Holiday Homes in Hillsborough County

Central Florida Vacation Stilt Home with pool!

Your family will be close to most everything FL has to offer when you stay at this centrally-located home. I am within an hour drive of all theme parks, major beaches, sports stadiums and concert venues. Located in the center of town close to grocery stores, fast food locations and all of the local restaurants as well! Most importantly, to me anyway, minutes from several boat ramps that lead into beautiful Tampa Bay and little Manatee River which are great for boating leisure, sport and fishing

Stylish Beach Retreat • 2-Min Walk to White Sand

Experience the best of Indian Rocks Beach in this stylish 2-bedroom apartment, perfectly located just steps from the sand. This spacious retreat features 3 beds, 1 bath, and a comfy memory foam sleeper sofa—perfect for families or small groups. Walk across the street to the sand and enjoy nearby bars, restaurants, and shops. Around the corner, Kolb Park offers a playground, tennis, pickleball, and a skate park. Everything you need for the perfect beach getaway is right at your doorstep. BTR#1936

FREE Decor AnyOccasion*Romantic Getaway*Relax Bath

A modern & cozy place in Tampa,private entrance and parking.We include decorations for all occasions:birthday,wedding,special day, show your love, and more!Perfect romantic getaway to enjoy with your loved one.Located in a central area of ​​Tampa,close to Bush Garden/Adventure Island,Raymond James Stadium,Tampa International Airport, Ybor City, Downtown Tampa,Amalie Arena,River Walk,Clearwater/St Pete Beach and more! Peaceful and centrally-located place with very good restaurants and many shops.

#17 Home near Stadium, 2/2, 1 King Bed

Leave the stress of everyday life behind and head to this 2-bedroom, 2-bathroom home in Tampa. This well-appointed vacation rental has enough room for your group and is conveniently located near plenty of family-friendly activities. At this home, you’ll also be far enough from downtown that you can relax, but close enough to take advantage of all of the professional sports games, museums, and parks that the city offers. After a day out enjoy the backyard and the Beautiful Lake. pictures to come

Modern Home Great Location

Welcome to your home away from home. Our guests’ comfort is our priority. Equipped with all your creature comforts and surrounded by modern fixtures and decor to ensure a wonderful vacation. Open Floor plan, huge kitchen, and two cozy bedrooms. Walking distance to all the local restaurants and attractions, without the noise to keep you up at night; you couldn't choose a better location Please note: this is a duplex property, so you'll be sharing the building but enjoying your own private space.

Sun & Salt Air House-3BR home w/patio,pool,firepit

The search for the perfect sunset with friends and family is over. Minutes from one of a kind shopping, diverse dining, horse racing, and hiking. There is something for everyone. Home is completely renovated with gorgeous stone floors, chef kitchen, and custom outdoor space. Watch the Game on the 75" TV, or relax on the oversized patio/pool area. Enjoy the picturesque sunset before taking an evening dip in the LED lit salt water pool while staying warm by the gas firepit with loved ones.

Cozy Family Home Near Beach w/ Everything You Need

Relax & Recharge in a Stylish Mid-Century Tropical Getaway - Just Minutes from the Beach! 2BR/2BA with a bonus bedroom in the Florida room - sleeps up to 8. Nestled in a quiet neighborhood just minutes to Indian Rocks and Clearwater Beach, with great dining and shopping. Enjoy a private fenced backyard and BBQ area. Perfect for families or groups seeking comfort and convenience. Pet-Friendly! One well-behaved dog is welcome (an additional $225 pet fee applies). Sorry, no cats.

Orange Blossom Cottage heated pools 2 Min to beach

Escape to Orange Blossom Cottage, a freshly renovated 2-bedroom, 1-bath retreat just 2 blocks from Clearwater Beach. Relax in the bright living room with modern tile floors and stylish décor, rest easy in 2 spacious king bedrooms, and enjoy the charm of a retro aqua-tile bathroom. Surrounded by tropical gardens with access to 2 heated pools, our quiet cottage feels private yet is only steps from shops, dining, and the white sands — the perfect blend of relaxation and convenience.

4-bedroom Vacation home with heated pool family

🎊🎉🎊🎉A new surprise for you, the house has been completely renovated .2025 🎉🎊🎉🎊Bring the whole family to this great place with lots of room for fun. Fishing lake. Free one bottles of wine. **Near Amenities:*** Our location is very convenient, just a short distance from key tourist attractions and local shops. You can easily explore local culture and enjoy new experiences. Contact us to book now and experience our comfortable and warm space!

Reinel’s private apartment in Tampa

Close to the Tampa Zoo,Bush Gardens,adventure Island, and more ————————————————————— St Joseph’s hospital 7 minutes away ————————————————————— Multiple malls close ————————————————————— 10 Minutes away from Downtown Tampa ————————————————————— Tampa International airport 10 minutes away ————————————————————— Raymond James stadium 8 minutes away ————————————————————— ⭐️ ⭐️ ⭐️ ⭐️ ⭐️

Maximalist space w/eclectic style/Bars close by

Welcome to my little slice of paradise! This sunny 2-bedroom retreat sits on the top floor of a charming Floridian townhouse, right in the heart of trendy Seminole Heights. Just a short stroll or bike ride to buzzing cafes, cool bars, local breweries, and foodie hotspots—Tampa’s tastiest treasures are all around you! Whether you're here with family or friends, you're in for a fun-filled stay packed with flavor, flair, and good vibes.

Beautiful Clearwater home!

Enjoy a relaxing stay in this centrally located home just minutes from Pier 60, Honeymoon Island, Dunedin and beautiful Gulf beaches. This spacious retreat features fully equipped kitchen, large bathroom with shower and tub, walk- in closet and everything needed for a comfortable stay. Step outside to your private screened-in heated/cooled pool area with patio, BBQ grill, and outdoor dining space-perfect for families and groups.