Waterfront vacation rentals in Sarasota County

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

Super rare 2 week opening just popped up Feb 2027! Whisk your favorite person away to BayDreaming! Retreat to this quiet 1BR/1.5BA condo,just an 8‑minute walk from Turtle Beach. Perfect for couples, it offers a private deck with canal and Gulf views, a heated pool for sunset swims, two supyaks, and a plush king bed for cozy nights.Enjoy garage parking, beach gear, and a peaceful community.Whether you’re here to relax or reconnect, this coastal retreat blends romance with Siesta Key serenity.

Winter Haven Retreat – Steps to Bay & Ringling

Tropical Paradise by Sarasota Bay – Walk to Ringling Museum, Asolo Theatre! Just a two minute walk to New College and its beautiful bayfront promenade, this 2,200 sq ft tropical retreat beacons you to unwind. Enjoy 3 very private bedrooms, an office area, spacious living room, and a huge fenced-in backyard perfect for kids and pets—all less than 15 minutes from Lido Beach and café-lined St. Armands Circle. Kayaks, hammock, grill, foosball, sandbox, basketball hoop, and more await your stay!

Superhost! Fully Renovated Sarasota Home

Fully renovated, centrally located cozy home only 5 Min from SRQ Airport. Attractions: 15 Minutes to world famous Siesta Key (Ranked America's #1 beach)! 8 Min to Lido Beach and St Armands Circle where you can enjoy all the world class restaurants & shopping. 10 Min to Longboat Key & Ana Maria. 5 Min to Historic Downtown where you can enjoy restaurants, music, opera house, and art exhibits.Only 15 Min away UTC offers your favorite shopping, dining and lifestyle destination. 26-VR-000041

@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)

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 :-)

Bee Keepers Cottage

Welcome to Bee Keepers Cottage! Your country in the city. New guest home, private parking (2), designer interior, new stainless kitchen, microwave, dishwasher, stove with oven. Full sized washer and dryer, great high speed internet, screened porch on its own pond. Located on a 16 acre wooded property with many bird feeders, nature wildlife photo ops abound in own your backyard. See deer, wading birds, Bald Eagles, song birds and acres of privacy.

Coastal Paradise w/ Pool & Dock, Minutes to Siesta

Wake to the sounds of birds and enjoy the slower pace of waterfront living. Escape to Coral Harbor, a private one-acre waterfront retreat just 3 miles from world-famous Siesta Key Beach. Whether you're soaking up the Florida sun, enjoying cocktails under the tiki bar, feeding turtles from your private dock, or relaxing in the complimentary heated saltwater pool, Coral Harbor is designed for unforgettable family vacations and group getaways.

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.

Private Beach | Gulf Views | Pool | Walk to Dining

Wake up to Gulf views, spend the day on the white quartz sand of Crescent Beach, and watch the sunset from your private balcony. Our 2-bedroom, 2-bath condo offers private beach access, a heated pool, beach chairs, umbrellas and towels, plus a fully equipped kitchen and free parking. Restaurants, bars, coffee and ice cream are within walking distance, so you can enjoy Siesta Key without spending your vacation in the car.

Lakefront Getaway in Sunny FL

Welcome to your lakeside retreat in sunny Florida! Our house offers stunning lake views and spacious, immaculate rooms. Just a short drive to Siesta Beach (#1 in the USA). The main house has 3 beautifully furnished bedrooms. The separate guest house it can be available for an extra fee. Relax by the large, clean pool in our private, gated property. Well-equipped kitchen, gazebo, grill, and family-friendly features await!

Modern Garden Condo w/ Heated Pool | 1BR

Ground-floor 1-bedroom condo in the quiet Sienna community of Sarasota with a private fenced garden. Siesta Key Beach is a 5–10 minute drive (traffic dependent). Pet-friendly home — all pets welcome with a flat $10 pet fee per reservation, regardless of the number of pets. Guests enjoy access to a heated community pool and a calm residential setting close to shopping and dining.

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

Welcome to your dream oasis near the world-famous Siesta Key! ✨ This immaculate 2BD/2BA home is a true coastal gem, offering a serene retreat with stylish design and luxurious amenities. Just 1 mile from the sugar-white sands of Siesta Key Beach, this home provides the perfect blend of comfort and convenience—an ideal spot to embrace relaxed Florida living at its finest. 🌴