastal style. Beach chairs, wagon, coolers & more are provided—so pack light and settle into the IRB lifestyle.

Bay Lake Cottage

You’ll have the Entire 500sq ft Cottage & private entry, deck/dock, all to yourself. Located on a 37-acre private ski lake. Key-pad entry, private parking. 1 king bed, 1 bath, queen sofa bed, washer/dryer, WiFi, smart TV’s, blackout curtains,shampoo,conditioner,hairdryer,WiFi. Fully stocked kitchen, smokeless grill, wine fridge upon request, k-cup/drip coffee machine. The lake has bass, we provide fishing poles/tackle box. Rentable Kayaks & Canoe.

Best Location! Walk to Dining, Trail & Stadium

Charming 1920s cottage in Dunedin just 3 blocks from the water and lively downtown! Walk 2 blocks to the Pinellas Trail, Fenway Hotel, and TD Ballpark. Enjoy a private outdoor retreat surrounded by lush greenery—perfect for morning coffee. Bright, inviting interiors with a sunny kitchen, spacious living area, and cozy beds make this the perfect getaway for beach days, biking, dining, and sunsets! Book early, dates fill fast!