Vacation rentals with a kayak in Anna Maria

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Top-rated kayak rentals in Anna Maria

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Guest favorite

Guest suite in Sarasota

4.94 out of 5 average rating, 477 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!

Oct 19 – 26

ﺩ.ﺇ398 per night

Guest favorite

Home in Anna Maria

4.93 out of 5 average rating, 152 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!

Sep 2 – 9

ﺩ.ﺇ1,753 per night

Superhost

Condo in Siesta Key

4.83 out of 5 average rating, 235 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!

ﺩ.ﺇ610 per night

Guest favorite

Tiny home in Sarasota

4.9 out of 5 average rating, 172 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.

Jun 5 – 12

ﺩ.ﺇ552 per night

Guest favorite

Condo in Tierra Verde

4.96 out of 5 average rating, 237 reviews

Natural Beauty on Tierra Verde, Waterfront Condo

Feels like the Florida Keys! Fully renovated & well appointed second floor, 1 bed, 1 bath condo in Holiday Island condo resort. The condo features a beautiful waterfront & pool view, tennis, bicycles, hot tub, dock with grills, gym, and more. Remodeled in 2015 the condo features a fully equipped kitchen, Keurig coffee maker, beautiful views from the living room, dining room, kitchen, balcony. Walking distance to many local restaurants & minutes away from St. Pete Beach & Fort DeSoto.

Dec 2 – 9

ﺩ.ﺇ481 per night

Guest favorite

Guesthouse in Sarasota

4.97 out of 5 average rating, 408 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.

Jun 10 – 17

ﺩ.ﺇ512 per night

Guest favorite

Home in Ruskin

4.94 out of 5 average rating, 162 reviews

Private Beach Nature 2 ppl pets Work space remote

Unique, modern beachfront guest house-sits on a MULTI million $ property. Blend of Frank Lloyd Wright & Luis Barragan design. Located on Tampa Bay btwn Sarasota and Tampa/St Pete. Surrounded by palm trees, mangroves, birds chirping, dolphins, manatees, waves gently lapping and breezes. Sand from door to private beach. Fresh sheets, outdoor shower, small fridge, microwave, air fryer, & in and outdoor seating areas. Kayak and paddle board available. SUNRISE'S UNIQUE We are DOG FRIENDLY!

Oct 7 – 14

ﺩ.ﺇ888 per night

Guest favorite

Guest suite in Largo

4.97 out of 5 average rating, 316 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.

Aug 16 – 23

ﺩ.ﺇ411 per night

Guest favorite

Place to stay in Bradenton

4.97 out of 5 average rating, 30 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!

Aug 18 – 25

ﺩ.ﺇ396 per night

Guest favorite

Home in Bradenton

4.92 out of 5 average rating, 118 reviews

Braden River Fishing Bungalow Oasis

Secluded bungalow situated on the Braden River, surrounded by a natural preserve. The river's hideaway is a real Floridian oasis, complete with a large deck that is directly on the river complete with outdoor furniture and grill. We supply everything for your Florida vacation, beach towels, chairs, toys & games. Just a few miles away are lots of shops, bars and restaurants for your enjoyment. We hope you love this oasis as much as our family and friends have.

May 3 – 10

ﺩ.ﺇ539 per night

Guest favorite

Guesthouse in Clearwater

4.98 out of 5 average rating, 191 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!

Jul 10 – 17

ﺩ.ﺇ432 per night

Guest favorite

Apartment in Bradenton Beach

4.87 out of 5 average rating, 326 reviews

Las Palmas Beach Rentals unit 2

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.

Oct 1 – 8

ﺩ.ﺇ904 per night