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Vacation rentals with a kayak in Winter Haven

Find and book unique kayak rentals on Airbnb

Quick stats about vacation rentals with a kayak in Winter Haven

  • Total vacation rentals

    Explore 20 vacation rentals in Winter Haven

  • Nightly prices starting at

    Winter Haven vacation rentals start at G$8,370 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,270 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Winter Haven vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Winter Haven rentals

  • 4.9 Average rating

    Winter Haven stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated kayak rentals in Winter Haven

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

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Top guest favorite
A family-friendly living area is presented with a large, comfortable sectional sofa facing a flat-screen TV. Adjacent, a vibrant children's bedroom features a whimsical Moana theme with a sandy beach mural, complemented by a canopy bed adorned with tropical accents. The ceiling displays playful elements, enhancing the kid-friendly atmosphere.
Condo in Kissimmee
4.97 out of 5 average rating, 215 reviews

303_To Infinity & the Ocean Breeze Apartment

Welcome to your ultimate family getaway near Disney! This spacious 3-bedroom apartment is perfectly located just minutes from the magic of Disney. Designed with families in mind, it features two beautifully themed kids’ bedrooms—a Toy Story adventure and a Moana-inspired tropical escape—guaranteed to delight the little ones. Enjoy full access to an amazing waterpark, included free of charge, making every day feel like a vacation. Whether you're unwinding after a day at the parks or splashing th

Top guest favorite
Condo in Orlando
4.99 out of 5 average rating, 134 reviews

Disney Area Updated Lake View Orlando Resort Condo

Updated Disney area condo Amazing private lakeview and location! Special Mickey touches Spacious one bedroom plus bunk bed nook & TWO full bathrooms King bed in main bedroom with ensuite Two bunk beds in hall nook Queen size sleeper sofa in living area 2nd bathroom has access from hall Upgraded Stainless Steel kitchen New Washer & Dryer New AC & Heat Balcony overlooking pools & lake New furnishings 885 sq ft No resort fees Free Parking Disney 1 mi Seaworld 5mi Convention Center 6mi Universal 8mi

Top guest favorite
An open dining area showcases a wooden table set for six with stylish plates and glasses. Adjacent to the dining space, a comfortable living area features a light blue sofa adorned with colorful pillows and a mounted flat-screen TV. Large sliding glass doors reveal a view of the outdoor space.
Condo in Kissimmee
4.9 out of 5 average rating, 170 reviews

3191-204 Resort Lake View Disney Universal Orlando

Minutes from Disney World Orlando Florida, Modern & Stylish 2bed/2bath fully equipped apartment for up to 6 guests, located in the family friendly Storey Lake Resort. FREE Clubhouse & WATERPARK amenities: Heated Pool, Hot Tub, Kids Splash Zone, Water Slides, Lazy River, Gym, Tiki Bar, Ice Cream Shop & more. The apt is located: 10 min drive to DISNEY, 25 min to UNIVERSAL STUDIOS, 18 min to SEA WORLD. FREE Parking. FREE Waterpark. No extra FEES. Gated Resort with Security 24/7 & Self check-in!

Top guest favorite
Villa in Davenport
4.98 out of 5 average rating, 132 reviews

9BR Magical Family Resort Vacation Home

9BR Stargazer Villas Guest Favorite! Your family will love this vacation home in Champions Gate Resort just outside Orlando! Occupancy up to 16 beautifully decorated masterpiece. A short drive to Disney Magic Kingdom and close to attractions, shopping and dining. This villa has a heated pool (no extra charge) to relax in after a day at the parks. Themed rooms featuring Frozen, Guardians of the Galaxy, and Lilo & Stitch bedrooms as well as two primary suites & full size Harry Potter game room!

Superhost
A vibrant children's bedroom features two beds with superhero-themed bedding. A wall mural showcases characters from a popular franchise, adding a playful touch. A ceiling fan is visible above, and natural light streams in through a window with an unobstructed view.
Villa in Kissimmee
4.88 out of 5 average rating, 113 reviews

Disney Themed home with Private Pool & Lazy River!

Discover magic at our Kissimmee villa, minutes from Disneyworld in Storey Lake! With luxury decor and fun-filled bedrooms, our home offers enough comfort and fun for the whole family. Take the fun and relaxation out to the private pool in the home. And when you want to take it to the next level, visit the resort clubhouses! Resort perks include lazy rivers, fast water slides, mini-golf, kayaking, jacuzzis, a restaurant and more! Your dream Central Florida getaway begins here!

Guest favorite
A modern living area features a comfortable sofa in neutral tones alongside two vibrant orange chairs. A round glass coffee table is positioned in front of the sofa, while a large television is mounted on a wooden accent wall. Floor-to-ceiling windows allow natural light to fill the space.
Home in Kissimmee
4.95 out of 5 average rating, 124 reviews

Modern 4bdr Storey Lake w/themed rooms near disney

Have fun with the whole family at this stylish place: themed bedrooms and a peaceful feeling. With Disney just 5 miles away and Universal Studios 15-20 minutes away, the resort offers endless fun. Storey Lake Resort also has many nearby shopping malls and dining options. From its resort-style pool, splash pad, and watersides to its clubhouse, poolside bars, fitness center, and lake-based activities, Storey Lake is the happy ending to your vacation rental search.

Guest favorite
Cottage in Auburndale
4.93 out of 5 average rating, 27 reviews

Lakefront Boho Cottage w/ Fire Pit | Still Waters

Welcome to Still Waters Retreat, a peaceful lakefront cottage just 10 minutes from Lake Myrtle Sports Complex and about 30–35 minutes from Disney (without traffic). Perfect for couples, families, and tournament stays, enjoy calming lake views, golden sunsets, cozy boho interiors, and s’mores by the firepit. Minutes from downtown Lakeland, dining, shopping, major highways, and easy day trips to Orlando or Tampa — serenity without sacrificing convenience.

Superhost
A private balcony offers seating with a view of the shimmering lake, highlighting the surrounding landscape. Adjacent images reveal family-friendly amenities, including a vibrant water park with slides, an elegant kitchen space, and a welcoming sleeping area featuring playful decor.
Condo in Kissimmee
4.89 out of 5 average rating, 199 reviews

NEW APARTMENT WITH WATER PARK AND NEAR DISNEY

Enjoy a carefree vacation at Storey Lake Resort. Located minutes from Disney, Falcon's Fire Golf Club, Universal, Epic Universal, SeaWorld, Orange County Convention, Premium Outlets. Less than 1 mile from Walmart, Target, and restaurants, your family will have everything they need. Water Park, gym, and all amenities FREE. Free parking, 24/7 security in this gated resort and with an automatic check-in with direct access code and elevator available

Guest favorite
A balcony is depicted with four cushioned chairs arranged around a small table. The railing provides a view of a serene landscape with water and greenery in the background. Light fabric drapes softly from the sliding door frame.
Condo in Kissimmee
4.91 out of 5 average rating, 154 reviews

Modern Condo with Lake View Near Disney 3151

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!

Top guest favorite
A spacious living area features a striking mural of a serene lake scene, complemented by a cozy seating arrangement. Tropical-themed decor and unique ceiling fixtures add to the ambiance. Natural light filters in, highlighting the stone floor and creating a welcoming environment.
Home in Winter Haven
4.99 out of 5 average rating, 148 reviews

Beautiful Lake House Boating Fishing near Legoland

Welcome to The Executive Lake House 15 minutes from Lego Land in beautiful Winterhaven, Florida. The brand new rental home sits on a lake and offers a dock, with boats, fishing gear and beautiful views of the lake. The home offers 2 bedrooms and a kids loft. A full kitchen and laundry and one full bathroom The backyard has a playground and pool area that is on the property in backyard and is shared with other guests who may be staying here.

Superhost
A scenic aerial view captures a resort layout featuring several interconnected pools, water slides, and lounge areas. Lush palm trees provide shade around the pools, traversing pathways lead to various recreational spots, and a serene lake reflects the clear blue sky in the background.
Townhouse in Kissimmee
4.85 out of 5 average rating, 200 reviews

Disney 4 miles *LazyRiver Club* Private Pool*4B/3B

Discover luxurious comfort at the beautiful Island Paradise home. For your vacation we provide the best family friendly tropical getaway. The entire Townhome is crafted with intentional love. We will enhance your vacation by feeling right at home paired with our amazing amenities that exude an all inclusive resort like experience: waterpark, beach volleyball, basketball, poolside service for our restaurant and bar, kayaking, and mini golf.

Guest favorite
A balcony area features dark blue cushioned seating and a wooden coffee table. A view of a calm lake is visible beyond the railing, under a sky filled with scattered clouds.
Vacation home in Kissimmee
4.91 out of 5 average rating, 236 reviews

Best Clubhouse Ever/Lazy River Near Disney

Welcome to your perfect Orlando getaway! This cozy 2-bedroom, 2-bath apartment is located in the beautiful Storey Lake Resort, just minutes from Disney, Universal, SeaWorld, shopping, and restaurants. Enjoy a fully equipped kitchen, Smart TVs, high-speed Wi-Fi, and relaxing lake views. Guests have access to pools, lazy river, water slides, fitness center, mini golf, and more. Perfect for families, couples, and vacationers!

Popular amenities for Winter Haven kayak rentals

When is the best time to visit Winter Haven?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$30,760 GYDG$35,782 GYDG$37,247 GYDG$29,923 GYDG$27,203 GYDG$28,249 GYDG$30,342 GYDG$28,458 GYDG$26,366 GYDG$28,668 GYDG$30,342 GYDG$32,853 GYD
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C17°C

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