Cottage holiday rentals in St. Petersburg

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.

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.

Artsy guest house; near downtown w/ private patio

This uniquely decorated guest house is a private oasis with a lovely, private patio. The house is decorated with Latin American art from the owner's collection & travels. Only 11 blocks to downtown and very close to grocery stores, art galleries and all the night light life St. Pete offers. The home has a full kitchen and a very comfortable bedroom for one or two people. A perfect location for those that want to experience a comfortable and relaxing place. Only 12 block walk to Tropicana.

Luxury Beach Bungalow | Walk to Dining & Sunset

Escape to paradise at Sunshine Escapes! Welcome to #MangoIRB, 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 of Mexico beckons, offering pristine fluffy sand and unforgettable sunsets. As the sister cottage of Coco, #MangoIRB invites you to immerse yourself in the laid-back beachy vibes of IRB. Your perfect beach getaway awaits!

Walk to Downtown and Waterfront - Private Yard

Steps to Main Street, yet tucked away ! Private yard with grill in a prime location. Short walk to Dunedin's waterfront and minutes to beaches. Stroll to Dunedin's restaurants, breweries, shops, and live music. Enjoy stunning sunsets or drive minutes to award-winning beaches such as Honeymoon Island and Clearwater Beach. Sleeps 6. Enjoy beautiful décor and two king suites. Loaded with beach & kids’ gear for easy escape. Treat yourself and book this Dunedin favorite by Lucky Guest today.

Beautiful Beachfront Cottage on the Water

Renovated, romantic 1937 beach front cottage. Last of its kind in the quiet family setting of Indian Shores Florida, halfway between Clearwater Beach and Treasure Island/John's Pass. Truly an "Old Florida" experience with original pine floors, Florida room and covered porches, as well as updated kitchen and bathroom. This house, uniquely built near ground level, allows it to be waterfront on the beach while shaded by huge pine trees. You won't find a more tranquil setting on the beach.

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.

New Beach Retreat– Hammock, Patio & Steps to Sand.

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 and pet fees if applicable.!

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.

Centrally Located - Early Check In

Welcome to your charming retreat in the heart of Tampa’s historic district! Minutes from I-275 & I-4, our cozy carriage house offers the perfect blend of convenience and comfort in this walkable neighborhood. Quick 10 min drive to TPA Airport, Busch Gardens, Fla Amphitheater, Raymond James Stadium, Aquarium, Cruise Port, USF, UT, Ybor City, Moffit & Downtown. 35 min to country's best beaches, 70 min to Orlando. Plus, great restaurants & breweries within walking distance.

Gulfport Art District - One Block From Beach!

Welcome to Uncle Finley's! Situated in the heart of Gulfport's Art and Waterfront District, This cottage listing is for unit A of the duplex. Step outside and walk to Gulfport Beach only one short block away, experience the highly-rated restaurants and shops, or browse local arts and crafts during the weekly Tuesday Morning Market during your stay. Want to experience more of Tampa Bay? Downtown St. Pete, St. Pete Beach, and I-275 access are only ten minutes away.