Vacation rentals with a kayak in Sarasota

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

Sunniland Hideway, minutes from Siesta Key Beach

Welcome to your retreat just minutes from Siesta Key Beach! This abode is tailor-made for those seeking a tranquil getaway or a longer stay in paradise. Our home features a fenced-in yard, ensuring your dogs can roam freely and while you relax. Take advantage of the nearby Legacy Bike Trail for leisurely rides or a short drive to fulfill all your basic needs. Whether you're here for a weekend or a few months, our property promises comfort, convenience, and endless opportunities for adventure.

@Tiffanythetinyhome| island | netflix|bike|hammock

You are about to book a famous HGTV 270ft² / 25m² tiny home on a private 1.5-acre island! ☆ Walk to dining, nightlife, and shopping ☆ Fully equipped kitchen (K-cup) ☆ Backyard fire pit + BBQ ☆ Screened-in outdoor lounge w/ hammocks ☆ 415Mbps ☆ Smart TV w/ Netflix ☆ Memory foam bed ☆ FREE Bikes + kayaks + beach gear 3 min → Siesta Key Beach 7 min → Downtown SRQ 12 min → Myakka River State Park (river kayaking + wildlife viewing) We use a compost toilet. Please read house rules for info.

Free kayak/bikes/walk to beach/full cottage #1

Unit #1 Beach cottage very private and quiet, has a full kitchen, King bed in the master and queen sofa bed in the tv room, very comfortable, fast WiFi, AC & heat. All you need to relax and just have fun. Outdoor shower and laundry area, Private parking, Enjoy amazing sunsets/fishing/and restaurants and bars, all walking distance to the beach and bay. Kayaks/snorkel gear/beach toys are included. So start enjoying the beautiful sandy beach on Manasota Key, Lots of sea life and turtles.

Quick and Easy Walk Downtown - Tons of Amenities

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.

Peaceful Waterfront Orchard 1

bring the whole family including your pets to this peaceful orchard and garden oasis. the action packed backyard of this duplex proudly boasts over 40 fruit trees of various varieties including banana, orange, lemon, fig, mango, papaya... and many more! choose to fish from the dock in the backyard canal, go exploring with the kayaks or paddleboards, play in the sandbox, try out the slackline, or even say hi to the chickens in the coop (maybe even grab a few fresh eggs for breakfast).

Waterfront Suite-20 min to Gulf Beaches

A hidden gem awaits you in this waterfront “Old Florida” style guest suite. You’ll be in an attached yet private suite with your own entrance, bedroom & cozy living area. The setting offers amazing days swimming in the pool, kayaking or fishing. Maybe you’ll see manatees in the creek or the ducks, turtles, our cats & resident Blue Heron parade around the property. Beach lovers can get to Anna Maria Island in about 20 minutes. Nightlife? We’re 15 min from downtown Sarasota.

Luxury Sport Vacation Pool House-Downtown Sarasota

Welcome to the Luxury Sports Vacation Pool House in Downtown Sarasota, the only vacation rental in Sarasota, featuring both a private multi-sport (pickleball, volleyball, basketball, or badminton) court and a heated enclosed pool with a spacious covered patio. Also there is a game room equipped with a ping pong table. This beautifully renovated and fully furnished single-family residence offers 3 bedrooms and 2 bathrooms, accommodating up to 8 guests and your lovely pets.

Rita Retreat - Beautiful 2/2 with private pool

Welcome to your dream vacation home! This charming rental offers a private pool and a lush green area for relaxation and fun. Situated just 4.6 miles away from the stunning Siesta Key beach, you'll have easy access to sun-kissed sands and sparkling waters. Seafood lovers will be delighted to find the renowned Phillippi Creek Oyster Bar nearby, offering some of the best seafood in town. Embrace the Florida lifestyle and make cherished memories in this wonderful retreat!

Waterfront Gem/ Pool Spa+ Dock/ Near Bridge Street

Anna Maria Waterfront oasis! **5 min walk to beach, private dock, pool heat included!!** Relax in the private heated pool, sip coffee on the dock, or walk to the beach. This bright, updated home has spacious living areas, a stocked kitchen, smart TVs, fast Wi-Fi, and cozy beds. Great for families or couples! Grill by the pool, dine under the stars, or fish from the dock. Includes washer/dryer, beach gear, and parking. Your peaceful, sunny getaway awaits—book now!

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 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.

Newly Renovated 1 Bedroom In-Law Apartment

1 Bedroom in-law apartment with private entrance and easy up front parking, sleeps 2. There is a pull out but not great for adults more suited to kids . Minutes to Siesta Key, Downtown Sarasota and Lido Beach, with easy access to I75. This quiet apartment is tucked into lush tropical landscape. Attention to detail throughout with new bed, pull out couch , coffee bar, Internet, Prime, Netflix, plush towels, crisp linen, soft pillows.