Cottage holiday rentals in St. Pete Beach

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...!

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.

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 ..

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 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. Loaded for kids, pets and beach days. Treat yourself and book this Dunedin favorite today!

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.

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.

Ground-floor, direct beachfront 1BR | on the Gulf

This rare ground-floor, direct beachfront one-bedroom sits right on the Gulf of Mexico with unobstructed water views and effortless beach access Step out the door and into a life where the Gulf of Mexico is your backyard — no elevator, no lobby, just you, the sand, and thirty seconds between your pillow and the water. Enjoy your private beachfront patio, a cozy recently remodeled interior, and your own stretch of sand with lounge chairs and front row views right outside your door.

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.

Steps2Beach-Walk everywhere-Bikes & gear Included

Welcome to Paradise by the Sea 🌴 Your comfortable Florida beach cottage just steps from the sand in the heart of Pass-a-Grille. This charming island home offers the relaxed, old-Florida vibe guests love — with the convenience of being able to walk everywhere and rarely move the car. The beach is a quick, easy walk, and restaurants, coffee shops, ice cream, and the local market are all nearby. Guests often say it feels like settling into their home by the beach.

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

Island Time Stay: Happy Hour

Check out our large studio cottage located on Gulf Blvd in Treasure Island, FL. It is located less than 300 steps from the beautiful sand of Treasure Island Beach and 5 blocks from the world famous boardwalk, shopping and restaurants of John’s Pass Village in Madeira Beach. We have a crosswalk conveniently located in front of the property. You can stop traffic with the push of a button to safely walk across the street toward the boardwalk.