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.

Tampa's Hidden Gem 5/ 2.5 pool/Game-Theatre room !

Welcome to your ultimate Tampa getaway in Temple Terrace! Minutes from Downtown Tampa, Busch Gardens Tampa Bay, Ybor City, and the Tampa Riverwalk. This fully renovated 5BR home features a game room with pool table, massage chair & theater, plus a resort-style backyard with pool, covered patio lounge, TV, ping pong, gazebo, putting green and outdoor games—perfect for unforgettable stays with family and friends. Enjoy easy access to shopping, dining, and nightlife. Book now for the perfect escape

"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.

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 T and C Club

Welcome to The T and C Club! A featured home for the Make-A-Wish Foundation. Located 6 miles from the Tampa Airport, 7 miles from Raymond James Stadium and only 15 miles from award winning Clearwater Beach, this home is convenient as it gets. Completely refurbished, there is plenty of space to sleep 10 individuals comfortably, dining table for 10, a large resort-like backyard, saltwater pool, propane grill and all the fun you can imagine. This will truly be a case of you won’t want to leave!

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.

Sun & Shade | Bayshore Beautiful

Nestled just two blocks from iconic Bayshore Boulevard, this luxury South Tampa retreat offers the perfect blend of relaxation and convenience. Minutes from downtown, Hyde Park, beaches, dining, shopping, and nightlife, you'll enjoy the best of Tampa. Unwind by the private pool beneath majestic live oaks, soak up the Florida sunshine, or relax in the cool shade with a book, your favorite music, and a gentle breeze. Perfect for families and friends.

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

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.

The Happy Palms Retreat/ Saltwater Pool

Welcome to The Happy Palms Retreat – a private tropical oasis created for the perfect family getaway. Featuring a sparkling saltwater pool, pet-friendly accommodations, brand-new interiors, and thoughtfully designed outdoor living spaces, every detail has been carefully curated for comfort, relaxation, and unforgettable moments under the Florida sunshine. 🌴 place to stay is perfect for group trips.

Cozy AF Jungle-House Hideaway

We invite you to the **Cozy AF Jungle House**! Step into the foliage and immerse yourself in the jungle vibes. With every glance, you'll discover something new—from the sabretooth tiger skull to the romantic hot tub and even a crystal hanging banana. Adventurers, dare to play Jumanji if you’re feeling bold! Our goal is not just to provide a place to stay, but an experience you’ll cherish forever.

South Tampa Haven | King Bed | Near MacDill AFB

This spacious two-story home sleeps up to six guests comfortably. The main level features an open-concept kitchen, family room, and screened patio with brick pavers — perfect for entertaining. Upstairs you’ll find all three bedrooms, including a spa-like owner’s suite with custom closets, plus a game room with a sofa bed. A full bath on the main level adds extra convenience.