Vacation rentals with a kayak in Sarasota Beach

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Sarasota Beach

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Guest favorite

Home in Longboat Key

4.88 out of 5 average rating, 127 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

Home in Osprey

4.98 out of 5 average rating, 42 reviews

Charming Florida Cottage - Kayaks Included

Welcome to the Spanish Point Cottage! Our Old Florida style cottage is conveniently located within steps of some of Sarasota's most historic sites making it the ideal place to experience true Florida. Enjoy exploring Historic Spanish Point, kayaking to a secluded beach, walking to Historic Bay Preserve, watching the sunset over the Bay, fishing at Osprey Fishing Pier, walking to dinner all from your well appointed and peaceful oasis. There is no better place to experience true Florida living!

Guest favorite

Home in Bradenton

4.95 out of 5 average rating, 143 reviews

WOW-King Bed w/86° Pool, Turf Golf green, Beaches

Location! Have fun with the whole family at this stylish home. Just minutes to Anna Maria Island beaches. This incredible newly built home sets the highest standards of luxury living. It’s the ideal retreat with its expansive views of the outdoors from the moment you enter. Open concept with large French doors throughout the home creates the perfect indoor-outdoor lifestyle. Spend the day lounging by the heated pool with a cold drink in your hand. Fun turf yard area with games and putting green

Superhost

Condo in Siesta Key

4.83 out of 5 average rating, 298 reviews

Siesta Key 1/1 King bed “Sunset Suite” Pool Kayaks

We pay your AIRBNB service fees for you! Updated & inviting coastal getaway, located on the island of Siesta Key in a small resort called Solitude Suites on Siesta Key. The “Sunset Suite” has a living/dining/kitchenette area w/ 65” TV, a separate bedroom & a separate bathroom. Off the bedroom is a private open wood deck. Table & chairs allow you to enjoy the perfect view of a Siesta Key sunset. New shower in Dec 2023! 2 min drive or 10 min walk to beach! Enjoy FREE Kayaks, SUPs & Tiki Huts!

Superhost

Home in Sarasota

4.83 out of 5 average rating, 23 reviews

Sapphire Shores | Luxury Pool, Game Room + 2 Bars!

BNB Breeze Presents: Sapphire Shores! Welcome to this breathtaking 3-story sanctuary, nestled in the heart of Sarasota, Florida! Just 15 minutes away from the beaches and downtown, this luxurious property offers a true haven of opulence and relaxation! This destination has an extensive amenity list, including: - Private 40' Lap Pool w/ Sun Decks - Ocean Views From The Home - 2 Fireplaces - Game Room - 2 Bars - Kayaks + Bikes - Jura x8 Espresso Machine - Private Balconies off of Each Room

Guest favorite

Tiny home in Sarasota

4.89 out of 5 average rating, 221 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 favorite

Home in Sarasota

4.91 out of 5 average rating, 11 reviews

Luxe 3BR Siesta Key Home Pool, Hot Tub, Near Beach

Escape to luxury in our serene Sarasota home! - 3 spacious bedrooms with comfortable beds and modern amenities. - Open-concept living area with natural light and a relaxing atmosphere. - Private pool and hot tub for ultimate relaxation. - Fully-equipped kitchen and elegant dining area for family meals. - Spacious fully-fenced backyard with BBQ grill and free bikes for exploring. - Prime location: 3 min drive to Siesta Beach, 10 min drive to Crescent Beach, 13 min walk to a local beach.

Guest favorite

Home in Bradenton

4.93 out of 5 average rating, 28 reviews

Birds and Sunsets

Some of the best Sunsets and more Birds than you can count. Very spacious for your family and friends The master bedroom is upstairs and has sliding glass doors to a large balcony overlooking the Bay. The other 3 bedrooms are downstairs, one of those has sliding glass doors that open to the pool deck. All living areas as well as the kitchen have beautiful views of the Bay as well. The living room has a huge sectional and offers a 70-inch HDTV. TV in rooms Smart TV's with Netflix

Top guest favorite

Guesthouse in Sarasota

4.97 out of 5 average rating, 462 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.

Top guest favorite

Home in Siesta Key

5 out of 5 average rating, 15 reviews

The Shore House Private Dock Hot Tub

This Three bedroom two bathroom property is located in a quiet neighborhood, just a short walk or bike ride to the heart of Siesta Key Village, a quaint beachfront neighborhood that offers plenty of restaurants, shops and entertainment. It’s also just a short walk from the beautiful white sand beaches of Siesta Key. The house has been thoughtfully designed and furnished to emphasize style, comfort, and convenience. The energy of this home is so soothing its truly a relaxing oasis.

Guest favorite

Home in Sarasota

4.95 out of 5 average rating, 102 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!

Guest favorite

Home in Sarasota

4.93 out of 5 average rating, 75 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.