Waterfront holiday rentals in South Sarasota

A modern dining area is highlighted by a marble table with an elegant vase and tableware arranged for a meal. Stainless steel appliances and a large television are visible in the background, with natural light flowing in from sliding glass doors leading to an outdoor space.

4.89 out of 5 average rating, 142 reviews

Crystal House on Siesta Key Beach

This is an updated and renovated two bedroom suite on Siesta Key. Complete with marble dining table, stainless appliances and large televisions. There is a computer in the spare bedroom for your convenience along with an Xbox and DVD player. We tried to think of everything so please feel free to make suggestions after your stay. Your satisfaction is our number one concern. The sofa is a Laz-Y-Boy and is not a sleeper but is very comfortable!!! There is a set of twin-twin bunks in the main room!

A spacious living area features a comfortable sofa and two cozy armchairs. A wooden coffee table sits at the center, complemented by a geometric area rug. Large sliding glass doors provide natural light and lead to an outdoor seating area, showcasing a view of the beach.

4.94 out of 5 average rating, 139 reviews

NO Stairs, Siesta beachfront. Walk to the village!

Welcome to your own private getaway directly on Siesta Beach! This ground floor unit is just steps from the powdery sands of Siesta Key. NO STAIRS Enjoy the updated bathroom with quartz countertops, new fixtures, paint, new furnishings, and décor. You literally walk out your door and directly onto the beautiful, fine, powdery white sand of Siesta Key Beach. Private Paradise directly on the white powdery sand of Siesta Key! 2 bedrooms 1.5 bathroom beachfront home with Gulf views that sleeps 6.

4.79 out of 5 average rating, 104 reviews

Beachwalk Townhouse with view of Gulf of Mexico

Townhouse with 1550 sq. ft. Private elevator, all new flooring, quartz countertops, sinks, faucets, shower. View of the Beach and Gulf of Mexico from Lanai and Master Bedroom. Only a few steps to Siesta Key Beach Heated Pool, garage, grill, all beach accessories. Relax on the lanai with a view of the beach/gulf or in the downstairs Florida room by the pool. Walking distance to the village of Siesta Key to the many restaurants and amenities. Have a relaxing stay on a wonderful island.

4.85 out of 5 average rating, 123 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

4.95 out of 5 average rating, 413 reviews

Tiny home in Sarasota

@Shellmateisland |tiny home| island| bikes| kayaks

⭑Octagonal 320ft² tiny home sitting on a private 1.5-acre island!⭑ ✯ Lake access ✯ Walk to dining, nightlife, and shopping ✯ Fully equipped + stocked kitchen ✯ Free bikes + kayaks +beach gear ✯ Backyard fire pit + BBQ ✯ Screened-in outdoor lounge w/ hammocks ✯ Smart TV w/ Netflix ✯ Memory foam bed ✯ 426Mbps wifi Ask which fruit trees are in season for a homegrown treat! 3 min → Siesta Key Beach 7 min → Downtown SRQ 12 min → Myakka River State Park (river kayaking + wildlife viewing)

4.92 out of 5 average rating, 144 reviews

Siesta Key condo, beach access, heated pool

This condo is set in the perfect location between the beach and the bay! Soak up the sun at the heated pool, enjoy the tiki bar, or try your luck fishing on the pier, all while viewing the boats on the intercoastal! Included is private deeded beach access that is just a easy 5 min walk. Hop on the free trolley right outside your door to go to Siesta Key Village with plenty of restaurants, bars and shops only .5 miles away. 65" tv free wifi Netflix Disney+. Boat slip available up to 24'

4.93 out of 5 average rating, 162 reviews

A vibrant sunset is displayed across the sky, with hues of orange, pink, and purple blending seamlessly. Silhouettes of palm trees are seen in the foreground, framing the tranquil water below, which reflects the striking colors of the sky. Nearby structures are softly illuminated in the fading light.

Guest suite in Sarasota

SIP & RELAX SPECTACULAR SUNSETS CLOSE TO SIESTA

Walk the No 1 beach in America, watch dolphins, wake up to sunny blue skies and the breeze from the bay. Watch spectacular sunsets daily whilst sipping your cocktail. Host your destination wedding - additional arrangements & cost. Located on the inter coastal waterway, a peaceful cul da sac & neighborhood close to Siesta Key. Gaze at the water & garden, spot the dolphins & birdlife. Close proximity to fabulous restaurants, boat/kayak rentals, Siesta Key, Downtown, & St Armands Circle.

4.91 out of 5 average rating, 380 reviews

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 :-)

5 out of 5 average rating, 106 reviews

Condo in Sarasota

Quiet Gulf & Canal View 1 BR -2 Supyaks-Htd Pool

Whisk your favorite person away to BayDreaming! Retreat to this quiet 1BR/1.5BA condo, just an 8‑minute walk from Turtle Beach. Perfect for couples, it offers a private deck with canal and Gulf views, a heated pool for sunset swims, two supyaks, and a plush king bed for cozy nights. Enjoy garage parking, beach gear, and a peaceful community. Whether you’re here to relax or reconnect, this coastal retreat blends romance with Siesta Key serenity.

4.94 out of 5 average rating, 118 reviews

A heated pool is framed by a screened enclosure, allowing for sunlit swims while providing shade. Comfortable lounge chairs are lined along the poolside, and greenery is visible in the background, creating a serene atmosphere for relaxation.

Home in Sarasota

2BR/2BA home w/ heated pool, 5 min to Siesta Key!

Charming 2BR/2BA Lakefront Home with Heated Pool – Just 2 Miles to Siesta Key Beach! Escape to this picturesque lakefront retreat, only 2 miles from the world-famous Siesta Key Beach. Perfect for families or groups, this spacious and beautifully furnished home offers a relaxing and memorable getaway. Lounge by the heated pool, soak in stunning lake views, or explore nearby attractions—this home is your ideal Sarasota vacation base.

4.98 out of 5 average rating, 113 reviews

Home in Sarasota

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

Welcome to your dream oasis near the world-famous Siesta Key! ✨ This immaculate 2BD/2BA home is a true coastal gem, offering a serene retreat with stylish design and luxurious amenities. Just 1 mile from the sugar-white sands of Siesta Key Beach, this home provides the perfect blend of comfort and convenience—an ideal spot to embrace relaxed Florida living at its finest. 🌴

4.98 out of 5 average rating, 360 reviews

A stunning pool area is surrounded by lush greenery and tropical plants. A prominent rock feature with multiple waterfalls is visible, providing a serene focal point in the outdoor space. The vibrant blue water complements the natural elements, creating a tranquil retreat.

Island in Sarasota

JULY AVAIL! Sarasota #1 Luxury Villa w/PRIV BEACH!

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!

Popular amenities for South Sarasota waterfront rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment accommodation

Apartment in Bradenton Beach

4.85 out of 5 average rating, 145 reviews

Low Tide @ Tides Inn

Apartment in Bradenton Beach

4.91 out of 5 average rating, 145 reviews

Newly Remodeled Beachfront Studio - On the sand!

4.91 out of 5 average rating, 98 reviews

A vibrant sunset is captured over the calm ocean waters, with the sun partially dipping below the horizon. A silhouette of a bird is seen flying across the sky, adding movement to the serene scene. The warm orange and yellow tones dominate the visual landscape.

Apartment in Siesta Key

Siesta Sunsets Suite

4.97 out of 5 average rating, 139 reviews

A spacious living room features a large grey sectional sofa with teal accent pillows, a wooden coffee table, and a light blue area rug. Large glass doors provide access to an outdoor area, while a vibrant seascape painting adorns the wall.

Apartment in Bradenton

Sweet Retreat at Shorewalk!

Apartment in Longboat Key

Tall grasses gently sway in the foreground, framing a serene beach scene. Soft waves lap against the shore, reflecting hues of orange, pink, and purple from the sunset sky. Cloud formations add depth to the view, enhancing the tranquility of the coastal landscape.

4.96 out of 5 average rating, 120 reviews

Longboat Key-OCEAN FRONT- on the beach

4.91 out of 5 average rating, 22 reviews

The exterior of the condo is shown, featuring a spacious deck surrounded by palm trees, with an umbrella providing shade. Large windows offer a view into the interior space, and ample outdoor seating is visible. A concrete path leads through the outdoor area.

Apartment in Sarasota

Cozy Condo in Siesta key with boat dock

Apartment in Longboat Key

5 out of 5 average rating, 26 reviews

Is this Heaven? No, it's Longboat Key

4.94 out of 5 average rating, 133 reviews

The enclosed Lanai features large bay windows showcasing views of the Gulf of Mexico. A seating area includes wicker chairs and a coffee table. Light-colored walls are contrasted by wooden accents and a ceiling fan, creating a bright and airy atmosphere.

Apartment in Siesta Key

Siesta Premier Location - The 'Calm of Siesta'

Waterfront house rentals

4.98 out of 5 average rating, 112 reviews

Home in Bradenton Beach

Gulf Front! Sunset Deck! + Walk to Bridge St Pier!

A spacious living area features a large sectional sofa, offering ample seating. A contemporary chandelier hangs from the ceiling, while a light-colored coffee table sits at the center. In the background, a modern kitchen is visible, accentuated by sleek cabinetry and bright lighting.

4.97 out of 5 average rating, 115 reviews

AMI/IMG/Boat/Bikes/Golf/Hottub/Kayak/Beach/pool

4.78 out of 5 average rating, 549 reviews

An inviting beach scene features a sun umbrella providing shade over a wooden lounge chair, set upon soft, sandy shores. The clear blue sky contrasts with the tranquil turquoise waters, creating a peaceful atmosphere near the shoreline.

Home in Siesta Key

Beachfront Getaway in Siesta Key

An inviting outdoor lanai is shown, featuring comfortable seating with colorful cushions. A wooden coffee table holds glassware, while a heated pool glistens in the background, surrounded by lush greenery. The screened area offers a seamless connection to the tranquil outdoor environment.

5 out of 5 average rating, 110 reviews

Heated Pool-Game Room-EV-Near AMI Beaches/IMG!

A charming house with a well-manicured lawn is framed by lush greenery. The front porch is accented by decorative red doors, and a stone walkway leads up to the entrance. Large trees provide shade over the landscaped yard.

5 out of 5 average rating, 104 reviews

Peaceful Braden River Oasis: Main House

A spacious rooftop terrace overlooks a marina filled with boats. Lounge chairs are arranged for relaxation, surrounded by greenery. Outdoor tables are set for dining, with views of water and distant shorelines under a partly cloudy sky.

4.98 out of 5 average rating, 130 reviews

Bradenton Gem | IMG & AMI | King Ste + Beach Gear

4.9 out of 5 average rating, 157 reviews

A serene beach scene is captured with gentle waves lapping against the shore. The clear water displays various shades of blue and green, while a sandy coastline extends into the distance. People can be seen enjoying the beach, with a bright blue sky overhead.

Home in Siesta Key

Sea Club II Garden House

4.98 out of 5 average rating, 180 reviews

The front of the Guesthouse is showcased, featuring a welcoming light blue door and a stone chimney. Black rocking chairs are positioned on the porch beside landscaped greenery. A decorative sign stating 'WELCOME' is prominently displayed on the side, adding to the inviting exterior.

Home in Myakka City

Charming Country Cottage (Near Lakewood Ranch)

Waterfront condo accommodation

A modern kitchen features white cabinetry and a spacious counter. Stainless steel appliances, including an oven and microwave, are visible. A decorative beach sign adorns the wall, and a bowl of fresh fruit sits on the counter, adding a pop of color to the bright space.

4.86 out of 5 average rating, 197 reviews

Best Gulf Coast Condo w/Private Beach & Bay view

A detailed map highlights the location of Siesta Key, showcasing nearby points of interest and roadways. The Gulf of Mexico is indicated to the southwest, while the surrounding areas and other keys are marked, providing context for travel and exploration.

4.88 out of 5 average rating, 116 reviews

Bayside Sunrise Cottage on Siesta Key!

4.92 out of 5 average rating, 157 reviews

Gulf Views | Walkable | Spacious

A view from above showcases the lush, landscaped grounds of the condo complex, featuring curving pathways and palm trees. In the foreground, a heated pool is visible, with beach access just beyond. The serene beach and expansive ocean create a welcoming atmosphere.

4.82 out of 5 average rating, 144 reviews

Sarasota Surf & Racquet Club Siesta Key Condo

4.97 out of 5 average rating, 149 reviews

The bedroom features a spacious bed with decorative pillows and a light blue throw. An accent bench sits at the foot of the bed, while a round mirror reflects soft lighting from a chandelier. A patterned wallpaper adds a coastal touch, enhancing the serene ambiance.

Condo in Bradenton

KING Bed + Anna Maria Island Beaches + Beach Gear!

4.99 out of 5 average rating, 173 reviews

A spacious living area features a blue sofa and striped armchair, complemented by a wooden coffee table. Large windows allow natural light to illuminate the room, showcasing views of the turquoise Gulf. Light-colored cabinetry and decorative shelving enhance the inviting atmosphere.

Condo in Bradenton Beach

★Right on the beach ★ Relax and Enjoy ♥ Sunsets!

Superhost

A heated pool is surrounded by lounge chairs set on a white deck, with palm trees and lush greenery nearby. A multi-story building looms in the background, along with a tennis court visible at the side. A safety sign is placed by the gated entry.

4.85 out of 5 average rating, 119 reviews

Siesta Key Beach (OHAB) Townhouse #1 beach