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Guesthouse holiday rentals in Clearwater

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Popular amenities for Clearwater guesthouses

Family-Friendly guesthouses

Top Guest favourite
Guesthouse in St. Petersburg
4.9 out of 5 average rating, 326 reviews

Carriage House in North St. Pete

GraceRating, 5 stars4 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 favourite
Guesthouse in Davis Islands
4.85 out of 5 average rating, 966 reviews

Charming private guest house.

RomanRating, 5 stars3 weeks ago
Felt right at home! I loved the location, within a 10 min walking distance to coffee and food! 5 min driving distance to Channelside and Harbour Island. The place itself was perfect for me, was super clean and had waters for me in the fridge. A beautiful spot that I would definitely stay in again!
Guest favourite
Guesthouse in Old Seminole Heights
4.86 out of 5 average rating, 923 reviews

Seminole Heights Riverside Paradise w/Pool

JRating, 5 stars6 days ago
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!
Top Guest favourite
Guesthouse in Seminole
4.95 out of 5 average rating, 245 reviews

Private Apt/3miles from beaches/Treehouse.like

RichardRating, 5 stars1 month 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, 341 reviews

The Lassing House

Michael & AprilRating, 5 stars1 week ago
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
Guest favourite
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 favourite
Guesthouse in North Downtown
4.88 out of 5 average rating, 188 reviews

The Uptown Treehouse - Downtown St. Pete 1Br Apt

PauloRating, 5 stars2 weeks ago
Great place in a great location. Fully furnished kitchen. Walk to coffee shops. Close to downtown. Laundry on premises but if you need to do laundry, bring quarters.
Guest favourite
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

Guesthouses with a patio

Guest favourite
Guesthouse in Tampa
4.89 out of 5 average rating, 171 reviews

Stylish guesthouse 1-BR 2 miles from Busch Gardens

YeslinRating, 5 stars1 week ago
Magy’s place was a cute little spot and I can’t complain about the cleanliness.. everything was clean and spotless. The only thing that bothered us was the WiFi, it didn’t seem to work properly which was a bummer but other than that - we enjoyed our stay. Thank you so much
Guest favourite
Guesthouse in St. Petersburg
4.9 out of 5 average rating, 115 reviews

Cozy Renovated Studio – Private Entry + Parking

JrRating, 5 stars1 week ago
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.
Top Guest favourite
Guesthouse in Tampa
4.99 out of 5 average rating, 163 reviews

Quiet and clean guest house!

MarthaRating, 5 stars2 days ago
Raysa’s place has become our go-to choice for staying in Tampa. It’s thoughtfully appointed and tastefully decorated. The surroundings are peaceful. The washer/dryer is an added plus! Raysa is quick to respond and very helpful. We’ll be back!
Superhost
Guesthouse in Tampa
4.88 out of 5 average rating, 265 reviews

Private Casita in the Heart of Tampa

AshleRating, 5 stars2 weeks ago
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.
Guest favourite
Guesthouse in Tampa
4.93 out of 5 average rating, 189 reviews

Cozy Palma Ceia Cabana close to Westshore & TIA.

AmyRating, 5 stars6 days ago
This cabana had everything we needed for our short stay. It was located so close to everything, very convenient. It was very clean and the bed was super comfy! Pam was very responsive to all communication with us.
Guest favourite
Guesthouse in Tampa
4.96 out of 5 average rating, 303 reviews

Tiny House Oasis Blue Vatican . Near MacDill Base

JessicaRating, 5 stars4 days ago
This is a beautiful little place in an amazing area of Tampa. Very cute decor, and everything was spotless. The a/c runs icy cold and everything works perfectly. We didn’t spend much time in the little outdoor area due to it being June in Florida, but that was very cute and cozy, as well. I saw one reviewer say the bathroom door doesn’t close all the way, but this isn’t true. It’s sort of an “accordion” style door that slides open and closed, but the edge of the door does sit securely in the frame, allowing it to close just fine. I would definitely stay here again!
Guest favourite
Guesthouse in St. Petersburg
4.91 out of 5 average rating, 126 reviews

St Pete Casita Studio with Salt Water Pool & Yard

MelanieRating, 5 stars2 weeks ago
Room was as described, pleasant and clean ( the cleaning product used was very strong so we did have to air the room out for a short time) We loved our stay very much, the pool was definitely a bonus and we really enjoyed it. We travel extensively for our careers and will definitely recommend this stay to our friends and colleagues. Thank you! Melanie and Chris
Guest favourite
Guesthouse in Seminole
4.92 out of 5 average rating, 105 reviews

Enjoy your privacy in this Unique retro style Apt.

VanessaRating, 5 stars2 days ago
Hi! Just wanted to leave some feedback about our stay as a couple, it really worked well for us. The area is very peaceful, and we were able to relax and enjoy a quiet weekend. I think it could also be a great spot for families. It was just right for our Father’s Day weekend. Also, we recommend Sugar Baby for breakfast or brunch it’s only 4 minutes away and totally worth it! Thanks again! 😊

Guest house rentals with a washing machine and dryer

Guest favourite
Guesthouse in St. Petersburg
4.96 out of 5 average rating, 108 reviews

Tropical 2BR Casita + Hot Tub Near It All

DevinRating, 5 stars2 weeks ago
The casita was in the ideal spot for a little weekend getaway for me and my mom! Great location in general and the casita is super cozy and welcoming. All instructions were clear, parking was simple, and the casita itself was very clean and had a cool vibe to it.
Guest favourite
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
Top Guest favourite
Guesthouse in St. Petersburg
4.99 out of 5 average rating, 334 reviews

The Bungalow in Downtown St Pete.

SarahRating, 5 stars1 week ago
We totally loved our stay in the Bungalow ... lots to do nearby in walking distance, near to great beaches and downtown St. Pete.
Top Guest favourite
Guesthouse in Seminole Heights
4.97 out of 5 average rating, 193 reviews

Coastal in the Heights

ScottRating, 5 stars1 week ago
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
Guest favourite
Guesthouse in Tampa Heights
4.94 out of 5 average rating, 145 reviews

Caffeinated Bungalito near Armature Works /75in TV

CarlosRating, 5 stars3 days ago
Great host! Spent the weekend with my wife and 10 month old as a little getaway for my birthday/Father's Day. Would recommend highly with lots to do in this area and close to everything you need!
Guest favourite
Guesthouse in Tampa
4.94 out of 5 average rating, 277 reviews

Cozy Suite

JorgeRating, 5 stars1 month ago
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
Top Guest favourite
Guesthouse in Historic Kenwood
4.98 out of 5 average rating, 120 reviews

2 bedroom guesthouse in hip Grand Central District

GraceRating, 5 stars2 weeks 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.
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 stars3 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!

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

  • Wi-Fi availability

    50 properties include access to Wi-Fi

Destinations to explore