Cottage holiday rentals in Tampa Bay

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.

1930s Cottage + Pool 12 miles to Beach

Located in the heart of historic Palmetto FL, you will find this adorable cottage. This home has 2 bedrooms & 1 bath in the main home with a pull out sofa, as well as, a pool house with a full bath & daybed. You will love the southern charm of this home while relaxing by the pool or having morning coffee on the front porch. There are many restaurants & shops w/in walking distance as well as local parks & preserves. If you love the beach, this home is just a short drive to FL's beautiful beaches.

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 terrific location. Walk to restaurants, breweries, shops, and live music. Stroll to Dunedin's stunning 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!

Pass-a-Grille Historic Cottage Unit 1

PASS-A-GRILLE HISTORIC COTTAGE UNIT 1 A fully renovated historic beach cottage located in beautiful Pass a Grille, Florida. Steps from the Gulf of Mexico and Boca Ciega Bay. This is a duplex; Unit 1 - 1 bedroom/1 bath. Household linens, towels, cookware & dishes provided. Appliances include; dishwasher, washer/dryer, flat screen TVs and wi-fi. Vintage-style tiled bathroom and shower. High end window shades on all windows. Front patio area w/ BBQ grill. Private parking for 1vehicle on premises.

Beach Cottage | Walk to Gulf, Dining & Bikes.

Sandy Toes Cottage is a fully renovated beach home just 2 minutes from Indian Rocks Beach. Enjoy modern furnishings, a bright kitchen, spa-style bath, free Wi-Fi, and a backyard with fire pit and hammock! Walk to local dining and shops, your perfect coastal getaway 🌴 *NEW AIRBNB PRICING UPDATE** Starting mid-October 2025, Airbnb will show all-in pricing—including an increase fee of 15.5% Airbnb service fee (charged directly by Airbnb to me the host), cleaning fees, and pet fees if applicable.

Family Friendly Beach Cottage in Madeira Beach, FL

Mad Beach Cottage is a single family home in the Surf Song Resort on Madeira Beach 60 flip-flop steps to SAND! No streets, boardwalks or stairs! You'll enjoy a heated pool, 3 Weber grills, shuffleboard and sundeck with lounge chairs for gazing at spectacular sunsets every night. It's located across from famous John's Pass Fishing Village Boardwalk for shopping, dining, ice cream, coffee, live music, brew pubs, dolphin/fishing/sunset/pirate boat cruises, wave runner/kayak rentals. 5* LOCATION!

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 ..

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.

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.

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.