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.

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.

"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.

160 W. Tyler St | 2 bed @ AVE Tampa Riverwalk

Live Better at AVE Tampa Riverwalk with our heated pool, palm-lined courtyard, rooftop lounge, and 24/7 fitness center. 🌴 Your hotel-quality amenities, and modern furnishings feature a luxury bedding, stainless appliances, and washer/dryer. 🛋️ We're pet-friendly with no restrictions! 🐶 Steps from The Straz Center and minutes from Amalie Arena, our location puts you along the beautiful Tampa Riverwalk—with complimentary bikes to explore it all. 🚲 ✨ Resort Living on Tampa's Waterfront ✨

The Palm Tree Getaway

Ever stayed the night in the woods? Cross it off the bucket list with our ‘Tiny-Home’ style stay near the Hillsborough State Park. Rated #7 on PureWow as one of the 20 Best Airbnb Cabins. This Modern Luxury tiny home was thoughtfully crafted to capture the natural beauty of its old Florida virgin forest surroundings. Glamping at its finest with the best modern conveniences like a full gourmet kitchen, spa like shower, 5G FiberWi-Fi Internet, TV, and a super quiet Mini SplitAC & Heating.

Winter Season Getaway by the Bay, Close 2 Downtown

Steps from Bayshore & SOHO. Experience a blend of historic character and modern comfort. This revitalized bungalow, located in one of South Tampa's most desirable neighborhoods, offers a unique escape. It features a cozy sanctuary perfect for Tampa adventures. The front porch is ideal for morning coffee. The expansive ceilings, a gorgeous chandelier, and natural wood tones create a relaxing atmosphere. Scenic strolls along the waterfront are steps away. Book an unforgettable stay today!

Bay Lake Cottage

You’ll have the Entire 500sq ft Cottage & private entry, deck/dock, all to yourself. Located on a 37-acre private ski lake. Key-pad entry, private parking. 1 king bed, 1 bath, queen sofa bed, washer/dryer, WiFi, smart TV’s, blackout curtains,shampoo,conditioner,hairdryer,WiFi. Fully stocked kitchen, smokeless grill, wine fridge upon request, k-cup/drip coffee machine. The lake has bass, we provide fishing poles/tackle box. Rentable Kayaks & Canoe. Dogs okay, sorry no cats, pet fee $50.

Great For Couples + Work Trips • Central • PetsOK

🏙 Located in Tampa’s most vibrant neighborhood — walk to Bayshore Blvd, SoHo, and charming Hyde Park! 🌞 Perfect weekend escape or cozy work-travel retreat 🏡 Private guesthouse with exclusive rooftop access — enjoy your morning coffee or evening wine with a view 💼 Ideal for business travelers — comfortable, quiet, and centrally located ☕ Surrounded by local cafes, restaurants, nightlife, and boutiques 🚫 Please note: This unit is not handicap-accessible and requires stairs

Luxury Retreat~Private Hot tub~9 mins to Downtown

3-bedroom, 2-bathroom retreat that seamlessly blends urban convenience with cozy tranquility. Tucked in close proximity to downtown, you'll revel in the ease of accessing the city's dynamic attractions, exquisite dining, and abundant entertainment options. ✔ 3 Cozy Bedrooms ✔ Stand Alone Bathtub ✔ Hot Tub ✔ Airy Open Living Space ✔ Well-Appointed Kitchen ✔ Smart TVs in every Bedroom and the Living Room ✔ High-Speed Wi-Fi ✔ Convenient In-Unit Laundry ✔ Complimentary Parking

Hyde Park "Industrial-chic" with Private Backyard

This hand-crafted, urban-industrial loft-inspired apartment was designed to offer a most unique guest experience. The home is spotlessly clean, extremely comfortable, conveniently situated, and stocked with amenities. The apartment is located just a short stroll to SoHo (2 blocks) & Hyde Park Village (4 blocks), South Tampa's premiere spots for trendy restaurants, cafes, bars, and shops, AND minutes to downtown Tampa, Amelie Arena, Raymond James Stadium, & I-275

Tiny Tulum | Tropical Oasis in Tampa’s Heart!

Welcome to Our Romantic Tulum-Inspired Retreat! Escape to a tropical paradise at our enchanting Tulum-inspired oasis, designed with romance and relaxation in mind. Nestled in a serene neighborhood, our beautifully decorated retreat offers the perfect blend of luxury, comfort, and bohemian charm, creating an idyllic getaway for couples seeking a memorable experience. Why book a generic Airbnb when you can book a hand crafted Tropical Paradise?

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.