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17 creative staycation ideas in and around Tampa Bay

From tiny houses and beachfront mansions to tropical oases, the Tampa Bay area is full of unique places to stay that offer a change from the traditional.

The back of a gorgous beachfront Airbnb. The sun is setting over the ocean, deck chairs line the pool and palm trees divide the yard from the beach.

There are definitely worse places to spend a sunset.

Photo via Airbnb

Table of Contents

We all need a staycation or a trip to a different city from time to time. Whether you’re a Tampa Bay area local feeling a little cooped up or a visitor looking for a special experience in our beautiful area, picking the perfect home away from home is crucial.

We went looking for unique regional lodgings that capture the vast diversity of the TBAYspirit. So choose your ideal digs, pack your bags, and get ready for a memorable getaway.

Waterfront luxury

Oceanfront Villa, Redington Shores

This 8-bedroom, 6-bathroom villa sits right on the beach. Enjoy unencumbered views of the Gulf of Mexico from the pool, spa, or balcony, perfect for large groups or families looking to get away in style. You might have even spotted the villa in the background of the recent movie “80 For Brady.”

Coastal Theme Waterfront Home, Indian Rocks Beach

You could spot dolphins from the private dock at this 8-bedroom, 4-bathroom luxurious stay overlooking the ocean. The pet-friendly property also features a pool, spa, gym, a kitchen with a view of the water, and a golf cart for long-term stays

Waterfront Midcentury Ranch, Davis Islands

Staycation with views of Hillsborough Bay from this home which fits up to six guests. You can enjoy the sights of Bayshore Boulevard from the private dock, pool, hot tub, or even from the comfort of the living room inside.

A silver Airstream sits in front of a patio. There are chair around a fire pit, the sun is shining, and trees are behind a brown fence.

Airstream was founded in 1931.

Photo by StayTealDoor via Airbnb

Something a bit different

The Green Stream, Seminole Heights

Getaway in style at this unique rental. The retro feel of the fully equipped Airstream is perfect for up to three people and is accompanied by luscious outdoor greenery. Guests can enjoy a fire pit, a hammock, and a barbecue in the fully fenced-in backyard. There’s no shortage of things to do nearby as the shiny stay sits in the trendy Seminole Heights neighborhood.

The Boathouse, Old West Tampa

If being by the water isn’t enough for you, why not sit on top of it? This boathouse sits at the end of a dock above the Hillsborough River. As many as four people can stay here and enjoy tranquility by the water and views of downtown Tampa’s skyline, before heading inside to enjoy cozy living spaces.

Riverside Guesthouse, Seminole Heights

This cozy spot sits right on the Hillsborough River and is a wildlife watcher’s paradise. Watch for alligators, birds, turtles, fish, manatees, and even dolphins from the screened-in porch. We can’t guarantee you’ll see any, but the canopy of trees and water sounds are sure to help make your stay a relaxing one.

Island Soul Yacht, South Tampa

Bored of dry land? We’ve got you covered. This 90-foot yacht is a sea lover’s dream and gives guests the unique and luxurious opportunity to get a taste of life on the water. It can sleep up to eight people and it also hosts activities like day cruises, weddings, and birthday parties .

A view of this Southern Plantation Oasis Airbnb from above. There are fields surrounding the property and a fenced-in yard has a pool surrounded by palm trees.

Outdoor spaes like this are what dreams are made of.

Photo via Airbnb

Outdoor spaces

Southern Oasis, Lutz

Enjoy farm charm at this getaway where up to 12 guests can roam free. Soak under the waterfall in the pool, grab a drink at the pool bar, or play a game of pool inside. The home also sports a hot tub and nearby lake access. Pets are welcome to enjoy the oasis too.

Charming Home, Bayshore Gardens

Yard space is hard to come by in this part of town, but this place bucks that trend. The quaint backyard has fun for all the family, with a fire pit, outdoor furniture, a barbecue, and pool. Beach essentials and bikes are also provided for those who want to make the most of the beautiful local outdoor scene.

Paradise Peaceful, Clearwater

The outdoor space at this picturesque place will help ease you into a relaxing stay. The pool is surrounded by tropical plants and a cabana-style bar, plus enjoy the barbecue, fire pit, outdoor dining spaces, and screened-in lanai. Smaller pets are welcome too.

Tropical Oasis, Bay Crest Park

This secluded spot gives off serious resort vibes. With enough room for 14 people, the house boasts a glorious outdoor space with loungers, a pool, vibrant flora, a 55-inch TV, a grill, and even a putting green. Furry friends can practice their putting stroke too.

A small white house has an orange door and is surrounded by a white picket fence. There are chairs on the porch and tropical plants surrounding it.

A great spot for a minimalist.

Photo by Stephanie and David Bailey via Airbnb

Tiny homes

Big Tiny House, Ybor City

This rental is a great introduction to tiny homes, as it’s not quite as small as other ones you may find. Up to four people can stay here and enjoy the full range of amenities. Plus, the location can’t be beat — it’s in the heart of historic Ybor. The owners of this spot are tiny house aficionados with other similar listings too.

Tuck Away Tiny House, St. Petersburg

Try out this stay for a true tiny house experience. At just 100 sqft., this rental sits in the owner’s backyard, which has funky chilled-out vibes, a bar, a pool, and a bunch of yard games. If the place is too spacious for you, bring your pet along.

Watermelon Dome, Largo

Do you love watermelon? Then why not stay in one? This small watermelon-designed stay is sure to get your taste buds craving some sugar. From the green exterior walls, to the watermelon pillows, paintings, blankets, and murals inside, this thematic spot is a fruitful getaway for up to three people.

A couple is driving a pink car up the driveway toward The DonCesar hotel under sunny skies. Palm trees line each side of a paved road.

Barbie would be happy to call The Don home.

Hotels with a twist

The Don CeSar, 3400 Gulf Blvd, St Pete Beach

Also known as “The Pink Palace,” this hotel has been a happy getaway in Tampa Bay for almost 100 years. Built in 1928, The Don’s beautiful exterior is matched by its views of the Gulf of Mexico. For fans of the supernatural, this could be your spot. Some guests say they have seen the ghost of Thomas Rowe, the man who built the hotel, and his one true love, Lucinda, holding hands in the courtyard.

The Tampa EDITION, 500 Channelside Dr., Tampa

Tampa Bay’s first five-star hotel opened earlier this year in the Water Street Tampa neighborhood. Choose from a range of high class restaurants and bars, including a rooftop pool bar where DJs get guests into the partying mood. The 172-room hotel also has a 24-hour gym and spa services, with endless local spots within walking distance.

The Vinoy Resort & Golf Club, 501 5th Ave. NE, St. Petersburg

If one pink hotel wasn’t enough, here’s another one for you. The Vinoy’s grand opening was on New Year’s Eve all the way back in 1925. The resort offers views of Old Tampa Bay + has its own golf course. Enjoy a range of bars, restaurants, pools, a spa, as well as afternoon tea and a history gallery.

City Guides are presented by Water Street Tampa.

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