Vacation rentals with a kayak in Clearwater Beach Island

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Top-rated kayak rentals in Clearwater Beach Island

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Guest favorite

Cottage in Tampa

4.99 out of 5 average rating, 145 reviews

Bay Lake Cottage

You’ll have the Entire 500sq ft Cottage & private entry, deck/dock, all to yourself. Located on a 37-acre private ski lake.Key-pad entry, private parking. 1 king bed, 1 bath, queen sofa bed, washer/dryer, smart TV’s, blackout curtains,shampoo/conditioner,hairdryer,WiFi. Fully stocked kitchen, smokeless grill, wine fridge upon request, k-cup/drip coffee machine. The lake has bass, we provide fishing poles/tackle box. Rentable Kayaks & Canoe. Pet fee $50. Elope/Proposal packages IG lakepossibility

Feb 20 – 27

G$43,932 GYD per night

Guest favorite

Barn in Odessa

5.0 out of 5 average rating, 28 reviews

Cypress Lakes Barndominium

Rest & relax at this newly constructed barn loft apartment, located on a 4 acre hobby farm in Odessa, Florida on a private lake. This one bedroom, one bath and kitchen is clean, fun, and convenient. We have 2 daily feedings of farm animals at which you can participate including horses, cows, goats, & chickens; or you can choose to kayak on the lake. This memorable place is anything but ordinary, and is conveniently located 11 miles from the airport and is a quick drive to dining & shopping.

Jan 12 – 19

G$22,563 GYD per night

Guest favorite

Vacation home in Clearwater

4.88 out of 5 average rating, 112 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!

Jul 28 – Aug 4

G$30,860 GYD per night

Guest favorite

Condo in Tierra Verde

4.96 out of 5 average rating, 238 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.

May 26 – 31

G$26,241 GYD per night

Guest favorite

Cottage in Clearwater

4.94 out of 5 average rating, 31 reviews

Beach Access, Fenced Yard, Pets, Local Quiet Beach

Experience the ultimate beach getaway in our cozy 2/2! Welcome to Fairytale cottage, whimsical, bright and quaint home where bright colors, local art and copious sunshine await you. High quality bedding, non toxic cookware, kayak, bikes, grill, fenced in huge backyard, outdoor shower. This section of beach is less crowded. Walk to shops, restaurants and pier, come home to have dinner outside in the beautiful backyard under the magnificent tree, starry nights, warm Florida sea breezes

Apr 22 – 29

G$82,520 GYD per night

Guest favorite

Guest suite in Largo

4.97 out of 5 average rating, 317 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.

Oct 8 – 15

G$24,041 GYD per night

Guest favorite

Farm stay in Odessa

4.99 out of 5 average rating, 290 reviews

Farm and lake stay at Maison de L'eau Douce

LAKEHOUSE PRIVATE cabin-farmhouse décor-full kitchen/living room-cozy bedroom/full bath-W/D- 2.5 acres-2 flat screen TVs with Roku (Netflix, Spectrum cable app, and more)-bamboo hard wood flooring- high thread count sheets-very comfy queen bed. IKEA Sleeper sofa in livingroom. Kitchen: gas range-dishwasher-microwave-Keurig machine. Wooded setting-large deck with views of the lake. WIFI. Gas grill/firepit. HOUSEBROKEN PET FRIENDLY. WE NOW CHARGE A PET FEE (see below for details).

Oct 17 – 24

G$30,769 GYD per night

Superhost

Condo 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.

Oct 25 – Nov 1

G$27,169 GYD per night

Guest favorite

Condo 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.

Sep 2 – 9

G$49,618 GYD per night

Guest favorite

Guesthouse in New Port Richey

5.0 out of 5 average rating, 104 reviews

Palm Hideaway on the Cotee River

Relax on the river at Palm Hideaway-a luxury escape to the Gateway of Tropical Florida. Our cozy guest cottage was completely renovated in 2022 & is nestled amid lush greenery on the Pithlachascotee "Cotee" River in New Port Richey. Sleep in the king size bed & have coffee or tea on your Tiki patio rain or shine. Guests have shared access to the river from the park-like backyard & can enjoy a fire in the fire pit or paddle the kayaks.

Apr 27 – May 4

G$18,483 GYD per night

Guest favorite

Guesthouse 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!

Jul 22 – 29

G$24,169 GYD per night

Guest favorite

Home in Tarpon Springs

4.95 out of 5 average rating, 177 reviews

Tree House Treasure

We're a quiet, small, serene old neighborhood on the end of a cul-de-sac and nearly floating on a lagoon! Florida nature at it's finest. The home is just 4 feet off the sea wall so the home is best suited for adults that are looking for that quiet get-a-way. Upper has 2 beds & a tri-fold mattress. The lower is an office for the maintenance team. No smoking, vaping, or illegal drugs permitted.

Jul 24 – 31

G$23,951 GYD per night