Guesthouse vacation rentals in Sarasota County

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in Sarasota County

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Guesthouse in Sarasota

4.92 out of 5 average rating, 517 reviews

La Casetta: "the little house" near to the beaches

La Casetta means, in Italian, little house. Set in a private, peaceful, mature Florida tropical garden, a real hideaway. I am proud of the cleanliness of our property, however in this new reality that we live in, we do carry out enhanced cleaning and sanitizing between guests. We also practice social distancing, insofar as guests have their own part of our luscious back garden as well as your own entrance. La Casetta has 1 queen sized bed, bathroom & kitchenette. Wifi & Netflix available.

Guest favorite

Guesthouse in Sarasota

4.91 out of 5 average rating, 111 reviews

Super Clean Cozy and Quaint steps from the beach

The best of all worlds, cleanliness and steps from the beach. Avoid the crowds at the public beach in this beautiful private beach with lounge chairs already at the beach for your convenience. Literally yards from the beach, exit the ground floor condo and walk 100 yards to the gate to the private beach. Only 2 miles from the village, with an easy close by trolley stop just outside the complex. Beach cart, umbrella, cooler, beach toys and towels provided for your convenience! Look no further.

Guest favorite

Guesthouse in Sarasota

4.83 out of 5 average rating, 314 reviews

Sarasota Getaway Guest House

Fully private & not shared with others Seasonal rates commence Nov 1 2023 - April 30, 2024 Longer Term Lower Rate Rentals commence May 1, 2024 - Nov 24 (Long Term rental rates available - please contact) Enjoy the luxuries of staying in the Gillispie Park area Dog Park, Tennis, Pickleball...... Walking distance to downtown where guests can find wonderful dining, entertainment, Saturday morning Farmers Market and much more Close to beaches and Arts and Entertainment and St. Armands Circle

Top guest favorite

Guesthouse in Sarasota

4.97 out of 5 average rating, 276 reviews

Sarasota guest house only 8 miles to Siesta Key

Our Florida-themed guest house has everything you need to enjoy your vacation in beautiful Sarasota, Florida. It is a very comfortable, clean and private one bedroom and one bathroom guest house. It is a completely separate space and has it's own private entrance. It is conveniently located in a quiet, safe neighborhood near Interstate I-75, Shopping, Dining, Twin Lakes Park, Serenoa Golf Course, Myakka River State Park and just 8 miles from the #1 beach in the U.S. - Siesta Key Beach.

Top guest favorite

Guesthouse in Sarasota

4.92 out of 5 average rating, 180 reviews

Cozy Guesthouse in central Sarasota!

This cozy independent guesthouse is perfect for all ocations from a few business day stay to a vacacion getaway. Near to siesta key beach! Enjoy a private room with a comfortable bed, a bathroom with a great shower and hot water, plus a cozy bar-style area perfect for preparing snacks and coffee. You’ll also have access to a small patio where you can unwind, and we provide beach essentials. Perfect for travelers seeking comfort and peace, and a well-equipped space. We’d love to host you!

Guest favorite

Guesthouse in Sarasota

4.93 out of 5 average rating, 476 reviews

Clean and Modern Sarasota Studio

Our studio is private, comfortable, stylish, & efficient. Whether you are coming for business or leisure, we are sure you will have everything you need. Our home is newer (built in 2020) and we designed this space specifically with Airbnb guests in mind. Our neighborhood is central to almost all of Sarasota! We were born and raised here, and in our opinion this area is central to everything! Whether you are headed to Siesta, Myakka State Park, or UTC mall, you won't be driving for long!

Guest favorite

Guesthouse in Sarasota

4.92 out of 5 average rating, 110 reviews

University Pines Studio in Sarasota

Welcome to University Pines Studio, the perfect place to stay! Located in a quiet neighborhood situated in the heart of Sarasota off of University Parkway, it is close to restaurants, supermarkets and convenience stores, and has a beautiful park just a half mile away. It is minutes away from Lido Beach and Siesta Key Beach which is voted the #1 beach in the U.S. year after year, 4 miles from the SRQ airport., is near the UTC Mall, local shopping centers and the Nathan Benderson Park.

Guest favorite

Guesthouse in Sarasota

4.91 out of 5 average rating, 143 reviews

Perfect Florida location: Craftsman Carriage House

Beautiful, recently built accessory dwelling in downtown Sarasota designed to match and complement our historic 1920s bungalow main house, which can be booked separately on AirBnB. The 1BR/1BA carriage house apartment has all modern amenities, with a dedicated garage parking spot and a lovely outdoor porch. The carriage house features Craftsman-style details and is available for short- or long-term stays. Locally-based property management team on-call to ensure a pleasant stay.

Guest favorite

Guesthouse in Sarasota

4.89 out of 5 average rating, 123 reviews

City Garden Cottage

City Garden Cottage is a cozy and comfortable cottage located in the quiet Laurel Park neighborhood in Sarasota, only a few blocks from downtown. The studio is surrounded by lush gardens and trees. Inside you will find a kitchenette, equipped with a coffee maker, toaster, refrigerator, and hot plate. The studio also has a flat-screen TV, a queen bed & private bathroom. There is also shared use a gas grill and fire pit included with the rental.

Guest favorite

Guesthouse in Sarasota

4.99 out of 5 average rating, 140 reviews

Maggie's Hideaway

This adorable little bungalow is hidden away in one of Downtown Sarasota's oldest historical neighborhoods and only a couple miles from Sarasota Bay and surrounding beaches. Beautiful Lido Beach is only five miles west, Siesta Key is seven miles southwest, with Benderson Park being only seven miles east. Fabulous shopping and world class dining is plentiful in this downtown community. There is plenty to see and do in Sarasota - Come see us!

Guest favorite

Guesthouse in Sarasota

4.92 out of 5 average rating, 116 reviews

Have a great time

Your family will be close to everything when you stay at this centrally-located place. Lido beach is only 17 minutes away from the house. Siesta beach is only 19 minutes drive from the property. Downtown is a 6 minutes drive and a 34 minutes of walk. Beach chairs, cooler and beach umbrella available by request. Please let us know if needed and we leave it in house for your use.

Top guest favorite

Guesthouse in Sarasota

4.87 out of 5 average rating, 415 reviews

The Cottage, very close to Siesta Beach!

The cottage was built in 1926 and is in a Historic Neighborhood. Our location is a 10 min car ride to the #1 Rated Siesta Key Beach and a short stroll to popular eateries and shopping areas. The cottage is cozy and has all the essentials of home. Private entrance, backyard, kitchenette with a full fridge. Ideal for 2 people but can accommodate more. Dogs welcome