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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, 258 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, 168 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 Gulfport

4.96 out of 5 average rating, 144 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 St Pete Beach

4.96 out of 5 average rating, 180 reviews

Pass-a-Grille Historic Cottage Unit 1

PASS-A-GRILLE HISTORIC COTTAGE UNIT 1 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 1 - 1 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 patio area w/ BBQ grill. Private parking for 1vehicle on premises.

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, 143 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 Gulfport

4.95 out of 5 average rating, 262 reviews

Gulfport Cottage STEPS to Beach & Restaurants

Calling all beach lovers! Fall in love with this unique Gulfport Beach Cottage! Colorful, light & bright. Located on a corner lot STEPS from popular Beach Blvd & Gulfport beach, fishing pier, eclectic Gulfport shops, cafes and everything FUN! Gulfport has artsy and quirky shops, fabulous waterfront restaurants and a thriving art scene. Gulfport is a funky community all its own. Gulfport has an Art Walk on the First Friday and Third Saturday and a Tuesday market every week. Don’t miss it!

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, 101 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.

Cottage in Tampa

4.87 out of 5 average rating, 207 reviews

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.

Vacation rentals for every style

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Villas

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Bungalows

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A space thats all yours, with room for everyone

Popular amenities for Hillsborough County cottage rentals

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

Cottage in Tampa

4.95 out of 5 average rating, 95 reviews

Hot tub, 2 floors riverfront, Bush Gardens, kajaks

Cottage in Safety Harbor

4.9 out of 5 average rating, 67 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, 32 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, 78 reviews

Hidden Oasis #1, high&dry near the beach

Cottage in Tampa

5 out of 5 average rating, 5 reviews

Traveler's Sanctuary

Pet-friendly cottage rentals

Cottage in Tampa

4.96 out of 5 average rating, 79 reviews

River adjacent, Quiet neighborhood, King bed

Cottage in Clearwater

4.84 out of 5 average rating, 122 reviews

Beach Guest Cottage. Gulf Semi Private Area.

Cottage in Riverview

4.95 out of 5 average rating, 75 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 Tarpon Springs

4.92 out of 5 average rating, 49 reviews

Charming Blue Bungalow With Amazing Yard

Cottage in Thonotosassa

5 out of 5 average rating, 23 reviews

Tampa-Retreat I Homestead with 5th Gen Floridians

Cottage in Palm Harbor

4.96 out of 5 average rating, 46 reviews

Mango Cottage, pet friendly, steps to gulf

Cottage in St. Petersburg

4.95 out of 5 average rating, 43 reviews

Old Florida Paradise Secret Lair Cottage

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 Dunedin

4.97 out of 5 average rating, 71 reviews

Private and Romantic I The Highland Hideaway

Cottage in Dunedin

4.84 out of 5 average rating, 57 reviews

Cozy Cottage in the Heart of Dunedin

Cottage in Palm Harbor

4.7 out of 5 average rating, 69 reviews

Crystal Beach Yellow Cottage

Cottage in Madeira Beach

4.79 out of 5 average rating, 98 reviews

Water Front Super Chic 2BD/ 1 bath - Cottage Wi-Fi

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, 97 reviews

Palm Cottage * King Bed * Tropical Yard

Cottage in Gulfport

4.73 out of 5 average rating, 45 reviews

The Cottage at Wishing Well, Gulfport

Destinations to explore