Guesthouse vacation rentals in Clearwater

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Popular amenities for Clearwater guesthouse rentals

Family-friendly guest house rentals

Guest favorite
Guesthouse in Old Seminole Heights
4.97 out of 5 average rating, 177 reviews

Backyard Bungalow in Old Seminole Heights

NancyRating, 5 stars1 month ago
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.
Top guest favorite
Guesthouse in St. Petersburg
4.9 out of 5 average rating, 326 reviews

Carriage House in North St. Pete

GraceRating, 5 stars3 weeks ago
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!
Guest favorite
Guesthouse in Old Seminole Heights
4.86 out of 5 average rating, 922 reviews

Seminole Heights Riverside Paradise w/Pool

MelissaRating, 5 stars1 week ago
We loved Isla de Dij! Very peaceful, beautiful surroundings and pool. We would definitely recommend and hope to be back soon.
Top guest favorite
Guesthouse in Seminole
4.95 out of 5 average rating, 245 reviews

Private Apt/3miles from beaches/Treehouse.like

RichardRating, 5 stars4 weeks ago
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+
Superhost
Guesthouse in St. Petersburg
4.76 out of 5 average rating, 339 reviews

The Lassing House

GretchenRating, 5 stars1 month ago
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!
Guest favorite
Guesthouse in St. Petersburg
4.94 out of 5 average rating, 174 reviews

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

TomRating, 5 stars1 month ago
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.
Guest favorite
Guesthouse in North Downtown
4.88 out of 5 average rating, 186 reviews

The Uptown Treehouse - Downtown St. Pete 1Br Apt

HenryRating, 5 stars2 weeks ago
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
Guest favorite
Guesthouse in Pinellas Park
4.87 out of 5 average rating, 270 reviews

pet friendly on an equestrian farm

RoslynRating, 5 stars2 months 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

Guest house rentals with a patio

Top guest favorite
Guesthouse in St. Petersburg
4.97 out of 5 average rating, 219 reviews

Cozy Guesthouse Near Downtown (Non-Toxic)

AlanRating, 5 stars2 months ago
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!
Top guest favorite
Guesthouse in Tampa
4.99 out of 5 average rating, 161 reviews

Quiet and clean guest house!

AngelyaRating, 5 stars2 days ago
This was my third time staying at Raysa''s place. It's such a nice place. Quaint, quiet, and clean. Just as described.
Guest favorite
Guesthouse in Tampa
4.96 out of 5 average rating, 301 reviews

Tiny House Oasis Blue Vatican . Near MacDill Base

SandyRating, 5 starstoday
absolutely perfect for a couple or single person, super nice host, I felt very safe tucked away, I regretted not booking two nights.
Guest favorite
Guesthouse in St. Petersburg
4.91 out of 5 average rating, 124 reviews

St Pete Casita Studio with Salt Water Pool & Yard

DanielRating, 5 stars2 weeks ago
Very nice secluded stay had a great time no issues Priscilla responded timely to any questions great service would definitely stayvagain
Top guest favorite
Guesthouse in St. Petersburg
4.98 out of 5 average rating, 124 reviews

Relaxing & Charming Hideaway

IanRating, 5 stars2 weeks ago
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.
Guest favorite
Guesthouse in Seminole
4.92 out of 5 average rating, 103 reviews

Enjoy your privacy in this Unique retro style Apt.

CaitlynRating, 5 stars1 month ago
Super easy check in, and friendly hosts. Loved the space, it was close by everything I needed.
Top guest favorite
Guesthouse in Seminole
4.92 out of 5 average rating, 115 reviews

Beachy Bohemian Bungalow with all the perks!

CoralysRating, 5 stars1 week ago
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.
Superhost
Guesthouse in St. Petersburg
4.82 out of 5 average rating, 108 reviews

Grandma's House. Jacuzzi bathtub/Low cleaning Fee

JoeRating, 5 stars2 weeks ago
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 washer and dryer

Guest favorite
Guesthouse in Tampa
4.89 out of 5 average rating, 170 reviews

Stylish guesthouse 1-BR 2 miles from Busch Gardens

LukeRating, 5 stars2 weeks ago
This was the perfect spot for a weekend escape to Tampa. The space was sparkling clean, stylishly decorated, and incredibly comfortable—exactly what I needed to unwind. The location is ideal: right near the Riverwalk, with beautiful views and easy access to downtown, great food, and the art museum (which I highly recommend!). The host was communicative and thoughtful, with clear instructions and great local tips. I felt right at home from the moment I walked in. Quiet at night, cozy bed, fast WiFi—everything worked like a charm. I’d absolutely stay here again next time I’m in town. Highly recommend!
Guest favorite
Guesthouse in St. Petersburg
4.96 out of 5 average rating, 107 reviews

Tropical 2BR Casita + Hot Tub Near It All

DavidRating, 5 stars1 month ago
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!
Guest favorite
Guesthouse in Tampa
4.88 out of 5 average rating, 183 reviews

Dee's 5-star Tampa Location Unit 1

DominicRating, 5 stars1 month ago
This was the perfect place for my getaway! Super clean, comfortable, and great location. Will definitely book when I return
Guest favorite
Guesthouse in Historic Kenwood
4.94 out of 5 average rating, 135 reviews

Oasis historic cottage w/Tropical Patio/Parking

MongkonRating, 5 stars2 weeks ago
Wonderful stay! The place was exactly as described—clean, comfortable, and located in one of the safest neighborhood we’ve stayed at. Would definitely book again!
Top guest favorite
Guesthouse in Seminole Heights
4.97 out of 5 average rating, 192 reviews

Coastal in the Heights

MarielaRating, 5 stars1 week ago
I loved the place; everything was very well laid out. It made me feel at home. I go to Tampa every year to visit family, and I think I found the perfect place. The neighborhood was beautiful and quiet. Thanks for all Nicole.
Superhost
Guesthouse in St. Petersburg
4.89 out of 5 average rating, 517 reviews

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

KayleighRating, 5 stars2 weeks ago
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!
Top guest favorite
Guesthouse in Historic Kenwood
4.98 out of 5 average rating, 120 reviews

2 bedroom guesthouse in hip Grand Central District

GraceRating, 5 stars1 week ago
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.
Guest favorite
Guesthouse in St. Petersburg
4.96 out of 5 average rating, 300 reviews

The Dollhouse in Downtown St Pete

DianeRating, 5 stars3 weeks ago
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.

Quick stats about guesthouse 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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