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Guesthouse holiday rentals in Sarasota

Find and book unique guesthouse rentals on Airbnb

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Popular amenities for Sarasota guesthouses

Family-Friendly guesthouses

Guest favourite
Guesthouse in St. Pete Beach
5 out of 5 average rating, 35 reviews

St. Pete Beach House

TedRating, 5 stars4 months ago
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.
Superhost
Guesthouse in Historic Old Northeast
4.78 out of 5 average rating, 97 reviews

Stylish Retreat| Walk 2Dtwn+beach |Bikes+Patio

MandolyneRating, 5 stars4 weeks ago
Super cute and comfortable. I can’t wait to stay again. Perfect walking distance to the pier and Dali museum.
Top Guest favourite
Guesthouse in Sarasota
4.99 out of 5 average rating, 117 reviews

Sarasota Pool House

DanRating, 5 stars1 month ago
This was our second time staying at Lubos pool house. We really enjoyed our stay and are already looking far time to escape back. Great location near restaurants, stores and beaches. Back yard and pool are a dream and very peaceful.
Guest favourite
Guesthouse in Uptown
4.85 out of 5 average rating, 486 reviews

Cute home in historic neighborhood

YuvalRating, 5 stars2 weeks ago
The place was cozy, comfortable, and a great value overall. Clean and well-equipped, working AC, fresh sheets, clean kitchen and bathroom, and enough supplies for a short stay. I did find a dead roach when we arrived, but being from Florida, that’s not shocking and didn’t bother me. If you're super particular about spotless perfection, you might notice minor things, but nothing that impacted our comfort. The neighborhood is clearly mid-gentrification so you may see some characters around; I came across a homeless person sleeping in the nearby playground one morning while walking my dog. That said, I never felt unsafe (as a 6 foot tall guy) and it seemed like a “keep to yourself and you’re fine” kind of area. I took my daughter to the playground another day without issue. The best part is the location: 5 min drive (or 10 min scooter ride) to Central Ave, for great bars and restaurants and a 10 min or less drive to the waterfront area.
Superhost
Guesthouse in Old Southeast
4.76 out of 5 average rating, 340 reviews

The Lassing House

Michael & AprilRating, 5 stars5 days 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
Guesthouse in Arlington Park
4.74 out of 5 average rating, 102 reviews

One Bed Suite near Downtown Sarasota and Beaches

DianaRating, 5 stars14 months ago
We loved our stay here! Would highly recommend to anyone staying around the area. Has all the amenities you could ever possibly need and the host was super attentive. 10/10!
Guest favourite
Guesthouse in Uptown
4.88 out of 5 average rating, 188 reviews

The Uptown Treehouse - Downtown St. Pete 1Br Apt

PauloRating, 5 stars1 week 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.
Top Guest favourite
Guesthouse in Sarasota
4.87 out of 5 average rating, 415 reviews

The Cottage, very close to Siesta Beach!

PaulRating, 5 stars1 week ago
Fair price. Great Location. Awesome / quick communication.

Guesthouses with a patio

Guest favourite
Guesthouse in Sarasota
5 out of 5 average rating, 8 reviews

Coastal Hideaway: 2/1 guest house close to UTC!

DebbieRating, 5 stars1 week ago
Quiet and comfortable. Erinn thought of everything to make this an enjoyable stay. 🙂
Guest favourite
Guesthouse in Apollo Beach
4.95 out of 5 average rating, 109 reviews

Waterfront Studio Home in Paradise

MindyRating, 5 stars5 days ago
Perfect for our needs! We were in town for a wedding. Location was within 15-30 mins of all the places we needed to be! Wish we had more time to enjoy the pool and the sunset by the water!
Top Guest favourite
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 favourite
Guesthouse in Sarasota
4.94 out of 5 average rating, 94 reviews

Downtown Garden Studio close to everything

JeromeRating, 5 stars4 days ago
We had a wonderful weekend at Andrea’s place. From the beginning, she was very responsive and ensure that all of our questions were answered. The space was easy to find, easy to enter and quite private. When we arrived, it was perfectly clean and was just as described. The home is very bright and comfortable, and the hosts accommodated us with bicycles that we were able to use to explore the area. We had a great time in Sarasota, and this Airbnb was certainly part of the reason. Would definitely recommend!
Guest favourite
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 favourite
Guesthouse in St. Petersburg
4.98 out of 5 average rating, 125 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 favourite
Guesthouse in Gulf Cove
4.93 out of 5 average rating, 119 reviews

the Pool House

CarolinaRating, 5 stars2 weeks ago
We had a wonderful stay! The house was fully equipped with everything we needed to cook and feel right at home. We really appreciated the peaceful atmosphere and privacy the property offered. It was the perfect getaway to disconnect and recharge. Highly recommend!
Top Guest favourite
Guesthouse in Sarasota
4.94 out of 5 average rating, 53 reviews

Sea Turtle Cove private oasis near beaches

AshleyRating, 5 stars4 weeks ago
We had a wonderful stay at Tina’s Airbnb while visiting my hometown in Sarasota. The location was perfect—centrally located and made it easy to get around to all our favorite spots. The neighborhood was peaceful and quiet, which made for a relaxing stay. Tina was a great host—everything was clean, comfortable, and just as described. We’d definitely stay here again next time we’re in town!

Guest house rentals with a washing machine and dryer

Guest favourite
Guesthouse in Sarasota
5 out of 5 average rating, 15 reviews

High Life | Cozy Duplex Retreat

JayRating, 5 stars2 weeks ago
Amazing home! Easy check in and good lighting outdoors. Well decorated for aesthetic and functional purposes. Well established kitchen with everything you need. Rooms and bathrooms are cozy- beds and pillows feel very comfortable. There’s board games, card games, workout and yoga equipment, working tv’s in every room. Everything was thought out just like a home would be. Ethan was very helpful, friendly, and professional. Very glad I picked this home for vacation!
Guest favourite
Guesthouse in Gillespie Park
4.94 out of 5 average rating, 69 reviews

Downtown Sarasota Guest House

MelissaRating, 5 stars3 weeks ago
We had such a great stay at Greg’s place! It was very clean and it was close to all that we wanted to do. It’s 10 minutes from St.Armond’s circle and Lido beach which is exactly what I wanted. I’m so glad I chose to stay at Greg’s Airbnb. A great find and lovely spot!
Guest favourite
Guesthouse in Sarasota
4.93 out of 5 average rating, 88 reviews

Cabana/Guest house w/spa/pool 5min to Siesta key.

СергейRating, 5 stars3 weeks ago
We are very glad that we managed to choose this house. Large, spacious, with all the amenities and close to all the beautiful beaches. John is a big and kind person with an open heart and a bright soul. He does everything to make his guests feel comfortable. Thank you John.
Top Guest favourite
Guesthouse in Uptown
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 Historic Old Northeast
4.98 out of 5 average rating, 248 reviews

Historic Old Northeast Get A Way

Cory LeeRating, 5 stars1 week ago
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.
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!
Guest favourite
Guesthouse in Pass-a-Grille Beach
4.92 out of 5 average rating, 198 reviews

A Hidden Gem Steps to Pass-a-Grille Beach Dogs Ok!

KristieRating, 5 stars3 weeks ago
Amazing location, beautiful space and seamless check-in/out
Guest favourite
Guesthouse in Sarasota
4.92 out of 5 average rating, 39 reviews

Sarasota Bayside Hideaway

CameronRating, 5 stars4 days ago
This place was perfect for what we needed. We needed a little space to just be able to pop in and out of for the weekend. Getting in and out was very easy! It was clean, super cute and we felt very comfortable there.

Quick stats about guesthouse rentals in Sarasota

  • Total rentals

    50 properties

  • Total number of reviews

    3.9K reviews

  • 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

  • Popular amenities

    Kitchen, Wi-Fi and Pool

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