Crestwynd Bay vacation rentals

We found 2,081 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 14 - Nov 21
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Find out more about Crestwynd Bay

Find out more about Crestwynd Bay

Why visit Crestwynd Bay

  1. Family-Friendly Adventures: Crestwynd Bay is perfect for families seeking a variety of outdoor activities, including access to thrilling theme parks.
  2. Scenic Golf Courses: Enjoy picturesque golf courses that cater to both novices and seasoned players.
  3. Beautiful Lakes: Relax by the charming lakefront, ideal for picnics and leisurely strolls.
  4. Convenient Location: Crestwynd Bay serves as an excellent base for exploring nearby Orlando's attractions.
  5. Diverse Accommodation Options: Choose from private homes, villas, and condos to suit your vacation needs.

Popular types of accommodation around Crestwynd Bay

At our vacation rental platform, we offer a variety of options in Crestwynd Bay, including houses, villas, and condos. Whether you’re seeking the charm of Crestwynd Bay homes or the amenities of Crestwynd Bay resort, we have the perfect rental to suit your needs. Discover the ideal accommodation for your getaway and enjoy transparency, savings, and reassurance throughout your booking experience.

  • Houses: The top choice for visitors to Crestwynd Bay, offering spacious and comfortable settings ideal for families or groups.
  • Villas: A popular option, these luxurious properties provide ample amenities and private spaces for relaxation.
  • Condos: A convenient choice, perfect for those seeking a blend of comfort and community in a resort-like atmosphere.
  • Apartments: An economical alternative, great for couples or solo travellers wanting a home-away-from-home feel.
  • Cottages: These quaint and charming accommodations offer a cozy retreat for a more intimate experience.**

Top attractions around Crestwynd Bay

Crestwynd Bay in Four Corners, Florida, is an ideal destination for families seeking outdoor and entertainment-themed vacations. Visitors can enjoy a range of attractions, including thrilling theme parks, scenic golf courses, and beautiful lakes. Whether you're travelling with loved ones or exploring solo, there are plenty of activities to ensure a memorable experience in this vibrant area.

  1. Walt Disney World® Resort: A magical theme park just 9.7km from Crestwynd Bay, offering unforgettable entertainment for families, with thrilling rides, character meet-and-greets, and enchanting shows that create lifelong memories.
  2. Orange County Convention Center: Located 16.1km away, this arts centre showcases vibrant cultural events, exhibitions, and conventions, making it a hub for art enthusiasts and those seeking to experience local creativity.
  3. ChampionsGate Golf Club: Only 6.4km from Crestwynd Bay, this family-friendly golf course offers scenic views and friendly interactions, perfect for a relaxing day of golf or excursions with loved ones.

Things to do recommended for couples

Looking for a romantic getaway in Crestwynd Bay? Enjoy a fun-filled evening at Disney's Winter Summerland Miniature Golf Course, indulge in a delightful meal at Pirate's Dinner Adventure, or unwind in luxury at Ridgewood Lakes Golf and Country Club. Perfect experiences await you!

Things to do recommended for families

Families will have a blast at ESPN Wide World of Sports, just 3.2km from Crestwynd Bay, while Disney's Typhoon Lagoon Water Park offers fun and adventure 8.0km away. For a relaxing day, Northeast Regional Park, located 6.4km away, is perfect for wellness and leisure activities.

Things to do recommended for groups

Experience the magic of Disney Springs™, just 9.7km away for shopping and dining. Explore Old Town, a lively shopping centre 8.0km away, perfect for entertainment. For outdoor fun, play a round at Mystic Dunes Golf Club, only 1.6km from Crestwynd Bay.

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

If you're planning a trip with a group, family, or pets, or seeking an extended stay, be sure to prioritize your preferences when filtering options. Here are some helpful Vrbo booking tips for you.

  • Traveling to Crestwynd Bay with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor area for group gatherings. Thankfully, you can easily apply filters for all of these options, and much more, on Vrbo.
  • Traveling to Crestwynd Bay with young kids: Traveling with young children can present its own set of challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about your closeness to attractions that are family-friendly.
  • Taking your pets with you to Crestwynd Bay: For many families, a vacation isn’t truly fulfilled without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Crestwynd Bay: If you're searching for vacation rentals that offer discounts for month-long stays, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay around Crestwynd Bay

Crestwynd Bay, nestled in Four Corners, Florida, offers a delightful blend of family-friendly adventures and luxurious relaxation. This picturesque neighborhood serves as an ideal base for exploring nearby Orlando, renowned for its entertainment and theme parks. With a charming lakefront and a welcoming community, visitors can enjoy outdoor excursions and friendly atmospheres, making their vacation unforgettable. Experience the best of Florida's attractions while basking in the serene beauty of Crestwynd Bay.

  • Lake Buena Vista: Located a mere 9.7km from Crestwynd Bay, Lake Buena Vista is a vibrant city known for its family-friendly attractions and entertainment options. This area is famous for its resorts and shopping area, offering a delightful mix of leisure and retail therapy. Visitors can explore nearby iconic landmarks like theme parks, film studios, and a stadium, making it a prime destination for thrill-seekers and those looking to indulge in the magic of Florida's attractions.
  • Windsor Hills: Just 483m from Crestwynd Bay, Windsor Hills is a charming neighbourhood that caters to families and outdoor enthusiasts. The area is well-known for its resort-style amenities and proximity to shopping areas and golf courses. Visitors can easily access nearby theme parks and film studios, ensuring a fun-filled experience. Windsor Hills offers a relaxed atmosphere while still being close to the excitement of the attractions, making it a perfect base for your Florida vacation.
  • Indian Ridge: Approximately 3.2km from Crestwynd Bay, Indian Ridge is a welcoming neighbourhood ideal for families and those who enjoy outdoor activities. With its picturesque golf courses and resort facilities, it provides a serene retreat after a day of exploration. The neighbourhood is close to major landmarks such as theme parks, film studios, and a stadium, allowing visitors to easily dive into the local entertainment scene. Indian Ridge combines relaxation with adventure, making it a great spot to unwind while still being connected to the action.

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 August to October 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 SunnySlightly LowAverage
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 SunnyAverageAverage
December64.4°F (18.0°C)No Rain (Dry)Mostly SunnyAverageSlightly High

Booking with Vrbo is simple

Are you hoping to save on your next adventure? Being flexible with your travel dates can help, as prices tend to vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that suits your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to help you make the most of your travel experience!

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a convenient way to plan new trips, pick up from where you last left off, or manage your travel arrangements. You can easily access the properties you've saved or booked, now categorized under Potential, Upcoming, or Current Trips. To start using Trip Boards, please 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 approximately 42 available throughout the area. These houses typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and private outdoor spaces, making them ideal for families or groups. Additionally, there are several apartments, condos, and villas, which also offer modern amenities such as pools, fitness centres, and communal areas for relaxation.
Are there any beach house rentals in Crestwynd Bay?
In Crestwynd Bay, Florida, there are several beach house rentals available, primarily suiting families and groups looking for a spacious and comfortable getaway. These properties typically feature multiple bedrooms, fully equipped kitchens, and open living areas designed for relaxation after a day at the beach. Many homes also come with outdoor patios or decks, great for enjoying the warm Florida evenings. Located close to attractions like Walt Disney World and other theme parks, these rentals provide an ideal base for those wanting to explore the area while still having a tranquil retreat to return to.
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 travelling 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.
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.
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 travellers 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.
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. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Crestwynd Bay for a vacation rental?
July is the most popular time to visit Crestwynd Bay, Florida, as it coincides with the peak tourist season in this vibrant destination. During these summer months, the area comes alive with families and adventure seekers eager to enjoy the warm, sunny weather, great for beach activities and exploration. Visitors can indulge in a range of outdoor pursuits, from swimming and sunbathing on the beautiful shores to engaging in water sports and local attractions nearby.

The climate in Crestwynd Bay during July typically hovers around the mid-30s Celsius, making it ideal for those who love the heat and the lively atmosphere that summer brings. Families will appreciate the convenience of having everything close by, including dining options, shopping, and entertainment, ensuring a comfortable and enjoyable experience for all.

For those looking for a more budget-friendly option, October can be a wonderful time to book a vacation rental. This month offers milder temperatures and fewer crowds, allowing you to explore the area at a more leisurely pace. While the summer bustle may be absent, visitors can still enjoy the pleasant weather and the beautiful natural surroundings.
Are there any remote work vacation rentals in Crestwynd Bay?
In Crestwynd Bay, Florida, there are plenty of remote work vacation rentals available, with around 45 options to choose from. This vibrant area, located near the attractions of Orlando, is ideal for those looking to combine work and leisure. Many properties come equipped with essential amenities for remote work, including reliable Wi-Fi, dedicated desks, and comfortable office chairs, ensuring a productive environment. 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.
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 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 travellers 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 cosy 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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