Vacation rentals with a kayak in Winter Haven

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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 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.
Apartment in Winter Haven
4.98 out of 5 average rating, 162 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!

Guest favorite
An open living area features a modern design with a spacious layout. A comfortable sofa with accent pillows and a coffee table is set in front of a large window. The adjacent kitchen is equipped with sleek cabinetry and modern appliances, complemented by a dining space visible in the background.
Apartment in Kissimmee
4.93 out of 5 average rating, 105 reviews

3180-207 Resort Pool View Disney Universal Orlando

Brand New Bohemian & Chic 2bedroom /2bath fully equipped apartment . Pool View for up to 6 guests. Located in the family friendly Storey Lake Resort minutes from Disney. The open floor plan blends kitchen, dining, living room with 70"TV & Relax Room. Master suite has a King bed & 65"TV. Second bedroom has a Queen & Twin bed w/ Smart TV. Close to outlet malls & retail stores. FREE Water Park & Amenities: POOLS, KIDS SPLASH ZONE, WATER SLIDES, LAZY RIVER, GYM, TIKI-BAR, ICE CREAM SHOP & More.

Guest favorite
An aerial view captures the serene waterfront landscape, showcasing a canal bordered by lush trees. The expansive body of water reflects the sky, with residential homes dotting the shoreline. The image highlights the peacefulness of the surroundings, inviting outdoor activities and relaxation.
Home in Lake Wales
4.97 out of 5 average rating, 106 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.

Top guest favorite
Villa in Championsgate Village
4.98 out of 5 average rating, 117 reviews

9BR Highly Themed Villa 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!

Guest favorite
Home in Kissimmee
4.94 out of 5 average rating, 104 reviews

Themed Resort Villa with Pool + Spa

Come to Kings Castle, & live like royalty! Enjoy the lux amenities of your family-friendly home: themed rooms, a private swimming pool, & hot tub. Venture out around the resort with heated swimming pools, lazy riverside flow rides, & more. After all that fun in paradise - you're only minutes away from whatever attractions take your group’s fancy while there! Is this home booked? Check out our Vacation Alchemy Profile & choose from over a dozen magical properties suited for every group size!

Top guest favorite
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!

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
4.97 out of 5 average rating, 103 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
A welcoming living area features a large screen TV mounted on the wall above a stylish cabinet. Comfortable seating options include a brown leather couch and a fabric armchair. Natural light filters through the sheer curtains, while a green plant adds a touch of nature to the space.
Home in Kissimmee
4.88 out of 5 average rating, 108 reviews

Wonderfull home near Disney & FREE Waterpark 2421

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 large resort-style pool, shaped like a Mickey Mouse head, is surrounded by palm trees and lounge chairs. Guests are seen relaxing on sun loungers and enjoying the water, with umbrellas providing shade in certain areas. Additional smaller pools are visible nearby.
Apartment in Kissimmee
4.91 out of 5 average rating, 136 reviews

Amazing Apartment in Orlando - Kissimmee

Located in Orlando-Kissimmee, just minutes from Disney, theme parks, shopping, and dining. Enjoy free access to a stunning resort with everything you need for an unforgettable vacation: pools, gym, jacuzzi, lazy river, kayaking, mini-golf, restaurant, water slides, and basketball and volleyball courts, plus more amenities. Experience the comfort of home with all the fun of a resort in one place. Perfect for families and groups!

Guest favorite
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.

Top guest favorite
Condo in Kissimmee
4.91 out of 5 average rating, 180 reviews

P-Gated Resort-5 miles to Disney-2 FREE Water Park

Is this home booked? We have more! Click on the circular profile image, then scroll down till you see James's Listings. Gated/24 hour security. Resort living with 2 main clubhouses and a few other extra quieter pools, playground and a soccer field. 10 min to Disney 15 min to Universal 10 min to the Convention Center Within a 5 min drive: Publix Grocery Walmart Target 10-15 restaurants

Guest favorite
Townhouse in Kissimmee
4.93 out of 5 average rating, 120 reviews

Private Pool•StoreyLakes Resort•Near Disney•Themed

Enjoy your own private heated pool overlooking a peaceful lake, just 5 minutes from Disney! Located in the award-winning Storey Lakes Resort, this family-friendly home features themed kids rooms, a first-floor king suite, fast WiFi, a fully equipped kitchen, and full access to the resort waterpark with lazy river, splash pad, water slides, tiki bar, and gym. Pets welcome!

Popular amenities for Winter Haven kayak rentals

When is the best time to visit Winter Haven?

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Avg. priceﺩ.ﺇ496ﺩ.ﺇ540ﺩ.ﺇ544ﺩ.ﺇ525ﺩ.ﺇ477ﺩ.ﺇ496ﺩ.ﺇ533ﺩ.ﺇ499ﺩ.ﺇ463ﺩ.ﺇ503ﺩ.ﺇ533ﺩ.ﺇ577
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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 ﺩ.ﺇ147 per night before taxes and fees

  • Verified guest reviews

    Over 1,560 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!

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