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.

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

Whisk your favorite person away to BayDreaming! Escape to this quiet 1BR/1.5BA condo - just an 8-minute walk to Turtle Beach! Perfect for couples, it features a private deck with canal and Gulf views , a heated pool for sunset swims, 2 supyaks and a plush king bed for cozy nights in. Enjoy garage parking, beach gear, and a peaceful, welcoming community. Whether you're here to relax or reconnect, this coastal retreat offers the perfect mix of romance or just plain serenity on sunny Siesta Key!

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

MCM Waterfront Retreat • Dock, Kayaks & Beaches

Welcome to our Mid-Century Modern waterfront escape on Curry Creek, minutes from Nokomis Beach (2 miles) and Venice Beach (3 miles). Spend your days fishing from the private dock, paddling one of 4 kayaks, or biking the Legacy Trail with 6 bikes. Evenings are for the firepit, grilling on the charcoal BBQ, or cornhole under the stars. We’ve stocked shark tooth gear, beach essentials, toiletries, coffee, tea, olive oil, spices, and a welcome bottle of wine — so you can arrive, unpack, and relax.

North Port Home on Canal

Relax in this well appointed guest house as you enjoy the warmth of the Florida sunshine. Read a book on the garden swing next to the canal while you watch the birds, fish off the dock or canoe. Immaculate 2 bed/2 bath home with sun porch and patio complete with BBQ grill located in lovely neighborhood next to lighted bike paths. Close to Routes 41 and 75 for beaches, shopping, restaurants, sports events etc. Our favorite thing to do is beach combing the fabulous beaches -equipment provided.

Heated Pool, Dock, Kayaks, 1-mile to Turtle Beach

The Siesta Key Bungalows offer a heated pool, courtyard, sun loungers, gas-grills, laundry facilities, kayaks & a private dock on Heron Lagoon. The Dolphin Bungalow's one bedroom space; connects a welcoming living room, full-kitchen, and a private backyard patio. A king bed, two HDTVs and a full bathroom will further enhance your overall experience. Fully stocked with linens, care essentials, eating & cooking utensils. A queen sofa bed in the living room, allows for a capacity of three.

@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.

Relaxing Retreat, King Bed, Beautiful Scenic 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.

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 2.2 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). If you bring a truck, enjoy our double seat kayak!,no overnight guests who are not part of the advanced Airbnb reservation without permission from the host,guests fees apply,.

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.

Sunset and beach view from your balcony Unit 403

A luxurious experience on the beautiful beaches and emerald waters of the Gulf of Mexico awaits you when you check into this fabulous, fully renovated unit. It is one of the best one-bedroom, one-bath condos on Longboat Key, offering exceptional value. While the breathtaking views from the balcony capture the beauty of the Gulf, the interior has been thoughtfully redesigned to bring the outdoors in, creating a seamless blend of comfort and coastal elegance.