Guesthouse vacation rentals in Sarasota

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in Sarasota

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

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Top guest favorite

A charming outdoor area features tropical landscaping with a large palm tree surrounded by gravel. Two red chairs and a small table offer a cozy seating arrangement, while colorful flowers provide a vibrant touch to the setting.

Guesthouse in Fort Myers

4.99 out of 5 average rating, 113 reviews

Private guest house—minutes to the best beaches!

Experience the charm of Fort Myers in this quaint, private guest house located in the historic district. Perfectly situated near Fort Myers Beach (12 miles), Sanibel Island (16 miles), downtown (4 miles), some of the areas best restaurants (some even walking distance), grocery stores, & convenience stores. Easy access to Southwest Florida International Airport & FGCU. Uber and Lyft are easy access. The neighborhood is peaceful, safe, & walk friendly. Book now for a convenient and memorable stay.

Guest favorite

An open living space is showcased, featuring a cozy brown leather loveseat, a wooden coffee table, and a spacious bed with a light-colored throw. The kitchen is equipped with stainless steel appliances set against a white brick wall, while industrial-style pendant lights hang above the granite counter.

Guesthouse in Riverview

4.9 out of 5 average rating, 127 reviews

Spacious Industrial Style Studio Guesthouse

Welcome to Riverview Cottage - A beautiful, fully renovated, industrial/modern guest house only 10 miles from Tampa Bay! In this 450 square foot guest house, you'll enjoy all the regular luxuries of a full-size home without sacrificing comfort! Best of all enjoy a FULLY fenced-in entrance and private yard + parking for up-to 2 vehicles! Whether stopping by for work or leisure, you are sure to enjoy this thoughtfully designed space complete with full-size kitchen, bathroom, and living space.

Guest favorite

A vibrant hammock is suspended between two palm trees, positioned on a sandy beach with gentle waves lapping at the shore. The clear blue sky highlights the serene coastal environment, creating an inviting space for relaxation by the water.

Guesthouse in Historic Old Northeast

4.89 out of 5 average rating, 296 reviews

Private Guest Studio w/Courtyard

Enjoy your own private guest studio separate from the main house (no main house access). Located 1 mile from downtown and 1/2 mile from Tampa Bay. Guest studio includes one queen size bed, one full bathroom with shower (no tub), brand new air conditioner, mini fridge, 32" smart TV (login to your favorite streaming options and enjoy, no cable provided), a microwave and a coffeemaker. Great walking ability. We do not allow animals, any pet related questions please inquire with us prior to booking!

Guest favorite

The exterior of a Spanish-inspired structure exhibits textured walls and decorative elements. Two garage doors are centered within the façade, flanked by natural landscaping. A spacious driveway is visible, with sunlight casting soft shadows across the surface.

Guesthouse in Fort Myers

4.88 out of 5 average rating, 101 reviews

1920s Cozy Private Charming Tiny Home

Discover this charming 1925 stand-alone house in a scenic river-view neighborhood, close to eateries & shops. Enjoy private parking, security system, Wi-Fi, &Smart TV. Just 2 miles from vibrant downtown river district with dining, art, shops, music, & museums. Nearby amenities include; public golf course (.5 mi), community pool (1 mi), laundry (2 mi), and several beaches (5 mi). Experience tranquility and modern updates in this cozy 366 sq ft home, discreetly located behind a private residence.

Superhost

A wooden boardwalk extends over calm waters, lined by tall reeds. Clear blue skies dominate the scene, with a few clouds scattered above. In the distance, several boats can be seen near the shoreline, enhancing the tranquil lakeside setting.

Guesthouse in St. Petersburg

4.83 out of 5 average rating, 125 reviews

Guest House by the Lake

Large guest suite less than 10 minutes to both downtown St Pete and St Pete Beach. Walk out the back and you'll find yourself only a minute away from a large lake and a beautiful park. There is a golf range and practice green area located in the same park. The space is large and completely private. You will find everything you need - full bathroom, large closet, full table/desk, kitchenette, wifi/Netflix, yard/grill, etc. Also available to use: kayak, golf clubs, beach towels, fishing poles

Guest favorite

The image features a hot tub with illuminated water, set against a backdrop of lush greenery and colorful landscaping. Soft lighting highlights the features of the surrounding area, creating a serene outdoor environment perfect for relaxation.

Guesthouse in St. Petersburg

4.96 out of 5 average rating, 106 reviews

Tropical 2BR Casita + Hot Tub Near It All

NO CLEANING FEES!! This cozy 2-BR 1-Bath guesthouse is close to everything, making it easy to plan your visit. Two queen size beds. Private, fully fenced in yard with gorg landscaping! Only 8 min away from Downtown St Pete & St Pete Pier with tons of restaurants, bars, cafes & world class shopping. Great attractions like the Sunken Gardens are only 5 min away, beaches are only a 20 min drive. Tampa Intl Airport is a 15 min drive & St Pete/Clearwater Intl Airport is only 12 min away.

Guest favorite

A welcoming outdoor porch is featured, with a comfortable seating area consisting of a wicker loveseat adorned with colorful cushions. A coffee table sits in front, and a ceiling fan is installed overhead. Lush greenery surrounds the space, providing a tranquil atmosphere.

Guesthouse in Rosemary District

4.91 out of 5 average rating, 140 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.

Top guest favorite

A warm wooden staircase leads upwards, flanked by vibrant green foliage. The outdoor stairs feature subtle lighting along the sides, creating a welcoming entrance to the second-story carriage house apartment.

Guesthouse in Gulfport

4.98 out of 5 average rating, 104 reviews

Gulf Guesthouse - king bed, 3 blocks to downtown.

Be our guest! Welcome to our family compound where you will enjoy the treetop views from our second story carriage house guest apartment. You'll be surrounded by the tropical serenity of lush palms and plants, both inside and out, while being just around the corner from the excitement of downtown Gulfport. Our updated one bedroom apartment is fully furnished and stocked with all of the things you'll need for an extra comfortable, enjoyable stay. We look forward to hosting you!

Guest favorite

A sleek white convertible car is positioned in front of a modern architectural building, characterized by striking glass panels and the presence of palm trees. The clear blue sky adds to the bright and vibrant setting.

Guesthouse in St. Petersburg

4.9 out of 5 average rating, 243 reviews

Crescent Heights/St. Petersburg Entire Guest House

If you are looking for a clean, cute place to stay, you’ll love our studio guesthouse! Our contemporary 350-square-foot remodeled garage apartment is located in the tranquil, tree-lined neighborhood known as Crescent Heights. We are a 5 minute ride to downtown St. Pete where you can sample many great restaurants, breweries, museums and shops. The Gulf beaches are 25 minutes away and downtown Tampa is a 40 minute ride. Unit has private parking and queen size bed.

Guest favorite

A sandy pathway leads through lush greenery towards the beach, framed by swaying beach grasses. Gentle waves can be seen in the distance under a sky filled with soft clouds, creating a serene coastal scene.

Guesthouse in Pass-a-Grille Beach

4.92 out of 5 average rating, 195 reviews

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

Get ready to relax and enjoy the island life at this "Key West" style guest house! This Pass-A-Grille 1 bedroom apartment is located less than two blocks from the beach. This is the Upstairs 2nd floor unit of a two apartment cottage that is situated on the property, behind the owner's main house. The apartment has a full kitchen, living area and a side nook with a set of bunkbeds. There is also a small upstairs porch to sit and enjoy the view!

Top guest favorite

A covered porch area is visible, framed by white railings and blue siding. The door leading inside features a screen, providing ventilation. Bright sunlight filters through, highlighting the outdoor space and views of greenery in the distance.

Guesthouse in Fort Myers

4.99 out of 5 average rating, 100 reviews

Charming Carriage House in Historic Neighbourhood

This lovely carriage house backs onto the famous Edison Ford Estates making it a truly unique location- you really don’t have far to go to explore its beautiful gardens! Hit the Downtowns restaurants, bars and shops nestled within Art Deco architecture in stunning pastel colours for a real ‘Old Florida’ experience! DT is a 20 minute walk away or take advantage of the free trolley service from Nov-May 1. SWF airport 17 miles.

Top guest favorite

A wooden dock extends into calm waters, bordered by lush greenery and palm trees. A stately two-story building is visible in the background, featuring a prominent white facade. The surrounding landscape is serene and enhances the natural setting.

Guesthouse in Osprey

4.99 out of 5 average rating, 123 reviews

Terrific Treehouse by the Bay

Enjoy this modern yet rustic looking second-floor guest cottage in historic Osprey, one of Sarasota County's first settlements. Walk to the bayfront, restaurants, shopping, library, and parks. A short drive takes you to our famous Gulf beaches and all that Sarasota and Venice has to offer. Hurricane Milton: Yes, we are cleaned up and have power and internet!