Guesthouse holiday 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, 237 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

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, 287 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, 193 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!

An open-layout studio is illuminated by natural light, showcasing a comfortable queen size bed draped in white linens. Shelving units are positioned in the room, accompanied by a small dining area and kitchenette with modern appliances. A wall-mounted smart TV is visible, enhancing the living space.

4.94 out of 5 average rating, 109 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.

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, 492 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.

A spacious living area features a billiard table, a sectional sofa, and a kitchen area with wooden cabinetry and modern appliances. Natural light is provided by ceiling lights and side windows, set against a neutral grey wall.

4.84 out of 5 average rating, 459 reviews

Spacious guest suite near the bay, IMG, Anna Maria

This condo is attached to my home but is totally independant with private access. The condo is upstairs and accessible by a spiral staircase ( avoid large suitcase, may be challenging for some people) A large bedroom with a queen bed, an equiped kichen ( combined microwave/ oven), a bathroom ( large shower) and a living room with high ceiling. We follow cleaning recommendations. You can arrive anytime after check in time.PARKING is in the dead end street in front of my garden

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, 150 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 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, 191 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 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.

4.89 out of 5 average rating, 133 reviews

City Garden Cottage

City Garden Cottage is a cozy and comfortable cottage located in the quiet Laurel Park neighborhood in Sarasota, only a few blocks from downtown. The studio is surrounded by lush gardens and trees. Inside you will find a kitchenette, equipped with a coffee maker, toaster, refrigerator, and hot plate. The studio also has a flat-screen TV, a queen bed & private bathroom. There is also shared use a gas grill and fire pit included with the rental.

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, 281 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 offers. 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 guesthouses

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

Superhost

A screened-in lanai offers a comfortable seating area with a light-colored sofa and accent pillows. A glass coffee table is positioned on a textured area rug. A television is mounted on a cabinet, set against a vibrant mural featuring tropical designs.

Guesthouse in Gulfport

4.91 out of 5 average rating, 46 reviews

Treetop Serenity Near Gulfport Beach.

5 out of 5 average rating, 14 reviews

An outdoor cabana area is highlighted by a shaded seating arrangement and a built-in grill. Surrounding the space are white fences and paved flooring, creating a private and inviting atmosphere for gatherings. An umbrella stands in a relaxed position nearby.

Guesthouse in Venice

Modern, cozy family get-a-way: Bottomless Mimosa

4.98 out of 5 average rating, 44 reviews

A modern kitchen features white cabinetry and a large wooden island with blue accents. Shelves display green glassware and plants, while stainless steel appliances, including a microwave and dishwasher, are neatly arranged. Art adorns the wall, adding a coastal touch to the space.

Guesthouse in Nokomis

Serenity near the Coast

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

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.

4.94 out of 5 average rating, 90 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 Gardens of Gulf Cove

A well-lit guest room features a spacious bed with a patterned quilt and neatly arranged towels on top. A small table and chairs are positioned in a corner, and wall decor adds subtle character to the space.

4.78 out of 5 average rating, 65 reviews

Private Affordable Suite

A bright and modern kitchen space features a sleek stainless steel refrigerator and oven. A dining table with white chairs is positioned beside a comfortable couch. Natural light fills the room through a sliding glass door, enhancing the overall open feel.

5 out of 5 average rating, 21 reviews

Pinecraft’s Newest Hideout

Guesthouses with a patio

A spacious living area features a large modular sectional sofa adorned with soft pillows. A natural wood coffee table sits in the center, holding decorative items. Bright light filters through two windows, complemented by minimalist wall art and a potted plant in the corner.

5 out of 5 average rating, 15 reviews

Coastal Hideaway: 2/1 guest house close to UTC!

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, 8 reviews

New! Siesta Beach Guest House with pool!

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, 227 reviews

Supercute Beach Themed Retreat Free Parking Wi-FI

A spacious studio layout features a comfortable queen bed draped in crisp white linens, complemented by a cozy sectional sofa. Decorative beach-themed artwork adorns the walls, while a potted plant adds a touch of greenery. A minimalist coffee table holds magazines and decorative items.

4.96 out of 5 average rating, 28 reviews

Private/Peaceful Studio -Pet Friendly, Fenced Yard

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, 202 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, 137 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, 193 reviews

Conch Cottage adorable one bedroom with pool.

Guest house rentals with a washing machine 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, 34 reviews

Alta Vida | Cozy Duplex Retreat

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.

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, 38 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, 217 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, 51 reviews

Sarasota Bayside Hideaway

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, 106 reviews

[Ocean Oasis] guest house on Siesta Key

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.