Waterfront vacation rentals in South Sarasota

4.89 out of 5 average rating, 217 reviews

An aerial view showcases a private island surrounded by water, featuring lush greenery and two tiny homes. A manicured lawn is visible with seating areas, umbrellas, and pathways that create a serene outdoor environment.

Tiny home in Sarasota

@Tiffanythetinyhome| island | netflix|bike|hammock

You are about to book a famous HGTV 270ft² / 25m² tiny home on a private 1.5-acre island! ☆ Walk to dining, nightlife, and shopping ☆ Fully equipped kitchen (K-cup) ☆ Backyard fire pit + BBQ ☆ Screened-in outdoor lounge w/ hammocks ☆ 415Mbps ☆ Smart TV w/ Netflix ☆ Memory foam bed ☆ FREE Bikes + kayaks + beach gear 3 min → Siesta Key Beach 7 min → Downtown SRQ 12 min → Myakka River State Park (river kayaking + wildlife viewing) We use a compost toilet. Please read house rules for info.

4.83 out of 5 average rating, 101 reviews

A light-filled living area features a comfortable white sectional sofa with decorative pillows, complemented by a wooden coffee table. Large glass doors lead to an outdoor space, while a television and two lamps enhance the room's functionality and warmth.

Condo in Sarasota

The Palm Bay Club on Siesta key Beach

Welcome to The Palm Bay Club on Siesta Key Beach Enjoy sunrise to sunset from our great resort that has private bay to beach access . Updated 2 bedroom 2 Bath ground floor with walk out balcony .Each bedroom offers private en-suite, Clean and bright open floor plan, well appointed kitchen ,Central A/C . Resort features 2 heated pools , enjoy the tranquility of the bay from the large hot tub or pool . Fishing pier, tennis & pickle ball courts, gym, laundry area we also offer boat slips

The living area features exposed wooden beams and large windows that fill the space with natural light. A comfortable sectional sofa is accented by a light throw and decorative pillows. A modern coffee table sits in the center, alongside a stylish armchair, with a dining area visible in the background.

5 out of 5 average rating, 14 reviews

Coastal Retreat near Siesta Key Beach and Downtown

Welcome to your Coastal Retreat in Sarasota's most desirable neighborhood. Minutes to beaches and downtown, this home offers a bright living space with coastal aesthetics creating a perpetual vacation vibe. Everything has been recently updated. You can take advantage of the convenient location within walking distance of bars and restaurants of Southside Village. This space is curated by a designer with comfortable beds and nice linens. Book your stay today, this is a truly special find.

A serene lakeside view is displayed, featuring a landscaped shore with a mixture of greenery and decorative stones. Palm trees and shrubs line the water's edge, contributing to a tranquil setting. The calm water reflects the surrounding vegetation, creating a peaceful natural atmosphere.

4.93 out of 5 average rating, 100 reviews

SPACIOUS 2bed/2bath house - 5 min to SIESTA KEY!

Just 2 miles to Siesta Key, this 3bed/2 bath home with heated pool on private lake with amazing view is the perfect place to escape with family! This charming home offers everything you need for your vacation retreat! Home is fully equipped with beautiful new furniture, artwork, linens, fully equipped kitchen. The house is located on a quite cul-de-sac close to grocery stores, international restaurants, mall, and about 5 minutes drive to the number one beach in the USA, Siesta Key.

The home's exterior features a welcoming entry with a blue door surrounded by greenery. The landscape includes various plants and flowers along the path, complemented by a driveway leading to the house. A covered porch is visible, enhancing the home's curb appeal.

4.89 out of 5 average rating, 101 reviews

Lakeview Oasis - 4bd/2ba overlooking the lake!

Charming home for rent with a cozy feel and scenic lake view. Conveniently located within a 2-mile radius, you can indulge in delicious coffee at Postal 98 and savor homemade Amish foods. Spend the day under the sun at local beaches, only 8.7 miles from Siesta Key beach and 7.1 miles to Lido Key Beach. Downtown Sarasota is just 4.5 miles away! This home offers the perfect balance of relaxation and urban living, making it an ideal retreat. The back deck overlooks a serene lake.

Top guest favorite

Condo in Siesta Key

4.97 out of 5 average rating, 315 reviews

On the Beach; Siesta Key SunBum Studio

Welcome back to paradise ! STEPS to your private beach without the tricks or gimmicks found elsewhere on the Siesta Key. This is the only studio in the Palm Bay Club tower on ground level with breathtaking views of the white sand and gulf waters. The Palm Bay Club offers 2 pools, hot tub, gym, boat docks, fishing pier, outdoor grills, tennis/pickle ball courts; not to mention FREE parking+ beach lounge chairs. Enjoy 2 free bikes day rental with booking!

4.9 out of 5 average rating, 328 reviews

The master bedroom features a large king bed and a double bed, both dressed in soft bedding. A wooden armoire and nightstand provide storage, while a decorative rug adds warmth to the tiled floor. Natural light streams through a window, creating a cozy atmosphere.

Guest suite in Sarasota

Siesta Keys stylish and affordable Airbnb.

Relax while you stay in a colorful and warm Siesta Key/Sarasota neighborhood home that is only minutes from the famous Siesta Key beach. Enjoy your private, safe, and comfortable suite while being in close reach to all that Florida has to offer. Your suite is spacious and accommodating, wether your an individual, couple, family, or group of friends we have the space and amenities for you to maximize both your comfort and fun time while here in Florida :-)

4.78 out of 5 average rating, 354 reviews

Clear turquoise waters stretch towards the horizon, with gentle waves lapping against the pristine shoreline. The beach features soft, white sand and is bordered by low vegetation. A few distant figures can be seen enjoying the beach against a backdrop of cotton candy clouds.

Townhouse in Sarasota

Relaxing Condo Retreat Minutes from Siesta Key

Welcome to Paradise! You will love this townhouse located in Sarasota and close to Siesta Key Beach. After a day at Siesta Key, Lido Key Beach or Nokomis Beach you can cool off in the beautiful swimming pool. You may like to go to Siesta Village and shop or eat at one of the many restaurants. You are just a few minutes away from St. Armand's Circle, where shopping is amazing and the restaurants known around the world.

4.94 out of 5 average rating, 106 reviews

A cozy seating area is visible, featuring two chairs and a round wooden table. Decorative lanterns and potted plants adorn the table. Through the large screened window, a vibrant sunset over the beach and palm trees is framed, providing a serene view.

Condo in Siesta Key

Siesta Key Beach Front Condo

Located at CRESCENT ROYALE CONDOMINIUMS - one of the finest gated communities on Siesta Key. Large HEATED outdoor pool - this 2 bedroom/2 bath PRIVATELY OWNED vacation condo is steps away from world famous, breathtaking Siesta Beach - consistently VOTED #1 BEST BEACH IN THE USA year after year! This condo is nicely situated on the 2nd floor. The large screened lanai provides spectacular gulf coast views.

4.97 out of 5 average rating, 324 reviews

Island in Sarasota

Now NEW AUG Openings! Sarasota #1 Lux BEACH Villa

BOOK 2025 NOW, and stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!

4.9 out of 5 average rating, 135 reviews

A cozy living area features a blue sectional sofa accompanied by decorative pillows and a side table with a lamp. A wall clock adds a modern touch, while large sliding glass doors offer views of the outdoor space. A dark blue accent chair complements the scene.

Condo in Sarasota

6 min to Siesta Beach | Heated Pool | Lake View

🌴 Stylish Retreat Near Siesta Key & Heated Pool! Welcome to your perfect Sarasota getaway! This 720 sq. ft. pet-friendly home offers a , heated pool access, and a prime location just 6 minutes from Siesta Key Beach. Whether you're here for a beach vacation, a family trip, or a remote work retreat, this home has everything you need for a comfortable and stress-free stay.

A bright living area features two blue chairs and a round coffee table placed on a textured rug. Natural light enters through sliding glass doors, leading to a deck with outdoor seating. Decor elements include wall art and decorative shells.