
Cottage holiday rentals in Hillsborough County
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Top-rated cottage rentals in Hillsborough County
Guests agree: these cottages are highly rated for location, cleanliness and more.

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!

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...!

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.

Lovely Loft Close to Everything in Tampa
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. Quick 10 min drive to TPA Airport, Busch Gardens, Fla Amphitheater, Raymond James Stadium, Aquarium, Cruise Port, USF, UT, Ybor City, Armature Works & Downtown. 35 min to countrys best beaches, 70 min to Orlando. Plus great restaurants & breweries within walking distance.

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.

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.

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.

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.

Walk Downtown and Waterfront, Mins to Beaches
Experience modern coastal luxury in this stylish, spacious upstairs 2-bedroom cottage with designer decor. Steps from Main Street Dunedin, short walk 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, & serene treetop views. Treat yourself! Book your getaway at the Barefoot Parrot by Lucky Guest.

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 cottage rentals in Hillsborough County
Cottage rentals with a hot tub

Turtle Cottage - Anna Maria Island

Pink Gulfside Cottage, Steps to Beach, Pets OK

Beachy Keen Cottage A only steps to the Beach

Sunny - Key West Vibe Cottage - Pool - Walkable

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
Pet-friendly cottage rentals

BEACH! Sunny Escape! Steps 2 Famous Beach w/2 Bike

Vintage Florida Beach Cottage B

Cozy up in a French Country nest NEAR EVERYTHING

Beachy Paradise

Gulfport Art District - One Block From Beach!

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

Old Florida Paradise Secret Lair Cottage

Cozy South Tampa Cottage Near Macdill AFB!
Private cottage rentals

Coral Cottage pool/firepit 2 bedr 2 bth sleeps 6

Close to Downtown/Sponge Docks/Beaches/Trails

Central Quiet Bright Cottage, near Skyway Bridge.

Safety Harbor Cottage

Alafia River Cottage

🏡Cottage near Clearwater & Belleair Beaches🏖🌴☀️

Cozy Cottage - Nature Lovers Dream - Horses - Lake

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