Holiday rentals with a kayak in Sarasota County

Cottage & Tree ~ by the Sea

This cute cottage is located on a cul-de-sac, close to downtown Sarasota (5 min), the incredible white sand beaches of the Gulf (10 min), and just a few blocks from The Legacy Trail. Sarasota has award winning restaurants, bars, shopping, and unlimited fun activities. Our home features a large open lot with a gorgeous huge Live Oak tree to relax under. Enjoy fresh cool brand new AC and cozy decor. There is a fully stocked kitchen and grill area for entertaining while in your home away from home.

Venice Pool Villa with Bikes Kayaks & fun!

Relaxing pool home with new AC , 2 bedrooms, 1 king bed, 1 queen bed, 1 sofa double bed and one single foldout bed. 2 bathroom pool home just a 8 minute ride away from Manasota beach. Venice beach and caspersons beaches close by too. A great selection of restaurants and plenty of shopping and convenient grocery stores just 5 minutes away!. Also close to bike trails with two FREE bikes at the house and FREE kayaks too. My home is great for everyone! Pets welcome with pet fee, large fenced yard!

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.

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).

Peaceful Oasis: King Bed & Incredible Views

You have arrived, upon entering you will go upstairs to your spacious duplex. You will be greeted by an amazing view of the intercoastal waterway. You will love kayaking on the waterway & seeing all the amazing wildlife. You can sit on your downstairs patio with a cup of coffee or you can take a stroll to Turtle Beach & enjoy the sunset. Hop aboard the trolley & go to the Village & eat and drink at one of our famous restaurants or one of our favorite hot spots. See Guidebook.

Lagoon, pool, the Ringling at Siesta Key Bungalows

The Siesta Key Bungalows offer a heated pool, courtyard and a dock on Heron Lagoon. This is a resort that has something for everyone. The Ringling Bungalow features a bright and airy one bedroom space; with a kitchen, bathroom, and a private deck overlooking Heron Lagoon. With a king-size bed you'll feel at home. The Bungalow is fully stocked with linens, care essentials, plus eating and cooking utensils. The sofa turns into a queen size bed, allowing for a max occupancy of three.

Blue Cottage Suite- Peaceful Old Englewood Charm!

This charming rental is in historic Old Englewood right at the edge of Lemon Bay. The Blue Cottage is in a quiet neighborhood just 4 blocks from Dearborn Avenue with all great entertainment, eclectic shopping and restaurants, live music, and more. The Front porch pictured is part of the main house and is NOT included for use while renting the Blue Cottage Suite. IF the main home is vacant during your stay, I will let you know and it can be used during that time.

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.