Holiday rentals with breakfast in Hillsborough County

Walk to Downtown and Waterfront - Private Yard

Bright and beachy with stylish modern décor and an open floor plan. Concrete construction, a private yard, and a gas grill makes this cottage feel like your personal oasis. Steps from Main Street Dunedin and a short walk to the waterfront. A quick drive to award-winning beaches like Honeymoon Island and Clearwater Beach. Enjoy stunning sunsets and easy access to restaurants, breweries, shops, live music. The perfect getaway in delightful Dunedin—come be our guest at the Barefoot Parrot Cottages.

Paradise in Lutz! w/Heated Pool!

Beautiful and Modern 4 bed/3 full bath home with over 3,100 square feet of living space! The house has 12 ft ceilings and hardwood floors throughout the house! The home can comfortably sleep up to 15 people. It is the perfect place for a large group looking to stay together! The home also has a large screened-in pool with covered lanai. Pool heating fee is an additional $75 a day. The covered lanai has an outdoor bar with marble countertops and two TVs. The backyard has over 1.5 acres of land!

Luxury 3-Bedroom Tiny House-Sleeps Six People!

Have you ever wanted to try out a Tiny house? Want to stay in Tampa? This is the listing for you. This is a THREE BEDROOM tiny house! It has a queen sized bed, and two king-sized beds, (or they can split into four twin sized beds!) Our kitchen has all the amenities of a regular kitchen! The bathroom has Laundry, and shower with Endless Hot Water! Outside you’ll find a Grill and outside seating! We are 15 minutes from the airport! We’re sure you’ll enjoy our beautiful 35 foot not-so-tiny home!

Historic Kenwood KING walkable to Central Ave

Welcome to our newly renovated beachy 2nd floor guesthouse in Historic Kenwood. This spacious 1 bedroom (King bed), 1 bath is an easy walk, bike, or short drive to St Pete restaurants, bars, breweries, antique shops, museums, live entertainment and so much more. Grand Central District is just a 5 min walk, Edge District is 1 mile, Downtown is 2 miles, and St Pete beach is 15 minutes away. Guests have a private deck with seating for 2, Wi-Fi, and laundry accessible via shared fenced backyard.

Lakeside Beachy Cottage

We have decorated our cottage with soothing colors, amenities and artwork to help you relax. You can paddle board and kayak, or just enjoy the sunset on the dock. Or take in any of the entertainment in close proximity... Busch Gardens, Tampa Zoo, the downtown Tampa River Walk, and Ybor City. Or almost any sport... Buccaneers football, Rays baseball, Lightning hockey. We are 15 minutes from Univ. of S. Florida, and 45 minutes from some of Florida's finest beaches. Come and enjoy as you please!

Private Guest Suite 2 miles from Beach

Private, small completely renovated Guest Suite with Private parking, private separate entrance with deck. Space is best for 1-2 people: small, but thought out. 2 miles from Treasure Island beach. 2.5 miles from the St Pete beach! Beautiful quaint neighborhood. Near great fishing spot Kitchenette Full Bathroom Comfy queen size bed Cool AC unit ❗️WE HAVE GREAT REVIEWS, but please view before booking “Is this guest suite right for you” below under “things to note” to have the trip you desire

Tarpon Fun'n Sun-Pool, Beaches + Backyard Chickens

This home is ideally located near Florida's beautiful Sunset Beach and Howard Park Beach - only 17 miles from Clearwater Beach. Take a short ride to world famous attractions like Disney, or Busch Gardens. Don't settle for a hotel when you and your guests can enjoy a home with a gas grill, multiple patios, large kitchen/family room, a large 4K TV and a private jacuzzi/pool with gas heater *option. It's a perfect place for creating family memories or getting together with old friends.

ONE Guest Tiny Ybor Mustard House

The tiny house is for ONE guest. Great stopover in Ybor...but it IS for ONE guest only....It has been recently remodeled. This listing is only available for extended stays: a minimum of 7 days is required for a reservation. Breakfast is supplied and there is the Tampa fave, La Segunda bakery if you care for the real Latin style eats only one block away. Walk to historic Ybor in 7 minutes. Take our free trolley from Ybor down thru Channelside and downtown !

The Guest House at Riverbend Retreat Fla.

True Florida-style living under the oaks and palms on the Alafia River with beautiful views and comfortable beds. We include use of the pool, spa, fire pit, hammock, putting green, yard games, BBQ and dock area. There are additional bedrooms in the adjoining house for larger groups. Fisherman can cast into the river with expectations of catching Sheepshead, Red Snapper, Speckled Trout, Snook, Spotted Bass and Florida Gar off the dock. We also catch blue crabs.