Holiday rentals with a kayak in Sarasota County

A Piece of Paradise at Serenity Ranch

A peaceful, pastoral setting with cottage-like atmosphere 3 minutes from Myakka State Park & less than 30 minutes from Siesta Key, Ringling Museum, downtown Sarasota, & St. Armand’s. Experience the best of both worlds in this quaint apartment with fully equipped kitchen, washer and dryer. You can ride bicycles through our equestrian neighborhood, take an adventure in the Park, or enjoy a family BBQ and picnic on the property as you commune with horses, chickens, and cows, then relax by the pool.

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!

Experience serene and luxury waterfront living.

Welcome to our luxurious 1-bedroom, 1.5-bathroom condo, located on the water at The Strand. The apartment offer a beautiful view on the water to enjoy beautiful sunset. This is perfectly situated in a secure, tranquil community just minutes from Sarasota’s top attractions. Enjoy free parking and access to exclusive amenities, including a pool, gym, hot tub, and a kayak launch ramp. Close from Main Street, St. Armand's Circle, the Sarasota Opera, Marie Selby Gardens, Lido Beach, Ringling Museum.

Heated Pool - Just 1 mile to Beach! Updated/Fun!

Fun for the whole family!! Only 1 mile to the Beach! This newly updated home comes fully furnished with 4 bedrooms and 3 bathrooms. With a total of 6 beds, the home sleeps 10 comfortably. The Heated Pool is perfect for swimming, and being only 1 mile to the world famous Siesta Key Beach Access 12, this home also makes beach going easy and convenient. Inside, the home is clean, spacious and newly updated and equipped with smart tvs, air hockey table, pool table foose-ball, Pac-Man - fun for all

Lido Key Beach Bungalow with Private Heated Pool!

Behind the privacy wall you will discover an oasis in this beautiful beach bungalow. The outside space is amazing and almost as large as the inside space. Your own private pool and covered lanai area is the perfect place to relax, gather for dinner, watch TV and just enjoy outside living. You are a two minute walk to the beautiful sands of Lido Beach. St. Armand's Circle is a 10 minute walk for shopping and dining. Kayaking is a 2 minute walk and you can spend the afternoon exploring!

Florida Cracker Cabin on cattle ranch/Myakka River

We are located in Myakka City, FL, which is a short drive to Siesta Key and Lido Beach and Sarasota! Enjoy a peaceful stay in our newly built, unique, air-conditioned cracker cabin. The cabin sleeps 4 guests (2 adults comfortably and 2 children) and is located in the middle of our 1,100 acre working cattle ranch. Step outside and you are right on the Myakka River and can sit by the fire-pit at night and enjoy the sounds of nature. While your visiting, enjoy a kayak down the Myakka River.

@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)

Coolest Downtown Neighborhood - Ebikes, Beach Gear

Are you coming to Sarasota on vacation or perhaps considering moving here? If yes, then the Carriage House is the perfect place to use as a base camp while you explore the area and experience the best Sarasota has to offer. Quick and easy walk to dozens of casual restaurants, cool bars and unique shops. 5 minutes to Selby Gardens. 10 minutes to the Sarasota Bayfront. Main street is half a mile away. We provide tons of amenities including bikes, kayaks, beach chairs and umbrella.

Water Access Retreat | Kayaks + Hot Tub

BNB Breeze Presents: Water Access Retreat! Nestled in the heart of Sarasota, Florida, Water Access Retreat is a delightful property that offers a serene escape with direct access to a nearby kayak ramp, making it the perfect base for exploring the stunning waters of Sarasota Bay. Step outside and soak up the Florida sun or unwind after a day of adventure. - Hot Tub - Two kayaks and direct access to nearby kayak ramp - Private yard and patio with outdoor seating - Smart TV - and More!

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

siesta breeze suite

Peaceful Guest Suite- Great Location near Siesta Key! Welcome to our cozy and peaceful guest suite-perfect for two adults ,,We're just 2.1 miles from Siesta Key Beach and only 6 minutes from downtown Sarasota. Includes private entrance and parking , outdoor shower, and beach gear. No pets (owner allergic) no overnight guests who are not part of the advanced Airbnb reservation without permission from the host,guests fees apply,.