
Cottage holiday rentals in Hillsborough County
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Top-rated cottage rentals in Hillsborough County
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Pass-a-Grille Historic Cottage Unit 1
PASS-A-GRILLE HISTORIC COTTAGE UNIT 1 A fully renovated historic beach cottage located in beautiful Pass a Grille, Florida. Steps from the Gulf of Mexico and Boca Ciega Bay. This is a duplex; Unit 1 - 1 bedroom/1 bath. Household linens, towels, cookware & dishes provided. Appliances include; dishwasher, washer/dryer, flat screen TVs and wi-fi. Vintage-style tiled bathroom and shower. High end window shades on all windows. Front patio area w/ BBQ grill. Private parking for 1vehicle on premises.

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!

Wonderful 2-Br, 2 Bath Cottage near the river.
Welcome to my little cottage in the city. The house was built in 1926 but has been fully remodeled with modern style, while keeping the charm of an older home. Even though it's close to everything Tampa has to offer, it still has the feeling of that little, quiet neighborhood near the river. This is my get away home. I love the front porch to sit on with a cold beverage and watch neighbors stroll by walking their dogs. The river park is very close by which is a nice walk from the cottage.

A little piece of Heaven
2 people max cozy cottage with all the amenities of home with a lakefront view. There's a firepit for those colder nights and kayaks & peddleboats for the more adventurous ones, or just sit back and take in some sun on our beautiful dock. Centrally located in between the Veterans Expressway and I 275, minutes from shopping, Lake Park, Adventure Island and Busch Gardens ...Lutz has something for everyone, don't let your friends and family stay in a hotel, we've got it all waiting right here!

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. Dogs okay, sorry no cats, pet 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.

Cool Breeze Cottage by the Bay in South Tampa
Great location for this cottage one block from Infamous Bayshore Blvd. Smart Tv's and quiet back porch with fire pit makes this location perfect for vacationers. Short walk to Bayshore blvd with scenic views of downtown Tampa and beautiful Tampa Bay water ways. Come and enjoy biking, running, skating or just walking along this 4 miles continuous waterfront walkway. You will have views of Tampa Bay on one side and views of multi-million dollar homes on the other during your stroll.

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 to Waterfront, Mins to Beaches
Experience modern coastal luxury in this stylish, spacious upstairs 2-bedroom cottage. Professionally designed and fully stocked. Steps from Main Street Dunedin, short stroll to gorgeous 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! Book your getaway at the Barefoot Parrot Cottages.

Serene Waterfront Cottage with Tranquil Setting
Bring your kayaks, paddle boards , and the whole family to this great place with lots of room for fun. There’s an outdoor fire pit, beach volleyball court, basketball hoop, ping-pong table, grill, swings, 2 hammocks, and lots more. Inside there’s a wood-burning fireplace, 2 large bathrooms, 3 bedrooms, separate master suite located upstairs with private bath, inside laundry room, separate dining area, spacious kitchen , and 2 large gathering areas.

Little Manatee River Cottage
This cottage is located on the Little Manatee River. Sun City Center 10 min Aquatic rentals walking distance. The cottage is updated. Abundant fishing charters, Little Harbor, manatee viewing center and Simmons Park all within minutes. Fully furnished, linens, kitchen utensils; bath towels; blankets pillows comfy furnishings. View sunsets out on the river, on the dock or at Little Harbor sipping your favorite drink.
Popular amenities for Hillsborough County cottage rentals
Cottage rentals with a hot tub

Harbor Oasis | Hot Tub | Private | Lush Backyard

Turtle Cottage - Anna Maria Island

Beachy Keen Cottage A only steps to the Beach

New Listing Hidden Gem 3 Bedroom Home

Sunset Beach cozy boutique cottage

Corner Cottage Sleeps 5, Steps to Beach, Pets OK.

Happy Camper Cottage | Cozy Oasis with Hot Tub

Family FUN~Pool, GameRoom+Bikes, Near Beach/Trail
Pet-friendly cottage rentals

Cottage by the Coast 2 bd - Pet Friendly

The Pelicans Roost / Gulfport

Vintage Florida Beach Cottage B

Beachy Paradise

Gulfport Art District - One Block From Beach!

Charming Blue Bungalow With Amazing Yard

ALL NEW! Coral Sands II ~Coastal Modern 2/2 IRB

Old Florida Paradise Secret Lair Cottage
Private cottage rentals

Tranquil Guesthouse Hideaway (Near MacDill AFB)

"Sweet Harbor Cottage" Walk to Downtown

6B Newly Renovated Casita at Coastal Cottages!

Central Quiet Bright Cottage, near Skyway Bridge.

Safety Harbor Cottage

Alafia River Cottage

Kamp Komfort Historic Family Beach House

Carriage House 1893
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- Anna Maria Island
- John's Pass
- Busch Gardens Tampa Bay
- Raymond James Stadium
- Dunedin Beach
- Weeki Wachee Springs
- Reunion Resort Golf Courses - Palmer & Watson
- Coquina Beach
- Lido Key Beach
- Vinoy Park
- Cortez Beach
- Anna Maria Public Beach
- Amalie Arena
- Island H2O Water Park
- Bean Point Beach
- Jannus Live
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club
- ZooTampa at Lowry Park
- Gulfport Beach Recreation Area
- North Beach
- River Strand Golf and Country Club
- Tampa Palms Golf & Country Club
- Bok Tower Gardens
- Things to do Hillsborough County
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