
Cottage holiday rentals in Hillsborough County
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Top-rated cottage rentals in Hillsborough County
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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 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 today and escape to the Barefoot Parrot Cottages.

Flipper's @ Mad Beach Cottage
Flipper's at Mad beach is a few steps away from the sugary sands of Madeira Beach, and close by the famous John's Pass Village & Boardwark where shopping and entertainment is always great. Completely renovated with light porcelain tile, nice furniture, queen bed with memory Thempur-Pedic mattress, exquisite modern shower, tall kitchen cabinets with plenty of storage. Huge private paved fenced backyard with gazebo, great for entertainment and outdoor grilling. You will love the beach decor.

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.

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.

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.

Adorable Villa 1 min to Downtown Dunedin
Welcome to our 1/1 cottage-style villa, which is minutes from Downtown Dunedin. Only a short walk to Main Street and a 12 min drive to Honeymoon/Caladesi Island! Walk to the Pinellas Trail, breweries, eateries, waterfront marina, and Blue Jay baseball stadium. Enjoy award-winning cuisine, live entertainment, and breathtaking sunsets before returning to the peace and quiet of your own private area. Dunedin is a gulf cart friend city with local rental available to cruise around town.

Ground-Floor Beachfront | Walk-Out to the Sand
Walk straight from your door onto the sand. This rare ground-floor, direct beachfront one-bedroom cottage sits right on the Gulf of Mexico with unobstructed water views and effortless beach access — no stairs, no elevators, no roads. Enjoy your private beachfront patio, a cozy and newly remodeled interior, and your own stretch of sand with lounge chairs just steps away. Perfect for couples or longer stays looking for a relaxed, front-row beach experience in Indian Shores.
Popular amenities for cottage rentals in Hillsborough County
Cottage rentals with a hot tub

Turtle Cottage - Anna Maria Island

Harbor Oasis | Hot Tub | Private | Lush Backyard

Beachy Keen Cottage A only steps to the Beach

Lemon Cottage Steps from Beach

Happy Camper Cottage | Cozy Oasis with Hot Tub

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

Cozy Cottage Near Beach | Hot Tub • Pet Friendly

"Dunes" Gulf-View Historic Beachside Cottage 1/1
Pet-friendly cottage rentals

The Pelicans Roost / Gulfport

Steps2Beach-Walk everywhere-Bikes & gear Included

Coral Sands I -2/2 Porch, Pool Tbl, Best Location!

Luxury Beach Cottage | Walk to Dining & Sunset

Vintage Florida Beach Cottage B

Cozy up in a French Country nest NEAR EVERYTHING

Beachy Paradise

Beautiful Beachfront Cottage on the Water
Private cottage rentals

Beautiful newly renovated beach cottage

Tranquil Guesthouse Hideaway (Near MacDill AFB)

"Sweet Harbor Cottage" Walk to Downtown

2BR Charming Beach House Steps To The Beach 2nd FL

Oceanside Cottage

Coveted Sunset Beach Rental: Beautiful 2 Bdrm

Safety Harbor Cottage

Alafia River Cottage
Destinations to explore
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- Loft rentals Hillsborough County
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- Rentals with a kayak Hillsborough County
- Rentals with a firepit Hillsborough County
- Rentals with beach access Hillsborough County
- Hotel rooms Hillsborough County
- Cottage rentals Florida
- Cottage rentals United States
- Anna Maria Island
- Raymond James Stadium
- Busch Gardens Tampa Bay
- John's Pass
- Weeki Wachee Springs
- Coquina Beach
- Vinoy Park
- Lido Key Beach
- Dunedin Beach
- Amalie Arena
- Cortez Beach
- Bean Point Beach
- Island H2O Live!
- Anna Maria Public Beach
- Southern Dunes Golf and Country Club
- Jannus Live
- ChampionsGate Golf Club
- Tampa Palms Golf & Country Club
- ZooTampa at Lowry Park
- River Strand Golf and Country Club
- Hard Rock Casino
- North Beach At Fort DeSoto Park
- Bok Tower Gardens
- Splash Harbour Water Park
- Things to do Hillsborough County
- Food and drink Hillsborough County
- Sports activities Hillsborough County
- Nature and outdoors Hillsborough County
- Tours Hillsborough County
- Sightseeing Hillsborough County
- Art and culture Hillsborough County
- Things to do Florida
- Entertainment Florida
- Tours Florida
- Nature and outdoors Florida
- Art and culture Florida
- Wellness Florida
- Sightseeing Florida
- Food and drink Florida
- Sports activities Florida
- Things to do United States
- Wellness United States
- Sports activities United States
- Food and drink United States
- Tours United States
- Entertainment United States
- Sightseeing United States
- Art and culture United States
- Nature and outdoors United States




