Vacation rentals with a kayak in Siesta Key

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Top-rated kayak rentals in Siesta Key

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

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Superhost
A heated pool is enclosed within a screened area, surrounded by lush greenery and outdoor seating. The pool area features a natural stone deck, with lounge chairs positioned for sunbathing. The peaceful environment offers a private retreat for relaxation and enjoyment.
Home in Sarasota
4.91 out of 5 average rating, 107 reviews

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

Superhost
A spacious bedroom features a large bed with a blue quilt, flanked by two bedside tables with lamps. Sliding glass doors open to a private deck, allowing natural light to flood the room. Soft blue walls complement the light-colored flooring.
Condo in Siesta Key
4.83 out of 5 average rating, 324 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
The outdoor area showcases a heated saltwater pool surrounded by lounge chairs and a covered seating area. A manicured artificial turf putting green is prominently featured, providing a playful touch to the spacious backyard, which is framed by lush landscaping and bright skies.
Home in Bradenton
4.79 out of 5 average rating, 362 reviews

Heated saltwater pool home - turf putting green

Private 3 bedroom single family home 4 miles to white sand gulf beaches Longboat Key and Anna Maria Island. HEATED SALTWATER POOL home with access to ride bikes to the beach. Spread out in the oversized backyard with your own private pool and sitting area, featuring artificial turf yard and putting green, and beautiful landscaping. All hurricane damage has been repaired. The fence is fixed and the backyard is again completely private. The pergola pictured in photos was lost in the storm.

Superhost
Home in Longboat Key
4.86 out of 5 average rating, 135 reviews

Summer House longboat key

Luxurious waterfront home with bay and and canal view, new custom kitchen with a view to the pool and your own private tiki bar, dock that can accommodate up to 21 ft boat , whole house just received a complete inside and out make over. Tropical 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. minutes from St Armand’s circle. feel free to reach out with any questions or requests

Guest favorite
Bungalow in Siesta Key
5 out of 5 average rating, 19 reviews

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.

Guest favorite
An inviting living area features a blue sofa with decorative pillows, complementing a rustic wooden coffee table. A mounted Smart TV displays the Netflix logo. Bright pink LED lights illuminate the ceiling, enhancing the compact kitchen area, which includes bar stools and stylish cabinetry.
Tiny home in Sarasota
4.95 out of 5 average rating, 395 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)

Top guest favorite
An outdoor common area features a decorative umbrella over a bistro table, surrounded by potted plants. A wooden deck leads to a staircase, with warm lights illuminating the setting. A grill is positioned nearby, creating an inviting outdoor space for relaxation.
Guesthouse in Laurel Park
4.97 out of 5 average rating, 502 reviews

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.

Top guest favorite
Condo in Sarasota
5 out of 5 average rating, 101 reviews

Quiet Gulf & Canal View 1 BR -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, 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!

Guest favorite
A serene view of the intercoastal waterway is captured, featuring calm waters reflecting the sky. Lush greenery lines the opposite shore, while a wooden dock extends into the water. Palm fronds frame the scene, emphasizing the tranquil coastal environment.
Townhouse in Sarasota
4.78 out of 5 average rating, 172 reviews

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.

Guest favorite
Condo in Longboat Key
4.88 out of 5 average rating, 125 reviews

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.

Top guest favorite
A private pool is surrounded by a tropical landscape, featuring palm trees and vibrant plants. The clear water reflects the blue sky, and a spacious deck with paver stones offers a welcoming area for relaxation. A canal can be seen in the background.
Home in Anna Maria
4.95 out of 5 average rating, 187 reviews

AMI favorite w/Private 30' Dock & Pool

* It doesn't get much better than being right on the water, located on a wide canal, and ½ block from the beach. * Enjoy the large 16' x 30' private pool in a picturesque tropical landscape along with a 30' fishing/boat dock. * Within walking distance of Pine Avenue, City Pier, Two Scoops, Waterfront Restaurant, Galati's Marina, and Island Ocean Star Restaurant. *Less than a 3 minute walk to Bay Beach and a 15 minute walk to Bean Point.

Guest favorite
A modern living area is presented, featuring a neutral sectional sofa and a light-colored coffee table. A round mirror reflects natural light, while a potted plant adds a touch of greenery. The entrance leads to a view of the outdoors, enhancing the bright and airy space.
Vacation home in Venice
4.89 out of 5 average rating, 113 reviews

~ Relax Here 2 BED Home 8 Min to Beach ~

Enjoy a bright Florida getaway just 8 minutes from the beach! Perfect for families or couples, our cozy home features fast Wi-Fi, a fully equipped kitchen, free parking, and all the essentials for a relaxing stay. Close to restaurants, local shops, and water activities, this is the ideal base for your Florida vacation. Book now for convenience, comfort, and easy access to Gulf Coast fun!

Popular amenities for Siesta Key kayak rentals

When is the best time to visit Siesta Key?

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Avg. priceﺩ.ﺇ1,014ﺩ.ﺇ1,726ﺩ.ﺇ1,825ﺩ.ﺇ1,238ﺩ.ﺇ1,072ﺩ.ﺇ1,010ﺩ.ﺇ1,010ﺩ.ﺇ959ﺩ.ﺇ1,050ﺩ.ﺇ1,234ﺩ.ﺇ757ﺩ.ﺇ1,076
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Quick stats about vacation rentals with a kayak in Siesta Key

  • Total vacation rentals

    Explore 70 vacation rentals in Siesta Key

  • Nightly prices starting at

    Siesta Key vacation rentals start at ﺩ.ﺇ514 per night before taxes and fees

  • Verified guest reviews

    Over 2,260 verified reviews to help you choose

  • Family-friendly vacation rentals

    50 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Vacation rentals with a pool

    60 properties feature pools

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    70 of Siesta Key vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Siesta Key rentals

  • 4.9 Average rating

    Siesta Key stays are highly rated by guests—averaging 4.9 out of 5!

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