Holiday rentals in South Sarasota

Ben's Bungalow | 8 min to Siesta Key | Gigabit Wifi

Ben's Bungalow is all about comfort and convenience. Just 3 miles and an 8 minute drive from Siesta Key Beach, it's the perfect home-base for your next Sarasota adventure and promises an unforgettable retreat for you and your crew. The large 3rd bedroom boasts an ultra-comfortable Nectar mattress and a 65” curved screen HDTV. Enjoy the Gigabit Wi-Fi, and the back-yard comes pre-stocked with fresh firewood, marshmallow sticks, and a privacy fence ready for you to make great memories with the fam.

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. Effortless access to Siesta’s white sand beaches, Sarasota’s dining/arts scene, St. Armand’s & Gulf Coast adventure! 2BR boutique bungalow • Sleeps 6 • 4 beds In Sarasota’s coveted ‘West of Trail’ Coastal District — marble chef kitchen, beach gear, Smart TVs, spa bath, laundry, fast Wi-Fi. Grill lobster under stars, unwind in your tropical garden & walk palm-lined lanes to cafés & glorious waterfront sunsets.

Specious and renovated 2 bed 2 bath house

Hello and thank you for visiting our listing of our freshly renovated house with brand new kitchen and new bathrooms! When you stay here you'll get a sense of a friendly quiet laid-back feeling in this nice house and neighborhood. When you walk in, you will immediately see how spacious it is. You have plenty of room to stretch out and relax in this lovely environment. This rental house is freshly renovated, and both baths are new along with a brand new kitchen. There is plenty space for doggies

New listing: Coastal Retreat 7-mins to Siesta Key

Bright mid-century modern 2BR/2BA retreat just 7 minutes from Siesta Key. Freshly upgraded with stylish coastal design, comfortable living spaces, and private outdoor space perfect for relaxing after beach days. Ideally located between the north and south bridges for easy access to Siesta Key Village, downtown Sarasota, Lido Beach, and St. Armands Circle. A perfect getaway for couples or snowbirds. No pets please. No parties or gatherings. No smoking of any kind. Yes to fun and relaxation

The Getaway

Relax in this comfortable and stylish space only 2 miles from Siesta Beach. The Getaway is the perfect spot to relax whether you're here on business or you've spent the whole day on the beach. The space is newly remodeled and you will lack nothing here! Enjoy the outdoor deck and two Nigerian Dwarf goats that live on the property. The Getaway is an apartment style space attached to the main home. It has it's own entrance and is completely private. The host lives in the main part of the home.

Tiki Bar Paradise! Heated Pool & Gaming Oasis!

Welcome to one of our beautiful properties, only 9 minutes to Siesta Key Beach! 24/7 Host Support - no AI messaging or hidden fees. Gorgeous HEATED POOL & Tiki Bar. Corn hole, ring game, or water pong on dry land or play volleyball, basketball, or beer pong in the pool. Bring the competition inside to the Game Room to play billiards or any number of family card/board games. Relax in the cozy living room w/ fireplace & fully equipped kitchen. Minutes to Siesta Key, the Village & Downtown SRQ.

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!

Modern 4BR Home *Heated Pool & Spa*

Discover elegance in this centrally located Sarasota gem, featuring four bedrooms and two bathrooms to accommodate up to eight guests. Enjoy a laid-back vibe while lounging at Sarasota's beaches or immersing yourself in local attractions. Siesta Beach and Lido Beach are within easy reach at 7.6 and 6.4 miles respectively. Rest easy knowing commitment to cleanliness aligns with your travel priorities. Your serene vacation awaits in this beautifully adorned home. *Brand new pool* VR24-00265

Private Eco Studio 10 min to Beach & downtown

This is a delightful, newly renovated eco-friendly PRIVATE SMALL studio with its own separate entrance, attached to the left side of the main house. It is bright and it has a private entrance, spacious bathroom, little outdoor area, and a parking space. There is a little table with some kitchen basics and a queen size bed. It is nested in very convenient location, close to everything. It is located a few miles from downtown Sarasota as well as 5-6 miles from Siesta Key and Turtle Beach

Luxe Modern Home - Private, Friendly & Stylish

Welcome to Lux Modern Home, a stylish modern home just minutes from the world-famous Siesta Key Beach. Thoughtfully designed with clean lines, coastal tones, and smart features, this 1,400 sq ft retreat offers the perfect balance of comfort, privacy, and contemporary living. Whether you’re here for beach days, sunset walks, or a relaxing getaway, this home is an ideal base for couples, families, or friends seeking a calm and upscale coastal experience.

Only 10 minutes to Siesta Beach!

Enjoy a comfortable stay in this charming apartment featuring private parking, a spacious backyard, and a cozy king bed for restful nights. Stay connected with fast, reliable WiFi and stream your favorite shows on the Smart TV. Perfect for business or leisure, this well-equipped space offers the convenience and comfort you need, all in a great location close to local attractions, dining, and shopping. Ideal for short or extended stays!

Family / Group Vacation Home Close to Beach

This newly remodeled 3 bed, 2.5 bath home with a separate 2 bed, 2 bath guest house is centrally located in Sarasota. With plenty of space to spread out, beautiful natural light that pours into every room. This is the perfect place to relax. This home is located in a quiet neighborhood just 15 minutes away from the #1 rated Siesta Key Beach and downtown Sarasota. This space is perfect for large family gatherings or groups.