Cottage vacation rentals in Longboat Key

Ty's Canal Cottage

"Welcome to Ty's Cottage in Historic Cortez Fishing Village, which is one of Florida's last working fishing villages. Located within walking distance to well known Starfish, Swordfish, Tide Tables Restaurants and Tyler's Homemade ice cream. A short 1.3 mile walk to Anna Maria Island with gorgeous beaches. Short driving distance to beautiful golf courses such as IMG Academy Golf and Manatee County Golf Course. Local fishing charters for outstanding fishing. Outdoor sitting area on canal."

Luxury Beach Bungalow | Walk to Dining & Sunset

Escape to paradise at Sunshine Escapes! Welcome to #CocoPalmsIRB, nestled in the heart of Indian Rocks Beach. IRB is a hidden gem that radiates a whimsical, small-town charm, evoking nostalgic memories of carefree childhood summers by the shore. The Gulf of Mexico beckons just two blocks away, offering pristine fluffy sands and unforgettable sunsets. As the sister cottage of Mango, #CocoPalmsIRB invites you to immerse yourself in the laid-back beachy vibes of IRB. Your perfect getaway awaits!

The Mermaid: Heated Pool, 4 Houses to Beach

This apartment is a first-floor unit with an open floor plan that sleeps 2 with a maximum of 4 people. The bed makeup in this rental is a king bed in the master and a queen size sofa sleeper. This rental is great for longer stays or guests who like to cook since you have a full kitchen and all the items to cook any meal. There is a washer/dryer in the apartment. Beach chairs and umbrellas are supplied to you at no charge. This is a duplex and has another 1 bedroom 1 bath apartment above you.

Private Heated Pool Casita Near Downtown & Beaches

Built in 1925, Our Casaita Verde 2 Bedroom, 1 Bath home still retains its vintage charm but with modern touches. Enjoy watching the 55 inch flat screen TV with HD cable and stay in touch with the world with WI-FI internet. Lounge by the private pool or take in the beautiful evenings on the deck with your favorite beverage. Pet Friendly! Conveniently located near Downtown Sarasota on Bahia Vista with easy drive to Lido Key, our World Famous Siesta Key or I-75 for longer adventures.

*GROUND FLOOR DIRECT BEACHFRONT COTTAGE!!*

Step out the door and into the sand! Ground floor DIRECT beachfront one- bedroom/one-bath cottage nestled in the sand directly on the Gulf of Mexico with awesome amenities for the perfect Gulf Beach getaway! Enjoy a cozy bedroom, living/dining area, fully-equipped kitchen, beachfront patio and private beach area with lounge chairs. Conveniently located near a trolley stop for easy access to local restaurants, shops, and attractions. Book now for an unforgettable beach vacation!l

Walk to Downtown and Waterfront - Private Yard

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

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, 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. Pet fee $50.

Darling Old Florida Beach Cottage Steps From Gulf!

Completely Remodeled! Welcome to Cottage By The Sea, a newly remodeled charming retreat just steps from the pristine Gulf of Mexico beaches on Anna Maria Island, nestled in the serene area of Bradenton Beach. This delightful getaway blends the nostalgic charm of one of the only "Old Florida" cottages left, with modern updates, featuring bright and sunny décor. It's time to leave your worries behind and embrace the tranquility of paradise!

Staycation Sanctuary

Our property is clean and welcoming. You can enjoy a relaxing, warm and peaceful getaway from the rest of the world just steps to the beach. This is the perfect "Old Florida-style" location to experience the comfort and hospitality you so deserve! Grab your bathing suit/flip flops and enjoy tranquillity of beach life, sunsets and lazy days of fishing and bird/dolphin/manatee watching and gathering sea shells-- all only 2 blocks away!