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.

Luxury 3B/3B waterfront home w/ pool + boat access

Escape to this luxurious 3BR/3BA Sarasota sanctuary! 5 minutes from Siesta Key, this Mid-Century Modern gem sits on a canal with direct Bay access (no bridges). Dive into the private pool & spa, lounge on the 1,000 sq ft porch, or relax inside on cozy furnishings. Includes a private dock, kayak/SUP/canoe, bikes, and a massive driveway for boat trailers. From the hanging bed swing to the gourmet kitchen, every detail is designed for your dream waterfront getaway. Your Florida paradise awaits!

@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

Grand Oak at Seaview | Waterfront + Heated Pool

BNB Breeze Presents: Grand Oak at Seaview Discover the enchanting Grand Oak, a stunning waterfront haven nestled in the heart of Sarasota, Florida. Experience the best of the Florida lifestyle with nearby attractions featuring beautiful beaches, local dining, and vibrant cultural spots just a short drive away. - Heated Saltwater Pool - heated at NO extra cost from Nov 21 - April 1st - Waterfront Views - Gas Grill - Outdoor Dining - Lux Design and Furnishings - and More!

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.

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

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.

Florida Funshine

This newly renovated haven puts you close to everything - shopping , rowing, beach. The home is only 8 miles from Siesta Key which has been regarded as the #1 beach in the nation many times! Close to Nathan Benderson Park and UTC shopping while only 5 miles from downtown Sarasota which boasts many art and cultural attractions, and multiple renowned restaurants. Enjoy the heated pool, read a book by the lake or take a nap after a great day.

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.

Experience "Old Florida" at the Coral Cottage

BRAND NEW REMODEL AND BETTER THAN EVER! Designer furnished, cozy, stylish Vintage Florida home on Phillippi Creek. Fishing rods, kayak and paddle board included. See an abundance of wildlife, including birds and manatees right at your waterfront deck! One bridge to the Bay. Dock space available! Eclectic, quiet neighborhood on the unbeaten path yet so close to beaches (3 miles!) shopping, restaurants and more!

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. 🌴