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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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Guesthouse in St. Petersburg

4.9 out of 5 average rating, 482 reviews

Private Guest House sleeps 4 w/POOL & near beach!

This adorable pool house is light and airy with plenty of room for 4. There’s a king size bed, queen pullout sofa, dining area, efficiency kitchen perfect for light cooking, oversized closet and a newly remodeled bathroom. Guests have private entrance with small yard and patio of their own, and are encouraged to use the pool and backyard anytime, which we enjoy along with our sweet dogs, Frog and Bella. 3 miles from beach and downtown, lots of restaurants and shopping centers within 1.5 miles.

Guesthouse in Sarasota

4.9 out of 5 average rating, 105 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.

Guesthouse in Gulfport

4.94 out of 5 average rating, 197 reviews

A slice of paradise!

The guest cottage (approx. 300 sq ft) is separate from the main house, where we reside, with a beautiful saltwater pool to cool off in after your day's adventures! The property is 5 blocks from downtown Gulfport, with waterfront restaurants, bars, arts district, unique shopping, and beach. Close access to new tennis courts, bayside beach and minutes away from modern downtown St. Petersburg, and world-famous beaches. We are not set up to host pets or children and no unaccounted for guests.

Guesthouse in Sarasota

5 out of 5 average rating, 150 reviews

Magical Guesthouse 1 mi from SRQ airport

@Aloe_Stranger Dreamy + fresh! This 1-bedroom guesthouse has a king bed, full bath, kitchen, washer/dryer, daybed + sleeper sofa. NEW STOCK TANK POOL! Full of style - it feels like you're in your own art installation. 1 mile from SRQ Airport, it boasts a great location as well cushy comforts. 1/2 mile from Sarasota Bay, 15 min from Lido Beach, 15 min from Siesta Key and many beaches around the Sarasota/Bradenton area. 10 min from downtown Sarasota, 1 mile from the historic Ringling Museum

Guesthouse in Sarasota

4.97 out of 5 average rating, 263 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.

Guesthouse in Sarasota

4.94 out of 5 average rating, 186 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!

Guesthouse in Historic Old Northeast

4.98 out of 5 average rating, 241 reviews

Historic Old Northeast Get A Way

Carriage house converted to cozy updated 1 bedroom plus separate den/office above garage apartment in historic Old Northeast. The den/office has a new queen Murphy bed which will allow a second private sleeping space. Two blocks walking distance to Vinoy Waterfront Park and downtown St Pete. Twenty minute car ride to the beautiful Gulf Beaches or downtown Tampa. Great weekend get-a-way or longer term rental. Parking is available on the street with a parking permit which we provide.

Guesthouse in Rosemary District

4.9 out of 5 average rating, 131 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.

Guesthouse in Sarasota

4.88 out of 5 average rating, 199 reviews

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.

Guesthouse in Bradenton Beach

5 out of 5 average rating, 148 reviews

Bradenton Beach Sunsets 1, Anna Maria Island, FL

Fully furnished water view beach cottage located on beautiful Anna Maria Island directly across the street from white sand beach and Gulf of Mexico. 1 Bedroom 1 bath unit that sleeps 4 with the queen pull out couch. Beach chairs/umbrellas/Boogie boards/laundry room, etc. provided. Three blocks from historic Bridge Street with lively restaurants and bars. Free island trolley and across the bridge from Cortez fishing village. Free off-street parking.

Guesthouse in Historic Kenwood

4.97 out of 5 average rating, 285 reviews

Charming apartment in Historic Kenwood

Cute, spacious apartment located in Historic Kenwood, which was named 2020 “Neighborhood of the year” by NUSA. Our apartment is above our large garage. Lots of charm and just enough space to spread out a little for some privacy. Located close to downtown, walking distance to lots of restaurants, breweries and bars but still a short drive to our beautiful beaches. You access the apartment through our side gate and up an exterior stairway.

Guesthouse in Osprey

4.99 out of 5 average rating, 307 reviews

Cozy Cottage by the Bay

Enjoy this modern yet rustic looking 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!

Vacation rentals for every style

Get the amount of space that is right for you

Villas

Luxurious estates for the ultimate escape

Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Sarasota guesthouse rentals

Free parking on premises

Air conditioning

Family-friendly guest house rentals

Guesthouse in Sarasota

4.93 out of 5 average rating, 476 reviews

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

Guesthouse in Sarasota

4.99 out of 5 average rating, 107 reviews

Sarasota Pool House

Guesthouse in Downtown Sarasota

4.97 out of 5 average rating, 439 reviews

Quick and Easy Walk Downtown - Tons of Amenities

Guesthouse in Saint Petersburg

4.84 out of 5 average rating, 449 reviews

Cute home in historic neighborhood

Guesthouse in Indian Beach-Sapphire Shores

4.78 out of 5 average rating, 18 reviews

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

Guesthouse in Saint Petersburg

4.76 out of 5 average rating, 311 reviews

The Lassing House

Guesthouse in Sarasota

4.74 out of 5 average rating, 102 reviews

One Bed Suite near Downtown Sarasota and Beaches

Guesthouse in Sarasota

4.98 out of 5 average rating, 253 reviews

Casita Lantana, a 1925 cottage in a Tropical Oasis

Guest house rentals with a patio

Guesthouse in St. Petersburg

4.98 out of 5 average rating, 158 reviews

Central Cozy Cottage w/ Heated Pool & Hot Tub!

Guesthouse in Bradenton

4.96 out of 5 average rating, 69 reviews

Modern-Fully Equipped Near Beaches, Downtown & IMG

Guesthouse in Bradenton

4.97 out of 5 average rating, 143 reviews

Sweet MERMAID #1

Guesthouse in Sarasota

4.91 out of 5 average rating, 47 reviews

Adorable Private Quiet Guesthouse with Patio

Guesthouse in Ruskin

4.88 out of 5 average rating, 8 reviews

Beautiful Waterfront Guesthouse

Guesthouse in Historic Kenwood

5 out of 5 average rating, 35 reviews

Kenwood Cottage

Guesthouse in Sarasota

4.94 out of 5 average rating, 17 reviews

Bayou Oaks Guest House

Guesthouse in Bradenton

4.99 out of 5 average rating, 153 reviews

Conch Cottage adorable one bedroom with pool.

Guest house rentals with a washer and dryer

Guesthouse in North Downtown

4.8 out of 5 average rating, 5 reviews

FREE NIGHT! Quant historic home downtown: 9 BR!

Guesthouse in Historic Kenwood

5 out of 5 average rating, 70 reviews

Kenwood Retreat - 1BR carriage house

Guesthouse in St. Petersburg

4.91 out of 5 average rating, 58 reviews

Ask About $35 Cleaning Fee - Cal King Beach House

Guesthouse in Bradenton

4.86 out of 5 average rating, 69 reviews

Brand new 1 bedroom, 1 bath Guest House! Sleeps 3

Guesthouse in Historic Kenwood

4.98 out of 5 average rating, 91 reviews

2 bedroom guesthouse in hip Grand Central District

Guesthouse in Port Charlotte

4.93 out of 5 average rating, 100 reviews

the Pool House

Guesthouse in Saint Petersburg

4.96 out of 5 average rating, 278 reviews

The Dollhouse in Downtown St Pete

Guesthouse in Bradenton

4.84 out of 5 average rating, 49 reviews

Newly Remodeled PRIVATE Guest House With Pool

Quick stats about guesthouse rentals in Sarasota

Total rentals
60 properties
Total number of reviews
4.3K reviews
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wifi availability
60 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool

Destinations to explore