Guest house holiday rentals in Hillsborough County

Minutes to Beaches w/King Bed Private Updated

This private home away from home near pristine beaches sits behind the main house in a quiet neighborhood conveniently located near downtown Clearwater, Clearwater Beach, Tampa, St Petersburg, Dunedin, Tarpon Springs, and other great towns. Restaurants, shopping, & entertainment venues. • Clearwater Beach= 4 miles / 8 minutes • Downtown Dunedin= 3 miles • Honeymoon Island= 9 miles • Tarpon Springs Sponge docks= 14 miles • Tampa Airport (TPA)= 14 miles • St Pete/Clearwater Airport (PIE)= 9 miles

Kenwood Retreat - 1BR carriage house

This newly constructed carriage house was built to embrace the character and charm of the main house, a 1928 craftsman bungalow. Your 2nd floor 1 BR apartment is well appointed with a full chef's kitchen, a living room with a pull-out sofa, and washer/ dryer. Enjoy a morning cup of coffee or a glass of wine in the evening on the large porch. 2 min walk to Grand Central restaurants, coffee shops, boutiques, or grab a bike or scooter for a 5 min ride to Downtown St. Pete or 15 to the beaches.

Pool Side Getaway, Walk/Bike Tampa River Walk

Experience Tampa from our little slice of Heaven right in the heart of Tampa Heights. This is a detached private Pool House in our backyard. At 264 sqft, It has a full Bath, Kitchen, and studio space with a Queen memory foam mattress, and work space / breakfast table. Enjoy the Pool and its tropical surroundings or just relax in a lounge chair. We are walking distance to Lee’s Pizza, Armature Works, River Walk, and much more... Included is a smart TV, WIFI, and Two Bicycles to go explore.

9 Mins to Downtown, Full Kitchen, KingBed, Balcony

Freshly remodeled second story apartment in a charming 1920's guest house located in trendy Seminole Heights just North of downtown Tampa with easy on/off from I-275. Features a full kitchen, living room, king bedroom, bathroom, and balcony. Walk to restaurants, hip bars, and shops, or stroll the tree-lined streets of 100+ year old houses. Minutes from all Tampa has to offer: Busch Gardens, Zoo, Downtown, Riverwalk, Hard Rock Casino, USF. Come and relax at this inclusive and welcoming space.

Beautiful Private Casita Close to Everything

Splendid newly constructed guesthouse near downtown Tampa! Private and quiet! Lots of great amenities, including free use of 2 bikes! Free parking on-site. Private entrance. Close to Tampa Airport, Raymond James Stadium, Benchmark International Arena and more! Walk to Tampa's Riverwalk and Armature Works entertainment complex. Free wifi, television and a designated workspace. Murphy bed stows away for extra living space during the day. Owners live on site to quickly address concerns.

Tiny House Oasis Blue Vatican . Near MacDill Base

Enjoy this small and beautiful Oasis, a perfect hideaway to forget about the noise of the city, relax with the aroma diffusers and your favorite music; In the mornings fall in love with our solarium while having a good coffee. We are located in South Tampa just 3 minutes away from the MacDill Airbase. 5 min Picnic Island Park, 10 min Port Tampa Bay Cruise and Downtown, 15 min International Airport. 15 min Raymond James Stadium, 40 min Clearwater Beach. Free Parking for up to 2 cars.

Cozy Tropical Guesthouse for Two

Welcome to our charming guesthouse in Riverside Heights, a safe and centrally-located neighborhood — 10 minutes from Downtown Tampa. This unique retreat for two has tropical vibes, a loft sleeping area, a well-stocked kitchen, and a private patio. Newly built from floor to ceiling, it is filled with stylish decor and luxurious furnishings. Your hosts include a Tampa native and food writer which means you’ll get the best recommendations on things to do and places to eat!

Nalas House | Full Living Room+Kitchen+Bedroom

Enjoy the comfort of a private suite at a single-room rate ✨ This inviting space features a cozy queen bed, a full kitchen + dining area, a spacious living room, and your own private patio—perfect for relaxing after a fun day out 🌱 Located just 4 minutes from Busch Gardens & Adventure Island 🎢, 15 minutes from the Hard Rock Casino 🎰, and only 20 minutes from Downtown Tampa and the vibrant Ybor City Historic District 🌆. We look forward to hosting you ✨

Eco-Friendly Tampa Cottage - Full Kitchen+Parking

Close to Tampa’s best eats and entertainment! Our peaceful and eco friendly fully renovated space includes a full kitchen, queen memory foam bed, and comfy sleeper sofa—perfect for couples, solo travelers, or small families. Walk to a classic arcade and craft beer bar at the end of the street, or explore a huge selection of international cuisine nearby. Enjoy expansive off-street parking, a relaxing patio, and a non-toxic, environmentally conscious space.

Sonia's Little House

Welcome to your perfect home base in Tampa! This charming and private efficiency unit offers everything you need for a comfortable stay—whether you're visiting for business, vacation, or an extended stay. Located in a quiet residential neighborhood just minutes from downtown Tampa, Raymond James Stadium, Midtown, and Tampa International Airport, you'll enjoy easy access to all the city’s highlights while coming home to a peaceful retreat.

Entire Guest House near Tampa airport

Welcome to our charming guest house! Located just 12 minutes away from Tampa Airport, 20 minutes from Raymond James Stadium, and a quick 35-minute drive from Clearwater, our entire guest house offers you convenience and comfort. With a private entrance, you'll have all the privacy you need. Whether you're here for a game, a beach getaway, or to explore the city, our cozy space is your perfect home base. Book now for an unforgettable stay!

Relax in the tampa bay area #1

I invite you to spend your vacation, a romantic getaway or simply a work stay in this accommodation decorated and equipped with everything you may need to just relax and enjoy. It is conveniently located: Tampa International Airport: 3.5 miles Bush Gardens: 15 miles. Clearwater Beach: 20 miles. International Plaza and Bay Street: 4.3 miles Raymond James Stadium: 6 miles.