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

Walk to beach shops food drinks “The Sweet”
Cozy, romantic, 1 king bed, super cute and super sweet! Just a short walk to beautiful Indian Rocks Beach, nature parks with trails, shopping, orange grove, and many restaurants and fun beach bars! Guests have private entrance, private full bath, kitchenette, sofa sleeper, large back yard with fire pit, bbq grill, beach chairs, wagon and cooler. Zoning permits 2 people per bed only and one on futon. All guests must be listed on the reservation. No Pets allowed. Florida State License # DWE6215889

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 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.

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.

Gasparilla Bayshore Good Vibes cottage
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.

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.

Trendy Seminole Heights Flamingo's
Beautiful completely remodeled house in the trendy Seminole heights Area, located minutes away from Ybor City, Downtown Tampa, Raymond James Stadium, Amalie Arena, Busch Gardens and Tampa Aquarium, It is about 15 minutes from Tampa Airport and a few blocks away from interstate 275, Easy access to Clearwater beach and St Pete Beach, The back yard has been accommodated to enjoy every minute of your stay.

𖤓Updated Stilt home: just steps to the beach!𖤓
Experience a stylish and relaxing beach vacation at our vacation retreat! We are a very popular spot for Honeymooners and anniversaries! As a 4-year Superhost, we offer a charmingly renovated home just steps away from the beach and local restaurants. Explore Indian Rocks Beach with our provided bikes and unwind in the bubbly spa. Escape the everyday and find paradise here! BTR #2292
Popular amenities for cottage rentals in Hillsborough County
Cottage rentals with a hot tub

Harbor Oasis | Hot Tub | Private | Lush Backyard

Turtle Cottage - Anna Maria Island

Sunset Beach; Oasis Stunning Views of Gulf

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

Cozy Cottage Near Beach | Hot Tub • Pet Friendly

Beachside Historic Cottage – Steps to Sand!
Pet-friendly cottage rentals

The Pelicans Roost / Gulfport

Vintage Florida Beach Cottage B

Luxury Beach Bungalow | Walk to Dining & Sunset

Beachy Paradise

Gulfport Art District - One Block From Beach!

Charming Blue Bungalow With Amazing Yard

Coral Sands II ~Seaside Coastal Modern 2/2

Old Florida Paradise Secret Lair Cottage
Private cottage rentals

Cottage by the Coast 2 bd - Pet Friendly

Close to Downtown/Sponge Docks/Beaches/Trails

Beautiful newly renovated beach cottage

6B Newly Renovated Casita at Coastal Cottages!

Safety Harbor Cottage

Alafia River Cottage

🏡Cottage near Clearwater & Belleair Beaches🏖🌴☀️

Tampa-Retreat I Homestead with 5th Gen Floridians
Destinations to explore
- Holiday home rentals Hillsborough County
- Serviced apartment rentals Hillsborough County
- Rentals with a washing machine and dryer Hillsborough County
- Rentals with a sauna Hillsborough County
- Smoking-friendly rentals Hillsborough County
- Rentals with a firepit Hillsborough County
- Apartment rentals Hillsborough County
- Tiny house rentals Hillsborough County
- Rentals with an EV charger Hillsborough County
- Luxury rentals Hillsborough County
- Boutique hotels Hillsborough County
- Resort rentals Hillsborough County
- Rentals with a fireplace Hillsborough County
- Private suite rentals Hillsborough County
- Rentals with a kayak Hillsborough County
- Rentals with breakfast Hillsborough County
- Rentals with an accessible-height toilet Hillsborough County
- Loft rentals Hillsborough County
- Beachfront rentals Hillsborough County
- Rentals with a hot tub Hillsborough County
- Rentals with beach access Hillsborough County
- Hotel rooms Hillsborough County
- Pet-friendly rentals Hillsborough County
- Rentals with lake access Hillsborough County
- Motorhome rentals Hillsborough County
- Farm stay rentals Hillsborough County
- Townhouse rentals Hillsborough County
- Fitness-friendly rentals Hillsborough County
- Rentals with outdoor seating Hillsborough County
- Rentals with a patio Hillsborough County
- Rentals with pools Hillsborough County
- Bed and breakfasts Hillsborough County
- Rentals with an accessible-height bed Hillsborough County
- Aparthotel rentals Hillsborough County
- House rentals Hillsborough County
- Waterfront rentals Hillsborough County
- Bungalow rentals Hillsborough County
- Family-friendly rentals Hillsborough County
- Guest house rentals Hillsborough County
- Rentals with a cinema Hillsborough County
- Villa rentals Hillsborough County
- Flat rentals Hillsborough County
- Cottage rentals Florida
- Cottage rentals United States
- Anna Maria Island
- Busch Gardens Tampa Bay
- Raymond James Stadium
- John's Pass
- Reunion Resort Golf Courses - Palmer & Watson
- Dunedin Beach
- Weeki Wachee Springs
- Coquina Beach
- Vinoy Park
- Lido Key Beach
- Cortez Beach
- Amalie Arena
- Anna Maria Public Beach
- Island H2O Live!
- Bean Point Beach
- Jannus Live
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club
- ZooTampa at Lowry Park
- Tampa Palms Golf & Country Club
- River Strand Golf and Country Club
- Gulfport Beach Recreation Area
- Adventure Island
- Bok Tower Gardens
- Things to do Hillsborough County
- Sightseeing Hillsborough County
- Tours Hillsborough County
- Nature and outdoors Hillsborough County
- Sports activities Hillsborough County
- Art and culture Hillsborough County
- Things to do Florida
- Tours Florida
- Wellness Florida
- Art and culture Florida
- Entertainment Florida
- Food and drink Florida
- Nature and outdoors Florida
- Sports activities Florida
- Sightseeing Florida
- Things to do United States
- Tours United States
- Food and drink United States
- Entertainment United States
- Sightseeing United States
- Wellness United States
- Art and culture United States
- Sports activities United States
- Nature and outdoors United States




