
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.

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

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.

9BR Fantastic Family Fun Resort 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!

Magical Disney's Minion themed & Water View 3161
Indulge in our magical vacation homes, fully equipped for your comfort. With spacious bedrooms & full equiped kitchens, just minutes from Disney's theme parks. Book your stay for 7 days or more and unlock an exclusive 5% discount ! Craft unforgettable memories with loved ones at Disney World. For extended stays of a month or more, enjoy an even greater 10% discount as part of our long-stay offer. (Discount will apply on selected stays) Reserve now! we would love to be your host!

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.

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!

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!

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.

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.

Disney Castle Cove (Pool & Community Boat Ramp)
Discover the perfect vacation rental: a Disney-themed 4-bedroom, 2-bath home just 34 miles from Disney World Resort. Enjoy the luxury of two spacious living rooms and a well-stocked kitchen for all your culinary needs. Relax by the private pool after a day at the parks. Each bedroom is uniquely decorated with beloved Disney characters, creating a magical retreat for families. Make unforgettable memories in this enchanting home, ideal for your family getaway.

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

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.
Popular amenities for Winter Haven kayak rentals
House rentals with a kayak

7256-ST 5 Bed, Private Pool + SPA

No Airbnb Fees! Themed Home/Pool/SPA/Resort 243621

6-Bed/5-Bath Modern Escape | Pool, Resort, Disney

Storey Lake DREAM POOL HOME-Walk to FREE WaterPark

Waterfront 8Br5Ba Game Room/Pool/Spa/Office Space

Luxury Home, 5Bdrm, 5Bath, near Disney, Pool / Spa

Lakefront Home with Fishing Dock

N-Magical 8 Bdr w/Pool & Hot Tub-5 Miles to Disney
Other vacation rentals with a kayak

Authentic Disney Fort Wilderness Cabin near WDW-1

Luxe Resort Near Disney POOL BBQ

~15 mins to Disney - Resort Townhouse

Lux Storey Lake Villa/Water Park/Pool/SPA/Themed

Modern Vacation Home Near Disney SL4962

4731_205 Minutes from Disney, Incredible Condo 2BR

Lakefront Resort | 5 Min to Disney |Sleeps 8+Views

Beautiful 2BR Condo with Great Views on Resort
When is the best time to visit Winter Haven?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $205 CAD | $239 CAD | $248 CAD | $200 CAD | $181 CAD | $188 CAD | $202 CAD | $190 CAD | $176 CAD | $191 CAD | $202 CAD | $219 CAD |
| Avg. temp | 16 °C | 18 °C | 20 °C | 22 °C | 25 °C | 27 °C | 28 °C | 28 °C | 27 °C | 24 °C | 20 °C | 17 °C |
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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- Universal Studios Florida
- Walt Disney World Resort
- Universal Orlando Resort
- Orange County Convention Center
- Disney Springs
- SeaWorld Orlando
- Raymond James Stadium
- Universal's Volcano Bay
- Busch Gardens Tampa Bay
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- Discovery Cove
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Camping World Stadium
- Reunion Resort Golf Courses - Palmer & Watson
- Amalie Arena
- Tampa Convention Center
- Aquatica
- ICON Park
- Disney's Hollywood Studios
- Island H2O Live!





