Cottage holiday rentals in Pinellas County

Walk to beach shops food drinks “The Cottage”

Island Rum Suites has another cozy little cottage on the list of awesome places to stay near Indian Rocks Beach only 1/2 mile away! Location is everything and this is it! 25 miles from TIA, and all major attractions in Tampa. You will be in walking distance to the beach (IRB), beautiful sunsets, nature parks, nature trails, bike trails, marina, boat launch, shopping, sports bars, restaurants, pizza and ice cream! There is even a water park less than 1/2 mile away! fall special stay 2 get 1 free

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...!

Walk to Downtown and Waterfront - Private Yard

Bright and beachy with stylish modern décor and an open floor plan. Concrete construction, a private yard, and a gas grill makes this cottage feel like your personal oasis. Steps from Main Street Dunedin and a short walk to the water. Enjoy gorgeous sunsets and easy access to restaurants, breweries, shops, and live music. A quick drive to award-winning beaches like Honeymoon Island and Clearwater Beach. The perfect getaway in delightful Dunedin—come be our guest at the Barefoot Parrot Cottages.

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.

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.

Mermaid Cottage

Located in a three unit 'Olde Florida Style Complex' and just 45 steps to Clearwater Beach! The Mermaid Cottage is located on the 1st floor at the back of the complex. This Florida style unit is adorned wood floors and charming island decor. Open to an outdoor patio with furniture. The cottage has two bedrooms, two full baths and an outdoor shower! Living room has a queen pull-out bed. The patio area is completely fenced for private use. Nice, park like charcoal grill.

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.

Remodeled Beach Cottage | Walk to Dining & Sand

Sandy Feet Cottage is a beautifully remodeled beach retreat just 2 minutes from the sand in Indian Rocks Beach, Florida. Enjoy an open layout, all-new furniture, a spa-style bathroom, and a private backyard with hammocks, fire pit, and patio seating. Walk to local restaurants, beach bars, and shops. Perfect for families, couples, or friends seeking a stylish, relaxing stay on Florida’s Gulf Coast!

𖤓Updated Stilt home: just steps to the beach!𖤓

Experience a stylish and relaxing beach vacation at our vacation retreat! We are a very popular spot for Honeymooners and anniversaries! As a 4-year Superhost, we offer a charmingly renovated home just steps away from the beach and local restaurants. Explore Indian Rocks Beach with our provided bikes and unwind in the bubbly spa. Escape the everyday and find paradise here! BTR #2292