House holiday rentals in South Sarasota

A light-filled entryway features a wall of glass shelving with decorative items. Double glass doors provide access to the outdoor space, which is partially visible through the glass. A small mat lies on the floor near the entrance.

4.91 out of 5 average rating, 206 reviews

Sunshine Suite, Minutes to Beach,Tropical Paradise

The Sunshine Suite.Lots of natural light in this totally updated modern 3 bed/1 bath home.It is a completely separate dwelling w separate entry from the other dwelling on the property sharing no common walls. Smart thermostat & door lock. Keyless entry.Brand new AC, gas oven, quartz counter w/ custom marble backsplash, modern & comfortable furniture, private outdoor area, gas BBQ grill, off street parking.Great location! Minutes to Siesta Key beach, shopping/UTC, interstate, hospital & downtown

A well-lit dining area features a modern table with four chairs, complemented by a floral artwork on the wall. Natural light enters through French doors, enhancing the bright and open atmosphere. A stainless steel refrigerator is visible, maintaining a clean and functional kitchen space.

4.9 out of 5 average rating, 105 reviews

Tropical Paradise minutes to #1 Siesta Key Beach

Location! Just minute to the #1 Beach in USA , Siesta restaurant and shopping. This cozy 2 bedroom/1 bath home feels very modern, comfortable and very functional. Tropical landscaping .Fully equipped kitchen. Beautiful private fenced backyard with Yoga platform. Beach chairs available. Perfect for a budget oriented traveler looking for immaculate home and convenient location close to Hwy 41 Siesta Beach and shopping and walking distance to restaurants. Primary guest must be 25 years of age.

A charming cottage is nestled among lush greenery, surrounded by tall trees and palms. A gravel pathway curves gently around the property, enhancing the serene outdoor setting. Sunlight filters through the foliage, creating dappled light across the landscape.

4.96 out of 5 average rating, 170 reviews

Sarasota Florida -Wild Orchid Creek Cottage Home

Come enjoy old Florida living at this completely renovated cottage style home on nearly seven acres. Relax and unwind in this 1000 square foot private home with king bed and queen sleeper to accommodate up to four people. Open concept living, dining room and full kitchen. Laundry facilities available. Equipped with WiFi and direct tv. While enjoying the private backyard space, it is common to spot abundant wildlife and wildflowers. Wild orchids in many of the oak trees bloom in early summer.

A charming outdoor patio features a wooden pergola draped with fabric, providing shade over a seating area with four chairs. Lush greenery, including a palm tree, surrounds the cottage, nestled on a gravel area, creating a serene and inviting atmosphere.

5 out of 5 average rating, 110 reviews

The Mango House Beach Cottage

Our cozy boho beach cottage, The Mango House is the perfect place for a couple or small family to relax and enjoy all the best Sarasota amenities. It’s conveniently located right between both Siesta Key entrances, walking distance to restaurants, grocery stores, Trader Joe’s, gym and a block from the popular Walt’s Fish Market. This gorgeous bungalow is the front house of a duplex on a large lot with plenty of cozy private outdoor space to relax and take in all the wonderful Florida weather!

A living area features wooden flooring with a large area rug at the center. Two gray armchairs are positioned near a media console, which supports a flat-screen television. Natural light is provided by windows adorned with sheer white curtains, and a green plant adds a touch of greenery.

4.95 out of 5 average rating, 520 reviews

The Cottage At Central Park

There is no more charming place to stay! From the minute you step inside this immaculate and cozy private residence you will feel right at home. With a beautiful open kitchen, natural light that pours into every room, a spacious back porch overlooking the pool and fenced in yard with a fire pit, this is the perfect place to entertain AND relax. Minutes from the #1 rated Siesta Key beach and downtown Sarasota in one of the areas most sought after neighborhoods you are in the middle of it all!

The outdoor area features a uniquely shaped heated saltwater pool with clear blue water. Surrounding the pool are loungers placed on a bright, white deck, complemented by tropical plants and palm trees that enhance the tranquil environment.

4.98 out of 5 average rating, 106 reviews

Tropical Oasis Heated Pool Hot Tub Near Siesta Key

Escape to The Funky Fish House! Your private 2BR/3BD/2BA tropical oasis boasts a heated saltwater pool, bubbling hot tub, outdoor shower, and BBQ grill for endless fun, relaxation, and sun-soaked adventures. Just 5 miles from world-famous Siesta Key Beach and steps from Trader Joe’s, this elegantly renovated, fully stocked, stylish retreat invites families or couples to lounge, entertain, soak up the Florida sunshine, and enjoy the ultimate Sarasota vacation in absolute comfort and style!

The studio apartment features a spacious bed with light-colored linens, complemented by two decorative pillows. A sleek brown sofa is positioned in front, adorned with a soft throw blanket. Natural light enters through the window, enhancing the clean and modern design.

4.81 out of 5 average rating, 199 reviews

Comfortable + Functional Private Studio Apartment

This comfortable, clean, and private studio apartment is the perfect spot to relax- whether you're here on business or you've spent the whole day on the beach! Recently remodeled with a dining table to take your meals, hot water, a comfortable bed, and well equipped kitchenette, you will be lacking nothing here. This apartment is a guest suite attached to the main living area of the home and is completely private, however there is a resident who lives in the main part of the home.

The kitchen area features a white cabinetry design with open shelving. A round dining table is set for four with a grey tablecloth. Modern appliances, including a stainless steel refrigerator and a mixer stand, are visible along with a sleek, well-lit countertop.

4.97 out of 5 average rating, 199 reviews

Adorable Bungalow Fire pit/outdoor shower 2/1 Cute

Charming and tranquil two bedroom home located in central Sarasota. This adorable bungalow is just 6 miles from world famous Siesta Key Beach. Located on a quiet street you are just minutes from great restaurants and shopping. The house is an adorable bungalow with a sweet cottage feel inside. The backyard is private with a fence all around. You can enjoy laying in the hammock and by night sit around the fire pit. There is an outdoor shower with cold and hot water to enjoy.

A modern living area features a gray sectional sofa with white throw pillows, positioned next to a light area rug. A sleek coffee table holds a yellow tray, and a round mirror is mounted on the wall above. Green plants add a touch of nature, enhancing the space.

4.91 out of 5 average rating, 269 reviews

Cozy Getaway Home in Sarasota Near Beaches & More!

Escape to our peaceful home in Sarasota. Conveniently situated near our famous beaches, UTC, Benderson Park, downtown, and only within a mile of grocery stores and other shops. Enjoy outdoor moments on the patio and spacious yard. Modern amenities include high-speed internet, smart TVs, and a well-equipped updated kitchen and workspace. Washer/dryer on-site as well. Your gateway to relaxation and Sarasota's charm awaits! Please reach out if you have any further questions.

A bright pink flamingo float adorns the clear, inviting waters of the heated pool. Two white umbrellas provide shade for the striped lounge chairs nearby. Flower pots add a touch of greenery to the poolside area, which is enclosed by a white privacy fence.

4.94 out of 5 average rating, 108 reviews

Oasis by Siesta Key Beach and Downtown SRQ w/pool

Enjoy Sarasota in one of the most desirable neighborhoods by Siesta Key! Truly an elite location, take Siesta Dr down to the well-documented #1 beach in the US in around 10 mins. Flourishing Downtown Sarasota is just 5 mins away. The house features a brand new heated pool, fenced in back yard with pavers, open concept living, beautiful kitchen with everything you need, upgraded bathrooms and plenty of space for a big family. We look forward to hosting you and yours!

A spacious backyard is shown at sunset, featuring a heated pool surrounded by a tiled patio. Tropical palm trees frame the area, and a tiki bar can be seen in the background. Soft outdoor lights create a welcoming ambiance as the sky fills with vibrant orange and purple hues.

4.94 out of 5 average rating, 140 reviews

The Sand Castle - Backyard Oasis Mins from Siesta!

*UPDATED!* Your family will feel at home in this spacious home that has it all! With a gorgeous backyard, alluring HEATED pool, tropical tiki bar, ping pong and other lawn games, cozy and comfortable rooms, and a kitchen stocked with everything you need to prepare meals for many... you will be more than comfortable here! The location is super convenient- minutes from Siesta Key, downtown Sarasota, and every grocery store and restaurant you could ever want!

An aerial view captures a serene landscape featuring lush greenery and a calm blue waterway. Homes are visible along the shoreline, with distant city buildings punctuating the horizon. The inviting neighborhood is framed by clear skies and gentle waves, exemplifying a tranquil coastal environment.

4.83 out of 5 average rating, 174 reviews

Siesta Beach, 5 minutes from downtown.

My place is close to art and culture, restaurants and dining, great views, the Siesta Beach, Turtle Beach, and family-friendly activities. You’ll love my place because of the neighborhood, the comfy bed, the kitchen, and the coziness. My place is good for couples, solo adventurers, business travelers, and families (with kids). Its located right next to the north bridge to Siesta Beach North Bridge Outlook Park, you can walk to the water.

Popular amenities for South Sarasota house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A private pool is surrounded by a spacious patio with paver stones, offering an inviting area for relaxation. Several lounge chairs and a small table with decorative seating are positioned near the water. Lush greenery borders the yard, enhancing the secluded feel.

4.77 out of 5 average rating, 112 reviews

Pool house by the bay

A light-filled living area features a comfortable sofa, a wooden coffee table, and a dining space with a round table and chairs. The kitchen is equipped with modern appliances and cabinetry, while beach-themed decor adds a casual touch to the environment.

4.98 out of 5 average rating, 178 reviews

New remodel- 150 Yds to Beach and Restaurants!

A screened outdoor area features a heated pool accompanied by a spacious seating arrangement. A dining table with chairs sits shaded under an umbrella, while lounge chairs are positioned nearby. Lush greenery provides a natural backdrop, enhancing the inviting space.

4.96 out of 5 average rating, 149 reviews

Beautifully Remodeled Home with Pool Near Siesta

Superhost

A swing chair hangs from the ceiling in a cozy living space, complemented by a dark sectional sofa and a round coffee table. A decorative rug adds warmth to the wooden floor, while a wall-mounted television and a piece of artwork provide visual interest.

4.81 out of 5 average rating, 162 reviews

1 House 1400sq. ft. 12 min from Siesta Key!

The spacious living area features a comfortable couch adorned with patterned pillows, a wooden coffee table, and colorful rugs. Natural light floods in through large windows, and an open layout connects to the dining area and kitchen, which is visible in the background.

4.97 out of 5 average rating, 120 reviews

Sunshine House, close to Downtown

A private pool area is surrounded by lush greenery, featuring a clear blue water pool and four lounge chairs positioned for relaxation. Umbrellas provide shade, enhancing the serene outdoor space. Tropical plants are situated along the edge, adding to the natural atmosphere.

4.98 out of 5 average rating, 109 reviews

SIESTA BEACH HOUSE HEATED POOL☀️🌴3 MIN TO BEACH!!

A private outdoor space is presented, featuring a heated saltwater pool illuminated by soft lighting. A hammock is hung nearby under a stylish frame, surrounded by lush greenery and a fenced area, enhancing the serene ambiance for relaxation.

4.96 out of 5 average rating, 112 reviews

The Wisteria Oasis W/swings, heated pool & hot tub

A distinctive triangular structure features large glass windows, showcasing vibrant lighting from within. The exterior is surrounded by landscaped greenery and decorative white stones, enhancing the inviting appearance. Palm trees and a tidy paved driveway contribute to the overall charm and unique architectural design.

4.95 out of 5 average rating, 216 reviews

Modern, Bright Downtown SRQ A-Frame West of Trail

Weekly house rentals

An outdoor dining area is presented next to a heated pool, featuring a table set with plates of food and drinks. A gas grill is nearby, and the pool is enclosed by a mesh screen. Lush greenery is visible through the enclosure, enhancing the serene environment.

5 out of 5 average rating, 7 reviews

Paradise on Prospect w/ Htd Saltwater Pool

4.94 out of 5 average rating, 16 reviews

Pineapple House Near SRQ Downtown 15 Min to Beach

A bright and airy living area features a sleek white sectional sofa with decorative pillows. A dark coffee table is centered in front, adorned with two gold vases. Framed art pieces are arranged on the wall, adding a touch of elegance to the space.

4.95 out of 5 average rating, 77 reviews

Siesta Key Escape-8 min to the beach,Spa,Bikes,BBQ

A well-lit bedroom features a spacious bed with a light-colored bedspread. Two large windows offer views of the outdoors, framed by sheer curtains. A ceiling fan hangs above, providing airflow. A comfortable chair and a dresser add practical elements to the inviting space.

5 out of 5 average rating, 11 reviews

The Palms Away

A spacious living area is furnished with comfortable grey sofas and a central coffee table. A wall-mounted television displays scenic Florida imagery. Natural light filters through sheer curtains covering large windows, enhancing the overall bright atmosphere. The open layout connects to the dining area and kitchen.

4.85 out of 5 average rating, 54 reviews

Siesta Getaway-Minutes to Beach

A spacious bedroom is illuminated by natural light from sliding glass doors. The area features a large bed with blue accents, a comfortable armchair, and a desk. A muted rug complements the wooden flooring, while plants and decor add a touch of greenery.

4.97 out of 5 average rating, 31 reviews

Resort-Style Vacation Villa

5 out of 5 average rating, 19 reviews

A private entrance features a white fence and gate with the number 1825 displayed prominently. The pathway is paved with bricks and flanked by lush greenery and colorful flowers, leading to the home's inviting entrance.

Home in Gillespie Park

The Gecko Bungalow - DT Sarasota

A modern kitchen is presented with warm wooden cabinetry and stainless steel appliances. A large island provides seating with two white stools. Sunlight illuminates the space through a window above the sink, where a bouquet of flowers adds a vibrant touch.

5 out of 5 average rating, 74 reviews

Siesta Breeze ~ Charming Coastal Cottage

Private house rentals

A single-story home is set back from the street, featuring a light exterior and a welcoming entrance adorned with a seasonal decoration. Lush greenery surrounds the property, complemented by a manicured lawn. A spacious driveway provides access to the home, with a mailbox positioned at the front.

4.92 out of 5 average rating, 13 reviews

Bay Vista Cottage

A serene pool area features a rectangular swimming pool surrounded by a spacious deck. Lounge chairs are positioned for relaxation, while lush greenery and a wooden fence provide privacy. A decorative statue adds an elegant touch to the tranquil environment.

4.99 out of 5 average rating, 94 reviews

The Oasis

An open concept living area features light grey sofas arranged around a minimalist coffee table, with natural light illuminating the space. A dining area with white chairs and a table is visible in the background, complemented by modern pendant lighting.

4.97 out of 5 average rating, 38 reviews

Beach & City Oasis: Moments from Siesta Key Beach

The exterior of a charming turquoise cottage is framed by a fenced yard, featuring a stony pathway and ample outdoor space. Large trees provide a natural backdrop, enhancing the serene environment of this peaceful neighborhood.

4.96 out of 5 average rating, 27 reviews

Costal Breeze Cottage. Pet friendly. King size bed

5 out of 5 average rating, 38 reviews

Peaceful Cottage

The exterior of the duplex presents a welcoming facade, featuring a covered entryway with a chair and potted plants. A paved driveway leads to the porch, surrounded by a grassy area. Ample natural light highlights the subtle blue sky and greenery in the background.

4.97 out of 5 average rating, 89 reviews

2 bedroom 1 bath 7 mins to the beach

An open living space features warm wooden floors and large windows that provide ample natural light. A circular dining table is surrounded by six wire chairs. A modern chandelier hangs above the table, while a comfortable chair is positioned nearby, creating an inviting gathering area.

5 out of 5 average rating, 30 reviews

Sanctuary by the Sea

An outdoor dining area is displayed, featuring a large black table surrounded by six black chairs. An oversized turquoise umbrella offers shade, and a grassy backyard is visible in the background, accented by palm trees and lush greenery.