Guesthouse holiday rentals in Sarasota County

Find and book unique guesthouse rentals on Airbnb

Top-rated Guesthouses in Sarasota County

Guests agree: These guesthouses are highly rated for location, cleanliness and more.

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Guest favourite

Guesthouse in Sarasota

4.93 out of 5 average rating, 459 reviews

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

La Casetta means, in Italian, a tiny 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.

7–14 Nov

$207 NZD per night

Guest favourite

Guesthouse in Sarasota

4.91 out of 5 average rating, 102 reviews

Jungle Shack in the Back

The "Jungle Shack in the Back" is a small, private studio guest house behind our 1925 cottage in the wonderful tree-lined neighborhood of Indian Beach. West of the trail. Just north of downtown Sarasota. "The Shack" sits just 3 houses from the bay and a little bayfront park with benches and public bay access. Drop your things in the small, clean, quaint furnished studio and walk down with your wine glass for the evening sunset ritual. It's not the Ritz, but we're in a fabulous neighborhood.

24–31 Jan

$191 NZD per night

Guest favourite

Guesthouse in Sarasota

4.96 out of 5 average rating, 248 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.

7–14 Aug

$200 NZD per night

Guest favourite

Guesthouse in Sarasota

4.93 out of 5 average rating, 173 reviews

1920s Cottage in a Private Tropical Wooded Setting

Your perfect Sarasota getaway! This lovely little cottage is very private & isolated but just minutes from downtown. Modern conveniences & comfort nestled in a charming and cozy period cottage. You will make yourself at home in this tranquil, cozy, and quaint 1920's Old Florida Guest House. Nestled under a canopy of ivy-covered oaks, pines and the tallest of palms - where the flowers are always in bloom! This captivating cottage is your woodsy home base for all your Sarasota adventures!

13–20 Feb

$255 NZD per night

Guest favourite

Guesthouse in Englewood

4.97 out of 5 average rating, 202 reviews

Shabby chic cottage with pool one mile from beach

This adorable shabby chic decor style studio cottage for 2 is located on one acre of old Florida landscaping. Great area for walking, biking, for exercise. Included with this home is access to a pool and large, lovely lanai, just outside the door. Head south for 7 min to historic Dearborn St or north for 3 miles to Venice. This location offers peace and tranquility combined with accessibility to endless activities nearby. 2 twins OR one King, per your preference. The pool is unheated.

18–23 May

$228 NZD per night

Guest favourite

Guesthouse in Sarasota

4.94 out of 5 average rating, 370 reviews

Clean and Modern Sarasota Studio w/ Beach Gear!

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!

2–9 Oct

$190 NZD per night

Guest favourite

Guesthouse in Sarasota

4.97 out of 5 average rating, 408 reviews

Quick and Easy Walk Downtown - Tons of Amenities

Are you coming to Sarasota on vacation or perhaps considering moving here? If yes, then the Carriage House is the perfect place to use as a base camp while you explore the area and experience the best Sarasota has to offer. Quick and easy walk to dozens of casual restaurants, cool bars and unique shops. 5 minutes to Selby Gardens. 10 minutes to the Sarasota Bayfront. Main street is half a mile away. We provide tons of amenities including bikes, kayaks, beach chairs and umbrella.

10–17 Sep

$258 NZD per night

Guest favourite

Guesthouse in Sarasota

4.91 out of 5 average rating, 114 reviews

Perfect Florida location: Craftsman Carriage House

Beautiful, new construction 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.

23–30 Jul

$227 NZD per night

Guest favourite

Guesthouse in Sarasota

4.99 out of 5 average rating, 130 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!

25 Aug – 1 Sep

$273 NZD per night

Guest favourite

Guesthouse in Englewood

4.92 out of 5 average rating, 198 reviews

1 bed apat/full kitchen 5 min.from Manasota beach

Want to get away from the cold? Englewood FL. has 3 nice beaches to choose from. Venice has nice shopping and lots of sharks teeth.This nice apt. is ideal for those that want to go to the beaches and look for sharks teeth,eat great local food and enjoy the beautiful Southwest Florida weather.The Wi-Fi is not the best but should run Netflix. A percent of our earnings goes to a few international charities

14–21 Sep

$207 NZD per night

Superhost

Guesthouse in Sarasota

4.91 out of 5 average rating, 150 reviews

Solitude at Waterside South

*******SEE ADDITIONAL INFO!******** Our apartment is at the back of our 1.5 acre property, set behind beautiful, mature oak trees and is definitely a quiet retreat! The apartment is attached to our workshop/barn but you will not have access, nor be bothered during your stay! We (Beth & Merlin) live in the main house. 15 miles from Siesta beach and 12.5 miles from St. Armands and Lido beach.

20–27 Jun

$226 NZD per night

Guest favourite

Guesthouse in Sarasota

4.86 out of 5 average rating, 371 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 or 25 min bike 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

8–15 Dec

$231 NZD per night