Orlando Vacation Homes » West Hwy 192 Resort Area » Crestwynd Bay
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Crestwynd Bay Townhomes for Sale
Crestwynd Bay is a small gated community of 3-bedroom vacation townhomes – holiday homes, as UK buyers call them – in Kissimmee, about 4 miles from Walt Disney World, where short-term rentals (STR) are allowed. Owners can use their townhome as much as they like and rent it nightly the rest of the year. Amenities are simple, but the location just off Hwy 192 and Old Lake Wilson Road, in front of Windsor Hills, puts guests close to Disney and Sunset Walk.
3
bedrooms per townhome
Unlimited
owner use
About 4 mi
to Walt Disney World
Crestwynd Bay Quick Facts
| Short-term rentals (STR) | Permitted – nightly rentals allowed |
| Owner usage | Unlimited – no county limit on owner stays |
| Rental management | 3rd-party management company or self-managed; no on-site rental program |
| Property type | Townhomes |
| Bedrooms | 3 |
| Size | About 1,190 to 1,595 sq ft |
| Year built | 2006 to 2007 |
| Gated | Yes (no guard) |
| Resort area | West Hwy 192 Resort Area, Osceola County (ZIP 34747) |
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Can You Rent a Crestwynd Bay Townhome on Airbnb or Vrbo?
Yes. Crestwynd Bay allows short-term rentals, so owners can rent to vacationers by the night or week through Airbnb, Vrbo or a management company. A short-term rental, or STR, is a home rented to vacationers instead of on a long-term lease. Many Orlando-area neighborhoods do not allow it; Crestwynd Bay does.
Most buyers use their townhome for a family trip or two each year and rent it the rest of the time to help cover the HOA fee and other costs.
How Much Can Owners Use Their Crestwynd Bay Townhome?
As much as you like. There is no county limit on owner use at Crestwynd Bay. See our list of resorts by maximum owner usage to compare.
Who Manages Rentals at Crestwynd Bay?
There is no on-site rental program. Owners hire a 3rd-party management company or manage bookings and guests themselves. Ask any manager about current fees and policies before you sign.
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What Are Crestwynd Bay Townhomes Like?
Crestwynd Bay townhomes were built in 2006 and 2007. All are two-story, 3-bedroom homes of about 1,190 to 1,595 square feet, in four floor plans with Mediterranean and contemporary styling. Each has a full kitchen, a family room and a back patio. There are no private pools; guests use the community pool.
Typical Crestwynd Bay Townhome Features
- Bedrooms: 3
- Size: About 1,190 to 1,595 sq ft
- Style: Spanish/Mediterranean and contemporary, two stories
- Interior: Full kitchen, family room, inside laundry
- Construction: Block, stucco and wood frame; tile or shingle roof
What Amenities Does Crestwynd Bay Have?
Crestwynd Bay is a small community with basic amenities. Location is its main selling point: Animal Kingdom and ESPN Wide World of Sports are close by, and the shops, restaurants and entertainment at Sunset Walk and the town of Celebration are a short drive away.
Crestwynd Bay Amenities
- Community pool with swim lanes
- Pool restrooms
- Playground
- Sidewalks
- Gated entry
Amenities and HOA services are set by the association and can change. Contact us to confirm current terms before you buy.
Where Is Crestwynd Bay?
Crestwynd Bay is off N Old Lake Wilson Road, south of Hwy 192 and north of Sand Hill Road, directly in front of Windsor Hills Resort, in Kissimmee, Osceola County (ZIP 34747). Open in Google Maps
How Far Is Crestwynd Bay From the Parks?
| Walt Disney World | approx. 4 miles |
| SeaWorld Orlando | approx. 10 miles |
| Epic Universe | approx. 12 miles |
| Universal Orlando | approx. 13 miles |
| Orlando International Airport (MCO) | approx. 19 miles |
Distances are straight-line miles from the resort.
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Is Crestwynd Bay a Good Fit for You?
- A good fit if you want a lower-cost townhome close to Disney, unlimited personal use, and the freedom to choose your own manager.
- Consider other resorts if you want a clubhouse with resort-style amenities, a private pool, or more than 3 bedrooms.
Other Resorts Near Crestwynd Bay
- Summerville Resort
- Windsor Hills Resort
- Sycamore Resort
- Galleria Palms Hotel
- Magic Village Views
- All Orlando vacation townhomes
- All West Hwy 192 area resorts
Crestwynd Bay Video Tour
Video courtesy of WY Vacation Home.
Crestwynd Bay FAQ
Are short-term rentals allowed at Crestwynd Bay?
Yes. Crestwynd Bay townhomes can be rented nightly or weekly to vacationers through Airbnb, Vrbo or a management company.
How long can owners stay in their Crestwynd Bay townhome?
There is no county limit on owner use. You can stay as long as you like and rent the home when you are not using it.
How many bedrooms do Crestwynd Bay townhomes have?
All townhomes have 3 bedrooms, in about 1,190 to 1,595 square feet over two stories.
Who manages rentals at Crestwynd Bay?
There is no on-site rental program. Owners use a 3rd-party management company or self-manage.
Is Crestwynd Bay gated, and what amenities does it have?
Yes, it has a gated entry without a guard. Amenities are a community pool with swim lanes and a playground.
How far is Crestwynd Bay from Disney World?
About 4 miles in a straight line to the center of Walt Disney World.
Rental rules, management policies and HOA fees can change. Contact us to confirm current HOA and Management Company fees before you buy.
Buying at Crestwynd Bay
The latest Crestwynd Bay listings appear below and update daily from the MLS – view all available Crestwynd Bay townhomes. To schedule a showing or ask about any home, Call/Text David Myers at 407.801.3286 or send us a message.
Photos courtesy of Airbnb.com.
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Latest Crestwynd Bay Listings
Beautifully remodeled and fully furnished 3-bedroom, 3-bathroom townhouse offering 1,187 sq. ft. of comfortable living space. Located at 2693 Andros Lane in Kissimmee, th...
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Beautiful end-unit Townhome located in a gated Community just 2.5 miles from Walt Disney World, and minutes from major highways I4 and Hwy 192 offering easy access to sh...
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MAJOR PRICE REDUCTION! NOW ONLY $269,900 — PREVIOUSLY $299,000! LOCATION, SPACE, AND INVESTMENT POTENTIAL ALL IN ONE! Discover this attractive 1,595 sq. ft. corner-uni...
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Welcome to 2691 Andros Lane, Kissimmee, FL 34747, a beautifully maintained two-story townhouse offering 3 bedrooms and 2.5 bathrooms in a desirable resort-style community...
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Welcome home to Maintenance Free Living in Crestwynd Bay! This 3 bedroom 3 full bathroom townhome is ready for its new owner. Featuring a modern, carpet-free interior...
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Short Sale. Fantastic Opportunity to Own a 3-Bedroom, 3-Bathroom Townhouse! Located in the desirable gated community of Crestwynd Bay, this stunning townhouse has an open...
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Short Sale. SHORT SALE OPPORTUNITY! Discover the perfect blend of investment potential and vacation-home convenience with this TURNKEY, FULLY FURNISHED 3-bedroom, 3-bath ...
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Virtually Staged. Click the Virtual Tour link to explore the 3D walkthrough of this inviting townhouse, offering a flexible and thoughtfully designed floor plan with comf...
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