Vacation rentals with a kayak in Osceola County

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Top-rated kayak rentals in Osceola County

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Guest favorite

Tiny home in Avon Park

5 out of 5 average rating, 29 reviews

Back to Nature!

Reconnect with nature at this unforgettable escape. There are acres of beautiful Hammock land to explore and enjoy nature. We also raise USDA grass finished beef for purchase to enjoy while you stay or take home! You can also purchase our beef at the Highlands FARMERSmarket held on our property most Sundays from 11-3pm. Our tiny house is the perfect getaway to recharge your batteries! NO HUNTING ALLOWED! Please note that sometimes cell service, depending on the carrier, can be limited!

Guest favorite

Townhouse in Kissimmee

4.92 out of 5 average rating, 138 reviews

Fall Superhost Special, Dogs OK

Escape to a whimsical wonderland at Bullseye's Disney Ranch! Located just minutes away from amazing theme parks & adventures, this home away from home was designed with families in mind. Mickey and Toy Story-themed bedrooms will delight kids of all ages while parents can relax by the private heated pool or take advantage of resort amenities. Is this home already booked? Check out our Vacation Alchemy Profile and choose from over a dozen magical properties suited for every group size!

Superhost

Guesthouse in Lake Wales

4.83 out of 5 average rating, 23 reviews

Cozy Cottage on Peaceful Lake

Property is on a beautiful pristine lake, with lake access and free amenities, to provide a wonderful experience on the lake. However, you can not view lake from the cottage window. It is a 1 minute walk from cottage to the lake edge. Chairs, fire pit and grill may be provided at lake edge or at unit. If you prefer a unit with a lake view from window, we do have another unit to rent that does have a lake view from window. Please message me if you need help locating this listing.

Superhost

Condo in Kissimmee

4.83 out of 5 average rating, 126 reviews

Modern Storey Lake Resort Disney Orlando 3171-107

Relax in our Stylish & Modern 2Bed/2bath fully equipped apartment for up to 7 guests, located in the family friendly Storey Lake Resort. Minutes from DISNEY World Theme Parks in Orlando Florida. Close to UNIVERSAL STUDIOS & SEAWORLD. Enjoy our lake view from the balcony. Close to restaurants, supermarkets, outlet malls & retail stores. Great amenities: Heated Pools, Kids Splash Zone, Water Slides, Lazy River, Gym, Mini Golf, Kayak, Tiki Bar & Ice Cream Shop, security guard!

Guest favorite

Home in Babson Park

4.97 out of 5 average rating, 110 reviews

Authentic "Old Florida" on Crooked Lake!

Authentic "Old Florida" on Crooked Lake! Surrounded by palmettos and Florida foliage, our 1930's rustic lakehouse is serene, private, and exceptionally relaxing. Spring-fed Crooked Lake is designated an "Outstanding Florida Waters" lake and is great for swimming, paddle boarding, kayaking, fishing, and waterskiing. Huge screen porch, ping pong table, fully-equipped kitchen, dining room table for 12, spacious living area (great for games) -- you won't want to leave!

Superhost

Townhouse in Kissimmee

4.87 out of 5 average rating, 105 reviews

NEWLY LISTED Townhouse Storey Lake, Free Waterpark

Brand New 4 Bedrooms, 3 Bathrooms Vacation Rental with private pool. Located in Storey Lake Resort. The bedrooms consist of one master bedroom downstairs, another master suite upstairs, One bedroom with Queen bed, one room with two twin beds. Closest community from Disney, Disney Springs, Malls, Walmart. Clubhouse Resort with great amenities, Two Pools including a lazy river, restaurant, gym and more. fun with the whole family at this stylish place.

Superhost

Townhouse in Kissimmee

4.84 out of 5 average rating, 137 reviews

Disney 4 miles *LazyRiver Club* Private Pool*4B/3B

Discover luxurious comfort at the beautiful Island Paradise home. For your vacation we provide the best family friendly tropical getaway. The entire Townhome is crafted with intentional love. We will enhance your vacation by feeling right at home paired with our amazing amenities that exude an all inclusive resort like experience: waterpark, beach volleyball, basketball, poolside service for our restaurant and bar, kayaking, and mini golf.

Guest favorite

Condo in Kissimmee

4.83 out of 5 average rating, 193 reviews

Farm style Safari in Disney & FREE Waterpark 3120

Indulge in our magical vacation homes, fully equipped for your comfort. With spacious bedrooms & full equiped kitchens, just minutes from Disney's theme parks. Book your stay for 7 days or more and unlock an exclusive 5% discount! Craft unforgettable memories with loved ones at Disney World. For extended stays of a month or more, enjoy an even greater 10% discount as part of our long-stay offer. Reserve now! we would love to be your host!

Guest favorite

Condo in Kissimmee

4.92 out of 5 average rating, 133 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

Guest favorite

Guest suite in St. Cloud

4.93 out of 5 average rating, 325 reviews

LAKE FRONT Suite with FREE USE of Kayaks & Canoes

Private Master Suite with it's own exclusive entry. It has a convenient kitchenette complete with mini refrigerator, microwave, toaster, toaster oven and an outside grill. Comfy Queen size bed with overhead ceiling fan. Private Bathroom and shower. Lake view from the front of property, unit is in the back overlooking wetlands. Plenty of parking, with enough room to bring a boat.

Guest favorite

Vacation home in Kissimmee

4.91 out of 5 average rating, 140 reviews

Lazy River Oasis Near Disney - Best Clubhouse!

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.

Guest favorite

Condo in Kissimmee

4.89 out of 5 average rating, 121 reviews

SL106 - Mickey's Hideaway - Resort Access included

Welcome to Your Dream Vacation at Storey Lake Resort! Step into this stylish and spacious 2-bedroom, 2-bathroom condo, designed to comfortably accommodate up to seven guests. Nestled in the heart of Storey Lake Resort in Kissimmee, FL, this vacation rental offers the perfect blend of luxury, comfort, and convenience for an unforgettable getaway.