Holiday houses in Hillsborough County

Guesthouse in Davis Islands

4.87 out of 5 average rating, 1117 reviews

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.

LocationAccessComfort

4.97 out of 5 average rating, 179 reviews

A private outdoor area features a golf putting green with a textured surface, a jacuzzi with soft blue hues, and a wooden pergola. Near the pergola, a grill is provided alongside comfortable seating. Vibrant green walls and string lights enhance the inviting atmosphere.

Guesthouse in Tampa

"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.

ValueHospitalityComfort

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, 140 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.

4.81 out of 5 average rating, 120 reviews

A modern open-concept living area features a sleek kitchen with granite countertops and stainless steel appliances. The space is well-lit by recessed lighting and natural light streaming through the windows. Comfortable seating arrangements are visible, along with a fireplace that adds a cozy touch.

Home in Carrollwood

Family-friendly getaway home in the heart of Tampa

Modern home in the heart of Tampa. Within great distance from amazing entertainment, restaurants, cafes, bars, breweries, and much more. Perfect for weekend getaway, business trip, staycation, work-from-home alternative, or cozy home base while exploring everything Tampa has to offer. Step inside to find a bright and spacious living room with tile floors and plenty of natural light. The modern kitchen boasts granite countertops, stainless steel appliances, and everything you need to cook.

4.98 out of 5 average rating, 234 reviews

Home in Clearwater

Specious home W/ Heated Pool ! ! ! Great Location.

Cozy, spacious home 🏡 w/ heated swimming 🏊‍♀️ pool, next to a golf ⛳️ course. Close to the famous beaches ⛱️, St.Pete and Tampa. This cozy open home has a large living room, big kitchen and pool deck patio. All 3 bedrooms have large TV's. The big back patio has a swimming 🏊‍♀️ pool, TV, fridge and BBQ for cook outs & R&R. Located in a quiet family-friendly neighborhood. Location! 15 min - Clearwater Beach, Dunedin, Safety Harbor 30 min from - St.Pete, TPA Airport, Tampa

PoolCleanlinessNearby

4.92 out of 5 average rating, 168 reviews

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

4.8 out of 5 average rating, 142 reviews

A serene outdoor space features a rectangular swimming pool, surrounded by a spacious paved area. Two chairs are positioned near the pool. A white fence provides privacy, while trees line the background, enhancing the tranquil setting.

Home in Town 'n' Country

Villa Paradise

Relax with family in this quiet place to stay. Spacious house to enjoy with family and friends, enjoy a beautiful pool and a very large backyard, outdoor kitchen (only for 6 people). NO MORE THAN 6 PEOPLE. I do not allow events. You do not have access to the garage. I live in an apartment that I have in the garage. I do not have access to the accommodation from anywhere while the house is reserved. I am informing you of this for my safety and peace of mind. Thank you.

LocationCleanlinessKitchen

A sparkling outdoor pool is surrounded by a spacious patio, featuring light-colored paving stones. A thatched-roof cabana is visible in the background, providing shaded seating. The clear blue water of the pool reflects the sunlight under a bright sky, creating a serene outdoor retreat.

4.94 out of 5 average rating, 139 reviews

Private House with Pool and Cabana

Beautifully updated house with pool and cabana. 3 Bedrooms with queen beds, upscale bedding, TV's in every room, full kitchen and dinning area, BBQ, ready to cook, outdoor pool with cabana with a TV, firepit, gardens, park like backyard. Great for families and business trips. Close to everything, all shopping, 15 minutes to downtown, airport, Hyde Park, International Plaza, Busch Gardens and more. Close to parks, beaches, fishing, Bayshore Blvd, Gandy Bridge.

4.97 out of 5 average rating, 459 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.

Apartment 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

Superhost

A modern kitchen features white cabinetry and stainless-steel appliances, including an oven and refrigerator. Large windows allow natural light to fill the space, enhancing the light wood flooring. A small potted plant rests on a woven mat, adding a touch of greenery to the room.

Home in Palmetto Beach

4.9 out of 5 average rating, 155 reviews

Cozy Historic & Chic Home ~ 6 mins from downtown

Step into Tampa history with this renovated 1910 home in Palmetto Beach! Blending historic charm with modern comforts, this cozy retreat is minutes from downtown Tampa, Ybor City, the cruise port, and Amalie Arena. Walk or bike to DeSoto Park for waterfront views or explore top dining and nightlife nearby. Cruise Port: 2 miles Convention Center: 2 miles Amalie Arena: 2.5 miles Sportsplex of Tampa: 6 miles Tampa Airport: 9 miles

LocationHospitalityCleanliness

Apartment in Historic Hyde Park

A cozy living area features a brown sofa paired with two woven stools. A fireplace is elegantly styled with stacked logs, while soft lighting illuminates the space. A small dining table with wooden chairs is positioned near a window, enhancing the inviting atmosphere.

4.98 out of 5 average rating, 187 reviews

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.

A cozy bedroom is highlighted by large windows that allow ample natural light. A spacious bed is adorned with soft bedding and decorative pillows in neutral and warm tones. A fresh plant is visible through the window, adding a touch of nature to the interior.