Crestwynd Bay vacation rentals

We found 2,068 vacation rentals — enter your dates for availability

Discover a selection of 47 homes and other vacation rentals in Crestwynd Bay that are perfect for your trip. Whether you're staying in a vacation rental with friends, family, or even just your pets, you'll have the amenities you expect and more, which might include WiFi and a washer and dryer. You'll be sure to find a rental for everyone's needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - Crestwynd Bay

Showing deals for:Nov 7 - Nov 14

Image gallery for Announcing Dreams Come True Villa, - Close to clubhouse

Relax by the pool
10 out of 10 rating
Exceptional
(17 reviews)

Announcing Dreams Come True Villa, - Close to clubhouse

Kissimmee, FL

7% off
Price is $310
$2,168 for 7 nights
All fees included
Announcing Dreams Come True Villa, - Close to clubhouse

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Find out more about Crestwynd Bay

Find out more about Crestwynd Bay

Why visit Crestwynd Bay

  1. Outdoor Adventures: Crestwynd Bay is perfect for families seeking fun, with nearby theme parks and beautiful lakefront activities.
  2. Golfing Opportunities: Enjoy a round of golf at local country clubs, catering to both beginners and seasoned players.
  3. Water Parks: Experience thrilling water parks that provide exciting entertainment for visitors of all ages.
  4. Diverse Accommodations: Choose from a variety of vacation rentals, including cozy homes and spacious villas, to suit your needs.
  5. Welcoming Atmosphere: The charming neighborhood of Crestwynd Bay ensures a relaxing and enjoyable vacation experience.

Popular types of accommodation around Crestwynd Bay

Crestwynd Bay offers a fantastic selection of vacation rentals, including private homes, villas, and condos, perfect for any traveler. Whether you’re seeking a cozy retreat or a spacious getaway, Crestwynd Bay’s diverse accommodations cater to families, couples, and groups alike. Explore the charm of the Crestwynd Bay neighborhood and enjoy the assurance of a seamless stay in this inviting resort area. Discover your ideal vacation rental today!

  • Houses: The top choice among travelers to Crestwynd Bay, these homes offer spacious and comfortable accommodations for families or groups.
  • Villas: A luxurious option, villas provide upscale amenities and beautiful surroundings, perfect for a relaxing getaway.
  • Condos: Convenient and often centrally located, condos are ideal for those seeking easy access to local attractions.
  • Apartments: A practical choice for visitors, apartments offer the comforts of home in a variety of settings.
  • Cottages: These quaint and cozy rentals are perfect for a charming and intimate vacation experience.**

Top attractions near Crestwynd Bay

Crestwynd Bay is an ideal destination for families seeking outdoor adventures and entertainment. Visitors can explore nearby theme parks, enjoy the picturesque lakefront, and play a round of golf at local country clubs. With options like water parks and various entertainment venues, Crestwynd Bay offers a treasure trove of activities for travelers of all ages, ensuring a fun-filled vacation experience.

  1. Walt Disney World® Resort: Experience the magic at this iconic theme park, located 6 miles from Crestwynd Bay. With thrilling rides, captivating shows, and beloved characters, it's the ultimate family destination brimming with entertainment and joy.
  2. Orange County Convention Center: Situated 10 miles away, this arts center is a cultural hub featuring a variety of events and exhibitions. It's a great place to immerse yourself in local art and community vibes.
  3. ChampionsGate Golf Club: Only 4 miles from Crestwynd Bay, this family-friendly golf course offers scenic views, friendly staff, and exciting excursions for golf enthusiasts and families alike.

Things to do recommended for couples

Embark on a romantic adventure in Crestwynd Bay! Enjoy breathtaking views on the Orlando Eye at ICON Park, challenge each other at Disney's Winter Summerland Miniature Golf, and savor a delightful meal at Pirate's Dinner Adventure for a perfect blend of fun and romance.

Things to do recommended for families

Your family will have a blast at the ESPN Wide World of Sports Complex, just 2 miles away, experiencing the thrill of sports. For water fun, visit Disney's Typhoon Lagoon Water Park, located 5 miles away, or head to Wonderworks, an arcade adventure zone, 11 miles away for more excitement!

What do I need to keep in mind when booking a vacation around Crestwynd Bay

If you're traveling with a group, with family, bringing pets, or seeking extended stays, it's important to prioritize your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Crestwynd Bay with a group: Think about how many bedrooms you require, along with features like a full kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and many more on Vrbo.
  • Traveling to Crestwynd Bay with young kids: Traveling with young kids can be tricky. It’s important to prioritize their comfort and safety, as well as look for age-appropriate amenities, like a private swimming pool. Additionally, thinking about how close you are to family-friendly attractions is a wise choice.
  • Taking your pets with you to Crestwynd Bay: For many families, a vacation isn't truly a getaway without their furry companions. If you can relate, explore Vrbo listings that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and cozy beds, ensuring that every member of the family feels at home.
  • Planning for a long term stay visiting Crestwynd Bay: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By utilizing the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include additional preferences like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Crestwynd Bay

Crestwynd Bay offers an idyllic setting for family-friendly vacations, blending relaxation with exciting entertainment options. Explore nearby attractions that promise memorable excursions and a welcoming atmosphere. With its prime location, you'll find opportunities for outdoor adventures and luxury experiences, making it the perfect vacation destination. Whether you’re seeking a new apartment or simply looking to unwind, Crestwynd Bay and its surrounding areas are sure to fulfill your travel dreams.

  • Lake Buena Vista: Situated 6 miles from Crestwynd Bay, Lake Buena Vista is a vibrant city known for its family-friendly atmosphere and entertainment options. Visitors flock to this area for its renowned resorts and shopping centers, making it a hub for both leisure and business activities. The city is also home to iconic local landmarks such as theme parks, film studios, and stadiums, ensuring a variety of attractions to suit everyone’s interests. Whether you're indulging in retail therapy or exploring thrilling rides, Lake Buena Vista offers an unforgettable travel experience.
  • Windsor Hills: Located a mere 0.3 miles away from Crestwynd Bay, Windsor Hills is a charming neighborhood perfect for families and outdoor enthusiasts. This area boasts easy access to resorts, shopping areas, and golf facilities, making it a convenient choice for visitors. Windsor Hills is surrounded by major attractions, including theme parks and film studios, ensuring that adventure is never far away. With its welcoming community and variety of outdoor activities, it serves as an ideal base for exploring the nearby attractions.
  • Indian Ridge: Just 2 miles from Crestwynd Bay, Indian Ridge is a delightful neighborhood that combines family fun with outdoor recreation. Known for its golf courses and stunning resort options, Indian Ridge is a fantastic spot for visitors looking to unwind and play. The neighborhood is close to popular local landmarks such as theme parks and sports facilities, offering a wealth of entertainment opportunities. Whether you're teeing off on the greens or enjoying nearby attractions, Indian Ridge promises a memorable vacation experience.

Best time to go to Crestwynd Bay

If you're planning a trip to Crestwynd Bay, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs in February to March and July, while off-peak times, like September to November tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January60.6°F (15.9°C)Light RainMostly SunnyAverageAverage
February64.4°F (18.0°C)Light RainMostly SunnySlightly HighSlightly Low
March67.6°F (19.8°C)Light RainMostly SunnySlightly HighAverage
April72.7°F (22.6°C)Light RainMostly SunnyAverageAverage
May77.2°F (25.1°C)Light RainMostly SunnyAverageAverage
June81.1°F (27.3°C)Light RainMostly SunnyAverageSlightly High
July82.4°F (28.0°C)Moderate RainMostly SunnySlightly HighSlightly High
August82.6°F (28.1°C)Moderate RainMostly SunnyAverageAverage
September80.4°F (26.9°C)Moderate RainMostly SunnySlightly LowSlightly Low
October75.2°F (24.0°C)Light RainMostly SunnySlightly LowSlightly Low
November68.5°F (20.3°C)Light RainMostly SunnySlightly LowAverage
December64.4°F (18.0°C)No Rain (Dry)Mostly SunnyAverageSlightly High

Booking with Vrbo is a breeze

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Additionally, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to search by price, location, and type of vacation rental. We're here to help you find the perfect getaway!

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash™ on the full booking amount. Being the planner has its perks! When you join our travel rewards program, One Key, you'll gain access to exclusive member discounts and earn OneKeyCash™ on eligible bookings. Sign up today and begin enjoying your savings!

Vrbo Trips: Planning as easy as it gets

Vrbo's user-friendly Trip Board offers you a dedicated area to plan new adventures, pick up right where you left off, and manage your travel arrangements effectively. You can easily access properties you've saved or booked, now categorized under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Crestwynd Bay?
In Crestwynd Bay, vacation houses are the most popular rental option, with around 40 available in the area. These properties typically feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups looking for a comfortable stay. Many houses also include outdoor amenities such as private pools or patios, superb for enjoying the warm Florida weather. Additionally, there are several apartments, condos, and villas available, offering travelers a variety of choices depending on their preferences and group size.
Are there any beach house rentals in Crestwynd Bay?
In Crestwynd Bay, Florida, there are about 21 beach house vacation rentals available. These properties typically feature spacious layouts with multiple bedrooms, making them suitable for families or groups. Amenities often include fully equipped kitchens, private pools, and outdoor patios for enjoying the warm Florida weather. Located near popular attractions such as Walt Disney World and various golf courses, these beach houses provide a comfortable and convenient base for exploring the area while offering a relaxing retreat after a day of activities.
How much does it cost to rent a vacation home in Crestwynd Bay?
Prices for vacation rentals in Crestwynd Bay vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Crestwynd Bay to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Crestwynd Bay vacation house rentals?
You can find great discounts on house rentals in Crestwynd Bay on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What are popular rental amenities in Crestwynd Bay?
In Crestwynd Bay, travelers can expect a variety of popular rental amenities that enhance their stay. Many vacation rentals feature fully equipped kitchens, allowing guests to prepare their meals conveniently. A shared pool is a common amenity, providing a refreshing spot to relax and socialize, and some rentals even offer heated pools for year-round enjoyment. Additionally, many properties come with patios, great for outdoor dining or lounging in the pleasant Florida weather.
Are there any family house rentals in Crestwynd Bay?
Crestwynd Bay, located in Florida, offers an impressive selection of family-friendly rentals, with around 40 options available. This area is ideally situated near popular attractions such as Walt Disney World and various shopping centers, making it a fantastic choice for families looking to enjoy both relaxation and adventure.

Many of these homes feature spacious living areas, multiple bedrooms, and fully equipped kitchens, great for preparing meals together. Outdoor amenities often include private pools, where kids can splash around, and spacious backyards for family gatherings.
Can I rent a vacation home with a pool or hot tub in Crestwynd Bay?
In Crestwynd Bay, Florida, travelers have a variety of vacation homes available for rent that feature pools and hot tubs, with around 40 properties to choose from. This charming community is conveniently located near popular attractions, making it an ideal base for family vacations or group getaways. Many of these rentals come equipped with private pools, outdoor patios, and hot tubs, offering plenty of options for relaxation and leisure after a day of exploring the area.

Amenities commonly found in these homes include fully equipped kitchens, spacious living areas, and outdoor dining spaces, superb for enjoying meals al fresco.
Are there any Crestwynd Bay vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Crestwynd Bay with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there pet-friendly vacation rentals in Crestwynd Bay?
In Crestwynd Bay, travelers can find a variety of pet-friendly vacation rentals, with around 21 options available. Many of these accommodations feature modern amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces like patios or backyards, ideal for those traveling with pets.

The neighborhood is conveniently located near several parks, including the nearby Lake Louisa State Park, which offers ample trails for walking and exploring with your furry companions. Additionally, the vicinity is close to local shops and restaurants, making it a practical choice for families or groups.
Can I find long-stay vacation rentals in Crestwynd Bay?
A long-stay vacation rental in Crestwynd Bay is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit Crestwynd Bay for a vacation rental?
The peak season for vacation rentals in Crestwynd Bay typically spans from February to April, attracting visitors eager for a warm escape. This time of year boasts comfortable temperatures, generally ranging from the mid-60s to mid-80s Fahrenheit, making it ideal for outdoor activities such as beach lounging, water sports, and exploring the nearby attractions. The pleasant climate and vibrant atmosphere draw travelers, creating an energetic vibe.

July stands out as the most popular month for visitors, with bustling crowds and a lot of events that cater to all ages. This time is superb for those looking to bask in the sun and engage in various recreational activities, from fishing to kayaking, all while enjoying the local community events that often take place.

For travelers seeking a more budget-friendly option, October emerges as a fantastic choice. During this month, you can relish the beautiful weather without the hustle and bustle of peak tourist times.
Are there any remote work vacation rentals in Crestwynd Bay?
In Crestwynd Bay, Florida, there are numerous remote work vacation rentals available, with about 41 options to choose from. This area is known for its family-friendly atmosphere and proximity to popular attractions like Walt Disney World, making it an ideal spot for those looking to blend work and leisure.

Travelers can expect a variety of amenities tailored for remote work, including high-speed Wi-Fi, dedicated office spaces, desks, and comfortable chairs, ensuring a productive environment. Many properties also feature additional conveniences such as fully equipped kitchens, outdoor patios, and swimming pools, allowing for relaxation after a day of work.

The neighborhood is well-connected, offering easy access to dining, shopping, and entertainment options, which can enhance the overall experience for remote workers. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Crestwynd Bay vacation rental?
Book your Crestwynd Bay vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Crestwynd Bay?
In Crestwynd Bay, visitors can enjoy proximity to popular attractions in the Orlando area. Located just a short drive away, the Walt Disney World Resort offers a range of theme parks, including Magic Kingdom and Epcot, making it a prime spot for families. The neighborhood is also conveniently situated near the bustling area of Kissimmee, where travelers can find dining, shopping, and entertainment options. For those looking for outdoor activities, nearby Lake Tohopekaliga provides opportunities for fishing and boating.
Can I change or cancel my Crestwynd Bay home rental booking on Vrbo?
To find Crestwynd Bay vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Crestwynd Bay vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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