Holiday rentals with a kayak in Anna Maria Island

Find and book unique kayak rentals on Airbnb

Top-rated rentals with kayak in Anna Maria Island

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

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Guest favourite

Guest suite in Sarasota

4.96 out of 5 average rating, 173 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!

Guest favourite

Home in Longboat Key

4.87 out of 5 average rating, 106 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

Guest favourite

Home in Anna Maria

4.93 out of 5 average rating, 153 reviews

Private 30' Pool and Boat Dock - Rated best on AMI

* 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. * There's no better way to unwind and forget all your troubles than staying at Sunshine Cottage, located in the City of Anna Maria!

Guest favourite

Tiny home in Sarasota

4.9 out of 5 average rating, 173 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

Guest suite in Largo

4.97 out of 5 average rating, 318 reviews

Private Pool, Jacuzzi, Walk to Beach.

This Guest Suite is a large Studio Apt(360 sq ft) attached to our home. It has a private entrance, a large bath, large bedroom with pool view and private deck. Also includes a kitchenette with full size fridge, toaster, coffee maker and microwave. No Stove. Complimentary breakfast snacks including Coffee and tea. Relax on the deck and watch the birds on the bird feeder or grab our bikes, beach chairs and head to the beach. Grill available. Please read house rules before booking.

Guest favourite

Place to stay in Bradenton

4.97 out of 5 average rating, 31 reviews

Seas The Day By The Bay

Location location near historic Cortez Fishing Village and only 1.2 miles away from Anna Maria Islands 7 miles of paradise! Our dog friendly remodeled One bed/one bath mobile home sleeps 5 people comfortably! 2 queen futons, one twin foldout chair and a double bed in private bedroom. Comes with full size washer and dryer, grill, 4 bikes, inflatable kayak, and private fenced in patio and yard. 3 beach chairs and toys for you to enjoy. Come “ Seas The Day” at our beach base camp!

Superhost

Apartment in Saint Petersburg

4.85 out of 5 average rating, 408 reviews

Waterfront condo on top floor @ Boca Ciega Resort

The view of water is fantastic. Especially beautiful sunsets! Top floor end unit for privacy. Pinellas trail across the street to ride your bike or hike, a beautiful 38 mile trail. Plenty of restaurants nearby and grocery stores. Only 8 min drive to beach. 15 min from downtown St. Pete. Enjoy pool and hot tub overlooking bay for the condominium guests or can stay indoors and enjoy puzzles and games. We have a kayak that can fit up to 2 adults for our guests to use.

Guest favourite

Apartment in Indian Rocks Beach

4.99 out of 5 average rating, 107 reviews

Villa Al Golfo Pristine Waterfront Oasis

Pristine villa in the lovely seaside Gulf town of Indian Rocks Beach, 2 short blocks to the beach & the Intracoastal in your backyard. All newly renovated, both inside and out, enjoy unobstructed water views, private entrance, personal patio & your own indoor/outdoor fireplace. When you aren't lounging outside or taking a glide on our paddle board, you'll love the gourmet kitchen, comfy living room, two large TV's, cable/wifi, luxe memory foam beds & secured safe.

Guest favourite

Apartment in Bradenton Beach

4.87 out of 5 average rating, 62 reviews

Luxury, Fully Stocked, Next to Pool & Beach-202

Fully stocked condo, full kitchen, all the beach supplies needed. See my other listings here www.airbnb.c0m/p/ryant (replace the zero in .com with an o to get to link) Largest saltwater pool on island. Private beach access, plenty of space. Self-check-in, no contact with anyone. All units have their own parking. Unit has a full kitchen, grocery store is a mile down the road, plenty of open-air restaurants. Professional cleaning following CDC guidelines.

Guest favourite

Guest house in Clearwater

4.98 out of 5 average rating, 193 reviews

Guest House close To Clearwater Beach

Welcome to Clearwater! Located just a short distance from a variety of restaurants, unique shops, and grocery stores, we offer convenient access to anything you might need during your stay. Our studio is 4 miles from Clearwater & 5 miles to Indian rocks Beach. There is no shortage of things to do in the area, local parks, museums, cruises, and a variety of nightlife. Enjoy jet skis, bike trails, tennis, parasailing, and pier fishing!

Guest favourite

Flat in Bradenton Beach

4.88 out of 5 average rating, 205 reviews

Las Palmas Beach Rentals Unit 1

Upstairs unit with limited beach view across the street. Just a few steps to the white powder sand beach. 1 parking spot provided. This unit is for Max 3 persons. Hot tub downstairs. Spa just a few buildings to the south great massage and wellness center. We offer luggage drop off if you plan to uber/lyft and arrive before the check in time. Free trolley will give you service around the island.

Guest favourite

Cottage in Anna Maria

4.96 out of 5 average rating, 25 reviews

Snail's Pace: On Canal, Kayaks & Dog Friendly

606 N. Shore Drive, #4, Anna Maria, FL 34216 North End AMI Canal Home! Steps to the Gulf Beaches! 1 Bedroom / 1 Bathroom Queen Bed Backyard Dock (shared with other 2 cottages) Kayaks - 3 Single & 2 Double (shared with other 2 cottages) Hammock Gas BBQ Grill Professional Linen Service, Washer & Dryer Complimentary WIFI Dog Friendly (with pet fee) Beach Chairs & Beach Towels Parking for One Car