Guesthouse vacation rentals in Sarasota

A private stock tank pool is surrounded by a wooden deck and lounge chairs. An umbrella provides shade over the pool area. Colorful towels and a stylish table with refreshments are visible, set amidst a landscaped courtyard with lush greenery.

4.99 out of 5 average rating, 238 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 Gillespie Park

An outdoor patio area is shown, featuring a round table with four red metal chairs. Potted plants flank the table, and string lights hang overhead, creating an inviting space. French doors lead into the interior, framed by lush greenery.

4.84 out of 5 average rating, 331 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

A spacious bedroom features a king-size bed adorned with a blue and white textured coverlet. Soft natural light filters through the window, illuminating the room, which includes a nightstand, dresser, and a comfortable bench at the foot of the bed.

4.97 out of 5 average rating, 289 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.

A well-appointed bedroom features a spacious bed with decorative pillows. Soft natural light filters through the window, which is adorned with brown and beige curtains. A vintage mirror adds an elegant touch, while a bedside table with a lamp provides functional lighting.

4.92 out of 5 average rating, 194 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!

A charming entrance features a white trellis adorned with vibrant pink bougainvillea, offering a welcoming touch to the greenery surrounding the cozy cottage. A stone pathway leads to the front door, enhancing the inviting atmosphere of this secluded garden.

4.93 out of 5 average rating, 198 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!

4.95 out of 5 average rating, 111 reviews

Downtown Garden Studio close to everything

Welcome to my brand new guest house! The original building has been rebuilt and completed in December 2024 to offer a more comfortable experience for my guests. Peaceful and centrally located, ideal for relaxation and easy access to explore historic Sarasota and the beaches. A quick drive, bike or a short walk to downtown Sarasota, Selby Botanical Garden and Pineapple Street antique shops. 1.5 miles to Sarasota Bay. 3.5 miles to St Armands Circle and Lido Beach. 6.5 miles to Siesta Key.

A spacious studio features a comfortable king-sized bed with decorative pillows and a cozy leather couch. A mounted TV is visible alongside a desk area, while a kitchenette is seen in the background. Warm light enhances the inviting layout, complemented by modern decor.

4.93 out of 5 average rating, 500 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!

Guesthouse in Laurel Park

An outdoor common area features a decorative umbrella over a bistro table, surrounded by potted plants. A wooden deck leads to a staircase, with warm lights illuminating the setting. A grill is positioned nearby, creating an inviting outdoor space for relaxation.

4.97 out of 5 average rating, 493 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.

Guesthouse in Gillespie Park

An outdoor area is shown with a walkway made of red pavers leading to a yellow building. A dining set with an umbrella is situated on a gravel surface, surrounded by potted plants. Decorative stones and landscaping enhance the inviting outdoor space.

4.91 out of 5 average rating, 151 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.

Superhost

A living area showcases a round dining table with four chairs beside a light-colored sofa. A large artwork featuring palm trees hangs on the wall. The spacious sleeping area is visible through an open doorway, featuring a king-size bed with a yellow accent pillow.

Guesthouse in Siesta Key

4.8 out of 5 average rating, 107 reviews

[Ocean Oasis] guest house on Siesta Key

Welcome to our charming guesthouse, located just steps away from the pristine beaches of Siesta Key! Our cozy 1 bedroom, 1 bathroom guesthouse is the perfect retreat for couples or solo travelers looking to experience the laid-back island lifestyle. Inside, you'll find a comfortable king-size bed, a fully equipped kitchen and a cozy living area with a flat-screen TV. The bathroom is well-appointed, with plenty of fresh towels and toiletries provided for your convenience.

A light blue bedroom features a spacious bed with a floral-patterned blanket and a ceiling fan overhead. Double glass doors provide a view of the pool area outside. Storage options include a white dresser and closet, while a small table and chair are positioned nearby.

4.99 out of 5 average rating, 142 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!

A charming outdoor patio area features a wooden pergola overhead, providing shade. Potted plants and herbs are arranged thoughtfully around the space. Two sets of double doors lead inside, complemented by white garden furniture, inviting relaxation and connection with nature.

4.98 out of 5 average rating, 282 reviews

Casita Lantana, a 1925 cottage in a Tropical Oasis

Welcome to my original 1925 Casita, built in the heyday of the John Ringling era. We are centrally located between Sarasota, Lakewood Ranch, and Bradenton, making it an ideal place to explore all the area has to offer. Getting around is easy since we are located very close to the Ringling Museum of Art. Plus, it is only a short 15-minute drive to downtown Lido Beach and St. Armands Circle.

Popular amenities for Sarasota guesthouse rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly guest house rentals

Guesthouse in Central Oak Park

A private backyard features a heated pool surrounded by lush tropical plants and trees. The pool has a gentle curve and is accompanied by stone steps leading into the water. A small seating area is partially visible in the background, set amongst vibrant greenery.

4.98 out of 5 average rating, 221 reviews

Central Cozy Cottage w/ Heated Pool & Hot Tub!

Guesthouse in Apollo Beach

A bright sleeping area features light wood flooring and a wooden ceiling. A spacious bed is paired with bedside tables and a small dining table for two. Wall-mounted lighting provides soft illumination, and an air conditioning unit ensures comfort.

4.96 out of 5 average rating, 113 reviews

Waterfront Studio Home in Paradise

A serene view of a calm lake surrounded by lush greenery and trees. The clear blue sky reflects over the water, providing a peaceful natural backdrop. The grassy area in the foreground adds to the tranquil setting, inviting relaxation and appreciation of nature.

5 out of 5 average rating, 13 reviews

Sunny's Suite- private + waterfront

Guesthouse in Historic Kenwood

A bright living area features a white sofa and a light grey wall, creating a calm ambiance. A small kitchen area is visible with a countertop and microwave. Decorative items are arranged on open shelving, and a large mirror enhances the space. Natural light illuminates the room.

4.93 out of 5 average rating, 15 reviews

The Sweet Kenwood Suite

Superhost

An inviting pool area is framed by a protective screen, with soft lighting illuminating the space. Lush plants hang from the ceiling, and a decorative piece is positioned on the wall, creating an atmosphere of relaxation and calmness.

4.9 out of 5 average rating, 99 reviews

Cabana/Guest house w/spa/pool 5min to Siesta key.

A comfortable sleeping area is featured, showcasing a queen-sized bed with light beige striped bedding. Two bedside tables with lamps are positioned on either side of the bed. A wall-mounted television is visible, and a door leads to the bathroom area.

4.95 out of 5 average rating, 91 reviews

Modern-Fully Equipped Near Beaches, Downtown & IMG

The exterior of a charming studio is showcased, featuring a light yellow facade and a wooden porch area. A small table is positioned near the entrance, and air conditioning unit is mounted on the side. Lush greenery and a fenced yard are visible in the background.

5 out of 5 average rating, 6 reviews

Private guest house in Sarasota!

Guesthouse in St. Petersburg

The bright living area features a green sofa with a decorative pillow, a white coffee table, and a dining table with four chairs. Vibrant wall art enhances the space, complemented by large windows allowing natural light. A doorway leads to the private side yard.

4.98 out of 5 average rating, 147 reviews

Relaxing & Charming Hideaway

Guest house rentals with a patio

A welcoming living space is visible through an opening, featuring a comfortable blue chair and a wall-mounted TV. Natural light filters through a window, illuminating the white walls and partially covering a cozy bed with blue and white bedding in the adjacent area.

4.89 out of 5 average rating, 228 reviews

Supercute Beach Themed Retreat Free Parking Wi-FI

Guesthouse in Bradenton Beach

A vibrant yellow cottage is depicted with a landscaped area featuring palm trees and a gravel yard. Colorful adirondack chairs in pastel shades of pink and blue offer seating options, creating a casual outdoor space. Nearby cottages are visible, enhancing the beachfront setting.

4.99 out of 5 average rating, 192 reviews

Bradenton Beach Sunsets 1, Anna Maria Island, FL

Guesthouse in Laurel Park

A private outdoor area features a cozy swing sofa under a wooden pergola, surrounded by lush greenery. Several comfortable chairs are positioned around a small fire pit, creating a welcoming space for relaxation. Natural light filters gently through the surrounding trees.

4.87 out of 5 average rating, 134 reviews

City Garden Cottage

A white gate opens to a well-maintained outdoor area, featuring a concrete patio with lounge chairs and a small table. Lush greenery surrounds the space, contributing to a serene outdoor setting. The pink exterior of the building is visible in the background.

4.92 out of 5 average rating, 132 reviews

Have a great time

A spacious driveway leads to a white privacy fence that encloses the property. Lush greenery and colorful plants are visible along the edges, while a large storage shed and towering trees provide a natural backdrop.

4.97 out of 5 average rating, 204 reviews

Sweet MERMAID #1

The cozy living room features a comfortable sofa and a sleek armchair, complemented by a decorative rug. A glass coffee table sits in the center, while a wall-mounted TV displays a scenic beach view, enhancing the serene atmosphere.

4.89 out of 5 average rating, 138 reviews

Secluded Retreat 25 min from the best beaches!

A charming exterior of a cottage is showcased, featuring a light-colored facade and a sturdy metal roof. A private patio area is visible with a blue picnic table and outdoor seating, surrounded by landscaping and palm trees, offering a relaxed outdoor space.

4.98 out of 5 average rating, 194 reviews

Conch Cottage adorable one bedroom with pool.

A modern living area features a dark sofa draped with a light throw blanket, paired with a wooden table displaying decorative items. Natural light filters through sheer curtains, accentuating the neutral tones on the walls and tiled floor.

4.93 out of 5 average rating, 181 reviews

The Enchantment, Cozy guesthouse,7mi to the beach!

Guest house rentals with a washer and dryer

A comfortable living space features a neutral-colored sectional couch and a wooden coffee table at its center. A dining table with seating for four is visible, along with a wall-mounted TV displaying a tranquil landscape. A ceiling fan provides airflow in the well-lit room.

4.94 out of 5 average rating, 35 reviews

High Life | Cozy Duplex Retreat

A modern living space is showcased, featuring a sectional sofa and a wooden coffee table. A wall-mounted television displays serene ocean imagery. The fully equipped kitchen, visible in the background, includes stainless steel appliances and a casual dining area with two chairs. Natural light enters through large windows.

5 out of 5 average rating, 9 reviews

New! Siesta Beach Guest House with pool!

An open loft living area features a spacious sectional sofa in soft grey, accompanied by a white side table. Natural light enters through a skylight and nearby window, highlighting the subtle coastal decor, including soft green accents and a textured area rug on the floor.

4.95 out of 5 average rating, 40 reviews

*Azure Guesthouse* Walkable! Patio! Beach 8 min!

Guesthouse in Pass-a-Grille Beach

A sandy path leads through coastal grasses towards the beach, with palm trees and picturesque homes visible in the background. The clear blue sky enhances the inviting beach atmosphere.

4.93 out of 5 average rating, 218 reviews

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

A modern studio space features a grey sectional couch accompanied by a tan throw blanket. A small dining table is positioned near the kitchenette, which is equipped with a stove and refrigerator. Natural light enters through window blinds, illuminating the neutral walls and wood flooring.

4.94 out of 5 average rating, 53 reviews

Sarasota Bayside Hideaway

Guesthouse in Gillespie Park

The interior space features a modern kitchen with a large island and bar seating. Above, industrial-style lights hang, illuminating the area. A vintage clock is mounted on the wall, while a doorway leads to a small balcony, allowing natural light to fill the space.

4.99 out of 5 average rating, 141 reviews

The Mermaid and Corkscrew Loft

A fenced outdoor area features a mini putt putt green, two blue lounge chairs, and a seating arrangement beneath an umbrella. The cottage is displayed in the background, framed by lush greenery and palm trees.

4.97 out of 5 average rating, 39 reviews

NEW cottage near Downtown with boat parking

A spacious bedroom features a king size bed with a white bedding set and decorative pillows. Soft blue walls provide a calming backdrop. A ceiling fan is installed overhead, and natural light streams in through the window adorned with light blinds. Complementary artwork adds a touch of coastal charm.