Vacation rentals in Hillsborough County

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Top-rated vacation rentals in Hillsborough County

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favourite

Guest suite in Tampa

4.97 out of 5 average rating, 124 reviews

Brand New Tiny Tampa, Entertaining Backyard & BBQ

Brand new 1+1 located in Tampa. Completely renovated, in a quiet neighborhood. Tiny Tampa is a cozy granny suite, separate unit from the main house rental, with private entrance and free parking for two vehicles. We have provided a beautiful private backyard patio with BBQ for you to enjoy. 🌟Walking distance to Busch Gardens & Adventure Island. 🌟1 mile from USF. 🌟20 min drive to downtown, airport, Sparkman Wharf, Amalie Arena, Raymond James Stadium, Ybor City & beautiful white sand beaches.

Feb. 22 – Mar. 1

$163 CAD per night

Guest favourite

Home in Tampa

4.97 out of 5 average rating, 107 reviews

Downtown Tampa Pool House! Walk to Armature Works!

Location! Location! Location! Enjoy Tampa at this modern brand new remodeled POOL HOUSE with the BEST LOCATION & with POOL access! SAFE & EASY location in downtown. Come Experience events, food, festivals & nightlife only 1 block from #1 destination, Armature Works- a famous destination for food, fine dining, events, & fun! Enjoy a quiet downtown getaway to enjoy the pool, biking, paddle board or walk the beautiful Riverwalk. Full kitchen, W/D & Everything you need provided for a NO stress stay!

Oct. 6 – 13

$217 CAD per night

Guest favourite

Cottage in Tampa

4.99 out of 5 average rating, 139 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, 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. Pet fee $50. Elope/Proposal packages IG lakepossibility

Aug. 21 – 28

$289 CAD per night

Guest favourite

Apartment in Tampa

4.98 out of 5 average rating, 209 reviews

La Casita | Port Tampa cozy home close to beaches.

Welcome to La Casita in Port Tampa City, just 15 mins from downtown Tampa & TPA Airport and 30 mins from Famous Beaches & Piers. Your well-stocked vacation home features 2 bedrooms with a comfy king & queen-sized bed, a fully stocked kitchen, washer & dryer, and free reserved parking. Enjoy contactless entry, 2 Smart TVs & fast free Wi-Fi with work station and wireless phone charging. Explore all that Tampa has to offer and create memorable moments with your loved ones in this peaceful home!

Sep. 1 – 8

$157 CAD per night

Guest favourite

Guesthouse in Davis Islands

4.84 out of 5 average rating, 892 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.

Jan. 14 – 21

$150 CAD per night

Guest favourite

Guesthouse in Tampa

4.96 out of 5 average rating, 188 reviews

Tiny House Oasis Blue Vatican . Near MacDill Base

Enjoy this small and beautiful Oasis, a perfect hideaway to forget about the noise of the city, relax with the aroma diffusers and your favorite music; In the mornings fall in love with our solarium while having a good coffee. We are located in South Tampa just 3 minutes away from the MacDill Airbase. 5 min Picnic Island Park, 10 min Port Tampa Bay Cruise and Downtown, 15 min International Airport. 15 min Raymond James Stadium, 40 min Clearwater Beach. Free Parking for up to 2 cars.

Jul. 7 – 14

$117 CAD per night

Guest favourite

Tiny homes in Tampa

4.92 out of 5 average rating, 123 reviews

"sensation of tampa" near/Busch Gard/usf/casino

Experience the challenge of an adventure in a different style THE TAMPA FEEL is a 60×12 HeartLand Shed in the side yard of my house. It is completely private since it has its own patio divided by a 6' fence, made inside with a unique style, it has a wonderful living room, shared Pool, a fully equipped modern kitchen for your comfort, a bathroom, it will also have a nice gazebo with plants that You will enjoy the atmosphere for any picnic or grill event, and you have a space to do BBQ.

Mar. 24 – 31

$150 CAD per night

Guest favourite

Apartment in Tampa

4.95 out of 5 average rating, 268 reviews

Private and cozy studio close to the Airport

This apartment is amazing ,completely remodeled and luxury , fantastic location! , fast internet .Very comfortable to work , quiet neighborhood. The apartment is equipped with everything you could need. Completely private with separate entrance ,without any connection to the main house. Very clean, fresh decoration to spend a beautiful vacation. (Approximately 40 minutes away from Clearwater beach) This apartment is close to supermarkets, attractions and downtown. We are available 24/7

Oct. 14 – 21

$134 CAD per night

Guest favourite

Apartment in Tampa

4.98 out of 5 average rating, 116 reviews

Perfectionist's Dream #1 Ybor,Down Town, close-in

Centrally located near the heart of downtown Tampa and the City of Ybor, our top floor Perfectionist Dream Too, places you near everything you need to do and see in Tampa. Careful attention has been paid to detail and comfort, so you may enjoy a restful and relaxing stay. A fully appointed kitchen, comfortable bed and convertible couch, accommodate up to four guests. Additionally you'll enjoy a beautiful night view from your spacious porch. We know you will love your stay.

Jun. 16 – 23

$190 CAD per night

Guest favourite

Condo in Tampa

4.95 out of 5 average rating, 131 reviews

Waterfront condo with sunset views of Tampa Bay.

This newly furnished condo features a balcony with waterfront views of Tampa Bay and amazing sunsets. Includes a heated pool, volleyball court, BBQ and fire pit as well as on-site laundry. Just minutes from Tampa International Airport. Near Clearwater and other desirable beaches. Nearby attractions include Busch Gardens, Adventure Island, the Port of Tampa, Historic Ybor City, Tampa Bay Performing Arts Center, Tropicana Field, Amalie Arena and Raymond James Stadium.

Oct. 1 – 8

$253 CAD per night

Guest favourite

Guesthouse in Tampa

4.97 out of 5 average rating, 271 reviews

Newly Renovated Private Eco Cottage

Welcome to our newly renovated adorable studio cottage located in the heart of many major attractions. A hidden gem and a foodie's paradise offering everything from Venezuelan to Vietnamese cuisine. Walk to a family friendly classic arcade and craft beer bar at the end of our street. Contains a full kitchen, off street parking, patio, queen memory foam mattress, and sleeper sofa. Eco friendly space - filtered shower/water pitcher - non-toxic cleaners and products.

Sep. 4 – 11

$127 CAD per night

Guest favourite

Guesthouse in Tampa

4.97 out of 5 average rating, 143 reviews

Coastal in the Heights

In the quaint historic neighborhood of Seminole Heights a tropical setting awaits you...This coastal cottage style getaway in Tampa, FL includes everything you'll need for a weekend getaway, including a queen sized bed, fully equipped and stocked kitchen, full bathroom with tub/shower combo, stackable washer/dryer, Iron, ironing board, and hair dryer. Grill your dinner and enjoy our Florida weather outside in your own private courtyard patio outside the cottage.

Aug. 13 – 20

$158 CAD per night