Holiday rentals with a kayak in Anna Maria Island

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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

4.94 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!

4–11 Jan

$196 SGD per night

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

25 Apr – 2 May

$802 SGD per night

Guest favourite

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!

6–13 Nov

$740 SGD per night

Guest favourite

Tiny home in Sarasota

4.89 out of 5 average rating, 171 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.

29 Jul – 5 Aug

$212 SGD per night

Guest favourite

Apartment 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.

5–12 Jan

$190 SGD per night

Guest favourite

Holiday home in Clearwater

4.9 out of 5 average rating, 111 reviews

Waterfront Courtyard Condo 2 Blocks to Beach

Renovated and conveniently located Clearwater Beach courtyard condo with water views of the Mandalay channel. Kitchenette and additional pull out sofa to easily accommodate additional guests if needed. Central location, being on the edge of residential and commercial districts, allowing for short walking distances to all popular attractions and food on Clearwater Beach. Watersports on-site with office, offering amazing Island Jet ski tours, kayak & paddleboard rentals, parasailing!

30 Oct – 6 Nov

$165 SGD per night

Guest favourite

Guest suite in Largo

4.97 out of 5 average rating, 315 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.

11–18 Sep

$160 SGD per night

Superhost

Apartment in Saint Petersburg

4.85 out of 5 average rating, 407 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.

29 Aug – 5 Sep

$181 SGD per night

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.

28 Jul – 4 Aug

$331 SGD per night

Guest favourite

Guest house in Clearwater

4.98 out of 5 average rating, 190 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!

10–17 Jul

$155 SGD per night

Guest favourite

Flat in Bradenton Beach

4.92 out of 5 average rating, 262 reviews

Las Palmas Beach Rentals unit 3

Las Palmas located on Anna Maria Island just steps to the Gulf of Mexico. Close to restaurants and shopping. Kayak, fishing, diving, nature trails, guided tours and more! Loads of adventure the challenge will be to just relax at the beach and catch the sunsets. We offer luggage drop off if you arrive prior to the unit being ready.

29 Aug – 5 Sep

$335 SGD per night

Guest favourite

Guest house in Bradenton

4.99 out of 5 average rating, 134 reviews

Conch Cottage adorable one bedroom with pool.

Take it easy at this unique and tranquil getaway. Conch Cottage is 5 minutes to Anna Maria Island. Walk to Portosueno park and see the Manatees watch the sunset from the park or bridge. Kayak, walk or bike Robinsons Preserve. So much to do in this historic Palma Sola Neighborhood.

26 Aug – 2 Sep

$200 SGD per night