Vacation rentals with a kayak in Winter Haven

Find and book unique kayak rentals on Airbnb

Top-rated accommodations with a kayak in Winter Haven

Guests agree: these accommodations with a kayak are highly rated for location, cleanliness, and more.

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Top guest favourite
Condo in Orlando
4.98 out of 5 average rating, 131 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 favourite
A serene lakeside seating area is highlighted by sandy ground and palm trees. Sturdy wooden posts are anchored with rope, creating a relaxed atmosphere. In the background, a tranquil lake reflects the sky, enhancing the peaceful outdoor setting.
Townhouse in Kissimmee
4.98 out of 5 average rating, 135 reviews

Luxury 5BR free heat private pool Disney Universal

Welcome to this gem near all major attractions: Disney (5 miles), SeaWorld (7 miles), Universal (12 miles), Convention Center (9 miles), and Airport (20 miles). Nearby are outlets, restaurants, and supermarkets. This luxurious home features 5 bedrooms, 4 bathrooms, a private heated pool/spa, fully equipped kitchen, laundry, and free stroller, playpen, and highchair. Resort amenities include a water complex, lazy river, bar, fitness center, mini golf, kayaking, and more! Pets friendly & welcome!

Guest favourite
A winding lazy river glides through a tropical landscape, surrounded by palm trees and colorful plants. A wooden bridge crosses above, leading to a play area. The clear blue water sparkles under a bright sky with scattered clouds.
Vacation home in Kissimmee
4.89 out of 5 average rating, 141 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.

Top guest favourite
An aerial view showcases a spacious yard bordering a peaceful canal, leading to a large lake. The well-maintained property features lush greenery and a swimming pool, inviting relaxation. The surrounding homes reflect a tranquil community atmosphere, enhancing the serene waterfront setting.
Home in Auburndale
5 out of 5 average rating, 39 reviews

Little Castle on the canal on lake Arietta

Serenity and Beauty in the wonderful canal front house sitting on nearly 1 acre lot hidden in a secluded cul-de-sac. Enjoy the pool, volleyball on the yard, kayaking, paddle board on the canal that leads to a big lake. Well landscaped yard. Enter the front door, you'll greeted by high vaulted ceiling great room. Total 2300 sqft with 3 bedrooms and 2 full bath. 2 indoor/1 outdoor dining areas. Open floor one story layout, with wood and tile floor throughout, no carpet. Immaculately clean.

Top guest favourite
Villa in Davenport
4.98 out of 5 average rating, 129 reviews

9BR Family Fun Resort Home with Free Pool Heat!

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!

Top guest favourite
The outdoor pool area features a heated saltwater swimming pool with colorful floats, including a swan and a duck. The patio is paved with light-colored tiles and is surrounded by comfortable seating and decorative lighting, reflecting a welcoming space for relaxation and fun.
Home in Cypress Gardens
5 out of 5 average rating, 85 reviews

Waterfront Heated Pool Putting Green Dock Legoland

Sunset Haven is a luxurious, contemporary 3,581-square-foot lakefront home set on nearly one acre along the shores of beautiful Lake Summit, part of Winter Haven’s famous Chain of Lakes. From the moment you step inside, your eye is drawn through the home to sweeping lake views beyond the pool deck, where breathtaking sunsets can be enjoyed almost every evening. Thoughtfully designed, this exceptional residence offers an impressive array of amenities for a truly unforgettable stay.

Top guest favourite
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
4.87 out of 5 average rating, 183 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 favourite
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
4.91 out of 5 average rating, 111 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!

Top guest favourite
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 ten 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 one bedroom a full kitchen and laundry and one full bathroom The backyard has a playground and pool area that is ( not) included at this price point. If wanting an additional charge of 20 dollars per night Will be charged. Let me know at booking.

Guest favourite
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, 120 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 favourite
A collection of four images showcases various bedrooms and living areas. A dining space is presented with modern furnishings. A colorful bedroom features mural accents and two full beds with vibrant decor. Another bedroom displays a spacious bed with soft linens, accentuated by warm lighting.
Condo in Kissimmee
4.95 out of 5 average rating, 206 reviews

201-Mickey Safari & Circus Dream Stay

Your Perfect Getaway Starts Here! Just completely remodeled! Welcome to our cozy apartment, thoughtfully prepared to make you feel right at home. Whether you're here for the thrills of Orlando’s parks or shopping, we've got everything you need for a relaxing stay. Plus, enjoy unlimited access to the amazing waterpark—it's the perfect way to unwind after a fun-filled day! About this space • Community: Storey Lake Resort • 3 Bedroom/2 Bathroom/Sleeps 10

Top guest favourite
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, 153 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!

Popular amenities for Winter Haven kayak rentals

When is the best time to visit Winter Haven?

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Avg. price$205 CAD$238 CAD$248 CAD$199 CAD$181 CAD$188 CAD$202 CAD$190 CAD$176 CAD$191 CAD$202 CAD$219 CAD
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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 $56 CAD 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 and kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Winter Haven vacation rentals include wifi 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!

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