Cottage holiday rentals in Tampa

4.99 out of 5 average rating, 379 reviews

A cozy living area showcases a modular blue sofa, adorned with soft pillows and a warm throw. A light wooden coffee table rests in the center, complemented by decorative items. Natural light enters through a window, creating a bright and welcoming atmosphere.

Cottage in Dunedin

Walk to Downtown and Waterfront - Private Yard

Steps to Main Street and minutes to beaches, yet tucked away on a quaint downtown street. Private yard with grill in a top prime location. Walk to restaurants, breweries, shops, and live music. Walk to Dunedin's stunning 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 leather couch that sleeps 2 more. Loaded for kids, pets and beach days. Treat yourself and book this Dunedin favorite today!

4.95 out of 5 average rating, 200 reviews

A charming cottage exterior is presented, featuring a green front door and a large screened porch. Lush landscaping, including diverse plants and flowers, frames the entrance. Spanish moss hangs from the trees, creating a tranquil outdoor atmosphere under a partly cloudy sky.

Cottage in Lutz

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

5 out of 5 average rating, 111 reviews

The three-story guesthouse features a blend of wood siding and large windows, surrounded by lush greenery. A spacious balcony is present on the second level, offering a shaded outdoor space. Tropical plants and trees frame the entrance, enhancing the serene ambiance of the property.

Cottage in Seminole

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 ..

The cottage features a welcoming front porch adorned with vibrant flowers and lush greenery. A stone pathway leads to the entrance, framed by well-maintained landscaping. Large windows allow ample natural light, enhancing the charm of the remodeled exterior.

4.96 out of 5 average rating, 166 reviews

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.

A cozy living area features a yellow sofa and two accent chairs flanking a wooden coffee table. A TV displays a calming fireplace scene, with decorative wall art and patterned accents adding character. Natural light filters through windows covered by white blinds.

4.91 out of 5 average rating, 101 reviews

River adjacent, Quiet neighborhood, King bed

Small and cozy, this Seminole Heights home sits among other adorable homes in a stellar neighborhood, just a block from the Hillsborough River, and is within walking distance to great places to eat and drink. The Seminole Heights part of Tampa is wildly convenient to all of this city’s must-see spots; downtown, bayshore boulevard, Hyde Park Village, Busch Gardens, The Tampa Riverwalk and more. Whether or not you book with me, I’m still thrilled to help you find things to do while here.

Two wooden Adirondack chairs are positioned on a deck overlooking a serene lake. A floating dock extends into the water, featuring two red lounge cushions. The clear blue sky enhances the tranquil atmosphere, with greenery visible along the shoreline.

4.98 out of 5 average rating, 265 reviews

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.

4.98 out of 5 average rating, 120 reviews

Cottage in Gulfport

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.

Cottage in Bayshore Beautiful

A comfortable seating area features two light-colored sofas with throw pillows, arranged around a rustic wooden coffee table. A decorative screen provides partial division from other spaces, and a textured rug is laid beneath the furniture, enhancing the warm ambiance of the room.

4.79 out of 5 average rating, 203 reviews

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.

Cottage in Clearwater Beach

4.76 out of 5 average rating, 239 reviews

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

Cottage in Indian Rocks Beach

4.98 out of 5 average rating, 164 reviews

Walk to Beach | Bikes, Hammocks & Fire Pit!

Sandy Feet Cottage is a newly remodeled beach retreat just 2 minutes from Indian Rocks Beach. Enjoy an open layout, new furnishings, a spa-style bath, and a private yard with fire pit, hammock, and patio. Walk to dining, bars, and shops—your stylish Gulf Coast escape. ***NEW AIRBNB PRICING UPDATE*** Starting mid-October 2025, Airbnb will display all-in pricing—including a 15.5% Airbnb service fee (charged directly by Airbnb to the host), plus cleaning fee

Cottage in Indian Rocks Beach

A vibrant tropical mural featuring large flowers adds a pop of color to the room, while a cozy seating area includes a sofa adorned with decorative pillows. A small dining table with tropical-patterned chairs provides a space for meals. The outdoor area showcases a lit pool, creating a serene evening ambiance.

4.99 out of 5 average rating, 214 reviews

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! 🥥

A comfortable living area is highlighted by a light-colored sofa and armchair, paired with decorative cushions. A ceiling fan and large windows allow natural light to fill the space. A coffee table sits in front of the sofa, adorned with a small plant and decorative items.