
Cottage vacation 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 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.
LocationFamilySolo travel

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!
ValueFamilyBiking

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.
ValueLocationAmenities

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.
LocationFamilyGetting around

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
LocationFamilyIndoor spaces

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.
ValueLocationGrill

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.
LocationValueOutdoor spaces

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.
FamilyLocationView

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.
ValueFamilyPets

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.
FamilyLocationWifi

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!
FamilyValueWifi

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.
LocationValueLong stay
Popular amenities for Hillsborough County cottage rentals
Cottage rentals with a hot tub

Turtle Cottage - Anna Maria Island
FamilyLocationSolo travel

Pink Gulfside Cottage, Steps to Beach, Pets OK
ValueFamilyNearby

Beachy Keen Cottage A only steps to the Beach
FamilyLocationQuiet

Happy Camper Cottage | Cozy Oasis with Hot Tub
ValueLocationView

Family FUN~Pool, GameRoom+Bikes, Near Beach/Trail
ValueFamilyLong stay

Cozy Cottage Near Beach | Hot Tub • Pet Friendly
FamilyLocationTV

Castle Keep Guest House
LocationValueNearby

Waterfront Beach Cottage w/Lagoon Pool & Spa
FamilyLocationHot tub
Pet-friendly cottage rentals

The Pelicans Roost / Gulfport
FamilyLocationWifi

River adjacent, Quiet neighborhood, King bed
LocationValueOutdoor spaces

Luxury Beach Cottage | Walk to Dining & Sunset
LocationFamilyGrill

Vintage Florida Beach Cottage B
LocationValueCheckout

Best Location! Walk to Dining, Trail & Stadium
FamilyLocationBiking

The Sunshine Cottage - Like Grandma's with WIFI
FamilyValueAccess

Cozy up in a French Country nest NEAR EVERYTHING
ValueLocationLaundry

Beautiful Beachfront Cottage on the Water
ValueLocationNearby
Private cottage rentals

Clearwater Cottage Short Drive to Beach & Dunedin!
ValueFamilyQuiet

B - BEACH HOUSE 3 MIN WALK TO THE BEACH
ValueFamilyWalkability

Family Friendly Beach Cottage in Madeira Beach, FL
ValueLocationAccess

Charming Newly Reno 1 min to Downtown Dunedin
FamilyValueParking

Private Peaceful Cottage-St Pete, Beaches & Trail!
LocationValueBackyard

Entire home and yard 2 /1 with two sleep sofas
ValueFamilyCheck-in

LUNA Retreat • Owner Managed • No Chores
LocationValueCleanliness

Cooper Cottage: Cozy, Convenient and Comfortable
LocationValueBathroom
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- 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!
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- Family travel hub Tips and inspiration
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- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes





