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.

Cooper Cabin: Cute, Adorable, Standalone Studio

Cooper Cabin is a super cute and sparkling clean stand alone studio with a full eat-in kitchen and bath. 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! Located within walking distance of all things Tarpon Springs and just a short 7 min drive to Fred Howard Beach, Cooper Cabin is decorated with fun decor and a relaxing front porch balcony with bistro set. Bikes and beach gear provided!

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

Vintage Florida Beach Cottage B

Just a short walk to the beach makes this a great beach getaway for couples or families. On your way you can stop at the Kooky Koconut for lunch, an awesome milkshake or a variety of snacks. With a totally new renovation in 2019, this unit is in updated, very clean and worry free condition. This cottage is located in a quiet residential neighborhood and a great place to relax. Common laundry on shared screened porch. Dogs allowed (extra $45 cleaning). Easy refund policy. Level 2 EV charger

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 and escape to the Barefoot Parrot Cottages.

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.

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.

#5 Beach Front Cottage w view- Indian Rocks Beach

LOCATION, location! Closest beach cottage to the water at Indian Rocks beach, view of the water from your porch & easy access to grass for pets. Perfect couples getaway. Enjoy some of Florida’s best beaches. Minimalistic living. *Kitchen recently updated* Shared gazebo & picnic table next door. Shared Washer & dryer takes quarters. Walking distance to local restaurants and bars. Minutes away from Clearwater beach, tourist attractions and mini golf. Property located next 2 public access.

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!

Cozy up in a French Country nest NEAR EVERYTHING

Very private, romantic and Stylish Apt w/free WiFi & Parking in a very walk/run/bike/golf carting friendly area. PERFECT LOCATION in the heart of everything! 10 mins away from Clearwater Beach, HONEYMOON & CALADESI ISLANDS, 10 mins walk from Downtown Dunedin with its Unique Restaurants, Boutiques & Breweries & 7mins to Blue Jay Stadium. Pinellas Trail is across the street from the apt and only 2 blocks down from the waterside! It's a perfect central place to cozy up away from home!

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.