
Guesthouse holiday rentals in Hillsborough County
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Top-rated Guesthouses in Hillsborough County
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Popular amenities for Hillsborough County guesthouses
Family-Friendly guesthouses

Charming private guest house.
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!

Adorable South Tampa Two-Story Guest House
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.

Hyde Park Tree House, Tampa, FL - Great location
Peaceful treehouse in the heart of Hyde Park. The location is great, bed very comfortable and we enjoyed the screened porch .

Cute home in historic neighborhood
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.

Private Apt/3miles from beaches/Treehouse.like
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!

The Lassing House
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!

The Uptown Treehouse - Downtown St. Pete 1Br Apt
Dirk & Erika are very responsive with very clear instructions. They're also very friendly!

pet friendly on an equestrian farm
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

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

Waterfront Studio Home in Paradise
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.

Suite The Marine
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.

Tiny House Oasis Blue Vatican . Near MacDill Base
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.

tinyhome en largo
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.

Cozy studio/Full Kitchen/Private Entrance
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.

Adorable 1 Bedroom Ybor Casita with outdoor patio
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!

Apartamento Casino 1
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

Bay Suite in Heart of Dunedin
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!

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

Private 2 BR Backyard Oasis, Walk to Downtown!
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!

Tiki Hut Cottage
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!

Cottage on Pinellas Bike Trail
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!

Caffeinated Bungalito near Armature Works /75in TV
This place was great. No surprises. Clean, comfortable. Good amenities and everything worked and was nice. Thank you!

Cozy Suite
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
Private Guest House sleeps 4 w/POOL & near beach!
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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- Anna Maria Island
- Anna Maria Public Beach
- Dunedin Beach
- Weeki Wachee Springs
- John's Pass
- Reunion Resort Golf Courses - Palmer & Watson
- Bean Point Beach
- Cortez Beach
- Lido Key Beach
- Busch Gardens Tampa Bay
- Amalie Arena
- Raymond James Stadium
- Gulfport Beach Recreation Area
- Reunion West
- Clearwater Beach
- North Beach
- Coquina Beach
- ChampionsGate Golf Club
- Vinoy Park
- Fort De Soto Park
- Tampa Theatre
- Curtis Hixon Waterfront Park
- Island H2O Water Park
- Streamsong Resort
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