Guesthouse holiday rentals in Pinellas County

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!

My wife and I stayed in the guest house for more or less the whole month of January after hurricanes Helene and Milton. Stone and Terra worked incredibly hard to make the property ready for us on our arrival date; during the restoration process, they kept us informed with photos and progress reports. I can't say enough about their honesty and work ethic. When we arrived, the guesthouse was pristine. The only difference between its current state and the photos in the listing is that they ripped out the flooring to reveal the terrazzo beneath, and laid out some rugs in the living room and bedrooms -- an improvement in our opinion. In short, we thoroughly enjoyed our stay there, and wish we could have stayed another month. With so many structures of its type on the beaches still uninhabitable, and some probably damaged beyond repair, this is truly a rare gem.

Super cute and comfortable. I can’t wait to stay again. Perfect walking distance to the pier and Dali museum.

Nice place that is close to downtown area. It is walkable to stores and restaurants. The place is clean and provides a good stay for those that are looking for a non-luxury place to stay that is welcoming, affordable and has everything you need. It is tucked away on an alley which makes it quiet as well. There is ample parking space.

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

Bebe's Casa O is at a quiet neighborhood with tranquility all around. Well maintained guest house, clean and cozy with a hospitable host. Looking forward to returning.

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!

Regina was super friendly and extremely helpful throughout our stay! The loft was such a cute fun spot to relax in after a busy day exploring downtown St. Pete!! Perfect mix of comfort and cute! Highly recommend as a home base for anyone curious abt exploring the city, with the added ease of a walkable distance to so many things right downtown! Thank you so much for hosting us!

Both Reynaldo and Dayne were gracious hosts. From the moment I reserved the suite all the way through my arrival and departure, they were thoughtful, friendly, and responsive. Since I was on a red-eye flight and got to town earlier, Reynaldo tried to accomodate me as much as possible for an earlier check-in. The entrance is private and the setting is beautiful. It was a little too hot for me to sit in the cute backyard but hope to do that next time.

Loved the place. Great AC. Had a humidifier that we had to dump out here and there but rather do that then feel muggy. The only complaint was the shower, tough to get the hot water going and water pressure wasn’t the best. But overall great stay.

Great place! Great location. Highly recommended

The house was exactly what I needed size and accommodation wise and was well worth the price. In a great location and was well kept and very clean. Had a great trip.

Perfect place, confort, privacy and security. Really close to the beach. I feel really good!! Thanks Maria

Our host was very helpful and responsive with clear instructions on how to enter the property. Everything was clean and appeared as listed. The host was even accommodating with check-out times.

Carlos and Ileana's was absolutely a dream. Peaceful and quiet perfect for relaxing. From the first hello the greeting was warm and friendly. I had mentioned it was my wife's bday and they took the time to decorate the room for her, had a balloon, card and a bottle of wine and magically it was mascato her favorite. They also had the place stacked with all the things you could think of. Snacks, drinks, coffee, tea, bathroom toiletries etc. Let me not forget the back yard which looked like a mini tropical resort with a hot tub, bar and mini refrigerator with drinks you can enjoy. Carlos also makes his own wine which is absolutely amazing we bought a bottle to take home. 10 out of 10 definitely recommend this place and will for sure be back!!

I absolutely loved my stay! The camper was beautifully renovated with a charming retro vibe, spotlessly clean, and surprisingly cool and comfortable, even in the heat. It felt very private, which made it easy to relax. I especially enjoyed the little patio setup! It was the perfect spot to sip my morning coffee and take in the peaceful surroundings. The location was ideal—quiet but walkable to everything in town. Highly recommend if you’re looking for a unique and cozy stay!

This was our second time staying at Nate’s place. It was just as wonderful as the first time we stayed here two years ago! Nate continues to maintain the upmost level of service with extremely clean, comfortable accommodations ready with everything you could hope for during your stay—including two bikes to use on the very nearby Pinellas Trail. We consider his place truly a little gem in Dunedin!

If we ever stay in St. Petersburg again, we’ll ask for Rob‘s place. It had everything we needed, and even the things we didn’t think we needed. Super clean and so close to many attractions. We walked the charming neighborhood frequently especially to the Bay parks.

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.

We loved our stay here! The pictures do not do it justice. Our space was perfect for our family of 4 and was much bigger than the pictures showed. There is plenty of storage space for your things and the loft is perfect for the kids to have their own space. The tiki porch was awesome and the pool is right outside the back door. My kids loved feeding the turtles and koi in the pond. It is a short drive to the beach and only a 5-minute drive to downtown Dunedin. We loved coming back and relaxing in the pool after a day out. The property is so peaceful and relaxing. We would definitely stay here again!

Kay’s home was exactly as described. Very welcoming and homey. The location was great and on street parking was always easily found. Kay is super responsive. I burned a hole in my (casual) wedding dress with the iron three hours before the ceremony-Kay suggested nearby stores and even said that she had a few dresses I could look at. She was an absolutely wonderful host. I would most certainly stay here again. We even met a neighbor walking his dog who was super friendly and personable. Great neighborhood.

Jennifer was a great host!! The place is very charming and perfect for two people! The home is very close to everything we wanted to do and would stay there again!

Stayed at Gregory’s place with my family and we found it a perfect place to access both the beach and the downtown area. We had everything we needed for a comfortable stay and felt right at home. Gregory was very friendly and communicative. We would stay again for sure.

'Twas a lovely little place to stay for the night! Highly recommend