Crestwynd Bay Vacation Rentals

Welcome to Crestwynd Bay, a gated community nestled in Kissimmee, Florida, where vacation dreams come to life. With its pristine landscapes, nature trail, and proximity to world-renowned attractions, Crestwynd Bay is the perfect destination for travelers seeking a memorable and rejuvenating getaway. Discover why renting a vacation home in this captivating community is an experience you won't want to miss.

View our Featured Crestwynd Bay Private Vacation Rentals at the bottom of this page.

Distance to Popular Orlando Area Attractions

  • Walt Disney World® Resort: 9 minutes (3.3 miles)
  • Universal Orlando Resort: 20 minutes (16 miles)
  • SeaWorld Orlando: 15 minutes (11 miles)
  • Orlando International Airport (MCO): 25 minutes (23 miles)
  • ESPN Wide World of Sports Complex: 9 minutes (4.9 miles)
  • Downtown Orlando: 25 minutes (24.6 miles)
  • Cape Canaveral: 61 minutes (67 miles)
  • Clearwater Beach: 87 minutes (88 miles)

Crestwynd Bay was originally built in 2007. As you enter the main gates, you'll be greeted by a tree-lined neighborhood featuring two-story townhomes that exude a sense of warmth and comfort. The community offers a range of spacious and well-appointed vacation homes that range from 1,300 square feet to nearly 1,600 square feet. Every home has tile roofs, a customary style for this vacation destination. Here you'll find the perfect accommodation to suit your needs, whether you're traveling with family, friends, or enjoying a romantic escape.

One of the standout features of Crestwynd Bay is its unbeatable location. Just a short drive away, you'll find the magical world of Walt Disney World Resort, where your favorite characters come to life and enchantment fills the air. Experience the thrills of Space Mountain, ride the Guardians of the Galaxy coaster at Epcot, or meet Mickey Mouse himself at the iconic Magic Kingdom. And when you're ready to explore beyond the magic, Universal Orlando Resort and SeaWorld Orlando are also within easy reach, ensuring endless entertainment for everyone.

If you're in the mood for some retail therapy, look no further than the nearby Orlando Vineland Premium Outlets and The Loop, both offering a treasure trove of designer brands, specialty stores, and enticing dining options. Indulge in a shopping spree, sample delectable cuisine, or catch a movie—the possibilities are endless.

Crestwynd Bay Photo Album

The pool at Crestwynd Bay

Back in Crestwynd Bay, take advantage of the community's fantastic amenities. Dive into the sparkling swimming pool to beat the Florida heat or relax poolside with a good book and a refreshing drink. The kids will have a blast at the playground, letting their imaginations run wild as they make new friends and create lasting memories.

For those seeking outdoor adventures, Crestwynd Bay is a gateway to the wonders of nature. Explore the nearby Kissimmee Lakefront Park, where you can take a leisurely stroll along the picturesque lakefront, go fishing, or enjoy a picnic with loved ones. If you're a golf enthusiast, you'll be delighted to find numerous world-class golf courses in the vicinity, catering to players of all skill levels.

As the sun sets, Crestwynd Bay continues to charm with its peaceful ambiance. Take a moonlit walk around the neighborhood, enjoying the tranquility and soaking in the beauty of the surroundings. Alternatively, venture into the vibrant city of Kissimmee, where you'll find an array of entertainment options, from live music and theater performances to trendy bars and restaurants.

Crestwynd Bay Highlights

  • Community pool with bathrooms
  • Children's playground
  • Secure, gated community
  • Nature trail
  • Natural lake
  • Excellent location

With its idyllic setting, convenient location, and an abundance of attractions and amenities, Crestwynd Bay is the perfect choice for your next vacation rental. Whether you're seeking adventure, relaxation, or a bit of both, this captivating community promises an unforgettable experience for travelers of all ages. So pack your bags, embrace the Florida sunshine, and let Crestwynd Bay welcome you to a world of magic, adventure, and endless possibilities. Your dream vacation starts here!

Crestwynd Bay Address

Crestwynd Blvd.
Kissimmee, FL 34747

Featured properties