Holiday rentals with a kayak in Winter Haven

4.83 out of 5 average rating, 120 reviews

No Airbnb Fees! Pool/ SPA/Game Room /Resort 242661

Unable to book this house? Don't worry! Check my profile for similar homes that might suit your needs WE HAVE A 24/7 CUSTOMER SERVICE! Escape the routine of visiting the parks every day and step inside of this 3,014 sqft house with 5 bedrooms, private pool, SPA and a game room with arcades specially designed to entertain your family. You can also have some fun at the Clubhouse, which offers a bar/restaurant, a big pool with water slides, a lazy river, a spa, a gym, a playground, and mini golf.

4.97 out of 5 average rating, 135 reviews

Flat in Kissimmee

3121-402 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, 44 reviews

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.

5 out of 5 average rating, 25 reviews

Home in Auburndale

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.

4.99 out of 5 average rating, 147 reviews

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!

4.97 out of 5 average rating, 65 reviews

Home in Winter Haven

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!

4.97 out of 5 average rating, 106 reviews

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

Our place is within the Storey Lake Resort, only minutes away from Disney. The house is STEPS away from the main clubhouse, the Hideaway Club. The second clubhouse, the Bronson Club, is just nearby. Enjoy the lazy river, heated clubhouse pools & spa, slides, splash park, basketball, volleyball, kayak, ping pong table, billiards, darts, poker table, fitness center and many more. The clubhouse is OPEN YEAR-ROUND. Private Pool/Spa. In-house washer and dryer. Free parking.

5 out of 5 average rating, 53 reviews

Home in Winter Haven

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.

4.91 out of 5 average rating, 108 reviews

Flat in Kissimmee

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!

4.89 out of 5 average rating, 56 reviews

Home in Winter Haven

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.

4.93 out of 5 average rating, 123 reviews

Townhouse in Kissimmee

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.

4.93 out of 5 average rating, 129 reviews

Q-Enchanted 8-Bd Sleeps 21 w/Pool 5Miles to Disney

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

Holiday rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Villas

Luxurious estates for the ultimate escape

Flats

Convenient locations with everyday essentials

Popular amenities for kayak rentals in Winter Haven

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

5 out of 5 average rating, 33 reviews

Home in Clermont

Lakefront home - country setting

ChelseyRating, 5 stars1 month ago

We had an amazing stay at this lake house—quiet, scenic, and right on the water. Waking up to the sun over the lake and enjoying coffee on the porch was absolute bliss. The cottage was clean, cozy, and had everything we needed for a relaxing escape. The host was responsive and made check-in a breeze. Whether you’re looking to fish, kayak, or just unwind by the water, this is the place. Highly recommend and would definitely stay again!

4.96 out of 5 average rating, 46 reviews

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

PamelaRating, 5 stars3 weeks ago

Staying at this spacious property was an absolute luxury. From the moment we arrived, we were welcomed with a thoughtful touch—a bottle of wine waiting for us, setting the tone for a relaxing and enjoyable stay. The home was spotless, beautifully maintained, and equipped with everything we needed for a comfortable visit. Each room was bright, inviting, and offered plenty of space to unwind. Access to the amenities was smooth and convenient, making it easy to enjoy everything the property had to offer. It truly felt like a well-curated retreat, and we wouldn’t hesitate to stay here again or recommend it to others looking for a peaceful, upscale escape.

4.97 out of 5 average rating, 97 reviews

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

NickRating, 5 stars2 weeks ago

Perfect location, only 20-30 minutes to all the major theme parks. Most enjoyable was the house, and the kids really enjoyed the waterpark, splash pad, lazy river and pool available at no cost. There is food and a tiki bar with all tropical drinks available. At night, we had our own private pool and hot tub, extremely relaxing, highly recommend!

4.94 out of 5 average rating, 18 reviews

*NEW* King Bed | Glow In The Dark Kid Cave

JordanRating, 5 stars2 weeks ago

Dillan’s place was perfect for the family. It was spacious and we loved the babe room for the kids. Dillan we’d very responsive and had clear instructions. Just make sure to read them carefully, they explain everything.