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Vacation rentals with a kayak in Siesta Key

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Siesta Key

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Home in Longboat Key

4.86 out of 5 average rating, 110 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

Home in Bradenton

4.97 out of 5 average rating, 111 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

Guest suite in Sarasota

4.94 out of 5 average rating, 505 reviews

Studio Apartment. Priv Yard. 5 min to Siesta Key!

Self checkin. Includes kayak and bikes! You’ll love my place because of the coziness, the high ceilings, and the location. My place is good for couples, solo adventurers, and business travelers. Converted garage space. Your own private fenced back yard, kitchenette, fridge, private bathroom, Amazon Firestick with Netflix, Hulu and dock/boat ramp just 30 sec from your door and in a beautiful neighborhood. Just a 10 min bike ride to Siesta Key. The #1 beach in America! What more could you ask for!

Tiny home in Sarasota

4.96 out of 5 average rating, 313 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)

Guesthouse in Downtown Sarasota

4.97 out of 5 average rating, 439 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.

Townhouse in Sarasota

4.77 out of 5 average rating, 131 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.

Vacation home in Venice

4.83 out of 5 average rating, 125 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!

Home in Venice

4.94 out of 5 average rating, 124 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

Home in Bradenton

4.94 out of 5 average rating, 158 reviews

4/2 house/pool we have power/wifi/water IMG blake

Welcome to West Bradenton, 3.5 miles away from IMG Academy! Convenient vacation destination just 5 miles away from the beaches, top sites and the best fishing spots! Enjoy nice Florida weather and have best time in this newly and completely renovated 4/2 pool/TIKI bar house with a huge fenced in backyard! We have lounge chairs, hammocks and kayaks for your use! The house is set up to make your vacation relaxing and full of fun. Just bring your swimsuit!

Home in Anna Maria

4.94 out of 5 average rating, 167 reviews

New Construction & Ready for Post-Hurricane Visits

* 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.

Home in Palmetto

4.78 out of 5 average rating, 144 reviews

Private Efficiency

LONG TERM Guests Welcome! To Check out is 11am Efficiency with fully stocked kitchenette is a living room with Murphy Bed. Living room by day, bedroom by night. Coffee, tea and creamer in stock. 15 minutes to Ellenton Outlet Mall with plenty of dining choices on the way. 30 minutes to St Pete or Sarasota. STRICT LIMIT TO (2) GUESTS, NO SMOKING INSIDE, NO cats No dogs For Local events see realizebradenton dot com

Rental unit in Bradenton Beach

4.88 out of 5 average rating, 350 reviews

Las Palmas Beach Rentals unit 2

No HOT TUB or Washer/Dryer due to flooding. Unit 2 Ground floor;800 sq ft; patio; limited beach view . Steps to the white sandy beach across the street. Fully equipped kitchen with markets nearby, Restaurants and shopping within walking or hop on the free trolly. Trolly stop nearby. Outdoor open air patio with Caldera Spa and screen porch for outside enjoyment. Linens and basic supplies are included.

Vacation rentals for every style

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Houses

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Apartments

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Bungalows

Intimate homes. inviting architecture

Popular amenities for Siesta Key kayak rentals

Free parking on premises

Air conditioning

House rentals with a kayak

Home in Venice

4.88 out of 5 average rating, 33 reviews

Venice Pool + Hot Tub Oasis (2 bed/2bath)

Home in Bradenton

5 out of 5 average rating, 66 reviews

Waterfront Home w/ Private Dock, Kayaks, and Yard!

Home in Venice

4.9 out of 5 average rating, 52 reviews

The Ripple Inn At Fennario

Home in Bradenton

4.87 out of 5 average rating, 55 reviews

Executive Bayside Retreat/Pool/IMG/Sarasota Bay

Home in North Port

4.99 out of 5 average rating, 84 reviews

North Port - Canal Home- Fish/Canoe/Bike

Home in Sarasota

4.89 out of 5 average rating, 90 reviews

Oceanfront home w/sunset views of Sarasota Bay

Home in Indian Beach-Sapphire Shores

5 out of 5 average rating, 43 reviews

Perfect Family Getaway+ping pong, mini golf, bikes

Home in Bradenton

4.9 out of 5 average rating, 81 reviews

1 lvl, 4bd htd salt pool, private, close to beach!

Cottage rentals with a kayak

Cottage in Holmes Beach

5 out of 5 average rating, 5 reviews

Steps To The Beach, Private & Heated Pool, Renovat

Cottage in Holmes Beach

5 out of 5 average rating, 5 reviews

Anna Maria Cottage w/Golf Cart

Cottage in Sarasota

4.96 out of 5 average rating, 74 reviews

Cottage by the Bay - free Level 2 EV charging

Cottage in Sarasota

4.81 out of 5 average rating, 155 reviews

Cozy clean cottage

Cottage in Nokomis

4.98 out of 5 average rating, 63 reviews

New Pool Tropical Waterfront Dock & Optional Boat

Quick stats about vacation rentals with a kayak in Siesta Key

Total rentals
40 properties
Nightly prices starting at
G$22,949 GYD before taxes and fees
Total number of reviews
1.8K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
30 properties have a pool

Destinations to explore