Vacation rentals with a kayak in Kissimmee

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Top-rated kayak rentals in Kissimmee

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Guest favorite

Guest suite in Orlando

4.98 out of 5 average rating, 254 reviews

Private En Suite W/ Office- Central Location!

Cute ensuite bungalow w/ office located in the heart of Orlando- perfect base for exploring the city. 2 rooms, bathroom, kitchenette. Snacks/coffee/tea and little touches make the place feel like home. Quiet and clean next to a church steeple on dead end street. Separate office room w/ spin bike, resistance band, and desk. Blackout curtains + white noise machine. Responsive host lives in main home sharing a living room wall w/ a water fall noise barrier. Indoor guest area is entirely private.

Jul 31 – Aug 7

G$19,153 GYD per night

Superhost

Guesthouse in Orlando

4.85 out of 5 average rating, 265 reviews

★ Lakefront Bungalow-5min Downtown ★Casa Pura Vida

Our little piece of paradise is located within 5-10 minutes of Downtown Orlando where some of the best restaurants, bars, and attractions Orlando has to offer. Winter Park & College Park are 10-15 minute drives, Disney/Universal only 20- 30 minutes. The interior is zen and inviting, with a homey feel. Enjoy the Lakefront view, play on the Lake with water toys , soak in the sun on the beach, curl up on the porch with a coffee and enjoy the view. So peaceful, you’ll have a hard time leaving.

Oct 14 – 21

G$28,569 GYD per night

Guest favorite

Condo in Kissimmee

4.87 out of 5 average rating, 164 reviews

Disney 4 miles NEW * Heated LazyRiver & Pool*2B/2B

Discover luxurious comfort at the beautiful Sunset Paradise Condo. For your vacation we provide the best family friendly tropical getaway. The entire Condo is crafted with intentional love. We have faith that your vacation will have you feeling right at home, enhanced with our amazing amenities that exude an all inclusive resort like experience: waterpark, beach volleyball, basketball, hammocking, full service for our poolside restaurant and bar, Kayaking, and mini golf. It's magical here.

Oct 16 – 23

G$35,879 GYD per night

Guest favorite

Condo in Kissimmee

4.89 out of 5 average rating, 47 reviews

The Summer Apt (5 Beds/2 Bdrm) Sleeps 6 Full Kitch

You and your family will be staying in our lovely home, and the whole place will be just for you. You will be less than 10 minutes away from many local fun places like, bowling course, hiking trails, roller skating, kayak paddling, shopping, movie theaters, dining and many more, staying in a clean and relaxing apartment that you can enjoy and rest as if you were at home. Places near: Shopping mall, Restaurants, Old Town, Disney Parks, Fun Spot, Universal Studios, SeaWorld, and many more!

Jun 20 – 27

G$22,417 GYD per night

Guest favorite

Condo in Kissimmee

4.94 out of 5 average rating, 124 reviews

Modern Storey Lake Resort Disney Orlando 3161-305

Minutes from Disney, stylish & modern 2bed/2bath fully equipped apartment for up to 6 guests, located in the family friendly Storey Lake Resort. Enjoy our pool view from the balcony. Master suite has a King bed. Second bedroom has 2 Twin beds. Living room with sofa bed. The open floor plan blends Kitchen, Dining and Living room. Close to outlet malls & retail stores. Great amenities: Pools, Kids Splash Zone, Water Slides, Lazy River, Gym, Mini Golf, Kayak, Tiki Bar & Ice Cream Shop.

Aug 15 – 22

G$31,334 GYD per night

Guest favorite

Townhouse in Kissimmee

4.93 out of 5 average rating, 122 reviews

Storey Lake, Themes, Dogs OK, Free Heated Pool!

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!

May 31 – Jun 7

G$45,960 GYD per night

Guest favorite

Home in Clermont

4.93 out of 5 average rating, 187 reviews

Lake Front Home with private Dock on Lake Louisa

Beautiful lake front home on Lake Louisa. The home sits under towering Cypress trees and is 15 feet from the waters edge. Enjoy breathtaking views of Lake Louisa in the very large great room. Enjoy a game of pool on the pool table, watch cable tv, or walk out onto our private shaded dock where you can fish, swim, enjoy the views, read, play a game of Bimini ring toss, or just relax and unwind. For the safety our guests we allow 2 days between to allow full disinfecting of the house.

Sep 22 – 29

G$35,777 GYD per night

Guest favorite

Guest suite in Orlando

4.92 out of 5 average rating, 316 reviews

Downtown Orlando Garden Retreat

This space is a mother-in-law suite, completely private from the main house, accessible through a private entrance outside and entering through the garage. THIS IS NOT THE ENTIRE HOUSE! There is a queen size bed... perfect for a couples getaway! It is conveniently located about 15 min. from OIA and 5 min. from downtown Orlando. There is a beautiful pool and hot tub with stunning sunset views of across the lake... so peaceful and you feel like you are in a resort

Aug 8 – 15

G$33,311 GYD per night

Superhost

Townhouse in Kissimmee

4.84 out of 5 average rating, 157 reviews

Luxury townhome with private pool

Brand new fully furnished townhome with private pool in gated community. Spacious living and dining rooms ideal for large family gatherings. Free parking situated in front of house. Walking distance from lake and short drive from attractions, malls, and golf course. The unit has fast Wi-Fi, and many smart devices can be connected to the Wi-Fi. Extra charges will be added to your reservation for pool heating, BBQ and others.

Aug 12 – 19

G$38,261 GYD per night

Guest favorite

Condo in Kissimmee

4.91 out of 5 average rating, 115 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

Jul 29 – Aug 5

G$34,746 GYD per night

Guest favorite

Guest suite in St. Cloud

4.93 out of 5 average rating, 293 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.

Nov 19 – 26

G$20,128 GYD per night

Guest favorite

Guest suite in Orlando

4.94 out of 5 average rating, 176 reviews

Private Apartment near Azalea Park!

Downtown Orlando 1 Bdrm, 1 Bath Apartment with full Kitchen in a Great Location! Within walking distance of beautiful parks, great restaurants, Lake Eola and Thornton Park, and the Milk District. Small, private deck and Outdoor Kitchen are also available to use. Perfect for 1 or 2 adults only. Shayna and Shawn are happy to help you with your stay!

Jun 4 – 11

G$21,087 GYD per night