Waterfront holiday rentals in South Sarasota

Oak Hammock on the Lake

Located in a quiet, safe neighborhood, at the end of a 400’ paver driveway, lined with old oak trees. Guest area is located in a large detached building with its own, secure, ground floor entrance. The unit is provided with its own AC and heat. The “Florida Shower” provides a large, private outdoor shower experience, with plenty of hot water, beneath the stars. Offers a ten acre lake view from inside or out. Many species of birds and wildlife are spotted, with 45 acres of bordering woodland.

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!

Siesta Key Beach Retreat-Heated Pool-Water View

Our Siesta Key condo is the ideal retreat for families seeking both relaxation & adventure. Situated just a short walk from the famous beaches.Ideally located on the Intracoastal Waterway, you can enjoy water views from the great room, lanai, and primary bedroom when you're not enjoying the sandy shores right across the street. After a day at the beach, unwind by the pool or take the elevator to your top-floor condo, where you can enjoy the sunset over the water from the private screened lanai

Coastal Retreat near Siesta Key Beach and Downtown

Welcome to your Coastal Retreat! Your gateway to the best beach experience in all of Florida. Located in Sarasota’s most desirable neighborhood, this light-filled home blends fresh coastal design with a relaxed vacation vibe. Just minutes from award-winning beaches and vibrant downtown, you’ll have easy access to everything that makes this region a hidden gem. Walk to the charming bars and restaurants. Everything has been recently updated. Book your stay today, this is a truly special find!

Siesta Premier Location - The 'Calm of Siesta'

My place is right across the street from Siesta Key beach, family-friendly activities, and nightlife. You’ll love my place because of the location, the ambiance, the outdoors space, and the neighborhood. My place is good for couples, adventurers, business travelers, and families. Walking distance to the village and is at less crowded section of the public beach which equals perfect location!! Updated and beautifully decorated condo with breathtaking view of the beach, You will LOVE it!

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

Whisk your favorite person away to BayDreaming! Escape to this quiet 1BR/1.5BA Siesta Key condo - just an 8-minute walk to Turtle Beach! Perfect for couples, it features a private deck with canal and Gulf views , a heated pool for sunset swims, 2 supyaks and a plush king bed for cozy nights in. Enjoy garage parking, beach gear, and a peaceful, welcoming community. Whether you're here to relax or reconnect, this coastal retreat offers the perfect mix of romance or just plain serenity!

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

Discover your perfect Siesta Key getaway in this vibrant 3BR, pet freindly duplex in the peaceful South Village. Just steps from the Gulf Coast beaches, this private retreat blends colorful décor, modern comfort, and playful outdoor fun. Lounge by the private 𝐡𝐞𝐚𝐭𝐞𝐝 𝐩𝐨𝐨𝐥, soak in the 𝐡𝐨𝐭 𝐭𝐮𝐛, or enjoy the backyard murals perfect for families, groups, and beach lovers. Book now for an unforgettable stay! <b>☀ Private Pool ☀ BBQ Grill ☀ Easy Beach Access</b>

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!

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!

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 :-)

Minutes to Siesta Key, heated pool & tiki on water

Coral Harbor is conveniently located in Gulf Gate Estates, just 3 miles to the beach. The 1 acre property sleeps up to 12, with a private heated salt water pool, mature trees, lanai, sun deck, and bonus "Tiki" bar. You'll love the deck overlooking the lake to feed the turtles! The home has all the modern amenities you would expect from a vacation home. Minutes to Siesta Key, easy access to Venice Beach, Lido Beach, downtown Sarasota, AMI & more!

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.