Guesthouse vacation rentals in Sarasota

Guesthouse in Historic Old Northeast

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.

4.89 out of 5 average rating, 295 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!

A bright and airy guest suite is presented with a sloped ceiling and large windows allowing natural light to flood the room. A cozy bed is positioned beside a woven basket and a decorative wall feature, while a warm rug adds comfort to the wooden floor.

4.97 out of 5 average rating, 219 reviews

Cozy Guesthouse Near Downtown (Non-Toxic)

Come relax in this calm, newly renovated guest suite. Clean, natural, & chemical free - diffusers and oils available on site. Amenities like central a/c, laundry, private patio, full kitchen, Netflix & Hulu. A short 5 minute drive from downtown - near tons of local restaurants, entertainment, and beaches. St. Pete loves the local vibe, be sure to check out our visitors guide for suggestions on spots to see while you’re here. It doesn’t get any better than St Pete! Book your stay with us today!

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.

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

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.

4.96 out of 5 average rating, 103 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.

Guesthouse in Rosemary District

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.

4.91 out of 5 average rating, 139 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.

4.98 out of 5 average rating, 102 reviews

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

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!

4.88 out of 5 average rating, 204 reviews

A shared swimming pool reflects shimmering blue water, with gentle ripples creating a serene effect. A stainless steel handrail is visible at one side, offering support for entry. Sunlight enhances the clarity of the water, inviting relaxation and enjoyment.

Guesthouse in Sarasota

Supercute Beach Themed Retreat Free Parking Wi-FI

Come and enjoy our newly remodeled 400 square foot laid back beached themed guest house. Located just 1.5 miles away from Sarasota/ Bradenton airport, and less than 10 miles away from our world famous beaches. Whether you are a single person in search of a long term stay or a family looking for a short vacation, we have the place for you. Our guest area is attached to our main residence and has a private entrance. Enjoy our shared swimming pool and outside patio areas.

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.

4.9 out of 5 average rating, 242 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.

Guesthouse in Pass-a-Grille Beach

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.

4.92 out of 5 average rating, 192 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!

4.99 out of 5 average rating, 98 reviews

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

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.

4.99 out of 5 average rating, 122 reviews

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

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!

A cluster of palm trees is framed against a white fence, surrounded by smooth white stones. Soft lighting is provided by ground-level fixtures, casting gentle shadows on the gravel pathway.