Cottage holiday rentals in Hillsborough County

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...!

Historic Heights Hideaway • Early Check-in

A perfect balance between suburban serenity & urban convenience in this historic Tampa neighborhood. Central air, Roku, strong Wi-Fi, coffee, tea, snacks. Easy self-check-in. The ideal home base for your Tampa adventures. Walk to Hillsborough River, Garden Center, & Florida Ave hotspots. 5 min to Zoo, 10 min drive to Amalie Arena, Busch Gardens, Ybor City, Ray Jay Stadium, Florida State Fairgrounds/Amphitheater, Riverwalk & Airport; 35 min to St Pete & nations best beaches, 70 min to Disney.

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.

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. Dog 30lb weight limit, no cats, fee $50.

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.

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.

Walk Downtown and Waterfront, Designer Getaway

Experience modern coastal luxury in this stylish, spacious upstairs 2-bedroom cottage. Steps from Main Street Dunedin. Walk to restaurants, shops, and breweries or take a short stroll to gorgeous sunsets at the waterfront. A quick drive to beaches such as Honeymoon Island and Clearwater Beach. This pet-friendly getaway boasts two king beds, a sleeper sectional, and serene treetop views. Your sunny, coastal escape awaits—book your getaway at the Barefoot Parrot today!

Hidden Oasis #1, just a few mins to the beach

Walk into this quaint cottage and step into relaxation! You'll find a homey space with shared access to a large courtyard featuring a propane grill, smoker, and outdoor tables and seating. Enjoy the peaceful surroundings, spend time with family and friends, and forget your worries in this Hidden Oasis! Working from paradise? Fast wifi & 2 desks w/ office chairs in the bonus room make it easy to meet your deadlines with time for a walk on the beach.