Holiday rentals in Sarasota Beach

Water's Edge: Charming Canal Oasis

*BOAT DOCK AVAILABLE* Escape to the serene waters of our canal-side retreat in Sarasota! Just minutes from downtown's vibrant entertainment scene and pristine beaches, this cozy haven offers a peaceful retreat. Relax on the dock, take a kayak or paddleboard out, or simply soak up the sun. Explore the city's arts and culture scene, indulge in fresh seafood, or unwind on the beach. This charming retreat is the perfect blend of relaxation and adventure. Book now and experience the best of Sarasota!

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.

A pool, hot tub, & espresso sleeps 4

Welcome to your Sarasota escape! This fresh, brand-new apartment offers the perfect blend of comfort, style, and privacy—ideal for a relaxing getaway on Florida’s stunning Gulf Coast. Step into your private oasis, where you'll enjoy exclusive access to a heated saltwater pool and hot tub, perfect shared spaces: ✨ entry way ✨ laundry ✨separate patio area (see layout photo) private spaces: ✨ kitchen ✨ living area ✨ bathroom/bedroom ✨ pool *rental agreement required, please see house rules

*Recently Updated* Cozy Oasis, centrally located

This cozy yet spacious apartment is very centrally located... Just 5 min from downtown, 10-15 min from Siesta and Lido bch and St Armands Crl, and within walking distance of the historic Amish district. The newly completed Legacy Trail (perfect for walking, biking...) is less than a 5-minute walk away. The space is very private and clean and Ive taken extra measures to ensure your absolute peace and comfort. It includes all the amenities you'll need to make your getaway a memorable one.

Caribbean Dream | Luxury Condo on SK w Heated Pool

🦩 Exclusive Amenities Include: • Semi Private, HOA Maintained, Heated Pool & Spa • Multiple Balcony Views • Located In Siesta Key Village • A Quick 3 Minute Walk to Siesta Key Beach • 2 Bedrooms, 2 Full Baths • 1 King Bed & 1 Queen Bed, 1 Queen Sleeper Sofa, 1 Twin Sleeper Chair • 2 Balconies With Dining & Lounge Areas • Poolside Dining & Lounge Space • Private Garage • Gated Entrance • Free WiFi & TV’s • Regular & Keurig Coffee Maker, Dishwasher, Washer & Dryer, & Kitchen Essentials Provided

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.

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.

Cottage by the Coast 6 min to Siesta Beach!

Welcome to Haven by the Coast, a calm and stylish 2BR/1BA coastal retreat in Sarasota’s Gulf Gate neighborhood, just 2.2 miles from Siesta Beach Access 12. With a serene king room, queen room, and spa-style rainfall shower, it’s ideal for couples or extended stays. Jodie and I built this space with the same care we look for when we travel—peaceful, clean, thoughtfully designed, and close to local restaurants, cozy cafés, and the sunsets that make Siesta unforgettable.

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

Modern Studio · 5 min from Siesta Beach

Stylish ground-floor studio designed for couples or solo travelers, just a 5-minute drive from world-famous Siesta Key Beach. A great choice if you’re looking for a calm, well-located space with thoughtful comfort. Pet-friendly stay – $10 one-time pet fee per booking, unlimited pets. An ideal base for beach days, local dining, or a relaxed Florida getaway. About 1 mile from the property, guests may also enjoy access to a beautiful community pool that is heated.

Private Pool +Game Room Near Siesta Key | Sleeps 9

Experience your own private family resort near Siesta Key Beach. This spacious Sarasota vacation home sleeps 9 and features a private pool, game room, soccer field, playground, and outdoor BBQ lounge in a fully fenced backyard. Bright coastal interiors, a fully equipped kitchen, fast Wi-Fi, Smart TVs, free parking, and easy self check-in provide effortless comfort. Minutes from beaches, dining, shopping, and top Sarasota attractions.