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, 136 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!

Superhost

A private swimming pool is surrounded by a spacious outdoor area featuring a variety of colorful seating options, including lounge chairs and patio furniture. The pool area is complemented by lush greenery and shaded spots, creating a relaxing atmosphere. A vibrant red umbrella provides additional shade.

Condo in Sarasota

4.8 out of 5 average rating, 215 reviews

Near beach. Pool view. King bed. Daily rentals

The ‘pool view’ overlooks the swimming pool & has a private covered open porch for shade 1 bed 1 bath w/ private entrance. The bedroom has a king sized mattress bed. The living room has a kitchenette area with a fridge, freezer, microwave, coffee maker and the essentials. There is a Smart TV. Separate bedroom with King size bed 3 mins walk to Crescent beach access #12 You can walk to a great choice of places to eat and drink Max 2 guests No smoking, No Pets, Great Location, Good Value.

4.84 out of 5 average rating, 119 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

4.96 out of 5 average rating, 401 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)

A private patio with a round wooden table and two chairs overlooks a manicured lawn leading to the beach. Palm trees sway gently beside the outdoor seating area, offering a serene view of the Gulf waters in the background.

4.97 out of 5 average rating, 366 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. If we are booked check out our additional units under our profile.

4.78 out of 5 average rating, 176 reviews

A serene view of the intercoastal waterway is captured, featuring calm waters reflecting the sky. Lush greenery lines the opposite shore, while a wooden dock extends into the water. Palm fronds frame the scene, emphasizing the tranquil coastal environment.

Townhouse in Sarasota

Relaxing Retreat, King Bed, Beautiful Scenic Views

You have arrived, upon entering you will go upstairs to your spacious duplex. You will be greeted by an amazing view of the intercoastal waterway. You will love kayaking on the waterway & seeing all the amazing wildlife. You can sit on your downstairs patio with a cup of coffee or you can take a stroll to Turtle Beach & enjoy the sunset. Hop aboard the trolley & go to the Village & eat and drink at one of our famous restaurants or one of our favorite hot spots. See Guidebook.

5 out of 5 average rating, 154 reviews

Home in Siesta Key

Beach, Village, Dock & Private Pool! One-of-a-kind

Fully Restored Post-Hurricane and Ready to Welcome You!! RCC in Siesta Key is a one-of-a-kind coastal cottage perfectly located between the beach, canal, and village. Enjoy a private heated pool, private dock, and one of the best locations on the island. This 1,500 square foot standalone bungalow has been fully restored with fresh post-hurricane updates. If you want a charming, private beach home with no shared walls and no condo feel, you have found the right place!

4.87 out of 5 average rating, 178 reviews

A cozy porch area features a hanging swing adorned with colorful cushions, complemented by a small dining table and chairs. The entrance is framed by green lattice work, creating a welcoming space. A sign with the text 'WELCOME' is mounted on the wall.

Cottage in Siesta Key

Adorable Cozy Silver Sands Cottage on Siesta Key!!

Adorable one bedroom "Old Florida Cottage" on the intracoastal bay side of Siesta Key. This is a stand alone cottage, ground floor, no elevators or flights of stairs to mess with. New Pool with a tiki hut, fishing dock, boat basin (up to 24'), beach access 4 min. walk across Midnight Pass Rd. to the #1 beach with the whitest, softest sand you'll ever see! Hi Def TV in LR , Wifi, TV in BR, Keurig in the kitchen, stocked with everything but your clothes and toothbrush.

4.97 out of 5 average rating, 104 reviews

A bright living space features a large window allowing natural light to fill the room. A modern coffee table sits atop a striped rug, with a sleek TV mounted on the wall. Decor items and a welcoming door can be seen in the background.

Home in Whitfield

Lovely Home by Sarasota Bay

Enjoy a stylish coastal bungalow in North Sarasota, just minutes from downtown’s restaurants, shops, and Sarasota Bay. Relax in modern comfort with central A/C, high-speed WiFi, and smart TVs in every room. Nearby, explore beaches like Siesta Key, Lido Key, and Anna Maria Island. The fully-equipped kitchen, comfortable bedrooms, and modern bath make for a relaxing stay. Plus, you’re close to top attractions like The Ringling Museum, Marina Jack, and more!

4.91 out of 5 average rating, 367 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 :-)

Superhost

The cabin's interior features warm wooden walls and ceilings. A spacious bed is positioned in the main area, while a small loft above is accessed by a ladder. Natural light fills the room through multiple windows, highlighting rustic decor including a painting and a green lamp.

Farm stay in Myakka City

4.88 out of 5 average rating, 151 reviews

Florida Cracker Cabin on cattle ranch/Myakka River

We are located in Myakka City, FL, which is a short drive to Siesta Key and Lido Beach and Sarasota! Enjoy a peaceful stay in our newly built, unique, air-conditioned cracker cabin. The cabin sleeps 4 guests and is located in the middle of our 1,100 acre working cattle ranch. Step outside and you are right on the Myakka River and can sit by the fire-pit at night and enjoy the sounds of nature. While your visiting, enjoy a kayak down the Myakka River.

Home in Gulf Gate Estates

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.

4.94 out of 5 average rating, 111 reviews

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.

Popular amenities for South Sarasota waterfront rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment accommodation

5 out of 5 average rating, 27 reviews

Beachfront Corner Condo | Sunset Gulf Views

4.87 out of 5 average rating, 136 reviews

Low Tide @ Tides Inn

4.91 out of 5 average rating, 137 reviews

Newly Remodeled Beachfront Studio - On the sand!

4.98 out of 5 average rating, 131 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!

A dining table showcases a glass top with intricately woven placemats. Each setting features decorative plates and neatly folded napkins secured with decorative rings. Sheer curtains frame the window, offering glimpses of lush palm trees outside.

4.88 out of 5 average rating, 229 reviews

Las Palmas Beach Rentals Unit 1

4.84 out of 5 average rating, 282 reviews

A bright blue entrance door labeled 'Poolside Suite' is visible, leading into the suite. The door is framed by a light blue exterior, with a view of the pool area and palm trees in the background. Sunlight casts gentle shadows on the patio.

Apartment in Siesta Key

Siesta Key - Poolside Suite - Studio - Free kayaks

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, 114 reviews

Longboat Key-OCEAN FRONT- on the beach

5 out of 5 average rating, 16 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

Waterfront house rentals

4.77 out of 5 average rating, 542 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

4.92 out of 5 average rating, 36 reviews

A bright living area features a spacious white sofa centered beneath a large woven light fixture. Tropical plants are situated near large windows that allow natural light to fill the space. A neutral rug complements the light-colored furniture and decor.

Home in Arlington Park

Coastal Retreat near Siesta Key Beach and Downtown

4.86 out of 5 average rating, 138 reviews

Home in Longboat Key

Summer House longboat key

4.99 out of 5 average rating, 165 reviews

A comfortable living area features a spacious gray sofa adorned with soft pink and white pillows. A round coffee table sits at the center, accompanied by patterned armchairs. Natural light filters through large windows, highlighting a serene ambiance.

Home in Cortez

My Peaceful place on the bay.

4.87 out of 5 average rating, 122 reviews

Home in Sarasota

Trendy & Relaxing: Close to Beach ~ Pool ~ Hot Tub

Home in Gulf Gate Estates

A screened lanai encloses a private saltwater pool, featuring a shallow entry and a vibrant pink float. Two lounge chairs are positioned nearby, surrounded by greenery that enhances the serene pool area.

4.95 out of 5 average rating, 110 reviews

Oasis on water near Siesta Key, Heated Pool, Tiki

4.95 out of 5 average rating, 187 reviews

A private pool is surrounded by a tropical landscape, featuring palm trees and vibrant plants. The clear water reflects the blue sky, and a spacious deck with paver stones offers a welcoming area for relaxation. A canal can be seen in the background.

Home in Anna Maria

2-night available 5/21 & 6/18-Boat Dock, 30' Pool

4.9 out of 5 average rating, 153 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

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, 189 reviews

Private Beach & Intracoastal Waterfront

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, 137 reviews

Sarasota Surf & Racquet Club Siesta Key Condo

4.97 out of 5 average rating, 138 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, 167 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!

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.

4.89 out of 5 average rating, 109 reviews

Siesta Key Beach (OHAB) Townhouse #1 beach

Superhost

A spacious screened lanai features a circular wooden table surrounded by two wooden chairs with patterned cushions. Potted plants and decorative items are placed on the table. Beyond the railing, palm trees and the vibrant blue of the Gulf coast are visible.

4.9 out of 5 average rating, 124 reviews

Siesta Key Beach Front Condo

4.98 out of 5 average rating, 227 reviews

A dining setting on a patio table showcases a plate of breakfast foods, including a toasted bagel, fruit, and a drink. Soft, rolled towels are stacked nearby, with a view of the beach and pool visible in the background.

Condo in Longboat Key

Sun-Kissed Memories: Open Thursday, March 26th!