Holiday houses in Hillsborough County

Charming private guest house.

Enjoy a private guest cottage tucked behind a beautifully restored historic Davis Islands home. The cottage, like the neighborhood, is exceptionally charming with a warm, coastal character that makes it special. It is close to so much, including downtown Tampa, Benchmark Arena, cruise port, waterfront parks, restaurants, cafes, and popular local attractions. Perfect for relaxing stays, it’s an ideal escape for couples or solo travelers looking for comfort, privacy, and a touch of island charm.

"Luxury Casita/Jacuzzi/Bush Gardens/USF/Casino"

Private townhouse style unit with its own entrance, parking, patio, and outdoor amenities. Attached to another Airbnb unit but completely separate with its own entrance and outdoor space. Enjoy this modern Tampa getaway with jacuzzi, pergola and putting green. Minutes from Busch Gardens, USF, and Seminole Hard Rock Casino. Features a modern kitchen, Smart TVs, Wi-Fi, and outdoor space. No parties, events, gatherings, or loud music permitted. Please respect quiet hours and neighboring guests.

The Jungalow SOHO - Pool/Hot Tub

The Jungalow is the ultimate urban oasis. Enjoy the luxuries of the home or venture out to local attractions like the iconic Bayshore Boulevard, Historic Hyde Park, SOHO, Downtown and more. This home was designed with comfort and convenience in mind. Fully equipped with a smart tv, high-speed WIFI, pool and hot tub - this place is paradise. Central to the action - walk to unique rooftop bars, restaurants and shops or Uber to local attractions like Water Street, Amalie Arena, and the Riverwalk.

3bd/2.5 bath townhome Bayshore Beautiful

Beautiful 3 bedroom, 2.5 bath in South Tampa. 2 blocks off Bayshore Blvd. Walk to Counter Culture and Barcelona Wine Bar. 1 mile to Hyde Park, 2 miles to downtown and Convention Center, 3 miles to Ballast Point, 4 miles to MacDill AF, 5 miles to Raymond James stadium, 13 miles to Busch Gardens, 24 miles to Clearwater Beach. Each bedroom has a queen bed. Additional queen air mattress is available. Each bedroom has smart HD TV. Keypad for entry and ring doorbell mounted next to door.

Traditional Home in Tampa

Our recently remodeled home features a beautiful private pool with fully automated controls for easy enjoyment. Inside, you'll find modern electronics and amenities designed for comfort and convenience. Located just 7 miles from Tampa International Airport, we’re also close to top attractions like Busch Gardens, Raymond James Stadium, and Downtown Tampa. Enjoy the privacy of a spacious pool home tucked away in a quiet cul-de-sac—perfect for relaxing after a day exploring Tampa Bay.

Heart of S Tampa| Near Beach, MacDill AFB| Hot Tub

Escape to your South Tampa sanctuary where tropical luxury meets ultimate convenience. • Perfect for families, business travelers, and military stays, this home features a private backyard oasis with a hot tub, treehouse-style deck, and fire pit. •Ideally located minutes from the pet-friendly Picnic Island Beach Park, MacDill AFB, TPA Airport, and top attractions like Busch Gardens 🎢✈️. • Enjoy a dedicated workspace, free parking, washer/dryer, and seasonal mango tree!

Tropical Paradise Tranquility Getaway

Cozy 2 bedroom/1 bathroom house centrally located to Downtown St Pete and beaches. Fenced backyard for your privacy and safety of children/pets. Walking distance to public library, neighborhood lake, restaurants and bus transportation. You will love backyard Pergola with dining and sitting area for your relaxation! Tropical back and front yards! 2 Grills provided for your delicious outside cooking! Included with your stay beach towels, beach coolers, no pet fee, etc..

Casita Palma ~ Old Hyde Park (Casita Palma)

Casita Palma is one of four residences in our beautiful, 100 year old home. The home sits on a quiet street in the Old Hyde Park neighborhood. This amazing location allows you to walk to beautiful Bayshore Boulevard and the shops and restaurants of the Hyde Park Village. The Casita is a place to relax and reset. Designed with a calming and minimalist vibe, our home is the perfect stay for couples, friends, or business travelers.

Private Pool Access Peaceful Retreat

Relax with family and friends in this peaceful and stylish retreat. Enjoy a private pool exclusively for your stay, a spacious covered porch, and all the comforts of home. This home is on a shared property with other separate units, each with its own private entrance and designated outdoor space. Guests have exclusive use of the house, pool, and patio. Ideal for vacations, business trips, or weekend getaways in a quiet community.

Chic cozy King Bed private Home

Welcome to your Tampa home away from home! Enjoy sunny beach days, top restaurants, and Florida fun. After exploring, relax in comfort with everything you need for a longer stay. Located at the end of iconic Bayshore Blvd and near MacDill Air Force Base, you’ll be close to the action yet tucked away in a peaceful spot. Whether you're here for work or play, this cozy retreat makes every stay easy, enjoyable, and memorable.

Hacienda Hideaway w/ heated pool

Welcome to the Hacienda Hideaway: a stunning Mediterranean-style retreat in historic West Tampa, Florida! Immerse yourself in the charm of this fully renovated and expertly designed home, boasting high-end finishes and luxurious touches throughout. Perfectly situated for convenience, the house is centrally located within ten minutes from the airport, stadium, downtown, shopping, restaurants, and the famous Riverwalk.

Cozy AF Jungle-House Hideaway

We invite you to the **Cozy AF Jungle House**! Step into the foliage and immerse yourself in the jungle vibes. With every glance, you'll discover something new—from the sabretooth tiger skull to the romantic hot tub and even a crystal hanging banana. Adventurers, dare to play Jumanji if you’re feeling bold! Our goal is not just to provide a place to stay, but an experience you’ll cherish forever.