Waterfront holiday rentals in Sarasota County

True Island Living House/beach/water views

Charming Bayfront Home in heart of Siesta Key. 3 bdrm/3.5 bath, full water views, spectacular sun rises, private, gas heated pool, boat dock/ lift, outdoor sitting area /lush tropical landscape. Open floor plan, contemporary decor, gas fireplace, hardwood floors throughout, updated kitchen, stainless steel appliances, granite counters and a full walk-in pantry. 2 Master Suites upstairs and one guest bdrm on main floor. Washer and dryer inside, 3 TV’s. Outdoor shower. Fishing. Parking for 2 cars.

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.

Gulf front romantic cottage in paradise

Gated and surrounded by lush scenery you will feel like you have suddenly escaped to the caribbean! The pressures of the world melt away as you get your first glimpse of the Gulf of Mexico. Eclectic design with mostly Caribbean influences. Marble floors, tile counter tops and a large shower with a sit down bench. Walk the custom pathways which reveal beautiful orchids and exotic plants. Go kayaking, fish off the beach or look for sharks teeth. Take a swim in the pool or work on your tan.

@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 Key Direct Beachfront incl kayaks & SUPs

Photos are all new after rebuilding from 2024 storms! This beachfront 2 BR condo is ground floor - literally walkout the back door and you are on the beach. includes use of owners kayaks and Stand Up paddle Bosrds. Boat docks are available for your use. Several restaurants within walking distance of condo or take the free trolley to the middle of the key or the village in the north end. Equipped with beach chairs, umbrellas, boogie boards and plastic to of fun beach toys

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.

Stylish Gray 2nd-Floor Condo w/ Heated Pool | 1BR

Stylish second-floor 1-bedroom condo with a modern gray design in a quiet residential area of Sarasota. 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 convenient location 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. 🌴

AUG SALE! Sarasota #1 Luxury Villa w/PRIV BEACH!

BOOK 2025 NOW, and stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!

Spacious Home with Private Pool

Escape to your private waterfront paradise in Sarasota! This modern 4-bed, 2.5-bath canal-front home comfortably sleeps 8. Enjoy a fully equipped kitchen, a private screened-in saltwater pool, and an unbeatable location just minutes from the world-famous Siesta Key Beach. Perfect for families and groups seeking a serene coastal retreat with modern amenities.

Siesta Serenity ~ Pool/Waterslide/Waterfront

Siesta Serenity is a luxury 4BR/4.5BA waterfront home just minutes from Siesta Key Beach 🏖️. Enjoy a private pool with waterslide and spa, outdoor dining, BBQ grill, ping pong table, and elegant coastal interiors. Every bedroom has an ensuite bath, plus a chef’s kitchen and stylish bar area—perfect for relaxing and entertaining in paradise 🌊✨.

Oceanfront home w/sunset views of Sarasota Bay

Treat your family, friends, and beloved small dogs 🐶 to an unforgettable oceanfront getaway ⛱️ in sunny ☀️ Florida! 🦅 🐬 🐠 🐚 🦀 Conveniently located near plenty of Sarasota's shopping and dining areas, your new home away from home is nice and isolated, surrounded by gorgeous views and just a quick walk from the waters of Sarasota Bay. 🌴