
Guesthouse holiday rentals in Sarasota
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Top-rated Guesthouses in Sarasota
Guests agree: These guesthouses are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Sarasota guesthouses
Family-Friendly guesthouses

St. Pete Beach House
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.

Stylish Retreat| Walk 2Dtwn+beach |Bikes+Patio
Super cute and comfortable. I can’t wait to stay again. Perfect walking distance to the pier and Dali museum.

Sarasota Pool House
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.

Cute home in historic neighborhood
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.

The Lassing House
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

One Bed Suite near Downtown Sarasota and Beaches
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!

The Uptown Treehouse - Downtown St. Pete 1Br Apt
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.

The Cottage, very close to Siesta Beach!
Fair price. Great Location. Awesome / quick communication.
Guesthouses with a patio

Coastal Hideaway: 2/1 guest house close to UTC!
Quiet and comfortable. Erinn thought of everything to make this an enjoyable stay. 🙂

Waterfront Studio Home in Paradise
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!

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!

Downtown Garden Studio close to everything
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!

Oasis historic cottage w/Tropical Patio/Parking
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!

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.

the Pool House
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!

Sea Turtle Cove private oasis near beaches
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

High Life | Cozy Duplex Retreat
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!

Downtown Sarasota Guest House
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!

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

The Bungalow in Downtown St Pete.
We totally loved our stay in the Bungalow ... lots to do nearby in walking distance, near to great beaches and downtown St. Pete.

Historic Old Northeast Get A Way
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.
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!

A Hidden Gem Steps to Pass-a-Grille Beach Dogs Ok!
Amazing location, beautiful space and seamless check-in/out

Sarasota Bayside Hideaway
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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- Anna Maria Island
- Siesta Beach
- Anna Maria Public Beach
- Crescent Beach
- John's Pass
- Turtle Beach
- Caspersen Beach
- Bean Point Beach
- Busch Gardens Tampa Bay
- Raymond James Stadium
- Cortez Beach
- Lido Key Beach
- Amalie Arena
- Coquina Beach
- Gulfport Beach Recreation Area
- Vinoy Park
- North Beach
- Fort De Soto Park
- Manasota Key Beach
- Streamsong Resort
- Tampa Theatre
- Jannus Live
- Curtis Hixon Waterfront Park
- ZooTampa at Lowry Park
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