Guesthouse holiday rentals in Hillsborough County

Find and book unique guesthouse rentals on Airbnb

Top-rated Guesthouses in Hillsborough County

Guests agree: These guesthouses are highly rated for location, cleanliness and more.

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Top Guest favourite

Guesthouse in Davis Islands

4.87 out of 5 average rating, 1116 reviews

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.

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Top Guest favourite

Guesthouse in St. Petersburg

4.97 out of 5 average rating, 255 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!!!

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Top Guest favourite

A private patio area is surrounded by wooden fencing adorned with greenery. Two blue chairs are positioned at a round table, creating a serene space for relaxation. Natural light filters through the nearby trees, enhancing the inviting atmosphere of the outdoor setting.

Guesthouse in St. Petersburg

4.97 out of 5 average rating, 268 reviews

Cozy Guesthouse Near Downtown (Non-Toxic)

Come relax in this calm, newly renovated guest suite. Clean, natural, & chemical free - diffusers and oils available on site. Amenities like central a/c, laundry, private patio, full kitchen, Netflix & Hulu. A short 5 minute drive from downtown - near tons of local restaurants, entertainment, and beaches. St. Pete loves the local vibe, be sure to check out our visitors guide for suggestions on spots to see while you’re here. It doesn’t get any better than St Pete! Book your stay with us today!

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Top Guest favourite

A charming guesthouse is seen from the front yard, featuring a green exterior with white trim. A welcoming porch is adorned with two chairs, and gentle landscaping with shrubs compliments the space. The surrounding grass is well-kept, enhancing the inviting presence of the home.

Guesthouse in Tampa

4.99 out of 5 average rating, 152 reviews

Stylish☀Mini Mint Bungalow☀10 mins from downtown

Our guesthouse is fenced in our backyard & there is a dedicated parking space on the right side of the driveway. Inside there is a fully equipped kitchen with new Samsung appliances, full size washer & dryer, a comfortable Queen size bed, en suite bathroom, Roku TVs, fast internet. I love the atmosphere in my neighborhood; you will find local & specialty stores (bakeries, vintage clothes, vinyl records, breweries), mix of cultures, the architectural style of the old city and a central location.

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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

4.97 out of 5 average rating, 177 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.

LocationFamilySleep quality

Top 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 Heights

4.89 out of 5 average rating, 439 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.

ValueFamilyAmenities

Top Guest favourite

A bright living area features a gray love seat and a colorful area rug with abstract patterns. A wall-mounted television is positioned above a wooden console. A Murphy bed is neatly stowed away, and light filters through the window with wooden shutters.

Guesthouse in Tampa

5.0 out of 5 average rating, 205 reviews

Private Casita Moments from Downtown Tampa

Splendid newly constructed guesthouse near downtown Tampa! Private and quiet! Lots of great amenities, including free use of 2 bikes! Free parking on-site. Private entrance. Close to Tampa Airport, Raymond James Stadium, Benchmark International Arena and more! Walk to Tampa's Riverwalk and Armature Works entertainment complex. Free wifi, television and a designated workspace. Murphy bed stows away for extra living space during the day. Owners live on site to quickly address concerns.

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Top Guest favourite

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, 379 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.

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Guest favourite

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

4.84 out of 5 average rating, 424 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).

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Guest favourite

The living area is furnished with a gray sofa and a coffee table positioned on a textured area rug. A flat-screen television is mounted on the wall, while natural light filters through two windows, complemented by minimalist decor featuring a black and white art piece.

Guesthouse in Palmetto Beach

4.89 out of 5 average rating, 287 reviews

cute comfy & cozy 2nd Floor Guest Suite (Seashell)

Welcome to my 400sqf one bedroom second floor Mother-In-Law private guest suite. Its very cute and cozy. Once you come up the stairs, you will find a deck with outside sitting to enjoy the great Florida weather. Inside there is a full kitchen with everything you need to cook a meal and relax on the sofa and watch some streaming shows before heading to your even or wonder around ybor city or down town. My place is in a neighborhood about 1-4 miles from most of what Tampa has to offer.

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Top Guest favourite

A spacious rooftop terrace is furnished with a shaded seating area, featuring dark wood chairs and a cushioned sofa, surrounded by potted plants. A large umbrella provides shade, while an area rug defines the seating space against the backdrop of lush greenery and clear blue skies.

Guesthouse in Tampa

4.93 out of 5 average rating, 104 reviews

Great For Couples + Work Trips • Central • PetsOK

🏙 Located in Tampa’s most vibrant neighborhood — walk to Bayshore Blvd, SoHo, and charming Hyde Park! 🌞 Perfect weekend escape or cozy work-travel retreat 🏡 Private guesthouse with exclusive rooftop access — enjoy your morning coffee or evening wine with a view 💼 Ideal for business travelers — comfortable, quiet, and centrally located ☕ Surrounded by local cafes, restaurants, nightlife, and boutiques 🚫 Please note: This unit is not handicap-accessible and requires stairs

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Superhost

An outdoor patio area is enclosed by a wooden fence, featuring a fire pit surrounded by two white adirondack chairs. Lush greenery and small shrubs border the space, which is accentuated by a stone path and grassy patches under a clear blue sky.

Guesthouse in Bayshore Beautiful

4.84 out of 5 average rating, 274 reviews

La Casa Azul - Private Detached Guest House

Please note the Hot tub has been removed. Charming, detached guest house in South Tampa. Just a short stroll to scenic Bayshore Blvd and stunning views of Tampa Bay. Shopping, dining and more. This guest house has lots of windows, providing a lot of natural light! It has off street parking and a gated patio/yard area. It's stylishly furnished, has an LED TV, surround sound, the Amazon Fire stick and Alexa. FREE Wifi. Bedroom has Tempur-Pedic Bed and inflatable mattress.

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