Holiday houses in Hillsborough County

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Top-rated holiday rentals in Hillsborough County

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Top Guest favourite
Guest suite in Tampa
4.96 out of 5 average rating, 264 reviews

"Chic/cozy Petite Studio •"Spa-Inspired Shower. 1”

Welcome to your serene hideaway in Citrus Park, where modern comfort meets thoughtful design. Just 11 minutes from Tampa International Airport, and free parking on premises this stylish and private studio is the perfect spot for couples, solo travelers, or business guests seeking a peaceful and rejuvenating stay. Located in a quiet, safe, and central neighborhood, you’ll enjoy a private entrance, free on-site parking, and easy access to restaurants, grocery stores, and major Tampa attractions.

Guest favourite
A serene pool area features a shimmering blue pool surrounded by lush greenery, including tropical plants. Two lounge chairs are positioned nearby on a brick patio, providing a comfortable spot for relaxation. A detached structure is visible in the background, set amongst a canopy of trees.
Guesthouse in Tampa
4.88 out of 5 average rating, 411 reviews

Pool Side Getaway, Walk/Bike Tampa River Walk

Experience Tampa from our little slice of Heaven right in the heart of Tampa Heights. This is a detached private Pool House in our backyard. At 264 sqft, It has a full Bath, Kitchen, and studio space with a Queen memory foam mattress, and work space / breakfast table. Enjoy the Pool and its tropical surroundings or just relax in a lounge chair. We are walking distance to Lee’s Pizza, Armature Works, River Walk, and much more... Included is a smart TV, WIFI, and Two Bicycles to go explore.

Top Guest favourite
A charming cottage exterior is framed by lush tropical plants and colorful flowers. Double French doors are highlighted with decorative glass, leading to a welcoming entrance. Brick flooring extends to the doorstep, adding to the cozy, inviting feel of the outdoor space.
Guesthouse in Tampa
4.86 out of 5 average rating, 1,042 reviews

Charming private guest house.

Our charming one bedroom guest cottage on Davis Islands sleeps 2 (queen-sized bed). Bathroom with large shower. Clean and cozy room has cable tv, wi-fi, mini fridge, microwave, Keurig coffee maker. Gorgeous neighborhood, walking distance to downtown DI restaurants, coffee shops, rentable bikes, Amalie Arena, the Riverwalk, Hyde Park, downtown Tampa, the Convention Center, Channelside & TGH. 2 miles from cruise port. 15 min. drive to Bush Gardens. Enjoy the sunset at the end of the island.

Top Guest favourite
A two-story guest house is shown with a well-maintained exterior. The image features a staircase leading to the upper level and a spacious pool area with surrounding pavers. An outdoor dining space with a table and chairs is visible, providing options for relaxation and enjoyment.
Home in Tampa
4.97 out of 5 average rating, 116 reviews

Entire Guesthouse - Tampa

Looking for a great stay in Tampa? This is the perfect place! One bed bedroom and one bath upstairs guest house that is detached from the main house. Located in a family-friendly neighborhood, this gem is centrally located to everything Tampa has to offer. Pool is not part of listing. Parking is in the street in front of house. No more than 1 vehicle per renter. Perfect for short term stay! Close to: TPA - 12 min Downtown Tampa - 8 min Raymond James Stadium - 10 min Amelie Arena - 9 min

Top Guest favourite
Guesthouse in Tampa
4.95 out of 5 average rating, 117 reviews

Easy Tampa | Fast WiFi | Kitchenette | Queen Bed

Newly Remodeled stylish and private studio suite with queen bed, bathroom, living/dining/work area, kitchenette (Dry), and shared laundry in the trendy Old Seminole Heights neighborhood. With an 83/100 walk score its easy to visit bars, restaurants, diners, bakeries, and quaint shops, or stroll the tree-lined streets of 100+ year old houses. This spot is perfect for the Tampa explorer with easy access to downtown. Free street parking, free WiFi, free shared laundry (in adjacent space).

Top Guest favourite
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
4.98 out of 5 average rating, 247 reviews

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.

Guest favourite
A modern two-story house features a clean white exterior and a staircase leading to the upper level. Potted plants flank the entrance, while outdoor seating awaits nearby, creating a welcoming space for relaxation.
Guesthouse in Tampa
4.87 out of 5 average rating, 201 reviews

Dee's 5-star Tampa Location Unit 1

1.7 miles from the Superbowl stadium!!!Beautiful completely remodeled house in the desired West Tampa area. This is the perfect location walking distance to Raymond James Stadium, within minutes from Downtown Tampa, Armature Works, Ybor city, Tampa International Airport, with easy access to Clearwater beach and St Pete beach. Forget about your mileage worries as every must-see place in Tampa is less than 10 minutes away. Leaving you stress-free vacations and pure enjoyment.

Top Guest favourite
The lounge area features a comfortable loveseat and accent chair, complemented by a coffee table. Natural light floods in from two skylights and several windows, creating a bright and airy environment. A small kitchen area is visible in the background, along with stairs leading to the loft.
Guesthouse in Tampa
4.97 out of 5 average rating, 101 reviews

Cozy Tropical Guesthouse for Two

Welcome to our charming guesthouse in Riverside Heights, a safe and centrally-located neighborhood — 10 minutes from Downtown Tampa. This unique retreat for two has tropical vibes, a loft sleeping area, a well-stocked kitchen, and a private patio. Newly built from floor to ceiling, it is filled with stylish decor and luxurious furnishings. Your hosts include a Tampa native and food writer which means you’ll get the best recommendations on things to do and places to eat!

Top Guest favourite
The room features a spacious bed with light bedding and accent pillows. Nightstands and lamps are located on either side. A desk and chair are visible in the corner, while a window with light curtains allows natural light to enter the room.
Guest suite in Tampa
4.97 out of 5 average rating, 152 reviews

Private Studio w/Free Parking Walk to Bucs Stadium

Charming private studio just minutes from Raymond James Stadium. Enjoy a private entrance, furnished outdoor area, kitchenette, A/C, smart TV, and free parking(for 2spots). Perfect for business or leisure travelers attending local events. Conveniently located near the airport and downtown. Relax in a quiet, well-equipped space with self check-in, fresh linens, coffee, and all the essentials for a pleasant stay. Great location, safe neighborhood, and fast Wi-Fi included.

Top Guest favourite
A circular sign featuring the word 'Welcome' in white, crafted with a decorative cursive font. The sign is accented with a black and white checkered bow and adorned with greenery, providing an inviting entryway touch.
Guest suite in Tampa
4.83 out of 5 average rating, 303 reviews

Quiet, clean and cozy room

This room is a great place to rest, cozy, clean and organized, close to city attractions such as 8 minutes from Busch Garden and Adventure Island, 7 minutes from Tampa Zoo, 13 minutes from Ybor City and Downtown Tampa, 14 minutes from the University of Tampa, 11 minutes from USF and Moffit Cancer Center, 15 minutes from the Port of Tampa and The Florida Aquarium, 12 minutes from Tampa Airport, 10 minutes from I 275 North and South. It is a quiet neighborhood,

Top Guest favourite
Guest suite in Tampa
4.95 out of 5 average rating, 231 reviews

A&A Suite Near Tampa International Airport

A&A, the place to arrive on time for your flight. If you are traveling by plane for business, vacation or personal matters, A&A suite allows you to be 4.1 miles from the TPA. The comfortable, spacious room, with private bathroom, independent access and free parking, workplace, Wi-Fi. Strategic location to explore Skyway Park with tennis courts and playground. Golf fan? Visit Rocky Point Golf Course and Cypres Point Park, to enjoy the beach and a sunset.

Top Guest favourite
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
4.96 out of 5 average rating, 114 reviews

"Luxury Casita/Jacuzzi/Bush Gardens/USF/Casino"

Welcome to Tampa Luxury Casita, a stylish and centrally located retreat featuring a relaxing jacuzzi and a private golf putting green. Located within walking distance to Busch Gardens, this beautifully designed space offers modern amenities, cozy comforts, and easy access to top attractions. Whether you're here for a weekend getaway or an extended stay, our casita promises a luxurious and unforgettable experience. Book now and enjoy the best of Tampa Bay!

Popular amenities for Hillsborough County holiday rentals

Destinations to explore