Holiday houses in Siesta Key

FlipFlopsOn III • ½ Mile Siesta Key • Walk to Bay

Experience life 4 blocks from the Gulf, ½ mile to Siesta Key — America’s #1 Beach. With effortless access to Sarasota’s dining & arts scene, Siesta’s white sand beaches, St. Armand’s, & Gulf Coast adventure! 2BR boutique bungalow • Sleeps 6 • 4 beds Situated in the coveted Coastal District (‘West of Trail’) — chef kitchen, beach gear, Smart TVs, marble spa bath, laundry, fast Wi-Fi. Grill lobster under stars, unwind in your tropical garden, & walk palm lanes to cafes, and waterfront sunsets.

Siesta Key, FL - Casa Berano

Quiet, private home on lovely Siesta Key. 1.6 miles from lovely #1 Beach in the country. 1.9 miles to Siesta Key Village. FREE shuttle to village & beach 7 days a week. Private saltwater pool/enclosed lanai. Spacious 3bd/3b. Pets, dogs only, welcome, pls add to your total guest reservation. Open floor plan, large living area. Kitchen opens into living area & 2 dining areas w/ large tables. 2 car gar. brick paved driveway, in home laundry. 6 Guests Max 2 pets Max (dogs only), under 50lbs

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!

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.

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!

Private Heated Pool Retreat for Two Families

🌴 Welcome to your private Sarasota escape - designed for easy, extended stays, where two families can relax together around a private heated pool. With generous living spaces and thoughtful touches throughout, the home balances comfort and connection. Located minutes from Siesta Key, Lido Beach, and downtown Sarasota, and within walking distance of a park with playground, public pool, courts, fitness areas, and scenic trails. Relaxed, comfortable, and ideal for memorable family getaways.

Sun-Kissed Memories!

This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in Longboat Key, Florida! On the second floor, overlooking the heated pool and ocean, this dreamy studio condo is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and secluded beach. Enjoy a relaxing vacation at our peaceful condo at The Beach at Longboat Key Resort! To see all four of our listings, click on my Host photo and scroll down...!

Heated Pool, Dock, Kayaks, 1-mile to Turtle Beach

The Siesta Key Bungalows offer a heated pool, courtyard, sun loungers, gas-grills, laundry facilities, kayaks & a private dock on Heron Lagoon. The Dolphin Bungalow's one bedroom space; connects a welcoming living room, full-kitchen, and a private backyard patio. A king bed, two HDTVs and a full bathroom will further enhance your overall experience. Fully stocked with linens, care essentials, eating & cooking utensils. A queen sofa bed in the living room, allows for a capacity of three.

Your private retreat near Siesta Key Beach.

Completely Remodeled Private Retreat. COME RELAX, UNWIND, AND MAKE LASTING MEMORIES! From the moment you arrive, you’ll feel the calm, welcoming atmosphere that makes this property stand out. This spacious 3brm 2-bath features an amazing heated pool, a private backyard, and stylish finishes throughout. Whether you’re lounging by the heated pool, enjoying meals in the bright open-concept living space, or exploring the nearby beaches this home is perfect for an unforgettable vacation

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.

Lux Pelican's Perch | Heated Pool + Hot Tub + Gym

BNB Breeze Presents: Pelican's Perch Welcome to Pelican's Perch, stunning Lux home. Located just a short drive from beautiful beaches and local attractions. Check out this fully loaded home. - Private Heated Pool - heated at NO extra cost from Nov 21 - April 1st - Built-in Hot Tub ​​​​​​​- Water filtration system - Beach Supplies - Luxe Modern New Construction - Garage Gym - Connected directly to the Legacy Trail with Bikes - Breville Espresso Machine w/ syrups

Luxury Canal-Front Home + Heated Pool Near Beach

This is a thoughtfully renovated canal-front residence near Siesta Beach. A private pool and screened patio offer a refined and tranquil retreat with direct canal views. Bright interiors and carefully curated details create an atmosphere of timeless, understated luxury. Just an 8-minute walk from the world-famous beach, yet surrounded by complete peace and privacy. This home is designed for guests who appreciate discreet luxury and elevated comfort.