Vacation rentals with a kayak in Winter Haven

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Top-rated kayak rentals in Winter Haven

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Guest favorite

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.

Apartment in Kissimmee

4.93 out of 5 average rating, 134 reviews

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!

Top guest favorite

A balcony view showcases a round table and two chairs facing the expansive lake. The serene water reflects the clear blue sky, while the railing provides safety and openness to the picturesque landscape.

Condo in Orlando

4.98 out of 5 average rating, 103 reviews

Disney Area Updated Lakefront Resort Condo 2 POOLS

Updated Disney area 18th floor condo Amazing lakeview and location! Special Disney touches Spacious one bedroom plus bunk bed nook & TWO full bathrooms King bed in main bedroom with ensuite Two bunk beds in corridor Queen size sleeper sofa in living area 2nd bathroom has access from hall Fully upgraded Stainless kitchen New Washer and Dryer New AC & heat Balcony overlooking pools & lake Many new furnishings Disney 1 mile Seaworld 5mi Convention Center 6mi Universal Studios 8mi MCO Airport 16mi

Guest favorite

A serene canal view is presented, featuring calm waters bordered by lush green grass. Neatly maintained properties line the opposite shore, and a small dock is visible in the distance, with trees and a cloudy sky adding to the tranquil setting.

Home in Auburndale

5 out of 5 average rating, 27 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.

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

4.99 out of 5 average rating, 149 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 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

4.97 out of 5 average rating, 75 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 favorite

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, 59 reviews

Lake*Walk2LEGOLAND*Pool*Putting Green*Dock*Sunsets

"Most beautiful home we’ve ever stayed at. Thank you for your sweet hospitality!" - Jessica "House felt like a spa!" - Kandy Sunset Haven is a luxurious contemporary lake house on beautiful Lake Summit in Winter Haven Florida. From the moment you enter, you are greeted with a view of the lake beyond the pool deck, where many beautiful sunsets can be seen almost nightly. This wonderful home boast an array of amenities for an extraordinary stay.

Guest favorite

Villa in Kissimmee

4.97 out of 5 average rating, 112 reviews

6BR Immaculate Orlando Home Minutes to Disney

Immaculate and well equipped Stargazer Villas vacation home at Storey Lake Resort! A short drive to Disney & within easy reach of attractions, shopping and dining. This Orlando area vacation home is a guest favorite and has a heated pool (no extra charge) for your family to relax in after a busy day at the parks. Featuring themed Toy Story & Mickey bedrooms, as well as three primary suites, along with Star Wars movie loft & Avatar game room!

Guest favorite

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.

Home in Winter Haven

4.88 out of 5 average rating, 59 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.

Top guest favorite

A sprawling resort pool area is displayed, featuring winding water slides, a lazy river, and lush landscaping with palm trees. Sun loungers line the pool, while shaded cabanas provide relaxation spots. Nearby, green spaces are visible, enhancing the recreational setting.

Townhouse in Kissimmee

4.93 out of 5 average rating, 129 reviews

5 miles from Disney - Full Waterpark, ALL nearby

Amazing decorated in One of newest resort communities in Orlando with stunning decorations and countless amenities, 12mins to Disney. 3 stories water slides, lazy river, tiki cocktail bar, and many more. you are only 4 miles away from Disney World. Fully equipped for BABY Pack n Play, TWO STROLLERS, HIGH CHAIR. Everything you can't bring any bulky, we got you covered. Make reservations now while it lasts.

Guest favorite

Townhouse in Kissimmee

4.85 out of 5 average rating, 468 reviews

A-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

Top guest favorite

The exterior of the main house is depicted, showcasing a blue facade with multiple windows. An expansive cement driveway leads up to the entrance, bordered by well-kept landscaping. Mature oak trees provide shade in the foreground, with the lake visible in the background.

Home in Auburndale

4.94 out of 5 average rating, 160 reviews

Lake Whistler Beach House with lakefront pool

The Lake house is a resort with Paddle boards/Kayaks at no cost to our guests. Enjoy the entire yard and non-public lake with a private beach which offers you fishing. The main house has a pool table,air hockey and live darts! Also there is a BBQ, 4 TV's, cable, internet, movie library and washer/dryer, Pool and pool Jacuzzi. Small fenced back yard for pets (pet fee required).

Guest favorite

An aerial view captures a spacious pool area surrounded by palm trees and lounge chairs. Water slides and splash pads are visible, alongside a large clubhouse. A serene lake reflects the nearby buildings, offering a tranquil environment for relaxation and recreation.

Vacation home in Kissimmee

4.94 out of 5 average rating, 185 reviews

Best Clubhouse Ever/Lazy River Near Disney!

Enjoy this comfortable, lovely, peaceful, pet friendly and centrally-located place just minutes away from Disney World, Sea World. and all other fun attractions of Orlando, Florida. The house is next to a beautiful quiet lake that you can enjoy every evening after a busy day playing. Enjoy the different pools and the amazing club house with your family; gym included.