Holiday rentals with a kayak in Winter Haven

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Top-rated rentals with kayak in Winter Haven

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

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Top guest favourite
A modern living area features a plush blue sectional sofa complemented by two stylish lounge chairs. A light area rug sits under a chic coffee table, while large sliding glass doors provide a view of the outdoors and allow natural light to enhance the space.
Apartment in Kissimmee
4.93 out of 5 average rating, 204 reviews

3171-206 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!

Guest favourite
Aerial view captures the resort's lazy river and multiple pools surrounded by tropical landscaping. An inviting bedroom features a comfortable bed with light teal bedding and decorative pillows. The dining area showcases a modern table set for six, with a large window letting in natural light. The private patio includes a heated pool surrounded by lounge furniture.
Townhouse in Kissimmee
4.96 out of 5 average rating, 165 reviews

❤Gorgeous New Home❤FREE Water Park☆15min to Disney

Welcome to this gorgeous new 5 bedroom 4 bathroom townhouse in the luxurious Storey Lake Resort Community! This beautiful vacation home with a private heated pool is located just around the corner from Disney, Universal and Sea World (~15 minute drive): ★ Walking Distance to Resort Clubhouse, 0.3 mile ★ - Animal Kingdom: 8 miles - Magic Kingdom: 9.6 mile - Hollywood Studios: 7.1 mile - Epcot: 7.7 mile - Sea World: 8.1 mile - Universal Studios: 12 mile - Orlando International Airport - 30 Mins

Guest favourite
A cheerful lake house is presented under a clear blue sky, featuring a yellow exterior with a metal roof. Lush palm trees are positioned by the entrance, complemented by manicured landscaping. The spacious driveway allows for parking, with a glimpse of the lake visible in the background.
Home in Auburndale
5 out of 5 average rating, 55 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.

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, 38 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. Two indoor dining areas. Open floor one story layout, with wood and tile floor throughout, there is no carpet. Immaculately clean.

Superhost
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.
Holiday home in Kissimmee
4.88 out of 5 average rating, 130 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
A balcony view overlooks a serene lake, framed by lush palm trees and vibrant green foliage. Bright blue skies and scattered clouds add to the tranquil setting, while glimpses of the driveway and nearby structures can be seen in the distance.
Flat in Winter Haven
4.98 out of 5 average rating, 163 reviews

Florida Penthouse in luxurious mansion!

Stay in your own themed Florida apartment . Tropical, palm trees, beaches ,marine life, flamingos throughout this stunning apartment in a multimillion dollar home. After parking on gated driveway walk up to your own private entrance way to paradise. Keyless entrance. One flight up and your viewing gorgeous lake views second to none. Executive kitchen with everything you need to cook a 5 course meal. Outdoor balcony that will leave you amazed. Opulence, security, with Florida Style awaits you!

Top guest favourite
An aerial view captures the expansive backyard featuring a large, fenced saltwater pool surrounded by a sunbathing area. The well-maintained lawn leads to the upgraded lakefront home, showcasing its brick exterior and covered patio, with trees and neighboring properties visible in the background.
Home in Winter Haven
4.98 out of 5 average rating, 97 reviews

Family Friendly Lake House W/ Pool Near Legoland

At this spacious, upgraded lakefront home, with a sandy beach and private dock, spend your days fishing, floating, and boating through the lake. Back at the house, the brand-new saltwater pool has a sun shelf, color-changing lights, and jets the kids will love! Relax on the expansive covered patio while you grill and grab drinks from the mini-fridge, or take a break to enjoy the 900 sqft game room with a pool table, foosball, basketball, darts, and arcade games. 10 min from Legoland!

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 Winter Haven
5 out of 5 average rating, 75 reviews

Waterfront*Heated Pool*Putting Green*Dock*Legoland

Sunset Haven is a luxurious, contemporary 3,581-square-foot lakefront retreat 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
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.
Apartment in Kissimmee
4.95 out of 5 average rating, 199 reviews

201-Luxury Apartment close to Disney - Free Waterp

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.
Apartment in Kissimmee
4.91 out of 5 average rating, 138 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 favourite
A modern kitchen features a spacious island with stylish wooden stools arranged around it. The cabinetry showcases a sleek gray finish, and a crystal chandelier hangs above. A large window allows natural light to illuminate the marble countertops, creating an inviting culinary space.
Home in Auburndale
4.98 out of 5 average rating, 62 reviews

Lake Arietta - Vacation and Events

Escape to our stunning vacation home on Lake Arietta! This serene oasis sleeps 8 comfortably, with room for an extra guest on an air mattress. Enjoy a fully equipped kitchen, a coffee bar, and aquatic adventures with a kayak and canoe. Three full bathrooms, including one with a charming claw foot tub, provide ultimate comfort. Dive into our pool, fish off the dock, and soak in the natural beauty of Lake Arietta - your perfect getaway awaits!

Guest favourite
A serene lakeside view is captured at sunset, with the sun reflecting on the water. Silhouettes of buildings are visible across the lake. A lush green tree and grass line the foreground, framing the scene. Utility poles and wires are present in the background.
Home in Winter Haven
4.89 out of 5 average rating, 53 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 kayaks and a paddle board she is happy to share. There are 2 small friendly dogs living on the property as well.

Popular amenities for kayak rentals in Winter Haven

When is the best time to visit Winter Haven?

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Avg. price£99£108£108£105£95£99£106£100£92£100£106£115
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Quick stats about holiday rentals with a kayak in Winter Haven

  • Total holiday rentals

    Explore 20 holiday rentals in Winter Haven

  • Nightly prices starting at

    Winter Haven holiday rentals start at £29 per night before taxes and fees

  • Verified guest reviews

    Over 1,560 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Winter Haven holiday 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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