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Guesthouse vacation rentals in Hillsborough County

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in Hillsborough County

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

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Top guest favorite
Guesthouse in St. Petersburg
4.97 out of 5 average rating, 234 reviews

Centrally Located Cozy 1-bed Private Cottage!

This charming private cottage is ideally located near beautiful views, beaches, art, culture, restaurants, and a variety of family-friendly activities. Guests love the space for its peaceful ambiance, great location, and inviting outdoor areas. It’s a perfect stay for couples, solo travelers, business guests, or anyone looking for a cozy getaway. Enjoy private parking just steps from the entrance, along with a BBQ grill, a brand-new hot tub, and an outdoor gas fireplace—perfect for relaxing!!!

Top guest favorite
A hot tub is positioned beside a fire pit, surrounded by greenery and decorative lighting. A projector screen displays images, creating an inviting atmosphere for outdoor entertainment. The space is enhanced by potted plants and gravel pathways, offering a serene retreat.
Guesthouse in Tampa
4.94 out of 5 average rating, 220 reviews

Hot Tub + Outdoor Theater + Free Wine! + Ping Pong

You will Experience serenity at The Loft House Retreat! Amidst lush Florida plants, unwind in a hot tub, challenge friends to ping pong, or cozy up by the fire pit and Projector. Inside, enjoy 2 full beds & refresh in a full bathroom with a walk in Shower. Explore Tampa's gems: Busch Gardens, Downtown Tampa, Waterstreet, Armature Works, Zoo Tampa, The Florida Aquarium, Raymond James Stadium, Sparksman Wharf, Michelin-starred restaurants, and historic eateries. Book your unforgettable escape now!

Guest favorite
Guesthouse in Tampa
4.89 out of 5 average rating, 159 reviews

Private Seminole Heights Guest Home

Nestled in Tampa's Old Seminole Heights (OSH) Neighborhood right along the Hillsborough River. This one bedroom, one bath with kitchenette cottage is sure to be a peaceful place to relax on your trip to the Tampa Bay Area. Our cottage has been recently renovated with all appliances, fixtures, and furniture brand new. It located on the backend of the property towards the end of the driveway and is located on a very quiet street. Parking is on-street parking, the driveway is for the main house.

Top guest favorite
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
4.97 out of 5 average rating, 147 reviews

"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.

Guest favorite
A modern suite features a cozy bed with a stylish headboard, complemented by patterned bedding. A glass-enclosed bathroom area showcases a freestanding tub. Natural light enters through the entryway, and the sleek kitchen is visible in the background, enhancing the open design.
Guesthouse in Tampa
4.96 out of 5 average rating, 278 reviews

K4 Mimi's Ste Casino

THIS SPACE IS FOR THE EXCLUSIVE USE OF ONLY TWO GUESTS. You get the entire suite. With a modern open concept this suite is private and convenient, ideal for a romantic getaway or just for a business travel or vacation. Walkable distance to Seminole Hard Rock & Casino. It has a kitchen, a cozy queen bed, bathroom, 55” TV (Roku) Internet (Wi-Fi) and private entrance. Located nearby many attractions (Bush Garden, Adventure Island Parks, Downtown Town, Restaurants and Florida State Fairgrounds.

Top guest favorite
A charming guest house exterior is showcased, featuring a sloped roof and large glass doors. The inviting solarium area displays comfortable seating arrangements. Lush green plants are positioned beside the entrance, and the space is surrounded by well-maintained artificial grass, enhancing the outdoor atmosphere.
Guesthouse in Tampa
4.95 out of 5 average rating, 369 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.

Guest favorite
A well-designed fire pit area is surrounded by vibrant landscaping, featuring five blue adirondack chairs positioned around a stone circle. Lush palm trees provide a tropical ambiance, and a gravel path leads to the space, inviting relaxation in the private backyard.
Guesthouse in St. Petersburg
4.85 out of 5 average rating, 405 reviews

NEW Luxury Casita w/Hot Tub, Fire Pit, Backyard🏝☀️🏖

Welcome to Casita Citron, a beautiful new tropical paradise in the heart of St. Pete! Tranquil & centrally-located: close to nature trails, shopping, downtown St. Petersburg, & Tampa. Minutes to St. Pete Beach, ranked #1 in USA! Washer & dryer on site. Private fully fenced in backyard with fire pit. Luxurious hot tub spa with speakers, water shooters, & LED lights. Heated outdoor shower. Memory foam mattress. SmartTV. Second queen size bed available upon request (AeroBed with foam topper).

Top guest favorite
A vibrant blue tiny house exterior is visible, featuring large glass double doors that lead inside. A green grass mat is placed at the entrance, and a hot tub is situated to one side, surrounded by a patio area and mature trees.
Guesthouse in Tampa
4.98 out of 5 average rating, 221 reviews

ZERO Cleaning Fees - Hot Tub Tiny House

Welcome to the Tiny Heights! Our quaint little tiny house features exclusive hot tub access, a full kitchen, private bathroom, shower and sink, wifi, AC, TV, Apple TV, and a beautiful private patio seating area. Tiny Heights Airbnb is located in the Seminole Heights area of Tampa and is within walking distance to an awesome selection of restaurants, bars, breweries, coffee shops and shopping. Just 4 miles from T.I.Airport and 2 miles from Raymond James Stadium, Ybor City & Downtown Tampa

Guest favorite
Guesthouse in Tampa
4.94 out of 5 average rating, 140 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 favorite
A spacious sleeping area features a modern white bed dressed in a black coverlet, complemented by matching throw pillows. A sleek dresser stands nearby, and the wall behind the bed showcases a stylish wavy pattern in black and silver. A small seating area with two chairs is visible.
Guesthouse in Tampa
4.97 out of 5 average rating, 362 reviews

Romantic Getaway*FREE Decor AnyOcassion*Relax Bath

A cozy place to have your vacation in Tampa, private entrance and parking.We include decorations for all occasions:birthday,wedding,special day, show your love, and more! Contact us with your ideas and we'll make this trip unforgettable! Located in a central area of Tampa, close to Bush Garden/Adventure Island, Raymond James Stadium,Tampa International Airport,Ybor City,Downtown Tampa,Clearwater Beach and more! Peaceful and centrally-located place to enjoy as a couple to your liking.

Top guest favorite
Guesthouse in St. Petersburg
4.98 out of 5 average rating, 264 reviews

Historic Old Northeast Get A Way

Carriage house converted to cozy updated 1 bedroom plus separate den/office above garage apartment in historic Old Northeast. The den/office has a new queen Murphy bed which will allow a second private sleeping space. Two blocks walking distance to Vinoy Waterfront Park and downtown St Pete. Twenty minute car ride to the beautiful Gulf Beaches or downtown Tampa. Great weekend get-a-way or longer term rental. Parking is available on the street with a parking permit which we provide.

Top guest favorite
Guesthouse in Town 'n' Country
4.99 out of 5 average rating, 335 reviews

Entire Guest House near Tampa airport

Welcome to our charming guest house! Located just 12 minutes away from Tampa Airport, 20 minutes from Raymond James Stadium, and a quick 35-minute drive from Clearwater, our entire guest house offers you convenience and comfort. With a private entrance, you'll have all the privacy you need. Whether you're here for a game, a beach getaway, or to explore the city, our cozy space is your perfect home base. Book now for an unforgettable stay!

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