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Cottage vacation 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.

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Cottage in Clearwater

4.73 out of 5 average rating, 263 reviews

Clearwater cottage

welcome to our Clearwater cottage located just minutes drive away from the world-renowned Clearwater Beach and just a short bike ride down to the waterfront where you can take in breathtaking sunsets and fishing the Pinellas trail is a 45 mile long biking/walking trail it is right around the corner from the house, there are two bikes available at no additional charge. the house has been renovated and comes completely furnished, pots pans silverware.. 6ft privacy fence, outdoor barbecue. pets ok.

Cottage in Tampa

4.98 out of 5 average rating, 171 reviews

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, 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. Pet fee $50. Elope/Proposal packages IG lakepossibility

Cottage in Madeira Beach

4.96 out of 5 average rating, 143 reviews

BEACHFRONT FAIRWINDS Cottage Lower

Bright, tropical-themed beach house located directly on Madeira Beach 1/2 block from John's Pass Village. This cozy 2 bedroom & 1 bath downstairs getaway has a huge covered 400 sq. ft. deck & ocean views. Toes hit the sand off the deck & just past the dunes is the Gulf! 1 wk stay for holidays + holiday rates. Decorative items removed due to COVID. Pics are preCovid, but cottage is still very cute! If guest loses house key, guest responsible for expense of locksmith, new locks, and new keys.

Cottage in Gulfport

4.96 out of 5 average rating, 146 reviews

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...!

Cottage in Clearwater

4.85 out of 5 average rating, 123 reviews

Beach Guest Cottage. Gulf Semi Private Area.

No Power outage. Come enjoy the Sun & Beach in french touch Design little Guest COTTAGE for 1-2 Persons in quiet Green Golf Area, own entrance Studio, lovely backyard under 2 big oaks. 2 mn to SEA by car, 7 mn to CLEARWATER BEACH. Self check-in from 3pm to late+ GOOD WIFI, ideal for remote work. KING Bed. Café & reading Corner with 2 armchairs, kettle & coffee, Organic teas and snacks, fridge & microwave. No kitchen or tv. Near downtown Clearwater. FREE PARKING on street. Safe neighborhood.

Cottage in St Pete Beach

4.96 out of 5 average rating, 128 reviews

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.

Cottage in Tarpon Springs

4.99 out of 5 average rating, 150 reviews

Cooper Cottage: Cozy, Convenient and Comfortable

Cooper Cottage is for cyclists, boaters, beach goers or those who just want to relax! The Cottage is the front half of a duplex in downtown Tarpon with all the amenities including bikes and beach gear! Walk/bike to Restaurants, Churches, Museums and Parks in under 12 minutes or drive to Fred Howard Beach or Sunset Beach in 7 minutes! 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.

Cottage in Lutz

4.95 out of 5 average rating, 145 reviews

Little piece of Heaven 2

This 2 bedroom cozy cottage is nestled on a 1.5 acre piece of property on a serene ski sized lake. The cottage is a laid back coastal feel with all of the amenities of home.Tucked away in between the hustle and bustle of Tampa without ever knowing it. Easy access the Veteran's Expressway that will take you to anywhere from Clearwater and our pristine beaches to Downtown St. Pete. I275 will take you to Downtown Tampa, Busch Gardens and Adventure Island. I-4 will take you to Orlando attractions

Cottage in St. Petersburg

4.96 out of 5 average rating, 114 reviews

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.

Cottage in Palm Harbor

4.78 out of 5 average rating, 180 reviews

Crystal Beach Cottage #1

The Cottage #1 is tucked quietly away underneath a canopy of oaks it is part of a duplex with 3 other cottages on the property. No storm damage but recently replaced all softgoods and furnishings for new snowbird season. Centrally-located apt in historic Palm Harbor. Restaurants, live music, tiki bars-finedining are all options. Take the Pinellas trail for biking enthusiasts, beaches of Honeymoon and Spring training nearby.. Walk to park and Sutherland bayou. Book and enjoy sunny Florida.

Cottage in Tampa

4.76 out of 5 average rating, 139 reviews

Good Vibes Cozy Cottage on Million $ Row

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.

Cottage in Ruskin

4.91 out of 5 average rating, 105 reviews

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.

Vacation rentals for every style

Get the amount of space that is right for you

Villas

Luxurious estates for the ultimate escape

Apartments

Convenient locations with everyday essentials

Bungalows

Intimate homes. inviting architecture

Popular amenities for Hillsborough County cottage rentals

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

Cottage in Dunedin

4.9 out of 5 average rating, 72 reviews

Sunny - Key West Vibe Cottage - Pool - Walkable

Cottage in Tampa

4.95 out of 5 average rating, 99 reviews

Hot tub, 2 floors riverfront, Bush Gardens, kajaks

Cottage in Safety Harbor

4.9 out of 5 average rating, 68 reviews

Downtown Luxe Comfort Cottage with Hot Tub!

Cottage in Dunedin

5 out of 5 average rating, 11 reviews

1000 Oaks Cottage 3bed/2bath with hot tub

Cottage in Palm Harbor

4.83 out of 5 average rating, 90 reviews

Happy Camper Cottage | Cozy Oasis with Hot Tub

Cottage in Largo

5 out of 5 average rating, 34 reviews

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

Cottage in Saint Petersburg

4.99 out of 5 average rating, 72 reviews

"TROPI COTTAGE"

Cottage in Largo

4.96 out of 5 average rating, 80 reviews

Hidden Oasis #1, high&dry near the beach

Pet-friendly cottage rentals

Cottage in Tampa

4.96 out of 5 average rating, 80 reviews

River adjacent, Quiet neighborhood, King bed

Cottage in Safety Harbor

4.94 out of 5 average rating, 48 reviews

6B Newly Renovated Casita at Coastal Cottages!

Cottage in Dunedin

4.99 out of 5 average rating, 305 reviews

Private Yard Walk to Downtown Dunedin & Waterfront

Cottage in Gulfport

4.73 out of 5 average rating, 45 reviews

The Cottage at Wishing Well, Gulfport

Cottage in Riverview

4.95 out of 5 average rating, 76 reviews

Alafia River Cottage

Cottage in Gulfport

4.99 out of 5 average rating, 263 reviews

Gulfport Art District - One Block From Beach!

Cottage in Thonotosassa

4.96 out of 5 average rating, 25 reviews

Tampa-Retreat I Homestead with 5th Gen Floridians

Cottage in Palm Harbor

4.96 out of 5 average rating, 48 reviews

Mango Cottage, pet friendly, steps to gulf

Private cottage rentals

Cottage in Largo

4.78 out of 5 average rating, 60 reviews

Cottage by the Coast 2 bd - Pet Friendly

Cottage in Tarpon Springs

5 out of 5 average rating, 26 reviews

New! Close to Downtown/Sponge Docks/Beaches/Trails

Cottage in Dunedin

4.97 out of 5 average rating, 73 reviews

Private and Romantic I The Highland Hideaway

Cottage in Dunedin

4.96 out of 5 average rating, 71 reviews

Adorable Villa 1 min to Downtown Dunedin

Cottage in St. Petersburg

4.94 out of 5 average rating, 17 reviews

Modern Cottage

Cottage in Palm Harbor

4.69 out of 5 average rating, 70 reviews

Crystal Beach Yellow Cottage

Cottage in St. Petersburg

4.99 out of 5 average rating, 90 reviews

St Petersburg Cottage- Beaches, Downtown & Trail

Cottage in Tarpon Springs

4.85 out of 5 average rating, 98 reviews

Palm Cottage * King Bed * Tropical Yard

Destinations to explore