Cottage holiday rentals in Pinellas County

2 bed/1 bath Hummingbird Beach Cottage (4 beds)

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.

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 4 get 1 free

Cooper Cottage: Cozy, Convenient and Comfortable

Cooper Cottage is for cyclists, boaters, beach goers or those who just want to relax! The Cottage is the front half of a duplex in downtown Tarpon with all the amenities including bikes and beach gear! Walk/bike to Restaurants, Churches, Museums and Parks in under 12 minutes or drive to Fred Howard Beach or Sunset Beach in 7 minutes! Due to allergies of visiting family & friends we do NOT ALLOW PETS OR COMPANION ANIMALS, so you can rest assured that animal allergens will NOT be an issue.

Modern Coastal Hideaway –Patio & Hammock by Beach.

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!

Flipper's @ Mad Beach Cottage

Flipper's at Mad beach is a few steps away from the sugary sands of Madeira Beach, and close by the famous John's Pass Village & Boardwark where shopping and entertainment is always great. Completely renovated with light porcelain tile, nice furniture, queen bed with memory Thempur-Pedic mattress, exquisite modern shower, tall kitchen cabinets with plenty of storage. Huge private paved fenced backyard with gazebo, great for entertainment and outdoor grilling. You will love the beach decor.

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.

Luxury Beach Bungalow | Walk to Dining & Sunset

Escape to paradise at Sunshine Escapes IRB! Welcome to Mango, 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, Mango invites you to immerse yourself in the laid-back beachy vibes of IRB. Your perfect beach getaway awaits!

Adorable Villa 1 min to Downtown Dunedin

Welcome to our 1/1 cottage-style villa, which is minutes from Downtown Dunedin. Only a short walk to Main Street and a 12 min drive to Honeymoon/Caladesi Island! Walk to the Pinellas Trail, breweries, eateries, waterfront marina, and Blue Jay baseball stadium. Enjoy award-winning cuisine, live entertainment, and breathtaking sunsets before returning to the peace and quiet of your own private area. Dunedin is a gulf cart friend city with local rental available to cruise around town.

Walk Downtown and to Waterfront, Mins to Beaches

Steps to Main Street ! Experience modern coastal luxury in this stylish, spacious upstairs 2-bedroom cottage. Professionally designed and fully stocked. Walk to Main Street Dunedin or take the short stroll to stunning sunsets at the waterfront. Quick drive to award winning beaches--Honeymoon Island & Clearwater Beach. Walk to restaurants, shops, & breweries. Pet-friendly w/ 2 king beds, a sleeper sectional, & lovely treetop views. Treat yourself today to this Dunedin favorite !

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.

Ground-Floor Beachfront | Walk-Out to the Sand

Walk straight from your door onto the sand. This rare ground-floor, direct beachfront one-bedroom cottage sits right on the Gulf of Mexico with unobstructed water views and effortless beach access — no stairs, no elevators, no roads. Enjoy your private beachfront patio, a cozy and newly remodeled interior, and your own stretch of sand with lounge chairs just steps away. Perfect for couples or longer stays looking for a relaxed, front-row beach experience in Indian Shores.

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.