Guesthouse holiday rentals in Clearwater

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Popular amenities for Clearwater guesthouses

Family-Friendly guesthouses

Guest favourite
Guesthouse in Old Seminole Heights
4.97 out of 5 average rating, 172 reviews

Backyard Bungalow in Old Seminole Heights

ShelleyRating, 5 stars1 month ago
We were displaced by the hurricanes. We spent several weeks in the backyard. Sonya was accommodating, responsive, and kind. She (and the family we met) made us feel welcome and made an unfortunate situation much better. Of course, we love the neighborhood. It’s been our home for many years. Our home is a 20 minutes walk from the Bungalow and depending on how we went there are bars, restaurants, coffee, and ice cream along the way. Who wouldn’t love that!
Guest favourite
Guesthouse in Tampa
4.85 out of 5 average rating, 332 reviews

Hyde Park Tree House, Tampa, FL - Great location

JulieRating, 5 stars4 weeks ago
We love staying at the Tree House and are regular guests here. The location is fantastic and you can easily walk into Hyde Park to the numerous shops, restaurants, bars and if course Buddy Brew Coffee Shop! We also enjoyed walking along Bayshore in the mornings too. Susan is a great host and always makes us feel very welcome. We highly recommend this cozy spot and will be returning again.
Guest favourite
Guesthouse in Saint Petersburg
4.85 out of 5 average rating, 467 reviews

Cute home in historic neighborhood

ColleenRating, 5 stars2 weeks ago
We loved our stay. We have stayed here multiple times and would recommend it.
Guest favourite
Guesthouse in Seminole
4.95 out of 5 average rating, 240 reviews

Private Apt/3miles from beaches/Treehouse.like

LisaRating, 5 stars3 months ago
Karen and Pete have been wonderful hosts! My husband and I were displaced by the recent hurricanes, and needed a place to stay while we get our house repaired. They have been very welcoming, friendly, responsive, and always willing to help out if needed. This is one of the cleanest Airbnb's we have ever stayed in. It's a large private space, with lots of windows and natural light, with a nice sized main room and kitchen. The home has reliable high-speed internet which has been great for my husband working remote. It's in a peaceful country-like setting with beautiful flowering vines and mature oak trees surrounding the property. Located across the street is Walsingham Park, a large county park with walking/biking trails, lakes, and picnic areas. It's also close to the Pinellas Trail, an awesome bike trail that runs the entire length of the county. The property is located in a quiet residential area with lots of shopping and restaurants within a short drive. Highly recommend!
Superhost
Guesthouse in Saint Petersburg
4.76 out of 5 average rating, 325 reviews

The Lassing House

NataleeRating, 5 stars2 weeks ago
Super cute place in a great location for a great price! We had a wonderful stay here.
Guest favourite
Guesthouse in North Downtown
4.88 out of 5 average rating, 180 reviews

The Uptown Treehouse - Downtown St. Pete 1Br Apt

MatthewRating, 5 stars10 months ago
One of the best Airbnb’s we’ve stayed at. We would have stayed and lived there if we could. Perfect combination of cozy, comfortable, cute, and great location for walking and exploring. Private parking out back and hangout area up top really made this stay enjoyable.
Guest favourite
Guesthouse in Historic Kenwood
4.91 out of 5 average rating, 265 reviews

Walk to St. Pete's Grand Central from Historic Apt

DamienRating, 5 stars2 months ago
Josh and Joy’s place is immaculate and near everything downtown St Pete. If this place is available book without hesitation. I’ll be back!
Guest favourite
Guesthouse in Pinellas Park
4.87 out of 5 average rating, 268 reviews

pet friendly on an equestrian farm

SandraRating, 5 stars2 days ago
Once again we had a wonderful time at Evie's place. We are never disappointed and look forward to our "Happy Place" every year!!

Guesthouses with a patio

Superhost
Guesthouse in St. Petersburg
4.86 out of 5 average rating, 309 reviews

NEW Luxury Casita w/Hot Tub, Fire Pit, Backyard🏝☀️🏖

AlexRating, 5 stars2 weeks ago
Great spot close to lots of things and a nice hot tub to end off your day. Would definitely stay again
Guest favourite
Guesthouse in Town 'n' Country
4.98 out of 5 average rating, 180 reviews

Entire Guest House near Tampa airport

BrendaRating, 5 stars2 days ago
We loved this place & Tatiana was great. The cleanliness & detail in decoration made the atmosphere and comfort amazing. The place was so peaceful and private. She had very nice new linen & towels. Also nice shampoo, conditioner, soap and coffee pods. Her TV was big & nice. The only small down side we would say, if you are in the rental a lot during the day, is the window blinds if you want the blinds open are facing the renter’s back yard & pool. Since we were on vacation this did not matter to us. There is a window in the living room & bedroom you can open the blinds. We highly recommend this place.
Guest favourite
Guesthouse in Apollo Beach
4.96 out of 5 average rating, 101 reviews

Waterfront Studio Home in Paradise

Pam And DanRating, 5 stars2 weeks ago
Rose and Charlie were very gracious, the cottage was a quiet and relaxing place to be and we enjoyed the outdoor space. A great value and close to everything we wanted to do in Apollo Beach.
Superhost
Guesthouse in Tampa
4.82 out of 5 average rating, 193 reviews

Suite The Marine

DominicRating, 5 stars2 weeks ago
Nice and easy check in clean place!
Guest favourite
Guesthouse in Tampa
4.96 out of 5 average rating, 270 reviews

Tiny House Oasis Blue Vatican . Near MacDill Base

DianaRating, 5 stars1 day ago
Cute little guest house. Has mini fridge, Keurig and microwave. Screened porch with TV and music. Outdoor sitting area for guests. Very clean, air conditioning, tile floors are nice and cool when the temperature outside is hot. Very responsive to messaging. There's a convenience store about 1/4 mile away, and restaurants/grocery/target about 1.5 miles away. Definitely walkable if you don't have mobility issues or a car.
Superhost
Guesthouse in Tampa
4.85 out of 5 average rating, 101 reviews

Cozy studio/Full Kitchen/Private Entrance

CarmenRating, 5 stars1 day ago
My stay was great. A comfortable, spacious location in a quiet residential neighborhood. I would gladly reserve a future stay!
Superhost
Guesthouse in Ybor City Historic District
4.84 out of 5 average rating, 175 reviews

Adorable 1 Bedroom Ybor Casita with outdoor patio

MikeRating, 5 stars3 weeks ago
Thank you Daniel for hosting us. Your place was a perfect little home, clean, felt right at home. Would stay again.
Guest favourite
Guesthouse in Tampa
4.92 out of 5 average rating, 107 reviews

Apartamento Casino 1

PatriciaRating, 5 stars5 days ago
This was our second stay, and once again, it was a fantastic experience. The property is exceptionally clean, peaceful, and offers complete privacy. Everything was just as we hoped, making for a truly relaxing stay. We would definitely return!

Guest house rentals with a washing machine and dryer

Superhost
Guesthouse in Tampa
4.85 out of 5 average rating, 223 reviews

Seminole Heights Flamingo's Little house

TomRating, 5 stars2 months ago
the place was advertised. It was our second stay and we will be back!
Guest favourite
Guesthouse in Historic Old Northeast
4.91 out of 5 average rating, 124 reviews

Private 2 BR Backyard Oasis, Walk to Downtown!

PatrickRating, 5 stars1 month ago
Place is well located within downtown, with all the amenities you could need. I would highly recommend this spot for anyone looking to stay in st. Pete
Guest favourite
Guesthouse in Bayshore Beautiful
4.84 out of 5 average rating, 239 reviews

La Casa Azul - Private Detached Guest House

BrianRating, 5 stars1 month ago
Beautiful home and well-mannered host.
Guest favourite
Guesthouse in Historic Old Northeast
4.98 out of 5 average rating, 243 reviews

Historic Old Northeast Get A Way

FrancoRating, 5 stars3 months ago
Really nice and comfortable apartment in a peaceful and quiet neighbourhood. The apartment is well stocked and felt really homely. Kay has gone to a lot of trouble to make her property feel like a home. Would definitely stay again. A fifteen minute walk from the centre of town so therefore a great location.
Guest favourite
Guesthouse in Brandon
4.88 out of 5 average rating, 57 reviews

Adorable Guesthouse

JohnRating, 5 stars1 month ago
Mom and I came down to Florida for some meetings and our stay was so nice and private in a quiet neighborhood in this guest house.
Guest favourite
Guesthouse in Tampa Heights
4.93 out of 5 average rating, 117 reviews

Caffeinated Bungalito near Armature Works /75in TV

DanRating, 5 stars1 week ago
Matthews Airbnb was great for my wife and I’s visit to Tampa. Worth a 5 star rating! Super clean, stocked with everything you need. Always responsive host! Highly recommend it!
Guest favourite
Guesthouse in Tampa
4.93 out of 5 average rating, 272 reviews

Cozy Suite

DajeRating, 5 stars2 weeks ago
This space was AMAZING! Very,Very,Very Clean and Spacious for 2-3 People. Outside porch with lights and comfortable seating. The check-in was a little skeptical at first, but once Mom came out with warm Florida hospitality felt right at home! Would definitely recommend!
Superhost
Guesthouse in St. Petersburg
4.9 out of 5 average rating, 499 reviews

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

LaurenRating, 5 stars4 weeks ago
We only had the opportunity to stay for a short time however it was perfect one night stay for my wife, kids and I. Cute cozy place and the best part was that I am familiar with the area considering I use to live a block over. Even though I didn’t need anything at the convenience store it’s nice to know that at the end of the alley (very short walk) I can get some adult beverages and a few other items had I needed it. Most definitely would book again!

Quick stats about guesthouse rentals in Clearwater

  • Total rentals

    60 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

    60 properties include access to Wi-Fi

Destinations to explore