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Guesthouse holiday rentals in Sarasota County

Find and book unique guesthouse rentals on Airbnb

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Popular amenities for Sarasota County guesthouses

Family-Friendly guesthouses

Guesthouse in Siesta Key
4.87 out of 5 average rating, 23 reviews

Siesta Key Luxurious Beach Cottage

KamiRating, 5 stars12 months ago
Location, location, location! Ilene and Al’s place was exactly what we were looking for… a private beach for our family (that includes fur babies) AND a pool! Just like we imagined and similar to our stay in Hawaii. Al and Ilene’s place is as described in the listing and focuses on the surroundings vs the accommodations. The cottage is comfortable and quaint and meets basic needs for two people, but this property is all about the very rare private beach and beautiful surroundings that are quickly disappearing from coastal FL due to the overtaking commercial properties. Get it while you can and enjoy this rare gem… it won’t be here forever!
Guesthouse in Port Charlotte
4.84 out of 5 average rating, 44 reviews

Exclusive Apartment in Park Setting

SusanRating, 5 stars14 months ago
What a lovely place to stay! Sandra and her daughter were always warm, welcoming and helpful. My dog loved the yard, and the surroundings were so peaceful. The apartment has everything we needed and more.
Guesthouse in Sarasota
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!
Guesthouse in Sarasota

'Osprey Landing', Sarasota, FL

JasonRating, 5 stars3 months ago
This was a great place to stay! This is more than a guest house, it's a home. The unit is attached to main house, but it is thoughtfully separated and the backyard is split with fence so there is a ton of privacy and feels like separate house entirely. The full size kitchen is well stocked, the bathroom is nicely appointed with beautiful tiled shower. The bedroom was comfortable with a huge roomy closet which was stocked with plenty of extra towels. The bed was very comfy!! Plus , there is a gas grill in the private backyard which was an added bonus. The property is in a very convenient location. It is across street from Gillespie Park, ample street parking, walking distance to downtown & marina, and bike-able to St. Armands and the beach. Best of all, the host is very responsive, friendly and super accommodating . We really appreciate the warm welcome and responsiveness!!
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.
Guesthouse in Sarasota
4.78 out of 5 average rating, 18 reviews

Guest House Get Away! Great Area. Private. Relax!

MichelleRating, 5 stars16 months ago
Susan's guest house is in a quiet neighborhood, yet convenient to everything. The pictures on the website are accurate; the house is comfortable, and equipped with everything we needed. There is a lovely private and fenced patio/yard that we enjoyed relaxing in with coffee in the mornings. The AC/heat unit was essentially silent, and worked great. Susan was friendly and quickly responsive to anything we needed. If we go back to Sarasota, I will definitely try to book Susan's house again.

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 stars2 weeks ago
Quiet and comfortable. Erinn thought of everything to make this an enjoyable stay. 🙂
Guest favourite
Guesthouse in Sarasota
4.94 out of 5 average rating, 69 reviews

Downtown Sarasota Guest House

MelissaRating, 5 stars1 month 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!
Top Guest favourite
Guesthouse in Venice
4.91 out of 5 average rating, 11 reviews

Peaceful/Private Studio -Pet Friendly, Fenced Yard

RileyRating, 5 stars4 weeks ago
Ellie & Dee’s place is amazing! It’s a small space that can accommodate solo or couple travel - brought my small pup along too! The space was clean with plenty of towels provided as well as beach towels and chairs. The neighborhood is quiet, peaceful, and beautiful to walk around. I felt very safe as a woman traveling alone. It’s less than 5 min from shopping centers and the beach. I loved staying here and would recommend this airbnb to anyone considering it!
Top Guest favourite
Guesthouse in Sarasota
4.94 out of 5 average rating, 97 reviews

Downtown Garden Studio close to everything

DannyRating, 5 stars2 days ago
Andrea went above and beyond to ensure we had everything we needed! No complaints at all, would definitely stay again.
Guest favourite
Guesthouse in Sarasota
4.91 out of 5 average rating, 22 reviews

Relaxing Retreat Near Siesta Key Beach

ManuelRating, 5 stars2 months ago
Excellent lugar para descansar, pequeño pero acogedor, todo funciona perfectamente, muy limpio, muy tranquilo, te da paz!! La pasé muy rico con mi novia! Excellent place to rest, small but cozy, everything works perfectly, very clean, very quiet, it gives you peace!! I had a great time with my girlfriend!
Top Guest favourite
Guesthouse in Port Charlotte
4.93 out of 5 average rating, 119 reviews

the Pool House

CarolinaRating, 5 stars4 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!
Guest favourite
Guesthouse in Sarasota
5 out of 5 average rating, 17 reviews

Pinecraft’s Newest Hideout

RomyRating, 5 stars1 month ago
Jane’s place is so beautiful very relaxing. Such a clean place exactly like the description! Me and my guest stayed for about a week and had everything we needed. Definitely recommend! Jane is super nice and even helped us check in early since we arrived sooner than expected.
Top Guest favourite
Guesthouse in Sarasota
4.98 out of 5 average rating, 52 reviews

Grove Getaway near beach + downtown with pool!

ErinRating, 5 stars2 months ago
The Grove Getaway was perfect for a long weekend, girls stay! The apartment is beautifully decorated, equipped with all essentials and smells wonderful of a citrus grove. Upon check in, we were greeted to a beautiful welcome basket, with a variety of local recommendations. With an easy 10 minute drive to the beach, Lauren’s place was perfectly equipped with beach essentials. The stay was also walkable to local restaurants and markets in the Southside village. Lauren was extremely responsive and helpful in answering any and all questions! Would highly recommend staying here to visit Sarasota and the surrounding beaches!

Guest house rentals with a washing machine and dryer

Top Guest favourite
Guesthouse in Sarasota
5 out of 5 average rating, 16 reviews

High Life | Cozy Duplex Retreat

JayRating, 5 stars3 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 Sarasota
4.93 out of 5 average rating, 89 reviews

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

KimberlyRating, 5 starstoday
We had a great stay at this Airbnb while on our vacation. John was the perfect host, with quick responses to our questions, friendly and kind, and offered a beautiful space for us that matched the description exactly. He also allowed my son, who loves dogs, to take his two dogs out into the backyard whenever we were around which made our downtime very enjoyable! The location was close to everything we did while there, including restaurants, parasailing, biking, state parks, hiking, the beach, and mini golf places!
Guest favourite
Guesthouse in Sarasota
4.93 out of 5 average rating, 197 reviews

1920s Cottage in a Private Tropical Wooded Setting

CarlRating, 5 stars2 months ago
This unit is very well decorated, has efficient space, and is in a gated private nook that feels a world away from the hustle & bustle of this part of Florida. It’s perfect for two adults. The host is respectful, responsive, and caring. We will definitely stay again the next time we are in the area!
Guest favourite
Guesthouse in Sarasota
4.92 out of 5 average rating, 79 reviews

Amazing Location West of the Trail

ErinRating, 5 stars3 weeks ago
Great place to stay, hope to be back soon!!
Guest favourite
Guesthouse in Sarasota
4.94 out of 5 average rating, 34 reviews

*Azure Guesthouse* Walkable! Patio! Beach 8 min!

AmyRating, 5 stars1 month ago
Nicole's AirBnb was one of my favorite in Sarasota! It's extremely walkable, close to both downtown and to Sarasota's famous Siesta Key. Also a super short walk to great restaurants like Libbys and an awesome little market called Mortons. The unit itself is cozy, clean, and well-stocked. I made myself breakfast every morning in the kitchen and had everything I needed to make eggs, bacon, etc. The bed is super comfy and the sheets and pillows were soft. The unit is quiet and peaceful and I slept great. Definitely recommend this AirBnb and hope to stay here again in the future!
Guest favourite
Guesthouse in Sarasota
4.93 out of 5 average rating, 41 reviews

Sarasota Bayside Hideaway

JamesRating, 5 starstoday
We enjoyed our stay. The host was responsive and friendly and the room exceeded expectations!
Superhost
Guesthouse in Siesta Key
4.83 out of 5 average rating, 94 reviews

[Ocean Oasis] guest house on Siesta Key

PethioRating, 5 stars2 weeks ago
Beautiful, clean, quiet home. Everything worked properly as well, no issues. Jayme was FAST to respond and very kind. The neighborhood was perfectly situated and very close to both Siesta and Lido beach. Would definitely come back.
Guest favourite
Guesthouse in Sarasota
4.97 out of 5 average rating, 35 reviews

NEW cottage near Downtown with boat parking

LynetteRating, 5 stars1 week ago
Roland was very responsive and his sister and nephews who live next door were friendly and very helpful. The home was very, very clean and had all the amenities we needed. Perfect for 2 people on a beach vacation. As 2 women traveling alone, we felt very safe. Great lighted parking in the driveway right in front of the door. Would definitely stay there again on our next visit to the area.

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