Holiday rentals with a kayak in Siesta Key

Find and book unique kayak rentals on Airbnb

Top-rated rentals with kayak in Siesta Key

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

0 of 0 items showing

1 of 3 pages

Guest favourite

Home in Bradenton

4.95 out of 5 average rating, 141 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

Apartment in Siesta Key

4.83 out of 5 average rating, 295 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!

Guest favourite

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.

Top guest favourite

Guest house in Laurel Park

4.97 out of 5 average rating, 461 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, 157 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, 137 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!

Guest favourite

Bungalow in Siesta Key

4.97 out of 5 average rating, 32 reviews

Heated Pool, Dock, Kayaks, 1-mile to Turtle Beach

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

Guest favourite

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 - Private pool and hot tub for relaxation - Fully-equipped kitchen and elegant dining area - Comfortable lounge with large flat-screen HDTV - Spacious fully-fenced backyard with BBQ grill and free bikes - Prime location: 3 min drive to Siesta Beach, 10 min drive to Crescent Beach, 13 min walk to a local beach Experience a High-End Vacation Getaway in Sarasota!

Guest favourite

Home in Sarasota

4.95 out of 5 average rating, 101 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 favourite

Home in Bradenton

4.92 out of 5 average rating, 77 reviews

Sea Gem | Waterfront w/ Pool, Dock + Paddle/Kayaks

BNB Breeze Presents: Sea Gem! This stunning waterfront haven in the heart of the Sunshine State is going to blow you away! Located just 30 minutes away from Siesta Key Beach, this beautiful and entertaining home includes: ✔ Private Dock on the Canal w/ String Lights! ✔ Heated Saltwater Pool ✔ Rooftop Deck w/ Picturesque Views! ✔ Kayaks + Paddle Boards ✔ Outdoor Kitchen! ✔ Dolphin Sightings From the Dock! ✔ An Outdoor Grill + Wine Cooler!

Guest favourite

Home in Sarasota

5 out of 5 average rating, 26 reviews

Stunning Home, Heated Pool and Boat Dock

Be among the initial guests to relish in the splendor of this charming 3-bed, 2-bath abode overlooking Phillippi Creek, with a rejuvenating pool and fresh, deluxe furnishings. It offers all you need for an unforgettable escape, featuring a well-equipped open kitchen, 2 fun large Roku smart TVs in the living spaces, and a 50" Roku Smart TV in the master bedroom. Essential bathroom amenities are provided for your comfort.

Guest favourite

Home in Siesta Key

5 out of 5 average rating, 8 reviews

Stroll to the Sea! Steps to the Village!

The house is a three bedroom, two bath ground level bungalow backing onto the intercoastal canal waterway. It has been beautifully renovated in a coastal style and is a five minute walk to Siesta Key Village and a ten minute walk to the beach. The house has its own private heated pool and hot tub. Enjoy fishing or just relax watching the tide come in or out.