Holiday rentals with a kayak in Winter Haven

4.94 out of 5 average rating, 156 reviews

A bright and airy dining area features a modern white table set for six. A stylish living space is shown with a beige sofa, two yellow chairs, and a large wall-mounted TV. Natural light streams in through sliding glass doors that lead to a balcony.

Flat in Kissimmee

3141-105 Resort Lake View Disney Universal Orlando

Minutes from Disney World Orlando Florida, Modern & Stylish 2bed/2bath fully equipped apartment for up to 7 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!

5 out of 5 average rating, 55 reviews

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

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.

4.98 out of 5 average rating, 163 reviews

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

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!

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!

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.

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!

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.

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.

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.

4.97 out of 5 average rating, 104 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.

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.

4.88 out of 5 average rating, 109 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!

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.

4.9 out of 5 average rating, 184 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

Two kayaks rest on a grassy area beside a brick pathway leading to the water. The serene lake sparkles under a blue sky dotted with fluffy clouds, while a palm tree stands in the foreground, adding a tropical touch to the scene.

4.88 out of 5 average rating, 76 reviews

Carefree Cove on Lake Connie - with Hot Tub!

Nestled on the shores of Winter Haven's Lake Connie, this charming 3-bedroom promises a tranquil escape. This cozy lake house has excellent views. Outside, a private hot tub awaits on the deck. A fire pit as well as a screened in patio perfect for lots of outdoor relaxation. A fully equipped kitchen complete with coffee bar. With comfortable bedrooms, and modern amenities, this lakeside retreat ensures a delightful stay.

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.

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.

An aerial view captures the expansive resort-style pool area, featuring tropical landscaping and winding water features. Sun loungers and cabanas line the poolside, while a lazy river and splash park invite guests to relax and enjoy. The serene water is bordered by a scenic lake.

4.94 out of 5 average rating, 168 reviews

O-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

Popular amenities for kayak rentals in Winter Haven

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

A themed game room is showcased with vibrant blue and red lighting, featuring life-sized character displays and two gaming consoles. Another area displays a modern living room adorned with a tropical mural, plush blue chairs, and a stylish area rug, creating a comfortable gathering space.

4.89 out of 5 average rating, 106 reviews

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

An elegant bedroom features a four-poster bed adorned with neutral blankets and decorative pillows. A dark wood dresser holds a flat-screen TV. Soft lighting highlights the plush carpeting, while a potted plant adds a touch of greenery. Doorways lead to adjoining spaces.

4.87 out of 5 average rating, 54 reviews

Serene Pool Home Just 13 Min to Disney

A screened patio features a well-lit spa and a inviting south-facing pool, surrounded by a spacious paver area. A lounge chair with colorful cushions is positioned nearby, alongside a seating arrangement with chairs and a small table, offering views of the tranquil waterfront.

4.97 out of 5 average rating, 107 reviews

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

A modern living area features a sectional sofa in dark leather, elegantly arranged around a round coffee table. A wall-mounted television is positioned above a sleek metallic console. Large glass doors allow natural light to fill the space, offering views of the outdoor area.

4.97 out of 5 average rating, 119 reviews

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

4.71 out of 5 average rating, 58 reviews

Home away from Home! 6BR, 5.5 BA

4.9 out of 5 average rating, 114 reviews

No Airbnb Fees!Themed Home w/Pool in Resort 231031

4.88 out of 5 average rating, 51 reviews

2932-SL 5 Bd Home, Game Room, Private Pool & SPA

4.8 out of 5 average rating, 30 reviews

A covered patio area overlooks Lake Bonnet, featuring a round table draped with a beige cloth and adorned with a potted plant. Two woven chairs with plush cushions are available for seating, alongside greenery and a peaceful water view.

Home in Lakeland

Lakefront - Private Fishing Dock - Ample Parking

Other holiday rentals with a kayak

4.83 out of 5 average rating, 12 reviews

Apartment in Orlando

Beautiful Lakefront Condo 1 Mile away from Disney

4.95 out of 5 average rating, 43 reviews

A large swimming pool is surrounded by palm trees, providing a tropical ambiance. Sun loungers are arranged around the deck, inviting relaxation. Clear blue skies reflect in the water, and a building with seating is visible in the background.

Townhouse in Kissimmee

Reunion Resort Townhome - minutes from Disney

An inviting bedroom features a Mickey-themed design with two spacious beds, ideal for children. The cozy living area showcases a comfortable sectional sofa, a flat-screen TV, and modern lighting. A stylish dining space with a table and six chairs is also visible, enhancing communal dining.

5 out of 5 average rating, 23 reviews

4731-103 Stay Magical • 2BR with Mickey Room & Mor

A contemporary living area features a dark sectional sofa adorned with orange and blue cushions. A circular coffee table sits at the center, while a flat-screen TV is mounted on a white entertainment unit. Natural light floods in from sliding glass doors leading to the patio.

4.95 out of 5 average rating, 41 reviews

Fabulous Storey Lake condo-walk to FREE WaterPark!

5 out of 5 average rating, 4 reviews

Modern Vacation Home Near Disney SL4962

An outdoor patio is visible, featuring a metal dining set with a rectangular table and four chairs. A small potted plant is centered on the table. The background includes a serene waterfront view with blue skies and greenery.

4.73 out of 5 average rating, 104 reviews

New -Bright & Charming Waterfront Condo

4.84 out of 5 average rating, 38 reviews

Villa in Kissimmee

6BR+Spa&Pool+Walk to Clubhouse+Theater+ThemedRooms

A living room features a large sectional sofa and a round coffee table, with a flat-screen TV mounted on the wall. A light-colored accent chair adds comfort. Natural light fills the space through sliding glass doors, leading to a balcony overlooking the lake.