Vacation rentals with a kayak in Winter Haven

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Top-rated kayak rentals in Winter Haven

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Guest favorite

A spacious living room features light green walls and hardwood flooring. A large flat-screen television is positioned on a white media console. Natural light enters through multiple windows, illuminating a comfortable cream-colored sofa adorned with pillows. A coffee table sits centered on a patterned area rug.

Home in Orlando

4.88 out of 5 average rating, 205 reviews

Charming Orlando Cottage - Close to Everything!

This charming 1920's cottage is the perfect retreat for either a brief stay visiting all that Orlando has to offer, or could be a quiet escape to stay for a few months working remotely. The home has one king size and one queen size bed, a separate office if you are needing to work out of the home. It's a private space but on a larger piece of property that also has two other homes and shares access to a beautiful lake - which our guests are welcome to use! Inquire for different terms available.

Superhost

Home in Winter Haven

4.73 out of 5 average rating, 200 reviews

Awesome Lake House W/ Private Dock, Kayaks & More.

Awesome lake house, with a private dock, kayaks, canoe, New Kitchen, & new master bathroom, game room w/ foosball, air hockey/small pool table, an arcade with 100s of games, hammock swings & the lake has boat ramp. This lake is a fishing paradise we have caught crappies, red ears, bluegills, and lots of bass, our 5 year old got a nice one on his 2nd cast. We love our vacation home & hope you will love it too. Disney 35 min, Legoland 10 min. Please read full description. Pets are not allowed

Top guest favorite

Home in Auburndale

5 out of 5 average rating, 40 reviews

Juliana Jewel on Lake Juliana

Welcome to our charming 3 bed/2 bath lake house in sunny Auburndale, FL! Enjoy stunning lake views and sunsets, Florida wildlife and private lake access. Take out our kayaks for a fun day on the water or bring your own boat! Grill up some delicious meals on the BBQ and gather around the fire pit to roast marshmallows under the stars. Sleeps up to 7 guests comfortably and has all the amenities you need for a memorable vacation. Located just a short drive from Orlando theme parks and attractions.

Superhost

Vacation home in Kissimmee

4.91 out of 5 average rating, 110 reviews

Urban Hip Disney condo with FREE Water Park!

Most central LOCATION in town! GORGEOUS, Brand NEW and super hip condo in the center of it all! Tastefully furnished and fully appointed to provide your family with a truly Magic vacation. Super fast Wifi, cable channels, parking immediately in front. Elevators, gated community. The resort offers FREE WATER PARK, lazy river, Tiki bar, a gym, sand volleyball, basketball court, kayak rentals and much more. Great shopping and restaurants in the vicinity and electronic lock for self check in.

Guest favorite

The home presents a charming façade with a spacious deck featuring colorful seating options. A hammock is seen suspended nearby, inviting relaxation. The lawn extends gently towards the waterfront, bordered by a wooden fence, with neighboring buildings visible in the background.

Home in Lake Wales

4.97 out of 5 average rating, 76 reviews

Crooked Lake House With Dock

Waterfront home! HOST PAYS SERVICE FEES Thoughtfully designed so that all spaces are used to their full potential. Traditional, cozy independent living & kitchen spaces which have more than enough room & seating. Luxurious touches & an at home vibe bring this wonderful stay to life. Fenced backyard & huge Deck. Public Boat ramp ,dock. This beautiful home has it all, firepit available after a day on the lake! Kayaks available at your own risk, missing or damaged parts will be billed to guest.

Guest favorite

A wooden billiards table is positioned in the room, with a vintage Budweiser sign hanging above. Large glass doors open to reveal serene water views and towering cypress trees outside. Natural light filters through the space, creating a relaxed atmosphere.

Home in Clermont

4.93 out of 5 average rating, 204 reviews

Lake Front Home with private Dock on Lake Louisa

Beautiful lake front home on Lake Louisa. The home sits under towering Cypress trees and is 15 feet from the waters edge. Enjoy breathtaking views of Lake Louisa in the very large great room. Enjoy a game of pool on the pool table, watch cable tv, or walk out onto our private shaded dock where you can fish, swim, enjoy the views, read, play a game of Bimini ring toss, or just relax and unwind. For the safety our guests we allow 2 days between to allow full disinfecting of the house.

Superhost

An open living area features a comfortable seating arrangement with two armchairs and a sectional sofa. A modern coffee table sits atop a soft rug. Large sliding glass doors lead to a balcony, offering a view of the tranquil lake.

Condo in Kissimmee

4.85 out of 5 average rating, 138 reviews

3171-107 Resort Lake View Disney Universal Orlando

Relax in our Stylish & Modern 2Bed/2bath fully equipped apartment for up to 7 guests, located in the family friendly Storey Lake Resort. Minutes from DISNEY World Theme Parks in Orlando Florida. Close to UNIVERSAL STUDIOS & SEAWORLD. Enjoy our lake view from the balcony. Close to restaurants, supermarkets, outlet malls & retail stores. Great amenities: Heated Pools, Kids Splash Zone, Water Slides, Lazy River, Gym, Mini Golf, Kayak, Tiki Bar & Ice Cream Shop, security guard!

Guest favorite

Townhouse in Kissimmee

4.93 out of 5 average rating, 99 reviews

Private Pool-StoreyLakesResort-Near Disney!

This gated community is perfect for your family &friends to create amazing memories! The home has a first floor bedroom (king) &a very PRIVATE LAKEFRONT pool (that can be heated at a reasonable fee). The resort is very lively.... has TONS AND TONS of amenities including a micky shaped pool, lazy river, tiki bar, slides, &kayaking. You are sure to enjoy your ultimate dream vacation! 5miles-Disney, 14 miles-Universal Studios. We provide all basic essentials, too!

Guest favorite

Condo in Kissimmee

4.84 out of 5 average rating, 213 reviews

Near Disney FREE Waterpark & Mickey Safari 3120

STOREY LAKE RESORT A premier vacation community just 8 miles from Disney and minutes from Universal & SeaWorld, this community is surrounded by restaurants, shops, and top malls. Only 30 minutes from Orlando Airport, it offers easy access to everything you need. Book your stay for 7 days or more and unlock an exclusive 5% discount ! Stay 30+ nights and save 10% (Discount will apply on selected stays) Reserve now! we would love to be your host!

Guest favorite

A tranquil outdoor space is presented, featuring a stone fire pit surrounded by lounge chairs. Lush greenery and palm trees frame the view of a serene lake, enhancing the inviting atmosphere for relaxation.

Home in Orlando

4.96 out of 5 average rating, 226 reviews

The Lake House - Next to Universal Studios - NEW ♥️

Luxurious, modern and completely remodeled single-family home with lake access in the prestigious Doctor Phillips neighborhood. Centrally located hops away from all Orlando has to offer, 1.1 miles (3 minutes) from Universal Studios Theme Parks, 9.5 miles to Disney World and 5 miles to Seaworld Orlando. No other Airbnb offers this upscale living space with stunning outdoor area to kick back and enjoy after a long day at the parks.

Guest favorite

Two bright yellow inflatable kayaks are anchored alongside each other on calm water. Lush greenery and tall trees line the shoreline in the background under a mostly cloudy sky.

Home in Winter Haven

4.91 out of 5 average rating, 44 reviews

Lakeside Bungalow - Winter Haven Chain-of- Lakes

The Lakeside Bungalow is located on Lake Howard, one of the most popular areas on the Winter Haven "Chain -of-Lakes". Enjoy easy access to lakefront bars, restaurants, the quaint downtown Winter Haven and LegoLand. Bring your boat and enjoy easy access to a boat ramp 1/2 mile away. The owner has two inflatable kayaks and a paddle board she is happy to share. There are 2 small friendly dogs living on the property as well.

Guest favorite

Villa in Kissimmee

4.88 out of 5 average rating, 115 reviews

Wonderful Villa at Storey lake Resort 6 Rooms Pool

Welcome to our luxurious and stunning vacation home located at STOREY LAKE RESORT, taking you on an adventurous journey filled with endless memories and exceptional selfies. We are 15 minutes from Disney and 2 minutes from Target, 5 minutes from Walmart and several other restaurants. All rooms have television and not to mention the private pool. Make some memories in this unique and familiar place.