Cottage holiday rentals in Safety Harbor

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.

Cooper Cottage: Cozy, Convenient and Comfortable

Cooper Cottage is for cyclists, boaters, beach goers or those who just want to relax! The Cottage is the front half of a duplex in downtown Tarpon with all the amenities including bikes and beach gear! Walk/bike to Restaurants, Churches, Museums and Parks in under 12 minutes or drive to Fred Howard Beach or Sunset Beach in 7 minutes! Due to allergies of visiting family & friends we do NOT ALLOW PETS OR COMPANION ANIMALS, so you can rest assured that animal allergens will NOT be an issue.

Walkable, fun, local Dunedin experience

Stay in this charming 1920s cottage, where you can walk to local restaurants, breweries, and shops, or take a short walk to the marina for a sunset. Perfectly located in the heart of Dunedin, this home makes it easy to explore the area on foot. Spend your days enjoying nearby beaches, biking the Pinellas Trail, or catching a game at TD Ballpark to watch the Toronto Blue Jays. After a day of beach fun, baseball, or exploring, then enjoy an easy walk for dinner, drinks, or live music downtown.

Charming Blue Bungalow With Amazing Yard

Don't miss a stay at the Blue Bungalow while enjoying the historic and beachy town of Tarpon Springs. This spacious 2-bedroom 1 bathroom home built in 1936 has been tastefully updated but still has much of it's original charm. Then there's the best backyard with a grill, dining area, a fire pit, cornhole court, and a spacious deck. The home is located minutes from several beaches, a dog park, the Pinellas Trail and Greek town. Restaurants, breweries and fun community events are abundant.

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. Dogs okay, sorry no cats, pet fee $50.

Cozy Cottage for Lovers

Relax, reconnect and revitalize in this private, intimate cottage that has everything you need to leave the hustle and bustle behind. Surrounded by lush tropical vegetation in the shade of giant live oaks and located in the Gulfport Arts District, you're a short walk or bike ride from excellent urban parks, restaurants, live music, fashion and art boutiques, dancing at the Gulfport Casino, community theater, and a beautiful beach that looks out over sailboats moored in Boca Ciega Bay.

Bright, Clean and Cozy Coastal Home in Ozona

Discover Old Florida Charm with Modern Luxury in Ozona. This newly renovated 2021 “Old Florida” fishing home blends turn-of-the-century charm with bright, contemporary interiors for a coastal escape. Walk to top restaurants, pubs, and the Pinellas Trail; stroll or bike to Honeymoon Island, and a short drive to Clearwater Beach. Sleeps 6–7 in stylish, relaxed spaces. Boat trailer-friendly, golf-cart neighborhood, and easy access to boat/kayak rentals. Unwind, explore, and reconnect.

Cozy up in a French Country nest NEAR EVERYTHING

Very private, romantic and Stylish Apt w/free WiFi & Parking in a very walk/run/bike/golf carting friendly area. PERFECT LOCATION in the heart of everything! 10 mins away from Clearwater Beach, HONEYMOON & CALADESI ISLANDS, 10 mins walk from Downtown Dunedin with its Unique Restaurants, Boutiques & Breweries & 7mins to Blue Jay Stadium. Pinellas Trail is across the street from the apt and only 2 blocks down from the waterside! It's a perfect central place to cozy up away from home!

Walk Downtown and to Waterfront, Mins to Beaches

Just steps to Main Street Dunedin and minutes to Honeymoon Island and Clearwater beach, this stylish upstairs 2-bedroom cottage blends modern coastal comfort with beautiful design. Enjoy gorgeous tropical murals, treetop views, two king beds, a sleeper sectional, and a fully stocked stay. Walk to dining, shops, breweries, and Dunedin’s stunning waterfront sunsets, then drive minutes to the beaches. Pet-friendly with every detail beautifully done—reserve the Barefoot Parrot today.

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.

Lemon Cottage Steps from Beach

1925 beach cottage with king size bed, new kitchen with granite countertops LG stainless steel double over, just 130 steps to the sand with no streets to cross. Sofa bed in living room total 2 sleeping areas. Great location with Frenchy s Rockaway Grill and Crabby s just 2 blocks away and Pier 60 5 blocks walk Enjoy a commercial size hot tub right out your back door with large wood party deck tin roof gazebo or private hot tub in Balinese style Cedarwood Hut

Luxury Beach Bungalow | Walk to Dining & Sunset

Welcome to Mango! Nestled in the heart of Indian Rocks Beach. IRB is a hidden gem radiating a whimsical, small-town charm that evokes nostalgic memories of carefree childhood summers by the shore. Just ✌🏽 blocks away, the Gulf beckons, offering pristine fluffy sand and unforgettable sunsets. As the sister cottage of Coco, Mango invites you to immerse yourself in the laid-back beachy vibes of IRB. Your perfect beach getaway awaits! 🥭