
Guest house holiday rentals in Clearwater
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Top-rated guest house rentals in Clearwater
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Popular amenities for guest house rentals in Clearwater
Family-friendly guest house rentals

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.

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!

Seminole Heights Riverside Paradise w/Pool
We loved Isla de Dij! Very peaceful, beautiful surroundings and pool. We would definitely recommend and hope to be back soon.

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
Absolutely wonderful, charming decor, very peaceful setting with delightful sounds of the fountain...I would definitely stay there again. The neighborhood is perfect, just a two block walk to Tampa Bay and a great place to watch families and dogs frolicking in the water. My daughter is relocating to St. Pete and now I'm considering it also! Thanks, Leigh Ann!

Casa O - Private In-Suite Studio in St. Pete
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.

The Uptown Treehouse - Downtown St. Pete 1Br Apt
I sincerely enjoyed every moment of my stay …I loved the apartment and never felt as though I was wanting for anything. Just as important as my apartment was how lovely the neighborhood and area was ….. it was such a pleasure to go for walks there …. D as o much nature and creativity to be enjoyed ..Im sure I’ll be reflecting on the times I spent at Round Lake every day …. My time in St Petersberg passed far too quickly , and my only regret was that it indeed came to an end and that I had to return to Miami. I believe I felt more at home there than I have anywhere for a long time

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
Guest house rentals with a patio

Cozy Guesthouse Near Downtown (Non-Toxic)
Our stay at this loft in Saint Petersburg was fantastic! The space was quiet, comfortable, and incredibly clean and well equiped. The cozy upstairs made it feel extra inviting, and the location couldn’t have been better—just minutes away from great restaurants and shops. The hosts were extremely accommodating and communicative, making the whole experience seamless. If you're looking for a perfect spot to stay in St. Pete, this is it!

Cozy Renovated Studio – Private Entry + Parking
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.

Private Casita in the Heart of Tampa
We enjoyed our stay while we were visiting to go to Busch Gardens. The place was cosy and was pretty close to the park. There was enough space for my family of four and comfortable for all of us.

Tiny House Oasis Blue Vatican . Near MacDill Base
We enjoyed the music playing upon our arrival. Super cute place. Thank you.

Relaxing & Charming Hideaway
It was a pleasure staying at Camila’s place. Everything was as described in the description of the property. I had no issues with my stay.

Enjoy your privacy in this Unique retro style Apt.
Super easy check in, and friendly hosts. Loved the space, it was close by everything I needed.

Beachy Bohemian Bungalow with all the perks!
Google GPS struggled with getting us to the exact house but we were able to figure it out. The check in was easy. The location was great. Everything we wanted to go to was 5-10 min away. We were able to unplug and relax completely for our baby moon because everything was so easy to get to. We enjoyed Madeira beach, John’s pass, studio movie theaters, and restaurants nearby. The place was really cute. Small but perfect for two people. Gwen was helpful. It was a bit humid but we turned down the AC and she had a small dehumidifier we were able to use.

Grandma's House. Jacuzzi bathtub/Low cleaning Fee
This was the Perfect stay for my emergency work need. The location was excellent, and the Eleanor was incredibly flexible with my situation and her communication was impeccable! I look forward to checking availability the next time I stay for the market.
Guest house rentals with a washing machine and dryer

Tropical 2BR Casita + Hot Tub Near It All
Jerry’s Airbnb in St. Pete was the perfect getaway — clean, comfortable, and just minutes from the beach. We loved the thoughtful touches throughout the space and felt right at home from the moment we arrived. It was the ideal spot for a relaxing, fun-filled trip, and we’d absolutely stay here 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.

Dee's 5-star Tampa Location Unit 1
This was the perfect place for my getaway! Super clean, comfortable, and great location. Will definitely book when I return
Private Guest House sleeps 4 w/POOL & near beach!
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!

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

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.

The Dollhouse in Downtown St Pete
Clean and beautifully decorated. Finding the parking was confusing but once I found it it was nice that it was gated at night and easy to open pull in and close. Ordering DoorDash I had to walk out to a well lit Ally at night to meet them bc they can not get in easily like they couldn’t follow my directions to get to my door. It’s close to hospital so it met my needs. Host is very responsive and nice. Overall stay was good.

Guesthouse in Downtown St Petersburg
Fantastic stay! The house was exactly as described - if not better. It's located in a beautiful, quiet neighborhood that felt very safe. It's walkable to a lot of great restaurants, and was so close to downtown and just a short drive from the beach. The hosts were incredibly kind and communicative. I'd 100% stay here again!
Quick stats about guest house rentals in Clearwater
Total rentals
50 properties
Total number of reviews
4K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
50 properties include access to wifi
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- Anna Maria Island
- Weeki Wachee Springs
- Dunedin Beach
- Anna Maria Public Beach
- John's Pass
- Bean Point Beach
- Busch Gardens Tampa Bay
- Raymond James Stadium
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- Lido Key Beach
- Amalie Arena
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- Tampa Theatre
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- Curtis Hixon Waterfront Park
- ZooTampa at Lowry Park
- Splash Harbour Water Park
- Adventure Island
- River Strand Golf and Country Club
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