Holiday rentals with a kayak in Sarasota County

Find and book unique kayak rentals on Airbnb

Top-rated rentals with kayak in Sarasota County

Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

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Guest favourite

Home in Sarasota

4.96 out of 5 average rating, 53 reviews

Large and Beautiful, Steps from Bay, Ringling!!

Tropical Paradise by the Bay – Walk to Ringling Museum, Asolo Theatre! Nestled between two university campuses and just a 5-minute walk to Sarasota Bay, 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!

Superhost

Home in Sarasota

4.8 out of 5 average rating, 30 reviews

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.

Guest favourite

Tiny home in Sarasota

4.88 out of 5 average rating, 224 reviews

@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.

Guest favourite

Home in Sarasota

5 out of 5 average rating, 6 reviews

Split Leaf Suite Amazing Pool, Hot Tub

Property Highlights • 5 Minute Walk to Beach (800ft) 5-10 Minutes to Village • Shared Heated Resort style Pool, Water Feature & Garden • 1 Bedroom, Bathroom, Living Room & Full Kitchen • 1 Queen Bed & Queen Sleeper Sofa (sleeps 4) • Outdoor Lounge Dinning Table for 8, Fire Table, Ice Maker, 2 Kayaks  • Clubhouse 1 w Ping Pong, Pool, Foosball, Pac-Man, Games • Starter Kit of Toiletry & Home Essentials • Free Private Parking, Laundry & Beach Essentials (Towels, Chairs, Cart, Umbrella)

Top guest favourite

Guest house in Sarasota

4.97 out of 5 average rating, 464 reviews

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.

Superhost

Townhouse in Sarasota

4.78 out of 5 average rating, 160 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 favourite

Holiday home in Venice

4.85 out of 5 average rating, 142 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!

Top guest favourite

Apartment in Sarasota

5 out of 5 average rating, 96 reviews

Quiet Canal Front 1 Bedroom- 2 Supyaks -Htd Pool

Whisk your favorite person away to BayDreaming! Escape to this quiet 1BR/1.5BA Siesta Key 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, 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!

Guest favourite

Home in Venice

4.94 out of 5 average rating, 143 reviews

MCM Waterfront Getaway w/ Private Dock + 4 Kayaks

Welcome to our Mid Century Modern waterfront getaway on the highly sought after Curry Creek. Perfectly situation between Nokomis Beach (2 miles) and Venice Beach (3 miles). Enjoy spending time fishing on the private dock or getting out on the water with our 4 kayaks and slip. We're located a half mile away from The Legacy Bike Trail (we have 6 bikes for guest use). large firepit, charcoal grill, cornhole, tons of supplies for shark teeth hunting and days spent at the beach

Guest favourite

Home in Sarasota

4.95 out of 5 average rating, 103 reviews

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!

Top guest favourite

Home in Port Charlotte

4.89 out of 5 average rating, 19 reviews

Peaceful waterfront home

Take it easy at this unique and tranquil getaway. Nestled alongside a serene canal, our home is a sanctuary of tranquility and natural beauty. From the moment you step onto the property, you are met with charm and allure that only canal front residence can offer. For those who enjoy outdoor activities, the canal provides a perfect venue for kayaking, fishing and lounging in the pool and hot tub. Surrounding sliding glass doors opens up to 3 separate patios.

Guest favourite

Home in Sarasota

4.93 out of 5 average rating, 76 reviews

Waterfront Home by Ralph Twitchell

Beautiful midcentury waterfront home on Phillipi Creek close to all that Sarasota has to offer. 5 miles to America's number 1 beach Siesta Key, and only a few short blocks from stores, nightlife, & other beaches. This quaint getaway includes a kayak to enjoy the pure bliss of the calm waters of Phillipi Creek as well as a game room including a pool table, foosball table, and a fireplace to lounge around and chat.