
Cottage vacation 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.

Pass-a-Grille Historic Cottage Unit 2
PASS-A-GRILLE HISTORIC COTTAGE UNIT 2 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 2 - 2 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 and back patio area w/ BBQ grill. Private parking for 2 vehicles.
LocationFamilyBeach

Walk to Downtown and Waterfront - Private Yard
Steps to Main Street and minutes to beaches, yet tucked away on a quaint prime downtown street. Private yard with grill in terrific location. Walk to restaurants, breweries, shops, and live music. Walk to Dunedin's stunning sunsets or drive minutes to award-winning beaches such as Honeymoon & Caladesi Island & Clearwater Beach. Sleeps 6. Two king bed suites and a luxury leather couch that sleeps 2 more. Loaded for kids, pets and beach days. Treat yourself and book this Dunedin favorite today!
LocationValueCheckout

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.
FamilyLocationBreakfast

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.
ValueLocationIndoor spaces

Cozy Cottage for Lovers
Relax, reconnect and revitalize in this private, intimate cottage that has everything you need to leave the hustle and bustle behind. Surrounded by lush tropical vegetation in the shade of giant live oaks and located in the Gulfport Arts District, you're a short walk or bike ride from excellent urban parks, restaurants, live music, fashion and art boutiques, dancing at the Gulfport Casino, community theater, and a beautiful beach that looks out over sailboats moored in Boca Ciega Bay.
LocationValueCheckout

Coral Sands II ~Seaside Coastal Modern 2/2
Welcome to Coral Sands Beach House II at Indian Rocks Beach! Your home away from home in the small beach town of Indian Rocks Beach. You will not want to leave this amazing property with a very coastal homey feel! Coastal chic on the inside and Laid back beach fun on the outside! Amazing location, 1 block to one of the best beaches in a Florida with spectacular sunsets. Lots of restaurants walking distance and we give you a wagon with all the beach gear you need! BTR Number: 1667
FamilyValueAir conditioning

Kooky Coconut Cottage, Indian Rocks Beach
Coconut Cottage only steps away from the beautiful beaches of Indian Rocks Beach. 2 bedroom,1 bath. The entire cottage has been renovated. Next door to the local famous Kooky Coconut Cafe. Perfect for couple, friends or small families. ONLY 3 GUESTS ALLOWED. NO sleeping on the sofa ALLOWED. If you bring more then 3 guests you will be charged $100.00 surcharge per night per extra guest. Due to cleaning restriction we DO NOT allow cooking with CURRY or FISH OIL in the cottage.
ValueFamilySleep quality

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.
ValueFamilyGrill

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.
FamilyValuePets

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.
ValueFamilyAmenities

Lush Harbor Oasis with Private Hot Tub
Escape to your private resort-style cottage in the heart of Safety Harbor! This renovated retreat is perfect for a relaxing getaway. Enjoy a private hot tub, a fully fenced yard, a dedicated office, and complimentary EV charging. Perfectly located for exploring Tampa, St. Pete, and Clearwater's famous beaches. Your ideal Florida home base awaits!
ValueLocationHot tub

Little Manatee River Cottage
This cottage is located on the Little Manatee River. Sun City Center 10 min, Moffit Cancer Center 3 miles. Abundant fishing charters, manatee viewing center and Simmons Park all within minutes. Fully furnished, linens, kitchen utensils; bath towels; blankets pillows comfy furnishings. View sunsets from the dock or front sitting area.
ValueFamilyCheck-in
Popular amenities for Hillsborough County cottage rentals
Cottage rentals with a hot tub

𖤓Updated Stilt home: just steps to the beach!𖤓
LocationFamilyHospitality

Private Heated pool/spa home!
LocationValueNearby

Turtle Cottage - Anna Maria Island
LocationFamilyTV

Pink Gulfside Cottage, Steps to Beach, Pets OK
LocationFamilyIndoor spaces

Beachy Keen Cottage A only steps to the Beach
LocationFamilyNearby

Family FUN~Pool, GameRoom+Bikes, Near Beach/Trail
ValueFamilyAir conditioning

Cozy Cottage Near Beach | Hot Tub • Pet Friendly
FamilyLocationWalkability

"Oasis" Historic Beachside Cottage 3/2
LocationFamilyHospitality
Pet-friendly cottage rentals

The Pelicans Roost / Gulfport
FamilyLocationKitchen

Charming Blue Bungalow With Amazing Yard
FamilyLocationParking

Luxury Beach Cottage | Walk to Dining & Sunset
FamilyValueBackyard

Best Location! Walk to Dining, Trail & Stadium
FamilyValueWifi

#5 Beach Front Cottage w view- Indian Rocks Beach
ValueFamilyCondition

Gulfport Art District - One Block From Beach!
ValueFamilyTV

Beautiful Beachfront Cottage on the Water
LocationFamilyParking

Cozy up in a French Country nest NEAR EVERYTHING
LocationValueKitchen
Private cottage rentals

Cooper Cottage: Cozy, Convenient and Comfortable
ValueLocationComfort

B - BEACH HOUSE 3 MIN WALK TO THE BEACH
LocationFamilyAmenities

Charming Newly Reno 1 min to Downtown Dunedin
FamilyLocationCleanliness

Island Time Stay: Happy Hour
LocationFamilyAccess

Florida Guest House
ValueLocationWalkability

Clearwater Cottage Short Drive to Beach & Dunedin!
ValueLocationOutdoor spaces

Entire home and yard 2 /1 with two sleep sofas
LocationValueAccuracy

LUNA Retreat • Owner Managed • No Chores
ValueFamilyAccuracy
Destinations to explore
- Boutique hotels Hillsborough County
- Resort rentals Hillsborough County
- Farmstay rentals Hillsborough County
- Townhouse rentals Hillsborough County
- Vacation home rentals Hillsborough County
- Rentals with beach access Hillsborough County
- Hotel rooms Hillsborough County
- Serviced apartment rentals Hillsborough County
- Rentals with a hot tub Hillsborough County
- Condo rentals Hillsborough County
- Tiny house rentals Hillsborough County
- Rentals with a sauna Hillsborough County
- Rentals with pools Hillsborough County
- Apartment rentals Hillsborough County
- Pet-friendly rentals Hillsborough County
- Rentals with a kayak Hillsborough County
- Rentals with lake access Hillsborough County
- RV rentals Hillsborough County
- Beachfront rentals Hillsborough County
- Villa rentals Hillsborough County
- Bungalow rentals Hillsborough County
- Rentals with breakfast Hillsborough County
- Luxury rentals Hillsborough County
- Aparthotel rentals Hillsborough County
- Loft rentals Hillsborough County
- House rentals Hillsborough County
- Waterfront rentals Hillsborough County
- Rentals with an accessible height toilet Hillsborough County
- Private suite rentals Hillsborough County
- Bed and breakfasts Hillsborough County
- Family-friendly rentals Hillsborough County
- Rentals with an accessible height bed Hillsborough County
- Guesthouse rentals Hillsborough County
- Cottage rentals Florida
- Cottage rentals United States
- Anna Maria Island
- Weeki Wachee Springs
- Anna Maria Island Beach
- Raymond James Stadium
- Busch Gardens Tampa Bay
- Coquina Beach
- Lido Key Beach
- Reunion Resort Golf Courses - Palmer & Watson
- Bean Point Beach
- Amalie Arena
- LEGOLAND Florida Resort
- Tampa Convention Center
- Dunedin Beach
- Hard Rock Casino
- University of South Florida
- Vinoy Park
- ChampionsGate Golf Club
- John's Pass
- Epperson Lagoon
- Fort De Soto Park
- Tropicana Field
- Sand Key Beach
- Southern Dunes Golf and Country Club
- Island H2O Live!
- Things to do Hillsborough County
- Sightseeing Hillsborough County
- Food and drink Hillsborough County
- Sports activities Hillsborough County
- Nature and outdoors Hillsborough County
- Tours Hillsborough County
- Art and culture Hillsborough County
- Things to do Florida
- Tours Florida
- Wellness Florida
- Art and culture Florida
- Entertainment Florida
- Sightseeing Florida
- Sports activities Florida
- Nature and outdoors Florida
- Food and drink Florida
- Things to do United States
- Food and drink United States
- Tours United States
- Sightseeing United States
- Sports activities United States
- Art and culture United States
- Entertainment United States
- Wellness United States
- Nature and outdoors United States





