Cottage holiday rentals in Hillsborough County

Little piece of Heaven 2

This 2 bedroom cozy cottage is nestled on an almost 1.5 acres piece of property on a serene spring fed lake. The cottage is a laid back coastal feel with all of the amenities of home & tucked away in between the hustle and bustle of Tampa without ever knowing it. Easy access to the Veteran's Expressway that will take you to anywhere from Clearwater and our pristine beaches to Downtown St. Pete. I275 will take you to Downtown Tampa, Busch Gardens and Adventure Island. I-4 will take you to Orlando

The Pelicans Roost / Gulfport

The Pelicans Roost is a remodeled home, with a new fully stocked kitchen with all your cooking and entertaining needs. All new furnishings, a screened in back porch and a patio with an outside table and grill. The yard is completely fenced and lined with tropical plants and trees for your privacy. This spacious and comfortable home is clean and in a quiet neighborhood just 5 blocks from all that downtown Gulfport has to offer- the Marina,Beach,Restaurants, Shops, Fishing, Galleries and more...!

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.

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 ..

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.

Wonderful 2-Br, 2 Bath Cottage near the river.

Welcome to my little cottage in the city. The house was built in 1926 but has been fully remodeled with modern style, while keeping the charm of an older home. Even though it's close to everything Tampa has to offer, it still has the feeling of that little, quiet neighborhood near the river. This is my get away home. I love the front porch to sit on with a cold beverage and watch neighbors stroll by walking their dogs. The river park is very close by which is a nice walk from the cottage.

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.

Gasparilla Bayshore Good Vibes cottage

Great location for this cottage one block from Infamous Bayshore Blvd. Smart Tv's and quiet back porch with fire pit makes this location perfect for vacationers. Short walk to Bayshore blvd with scenic views of downtown Tampa and beautiful Tampa Bay water ways. Come and enjoy biking, running, skating or just walking along this 4 miles continuous waterfront walkway. You will have views of Tampa Bay on one side and views of multi-million dollar homes on the other during your stroll.

Walk to Downtown and Waterfront - Private Yard

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

Adorable Cottage, Pet friendly, near beach & DT

The Cottage is a beautiful, comfy, clean, peaceful home where you will feel just at home, in the hearth of St Pete. It is in a great location, safe & quiet neighborhood, easy-to-access, just a short drive or bike ride away (5-10 minutes) to many good restaurants, grocery stores, museums, library, coffee place, breweries, hospitals, bars and night clubs in downtown & sandy white beaches. Jumped in the sun runner or public transport to downtown or beaches. Perfect for long stay.

Luxury Beach Cottage | Walk to Dining & Sunset

Welcome to Coco! Nestled in the heart of Indian Rocks Beach. IRB is a hidden gem that radiates a whimsical, small-town charm, evoking nostalgic memories of carefree childhood summers by the shore—the Gulf beckons just two blocks away, offering pristine, fluffy sands and unforgettable sunsets. As the sister cottage of Mango, Coco invites you to immerse yourself in the laid-back beachy vibes of IRB. Your perfect getaway awaits! 🥥