
Guesthouse holiday rentals in Hillsborough County
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Top-rated Guesthouses in Hillsborough County
Guests agree: These guesthouses are highly rated for location, cleanliness and more.
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Popular amenities for Hillsborough County guesthouses
Family-Friendly guesthouses

Carriage House in North St. Pete
We had a wonderful stay here! It was very close to everything we wanted to do and their hospitality was phenomenal. We hope to come back and stay again sometime!

Backyard Bungalow in Old Seminole Heights
It fit our needs perfectly. Sonya and Chris were both warm and welcoming and strived to make sure our needs were met. There was one glitch with washer/dryer but they made sure we still had the ability to use theirs. Very much appreciated. The bed was comfortable and the pillows as well. A pillow is often too big, these were just right. Having a granddaughter nearby, we hope it is available for future visits. A great two weeks.

Charming private guest house.
The guesthouse was perfect for my trip, I was traveling alone and in town to help a family member move in to their new home. I was busy during the day and it was nice to come back to the guesthouse in the evenings. The neighborhood is beautiful and quiet. There are a few restaurants and shops within short walking distance. Everything was very clean and the space is minimally furnished with just the bare necessities for a short stay.

Seminole Heights Riverside Paradise w/Pool
We felt at home-didn’t need anything extra-that had taken care of the details including every kitchen utensil/ item you would need. Ryan was great with communication and asked in advance if we had any needs. Such a peaceful property right on the river. We enjoyed the pool most afternoons-refreshing! Central location too! We will be visiting again for sure!

Private Apt/3miles from beaches/Treehouse.like
I stayed at Karens place for about a week while working and visiting family. It was beautiful and exceptionally clean. Check in very easy with the button lock box, and located nearby Walsingham park is good for walks and quiet views. Karen was really responsive with communication. Would happily stay here again. A+

The Lassing House
What a blessing! We really loved this cute beachy nest. It was so nice how the beach, as well as, a cute little market/restaurant was within walking distance! Their communication was super fast! They came over to help me with a stove issue almost instantly! We also had a friend show up at the last minute who needed a place to stay and they were so welcoming. We will definitely be back! God bless you, Michael & April

The Uptown Treehouse - Downtown St. Pete 1Br Apt
Dirk was an incredible host from the moment we booked. He replied quickly, sent clear check-in instructions, and even had the house ready earlier than expected. The home is located in a charming historic neighborhood that’s both central and peaceful—perfect for families. Everything was clean, and the bathroom was spotless. Having a private parking spot was a huge plus. One of our favorite details was the beach chairs available for guests—small touches like that made our stay even better. We truly felt at home and would happily return to the Treehouse. Thank you, Erika and Dirk, for a lovely experience!

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

Charming studio in the heart of Tampa
Perfect location in the heart of Tampa; it was close to everything we had planned. The room was clean and cute. Coffee was perfect every morning! Very worth the value!!

NEW Luxury Casita w/Hot Tub, Fire Pit, Backyard🏝☀️🏖
We have a nice time, So Beautiful and so extra Sooo clean, hot tub Amazing and we have all instructions easy to handle, Thanks for everything, we definitely come back!!!!

Suite The Marine
very quiet and peaceful neighborhood located in beautiful temple terrace, a lovely riverside park within walking distance with plenty to see and do. the space was so clean and cute, i felt right at home. thank you for helping make my little adventure even more special. :)

Stylish Studio-Perfect Location! 10min to DownTown
Went for the weekend to see Metallica and Justin’s place was the perfect spot to lay low and enjoy the weekend! It was close to everything and just a short Uber ride to the show! Would definitely stay again!

St Pete Casita Studio with Salt Water Pool & Yard
Priscilla was a great host! We really enjoyed the cozy house, and the pool. It’s a great place for 2 people. We are looking forward to staying there again.

Cozy studio/Full Kitchen/Private Entrance
Lissette's listing is so nice! Spotlessly clean and had everything I needed to make my stay pleasant. She's a great host. Responsive and friendly. I would definitely recommend her listing to anyone visiting the Carrollwood/Tampa area!

Casino 1 Apartment
Lovely place!! Stayed for a week place was cozy and i felt safe! Will book again!

No Cleaning Fee for Rentals in June, July & August
We've stayed at Bonnie's place multiple times. It is our absolute favorite Airbnb in the Riverside Heights area. We love the little extras that are provided that show how much she is thinking of her guests. Her communication is topnotch. We enjoy being able to use the bicycles. It is a short ride to the riverwalk and restaurants. Bonnie prints up a list of things going on in the area during your stay too! The Airbnb is nice and cozy and we will definitely book with Bonnie again and again. Thanks for a great stay every time.
Guest house rentals with a washing machine and dryer

Idlewild Guesthouse
Great private location. Feels like your own small apartment. Host was very responsive and place was roomy. Great value compared to others in the area.

Cozy Guesthouse Near Downtown (Non-Toxic)
Stylish and comfortable place with a convenient central location, minutes from downtown and a short drive to the beach. We loved it and would stay again!

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.

La Casa Azul - Private Detached Guest House
We enjoyed the quiet, small space. It was a nice retreat after a very long day at work. He was especially awesome at helping us locate our puppy after she got out of the backyard (No fault of his! She does her best to sneak out!) He immediately posted on his neighborhood app and she was found within mins!! We appreciate the cleanliness and would absolutely recommend!!

Palm Tree Guest Private Studio
Nima was a great host and the place was a cute little spot! Close by downtown!

Coastal in the Heights
I was in Tampa for the Metallica concert and found this place to be close enough to the venue. Nicole’s property is beautiful, cozy and private. Perfect place for two. Great neighborhood with lots of bars and restaurants close by. Next time I’m in Tampa and need a place to stay I’ll be coming back here! Great place

ONE Guest Tiny Ybor Mustard House
I enjoyed visiting Tampa and that I could bring my cat, Piper. The tiny house is pretty much a straight shot to a trolly stop & the trolly is frequent free which is great. Plenty of snacks and breakfast items were provided, which I really appreciated. The host even brought me a container of milk.

2 bedroom guesthouse in hip Grand Central District
I am frequently in St Pete's and love staying in Kenwood. This is a great place-perfect location, of course, but also perfectly clean, very comfortable bed and linens and fully equipped kitchen. I Really Loved the decor-unfussy, but with interesting touches everywhere. Wish my house looked like this! Would stay again any time.
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- Anna Maria Island
- Weeki Wachee Springs
- Anna Maria Public Beach
- Dunedin Beach
- John's Pass
- Bean Point Beach
- Raymond James Stadium
- Busch Gardens Tampa Bay
- Cortez Beach
- Lido Key Beach
- Amalie Arena
- Coquina Beach
- Reunion West
- Gulfport Beach Recreation Area
- ChampionsGate Golf Club
- North Beach
- Fort De Soto Park
- Island H2O Water Park
- Vinoy Park
- Jannus Live
- Streamsong Resort
- Tampa Theatre
- ZooTampa at Lowry Park
- Curtis Hixon Waterfront Park
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