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 TBAY spirit. 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
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 .
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 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.
Barbie would be happy to call The Don home.
Photo by The Don CeSar Shop
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 hotel is currently closed due to impacts from hurricane season. Please check with the Don for reopening updates.
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.
