Holiday rentals in Hillsborough County

Guest house in Davis Islands

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.

LocationValueNearby

4.86 out of 5 average rating, 1132 reviews

Superhost

A covered patio area is showcased, featuring comfortable seating arrangements that include two lounge chairs and a sectional with a coffee table. The space is framed by a screened enclosure, providing unobstructed views of the pool and surrounding greenery.

4.88 out of 5 average rating, 109 reviews

Bayshore - Pool - Outdoor Kitchen - Yard

Get away in elegance and soak up the South Tampa sun in this gorgeous 4 bedroom, 2 bath pool home. Visit with family and friends in the covered patio and pool area, cook in the outdoor kitchen or relax with a drink by the pool (not heated). Enjoy great restaurants or visit one of the many attractions nearby - The Aquarium, Armature Works, Sparkman's Wharf, just to name a few. Visit Bayshore Park Fitness Trail, just minutes away and explore the 4.5 miles of waterfront views. Enjoy all of Tampa!

ValueFamilyIndoor spaces

4.98 out of 5 average rating, 274 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, Private Dock, Romantic, Fishing

You’ll have the Entire 500sq ft Cottage & private entry, deck and fishing dock, charcoal grill, 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, soft water, WiFi, smart TV’s, blackout drapes, luxury hair products, high thread count linens. Fully stocked kitchen, reverse osmosis drinking water, k-cup/drip coffee machine. The lake has bass, complimentary fishing poles/tackle box. Rentable Canoe & Kayaks.

ValueFamilyOutdoor spaces

Superhost

Home in Pinellas Park

Private Pool • Boat Parking • Near Golf Beaches

home with private pool and 10-car parking. 3 bedrooms, 2 baths, 3 beds, sleeps 6. Full kitchen, washer/dryer, AC, wifi, TV, laptop friendly workspace A beautiful property located in Central Pinellas County close to the beaches st Pete Beach, Madeira Beach ,Indian rocks, Jons pass 15-25 min plenty of parking including boat up to 40 feet centrally located 15 minutes away from Tampa airport 15 minutes away from downtown St. Petersburg 5 to 10 minutes away from restaurants and shopping centers

ParkingNearbyOutdoor spaces

5.0 out of 5 average rating, 4 reviews

4.93 out of 5 average rating, 41 reviews

CASA SOLÉ | 5 Min MacDill AFB | Fenced Yard

Welcome to Casa Solé, a serene and stylish retreat in the heart of South Tampa, perfectly designed for relaxation and exploration. Our home combines modern elegance with cozy comforts, making it the perfect getaway for couples, families, or business travelers. Located just minutes from the West Shore district, and MacDill AFB, Casa Solé is near Tampa’s best dining, shopping, and entertainment. Whether enjoying sunny beaches or relaxing, Casa Solé offers the perfect home for your stay

ValueFamilyAir conditioning

4.97 out of 5 average rating, 100 reviews

Home in Town 'n' Country

Traditional Home in Tampa

Our recently remodeled home features a beautiful private pool with fully automated controls for easy enjoyment. Inside, you'll find modern electronics and amenities designed for comfort and convenience. Located just 7 miles from Tampa International Airport, we’re also close to top attractions like Busch Gardens, Raymond James Stadium, and Downtown Tampa. Enjoy the privacy of a spacious pool home tucked away in a quiet cul-de-sac—perfect for relaxing after a day exploring Tampa Bay.

FamilyLocationTV

4.98 out of 5 average rating, 194 reviews

Townhouse in Tampa

Luxe Meets Value | XXL Rooftop | KingBed | Sleep 8

Live the luxe Tampa life without the luxury price tag! This stylish 3BR, 2.5BA villa sleeps 8 and gives you room to relax, recharge, and enjoy Tampa your way. Unwind in the plush king bedroom, enjoy seamless indoor-outdoor living, or escape to your private fenced rooftop for morning coffee, sunset drinks, and good conversation. Enjoy upscale comfort, privacy, and plenty of space just minutes from Downtown Tampa, dining, nightlife, attractions, sports, and entertainment.

FamilyValueBack garden

4.92 out of 5 average rating, 172 reviews

Tampa 3BR | Hot Tub | Near Airport & 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

FamilyLocationGetting around

5.0 out of 5 average rating, 12 reviews

Heated Pool | Hot Tub | Pickleball • South Tampa

Enjoy a private South Tampa backyard resort with a heated pool, hot tub, pickleball/basketball court, putting green, and cedar outdoor shower, and on-site Level 2 EV charger. Pool heater is available for an additional fee. With four bedrooms and inviting guest spaces, the home is ideal for families and groups. Convenient to MacDill AFB for PCS moves, TDY stays, and visiting military families, with easy access to downtown Tampa and Gulf Coast beaches.

FamilyLocationPool

4.95 out of 5 average rating, 377 reviews

The entrance of a bungalow features a bright yellow front door framed by lush green tropical plants. A stone pathway leads up to the door, flanked by manicured landscaping, creating an inviting entryway. Two windows are visible, adding charm to the home’s facade.

Bungalow in Tampa

Lemon House near Downtown Tampa

Settle in at The Lemon House, our 1949 2/1 bungalow, offers a central location to all of what Tampa offers. North Hyde Park is minutes from UT & Tampa’s Downtown scene: Armature Works, Riverwalk, Historic Hyde Park, The Heights & Bayshore. Prime for conventions, concerts, the port, sport attractions, Zoo, Aquarium, Busch Gardens & Beaches (30mins). Overall central for an eclectic variety of restaurants, parks, breweries and nightlife.

LocationValueKitchen

A private pool area is surrounded by lush greenery, featuring a spacious pool with a spa at one end. Sunlight reflects off the clear water, highlighting the relaxing atmosphere of the outdoor space.

4.91 out of 5 average rating, 175 reviews

Tampa Waterfront Heated Pool/ Hot Tub Oasis w Dock

Enjoy this South Tampa waterfront pool home, centrally located off Westshore. Close proximity to Clearwater, downtown Tampa, and Orlando. Featuring brand new contemporary finishes and breathtaking views. This home Is monitored on video surveillance on the exterior corners of the home as well as the back yard and front door ring camera. Device will record during reservations. No parties of any kind will be permitted.

FamilyValueSleep quality

A covered patio area features a built-in seating arrangement with soft cushions, accompanied by a round coffee table. The space opens to a sparkling pool surrounded by wooden decking and lush greenery, offering a serene outdoor experience.