Holiday rentals with outdoor seating in Hillsborough County

The exterior of a charming bungalow is surrounded by lush greenery and colorful flowers. A pathway of distinctive patterned stones leads to a welcoming entrance with a blue door. The well-maintained garden complements the peaceful setting, inviting guests to explore the serene surroundings.

4.96 out of 5 average rating, 141 reviews

Bungalow Bliss on Highland

Enjoy our beautiful home privately for up to four guests. Perfect for friends, families, or a pair of couples looking to see and do the best Tampa has to offer! Located less than 15 minutes from the Tampa River Walk, Downtown Tampa and Ybor City, and less than 10 minutes from Busch Gardens Amusement Park and the famous Zoo Tampa, your options are many. From restaurants to kayaking, biking to BBQs, we welcome you to find your peace (or adventure) as you nestle into Bungalow Bliss on Highland.

A serene outdoor space features a sparkling pool framed by lush tropical landscaping. A relaxing spa is integrated into the pool area, accompanied by comfortable lounge chairs. A shaded cabana and grilling station are visible in the background, enhancing the inviting ambiance.

4.94 out of 5 average rating, 129 reviews

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.

The living room is furnished with a large sectional sofa adorned with red accent pillows. A wooden coffee table is situated on a patterned rug, complemented by contemporary artwork on the walls. A wall-mounted television is visible, along with a stylish clock.

4.98 out of 5 average rating, 243 reviews

Bucs Bungalow Stadium Home, King Bed Suite, Gym

Whether you’re here for business or pleasure, Bucs Bungalow is your place! Conveniently located at the heart of Tampa Bay less than 10 mins from the airport. A 0.6 mile walk to a football game or a concert at Raymond James Stadium. No expensive parking fee and have your own private parking in our driveway that can accommodate 4 cars. Have a worry-free good time without the drinking and driving. While our fully stocked kitchen, dedicated workspace and home gym is ideal for your longer stay!

4.98 out of 5 average rating, 265 reviews

Two wooden Adirondack chairs are positioned on a deck overlooking a serene lake. A floating dock extends into the water, featuring two red lounge cushions. The clear blue sky enhances the tranquil atmosphere, with greenery visible along the shoreline.

Cottage in Tampa

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.

4.94 out of 5 average rating, 109 reviews

Flat in Tampa

Mint House by Kasa | Studio in Tampa Downtown

Step into the energy of Tampa’s thriving Channel District (Channelside), close to the Sparkman Wharf, Benchmark International Arena, and the Florida Aquarium. Perfect for work trips and longer stays, you’ll find comfort in our selection of apartment-style suites with full kitchens and in-unit laundry, plus an outdoor plunge pool, grill area, and fitness center. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text, and Virtual Front Desk via mobile device.

The open-concept living area features a spacious sectional couch and modern chandelier providing ample lighting. Large windows allow natural light to illuminate the room and showcase the greenery outside. A stylish dining table complements the space, creating an inviting atmosphere for gatherings.

4.96 out of 5 average rating, 193 reviews

Luxe TPA Experience! 5 bedrooms, Walk to Hyde Park

Experience Tampa in a new way, professionally furnished, feel like you're at your favorite luxury hotel! We can't stress it enough, LOCATION! In the core of one of the best areas in Tampa, walk to Bayshore Blvd, Hyde Park, and the Soho District. This home is equipped with the highest end finishes and Thermador appliances to provide you with a one of a kind stay in Tampa. Nobody gets the short stick with 5 spacious bedrooms, 4 full baths, and half baths. We look forward to hosting you!

4.98 out of 5 average rating, 605 reviews

A rustic tiny house stands within a lush garden, featuring a wooden deck adorned with comfortable seating. The entrance showcases large glass doors, framed by greenery, while a charming pathway of stones leads toward the entrance. Subtle decorative elements enhance the inviting outdoor space.

Tiny home in Tampa

Cozy AF Tiny-House Oasis

Awarded a *Unique Stay* by Airbnb, welcome to the **Cozy AF Tiny-House Oasis**, a rustic tiny home that started its journey as a world-traveling storage container. Now transformed into a charming cottage, it’s filled with unique and fun details waiting to be discovered. Enjoy the entire backyard, complete with a hot tub, koi pond, fire pit, hammocks, greenhouse, and even a bunny garden! Our goal is not just to offer you a place to stay but an experience you’ll cherish forever

A cozy living area features a comfortable gray sofa adorned with an array of textured pillows. Two large paintings depicting tropical scenes are displayed on the wall above, complemented by lush green plants on either side. Natural light filters through white curtains, enhancing the inviting space.

4.95 out of 5 average rating, 280 reviews

Boho Bungalow close to Downt- SOHO - Hyde P- TIA

Beautiful historic bungalow located in the heart of Tampa, close to everything the city has to offer. Featuring a rustic boho design, our home provides a relaxing retreat just 5 minutes from Downtown Tampa. Enjoy the convenience of free parking and easy self check-in, along with a fully stocked kitchen, SMART TVs, and a laundry room. The bohemian atmosphere makes it ideal for vacations, romantic getaways, family visits, concerts, sporting events, or work trips.

4.97 out of 5 average rating, 440 reviews

A modern bathroom featuring a round mirror above an elegant wooden sink with a metallic bowl. Exposed brick walls and dark accents create an industrial feel. A sleek, black toilet complements the stylish glass shower, which is designed with contemporary tile.

Flat in Tampa

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

4.97 out of 5 average rating, 378 reviews

The exterior of a coastal cottage is shown, featuring a gravel driveway and tropical landscaping with palm trees. Two wicker chairs are positioned under a covered porch, inviting relaxation. Large windows allow natural light to brighten the welcoming facade.

Cottage in Dunedin

Walk Downtown and to Waterfront, Mins to Beaches

Just steps to Main Street Dunedin and minutes to Honeymoon Island and Clearwater beach, this stylish upstairs 2-bedroom cottage blends modern coastal comfort with beautiful design. Enjoy treetop views, two king beds, a sleeper sectional, and a fully stocked stay. Walk to dining, shops, breweries, and Dunedin’s stunning waterfront sunsets, then drive minutes to the beaches. Pet-friendly with every detail beautifully done—reserve the Barefoot Parrot today.

4.98 out of 5 average rating, 269 reviews

A serene sleeping area is defined by a wooden bed frame draped with sheer white fabric. The plush bedding features a subtle pattern. A vibrant green plant wall provides a backdrop, and a decorative neon sign reading 'Tiny Tulum' adds a modern touch.

Guest suite in Tampa

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?

The living area features a spacious layout with a comfortable gray sofa and a decorative wooden coffee table. A flat-screen TV is mounted on the wall, while a well-equipped kitchen with modern fixtures is visible in the back. Natural light enters through the windows, creating a bright atmosphere.