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Guesthouse holiday rentals in Hillsborough County

Find and book unique guesthouse rentals on Airbnb

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Popular amenities for Hillsborough County guesthouses

Family-Friendly guesthouses

Guest favourite
Guesthouse in Tampa
4.85 out of 5 average rating, 958 reviews

Charming private guest house.

IvyRating, 5 stars2 weeks ago
Wow! What a great stay! I was so impressed by the space and location. My friend and I stayed the night for a concert at Amalie Arena. We had no trouble getting there or back! Vera provided us with great directions to make our way. The space was clean and smelled AMAZING! My friend and I both said we wished we had more time at the location because it was so nice! If I am ever back in Tampa I will definitely try to book again!
Guest favourite
Guesthouse in Tampa
4.93 out of 5 average rating, 110 reviews

Adorable South Tampa Two-Story Guest House

JoanRating, 5 stars1 month ago
While the location of this home is in the midst of the city and near the airport, the neighborhood was quiet and walkable, stores and restaurants were nearby and there was easy access to highways. It was a comfortable place to return" home: to each day. The beds and couch were comfortable and the air conditioners really helped. James and his family were very friendly and helpful. The size of the unit was fine for two people, but with a small bathroom and kitchen, might be a challenge for 3.
Guest favourite
Guesthouse in Tampa
4.85 out of 5 average rating, 338 reviews

Hyde Park Tree House, Tampa, FL - Great location

HeatherRating, 5 stars3 weeks ago
Peaceful treehouse in the heart of Hyde Park. The location is great, bed very comfortable and we enjoyed the screened porch .
Guest favourite
Guesthouse in St. Petersburg
4.85 out of 5 average rating, 479 reviews

Cute home in historic neighborhood

KeithRating, 5 stars1 week ago
Jeff’s place was in a great location for my one night trip in st. Pete. Very close to local restaurants and bars. Located in a safe and quiet neighborhood. Will stay there again.
Top Guest favourite
Guesthouse in Seminole
4.95 out of 5 average rating, 244 reviews

Private Apt/3miles from beaches/Treehouse.like

KristopherRating, 5 stars3 weeks ago
Fantastic Stay at Karen’s Place! Our stay at Karen’s Airbnb was exceptional! From her warm welcome to the beautiful, clean, and well-equipped home, every detail was perfect. Karen’s genuine hospitality truly stood out. The location was both convenient and peaceful. Highly recommended—thank you, Karen, for a memorable stay! Looking forward to our next visit!
Superhost
Guesthouse in St. Petersburg
4.76 out of 5 average rating, 336 reviews

The Lassing House

TabithaRating, 5 stars2 weeks ago
This is actually my 3rd time staying here and I have loved everything! The place is just like the photos, has all basic needs with a family dollar right up the street, and a comfy bed and linens. The courtyard is quiet and peaceful with a privacy fence, perfect for having a coffee or end of the day drink/snack. If you get a chance, walk down and catch the sunrise over the water at Lassing Park. Def worth grabbing a sandwich or poke bowl at The Old Southeast Market a few blocks away too!
Guest favourite
Guesthouse in St. Petersburg
4.88 out of 5 average rating, 185 reviews

The Uptown Treehouse - Downtown St. Pete 1Br Apt

MichaelaRating, 5 stars1 month ago
Dirk & Erika are very responsive with very clear instructions. They're also very friendly!
Guest favourite
Guesthouse in Pinellas Park
4.87 out of 5 average rating, 270 reviews

pet friendly on an equestrian farm

RoslynRating, 5 stars1 month ago
As a solo 74 year old gal with an English cocker, safety is most important. I was very comfortable and felt safe. there. Just a lovely place and nice people

Guesthouses with a patio

Superhost
Guesthouse in St. Petersburg
4.85 out of 5 average rating, 324 reviews

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

MeganRating, 5 stars3 weeks ago
cute little studio, with a kitchenette and a big shower. Smart TV and they even left some popcorn and waters! The backyard was what really made this place shine. Beautiful jungle vibe, native plants, and a really peaceful set up, lots of birdwatching. A fire pit if it's cold ( did not try this out). The hot tub is incredible, multiple different seats with different jet configurations, super clean, good privacy. Great location near everything in St Pete. I will definitely be back!
Top Guest favourite
Guesthouse in Apollo Beach
4.95 out of 5 average rating, 108 reviews

Waterfront Studio Home in Paradise

KailaniRating, 5 stars3 weeks ago
We loved staying here for a few days! Gorgeous and peaceful corner of Apollo Beach and the outdoor area was such a great spot to enjoy our morning coffee. We're really grateful we discovered this place and Rose was so welcoming. Would definitely recommend for anyone looking for an escape in the area.
Superhost
Guesthouse in Tampa
4.82 out of 5 average rating, 202 reviews

Suite The Marine

Jade-LynnRating, 5 stars1 week ago
This was a last minute trip for us and it was a great stay. The host is very nice and the space was perfect for what we needed and the location is close to everything! would stay again.
Guest favourite
Guesthouse in Tampa
4.96 out of 5 average rating, 293 reviews

Tiny House Oasis Blue Vatican . Near MacDill Base

DougRating, 5 starstoday
The small and quaint little cottage was a perfect little get-a-way for the night after enjoying a concert to see Joan Jett and Billy Idol at Midflorida Credit Union Amphitheatre. The place was cute and precious and will visit again.
Guest favourite
Guesthouse in Seminole
4.85 out of 5 average rating, 105 reviews

tinyhome en largo

BillyRating, 5 stars4 weeks ago
Alejandro’s little home was exactly as described. It was very cozy and just enough space for two. The location was perfect! Overall Alejandro was a great host and the stay was exactly what we needed. We'd book again if back in the area.
Superhost
Guesthouse in Tampa
4.86 out of 5 average rating, 110 reviews

Cozy studio/Full Kitchen/Private Entrance

AllysonRating, 5 stars2 weeks ago
Lisette’s space was very clean, matched the photos, and good location / neighborhood. It was easy to access and had everything we needed for our short stay.
Superhost
Guesthouse in Tampa
4.83 out of 5 average rating, 185 reviews

Adorable 1 Bedroom Ybor Casita with outdoor patio

ChiRating, 5 stars4 weeks ago
A great place to stay for our short visit to Tampa! Close walk to Ybor area for great restaurants and bakery shops! Short drive to downtown Tampa. The apartment is clean and has everything we need. The hosts are very responsive to questions throughout our stay. High recommend!
Guest favourite
Guesthouse in Tampa
4.92 out of 5 average rating, 120 reviews

Apartamento Casino 1

VanessaRating, 5 stars1 week ago
We stayed here while attending an event at the Straz center. It was the perfect distance. There are plenty of nearby restaurants, stores, and the airport is a short drive from this place. We visited the beach once we realized it wasn’t that far (St. Pete is only about 40 min away)! Host gave me clear instructions on check in and we had everything we needed for our stay. Highly recommend staying here!

Guest house rentals with a washing machine and dryer

Top Guest favourite
Guesthouse in Dunedin
4.99 out of 5 average rating, 185 reviews

Bay Suite in Heart of Dunedin

SummerRating, 5 stars2 weeks ago
My nephew (14) and I stayed at Nate and Stefani’s Airbnb for the Alan Jackson concert in Tampa. The Airbnb is a nice in between from Tampa and beach! We walked to nearby restaurants and shopping areas. And Let me tell you. The pictures they have on here do not do this place justice. It was so stylish and comfy. There is so much space and unique little touches. I was so pleased. Nate and Stefani put a lot of thought into it. We felt at home instantly. The bed and pillows were so comfortable and the towels are so fluffy. We had a wonderful stay here. Even my Gen Z nephew started throwing out a bunch of slang words I didn’t know the meaning to. Like “lit” and “bussin”… I’m assuming he liked it… lol! Thanks, Nate and Stefani!
Superhost
Guesthouse in Tampa
4.81 out of 5 average rating, 158 reviews

Entire rental unit.Tampa .2B/1B Near to everything

LasheaRating, 5 starstoday
My stay wonderful. The location is private and quiet. It's also conveniently located near restaurants and grocery stores. The home is spotless and has all the amenities and supplies you need for your stay. And for those that work remotely like me the wifi is fast and the router/modem is easily accessible for hard-wiring. If I come back into town this would be my go-to place.
Top Guest favourite
Guesthouse in St. Petersburg
4.91 out of 5 average rating, 126 reviews

Private 2 BR Backyard Oasis, Walk to Downtown!

NicoleRating, 5 stars1 month ago
Cute historic place. Great location, easy to walk to downtown. Friendly hosts. Private tropical yard. Very well stocked, lots of supplies to cook there. Also comfy beds with extra blankets. Great water pressure in the shower!
Top Guest favourite
Guesthouse in Dunedin
4.95 out of 5 average rating, 168 reviews

Tiki Hut Cottage

AbbyRating, 5 stars4 days ago
This place is my favorite place we have ever stayed! It is beautiful and serene! Book this place and you will not regret it! I got to meet Lori, and she was such a sweetheart!
Guest favourite
Guesthouse in Clearwater
4.89 out of 5 average rating, 209 reviews

Cottage on Pinellas Bike Trail

AlejandraRating, 5 stars2 days ago
Cute little charming cottage by the trail and water. Kate was quick to respond if we needed anything. Our dogs had a great time and also felt comfortable. Quiet and peaceful, definitely would recommend. We had a great stay!
Guest favourite
Guesthouse in Tampa
4.94 out of 5 average rating, 137 reviews

Caffeinated Bungalito near Armature Works /75in TV

GeoffreyRating, 5 stars3 days ago
This place was great. No surprises. Clean, comfortable. Good amenities and everything worked and was nice. Thank you!
Guest favourite
Guesthouse in Tampa
4.94 out of 5 average rating, 277 reviews

Cozy Suite

JorgeRating, 5 stars2 weeks ago
Jose’s place was exactly what I needed for my stay and I’ll definitely be considering it for future stays. It was clean, cozy and had all the necessary resources for a pleasant stay
Superhost
Guesthouse in St. Petersburg
4.89 out of 5 average rating, 510 reviews

Private Guest House sleeps 4 w/POOL & near beach!

DougRating, 5 stars1 month ago
What a wonderful and welcoming experience when we arrived. Jennifer & Steve were finishing up and as described, the cleaning was meticulous ! We briefly met the pups and they are SO sweet. The grounds have a rustic beach vibe with vibrant colors and inside, a great beach decor with all you need! It was so comfortable! We will stay again when we get back to St. Pete!!!!

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