Vacation rentals with a kayak in Sarasota County

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Sarasota County

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Superhost

Home in Longboat Key

4.88 out of 5 average rating, 121 reviews

Summer House longboat key

Luxurious waterfront 3 Bedroom home with bay and and canal view with extra dock that can accommodate up to 21 ft+-heated pool, tropical landscaping with coconut palms, outside patio and grill. Fish on the dock and watch dolphins and manatee. Truly a tropical paradise just 7 minute Walk to your own private beach, It is a private home nestled on a canal that is 2 houses from Sarasota Bay. Our home is situated in the desirable quiet neighborhood of Country Club Shore minutes from at Armand’s circle

Top guest favorite

Condo in Nokomis

5 out of 5 average rating, 48 reviews

Family Friendly Beach Condo

Property located on Lyon’s Bay, in Nokomis, Florida. This three-bedroom upper Condo unit is situated within a ten minute walk to Nokomis Beach on the Gulf of Mexico. Open kitchen fully equipped, Office area. Wi-Fi Large master suite, second bedroom has a queen bed. Third bedroom features four twin beds, walk-in closet and its own full bath. Your stay comes with access to paddle boards kayaks, which can be launched from a floating dock. Also available for your use are beach chairs and coolers.

Superhost

Bungalow in Siesta Key

4.89 out of 5 average rating, 9 reviews

Lagoon, pool, the Catamaran at Siesta Key Bungalow

The Siesta Key Bungalows offer a heated pool, courtyard and a dock on Heron Lagoon. This is a resort that has something for everyone. Featuring a bright and airy one bedroom space; experience an open floor plan connecting a welcoming living room and full-kitchen. With a king-size bed and a private bathroom you'll feel at home. The Catamaran Bungalow is stocked with linens, care essentials, plus eating & cooking utensils. An additional single-roll-away-bed allows accommodations for three guests.

Guest favorite

Condo in Sarasota

4.98 out of 5 average rating, 47 reviews

Gulf Views! 2 BR- Quiet-Canal-Htd Pool-Kayak/SUP

Feb 2026 2 week min Feb 1-14 or Feb 14-28 Mar 2026 2 week min Mar 1-16 or Mar 16-31 Gulf View, Top-Floor Beach Condo! Escape to Paradise Seeking a peaceful summer escape? Discover our charming coastal retreat—a perfect blend of relaxation and adventure! Nestled along a quiet canal, this cozy two-bedroom haven has everything you need for a rejuvenating getaway. Tandem Kayak & paddleboard included! Heated pool! Small, quiet complex! Less than 1/2 mile to Turtle Beach and the free trolley!

Superhost

Home in Venice

5 out of 5 average rating, 3 reviews

Tarpon Bayou

Take a break and unwind at this peaceful oasis. Right off the Myakka river. On Tarpon Bayou! Bring your small boat, kayaks and bikes. Near Myakka State Park South. Fisherman’s paradise producing Tarpon, Snook, Redfish, Snapper, Catfish, Dolphin, Manatee, Bull shark & Alligators. Close amenities include the Wellen Park baseball stadium that houses Atlanta Braves spring training. 10 minute drive to downtown Venice, Englewood, Northport and Port Charlotte nearby shopping and dining. Best Beaches.

Top guest favorite

Home in Sarasota

4.95 out of 5 average rating, 21 reviews

Beautiful MidCentury Modern Home

Our charming 2BR/2Bath mid-century modern home just steps from the water. Explore Sarasota's beautiful mangroves and beaches with our kayak or bicycle to nearby attractions. Enjoy the open floor plan, modern kitchen, and comfortable living room with sectional couch and TV. The primary bedroom offers a queen bed and office space. The second bedroom has a full bed and TV. Recently remodeled bathrooms and a separate laundry room add convenience. Siesta Key Beach is only six miles away. No pets.

Guest favorite

Home in Englewood

4.93 out of 5 average rating, 88 reviews

20 Steps to Water! Sunsets, and Hot tub!

• The dock is being replaced and is not usable at this time. Gorgeous Sunsets: Enjoy stunning views • Spacious & Updated: Modern, comfortable stay • Relaxing Atmosphere: Your worries melt away • Wildlife: Watch dolphins & manatees play • Main Level Living: No steps, easy access • Private Entry: Lower duplex unit (others live upstairs) • Gourmet Kitchen: Granite counters • Outdoor Fun: Hot tub, enclosed porch, dock • Water Activities: 2 kayaks, 2 paddleboards • Beach: 2 miles away

Superhost

Condo in Sarasota

4.9 out of 5 average rating, 10 reviews

Beachfront - Siesta Key 2 BR walk out to beach

Sept 30, 2024. Condo was severely damaged in hurricane Helene see photos Located on the secluded south end of Siesta Key. This beachfront 2 BR condo is ground floor - literally walkout the back door and you are on the beach. includes use of owners kayaks. 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

Guest favorite

Condo in Sarasota

4.97 out of 5 average rating, 32 reviews

Bayside Escape-Condo w/ Dock, Pool, and Near Beach

This unique 2 bedroom/ 2 bath condo is right on the waterfront in Siesta Key! It is the upper condo of a two story complex that has a perfect view and feels like your own personal getaway! It comes with a full kitchen, living room, and two decks. Part of what makes it amazing is the private dock on the Pass. Perfect for kayaking and exploring! Or maybe you'd like to just relax and take a dip in the heated pool? Located in the quiet end, you can enjoy the calm, or head to Siesta Village!

Top guest favorite

Tiny home in Sarasota

4.96 out of 5 average rating, 344 reviews

@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)

Guest favorite

Townhouse in Sarasota

4.78 out of 5 average rating, 148 reviews

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.

Guest favorite

Vacation home in Venice

4.84 out of 5 average rating, 134 reviews

🌟Venice Cute Pool Villa with bikes Kayaks 🌈🐬

Escape to our charming Venice pool home, where relaxation meets adventure! Perfectly located near the water, this tranquil three-bedroom retreat is nestled on a quiet, palm-lined street. Enjoy easy access to bikes and kayaks for exploring, plus all the beach essentials: cooler, umbrella, and chairs. The pool awaits for sunny days and peaceful evenings (note: a brand-new pool cage is on its way, expected in December). Book now to experience Venice’s beauty from your private oasis!