Crestwynd Bay holiday lettings

We found 2,090 holiday rentals — enter your dates for availability

Discover a selection of 7 homes and other holiday rentals in Crestwynd Bay that are perfect for your trip. Whether you're staying in a holiday rental with your children or with friends, you'll find the amenities that you need and want, which might include a hot tub and garden. You'll be able to choose a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Crestwynd Bay

Showing deals for:24 Apr - 1 May

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Why visit Crestwynd Bay

  • Family-friendly atmosphere: Crestwynd Bay is perfect for families seeking a fun and entertaining getaway.
  • Proximity to attractions: Easily access nearby theme parks, scenic lakes, and golf courses.
  • Beautiful beaches: Enjoy a charming day at Clearwater Beach with its stunning shoreline.
  • Diverse accommodation options: Choose from private homes, villas, and condos tailored to your needs.
  • Outdoor activities: Experience leisurely excursions, recreation, and relaxation in a welcoming environment.

Popular types of accommodation around Crestwynd Bay

Crestwynd Bay offers an array of delightful vacation rentals, including private homes, villas, and condos to suit every traveller's needs. Whether you're seeking a tranquil retreat or a family-friendly getaway, our Crestwynd Bay holiday rentals provide the perfect base for your adventures. With options for Crestwynd Bay resort rentals and charming homes, you're sure to find the ideal accommodation for a memorable stay.

  • Houses: The top choice for visitors in Crestwynd Bay, offering spacious and comfortable settings ideal for families or groups.
  • Villas: A popular option, villas provide a luxurious stay with private amenities and often stunning views.
  • Condos: These offer excellent convenience and facilities, perfect for those seeking a home away from home.
  • Apartments: Affordable and practical, apartments are a great choice for shorter stays or couples.
  • Cottages: Quaint and charming, cottages provide a cosy retreat in a picturesque setting.**

Top attractions near Crestwynd Bay

Crestwynd Bay offers a delightful family-friendly getaway, perfect for those seeking outdoor entertainment. Explore nearby attractions like theme parks, scenic lakes, and golf courses at country clubs. For a charming day out, don’t miss the opportunity to visit Clearwater Beach, known for its stunning shoreline. Whether you're travelling with family or friends, Crestwynd Bay promises a memorable experience filled with fun and adventure.

  • Walt Disney World® Resort: A magical theme park offering enchanting entertainment and family-friendly attractions, just 3.7km from Crestwynd Bay. Experience the joy of beloved characters and thrilling rides that create unforgettable memories.
  • Orange County Convention Center: Located 6.2km away, this vibrant arts centre showcases a rich cultural vibe with various exhibitions, events, and performances, making it a hub for creativity and inspiration.
  • ChampionsGate Golf Club: Situated 2.5km from Crestwynd Bay, this welcoming golf course accommodation provides family-friendly excursions and a friendly atmosphere, perfect for both seasoned golfers and beginners.

Things to do recommended for couples

For a delightful couple's getaway in Crestwynd Bay, enjoy a fun round at Disney's Winter Summerland Miniature Golf, just 1.2km away. Indulge in romance at Pirate's Dinner Adventure, 11.2km from your stay, or relax in luxury at Ridgewood Lakes Golf and Country Club, located 5.6km distant.

Things to do recommended for families

Your family will have a fantastic time at ESPN Wide World of Sports Complex, just 1.2km away, where you can soak up the sports atmosphere. For water fun, visit Disney's Blizzard Beach Water Park, also 1.2km away, or unwind at Northeast Regional Park, located 2.5km from Crestwynd Bay.

Things to do recommended for groups

Groups staying in Crestwynd Bay can enjoy a delightful experience at Disney Springs™ for shopping, visit Old Town for entertainment and family activities, and challenge themselves at Mystic Dunes Golf Club for a round of golf in a beautiful outdoor setting.

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

Regardless of whether you’re travelling with a group, family, pets, or seeking extended stays, it's essential to apply the appropriate filters to match your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Crestwynd Bay with a group: Think about how many bedrooms you require, as well as features like a fully equipped kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for all these options, and much more, on Vrbo.
  • Traveling to Crestwynd Bay with young kids: Travelling with young children can indeed be a bit daunting. It's essential to prioritise their comfort and safety, alongside ensuring access to suitable facilities, like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Crestwynd Bay: For many, a family holiday wouldn’t feel complete without their furry companion. If you can relate, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations provide feeding bowls and beds, ensuring that every member of the family feels at home.
  • Planning for a long term stay visiting Crestwynd Bay: If you are in search of holiday rentals that offer discounts for stays of a month or more, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include additional features in your search, such as a parking space, a well-equipped kitchen, or a private pool.

Where to stay near Crestwynd Bay

Crestwynd Bay, nestled in Four Corners, Florida, offers a charming escape for families and outdoor enthusiasts alike. With its convenient location, you can easily explore nearby attractions while enjoying the warm, welcoming atmosphere. The community is perfect for leisurely excursions, recreation, and relaxation, making it an ideal base for discovering the vibrant local culture and entertainment options. Experience the delightful blend of fun and tranquillity that Crestwynd Bay has to offer during your holiday.

  • Windsor Hills: Windsor Hills is a delightful neighbourhood located a mere 186m from Crestwynd Bay, making it incredibly accessible for visitors. Known for its family-friendly atmosphere, Windsor Hills offers an array of entertainment-themed experiences and outdoor activities. Visitors can enjoy the local resort, explore the shopping area, or indulge in a round of golf. With nearby attractions such as a famous theme park, a film studio, and a stadium, Windsor Hills serves as an excellent base for adventure and relaxation.
  • Lake Buena Vista: Situated 3.7km from Crestwynd Bay, Lake Buena Vista is a vibrant city that caters to families and business travellers alike. This city is renowned for its entertainment-themed experiences, offering a plethora of resorts, shopping areas, and shopping mall centres. Lake Buena Vista is home to prominent landmarks and attractions, including a world-famous theme park, a film studio, and a stadium, ensuring that there’s something for everyone. Enjoy a day filled with fun activities or unwind with some retail therapy in this dynamic city.
  • Four Corners: Four Corners is a charming village located 1.2km from Crestwynd Bay, where visitors can immerse themselves in family-friendly and outdoor experiences. The village is noted for its accessible resorts and multiple golf courses, making it a great destination for relaxation and recreation. With nearby attractions like a theme park, a film studio, and a stadium, Four Corners offers a unique blend of leisure and excitement. This village is perfect for those seeking a tranquil yet entertaining getaway.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 simple

Are you hoping to cut costs on your next getaway? It might be worth considering some flexibility with your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often leads to substantial savings. To discover the perfect Vrbo property that fits your budget, make use of our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers an easy-to-use platform for planning your next adventures. You can seamlessly create new trips, resume previous ones, or manage your existing plans all in one place. Your saved or booked properties will be neatly organised under categories such as Potential, Upcoming, or Current Trips. To get started with Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of holiday rental in Crestwynd Bay?
In Crestwynd Bay, holiday houses are the most popular type of rental, with around 42 available in the area. These spacious homes typically feature multiple bedrooms, fully equipped kitchens, and private outdoor spaces, making them ideal for families or larger groups. The atmosphere is relaxed and home-like, allowing guests to unwind after a day of exploring the nearby attractions, such as Disney World and other theme parks. In addition to holiday houses, there are several apartments, condos, and villas available, offering a variety of options to suit different preferences.
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 seeking a spacious getaway. These properties typically feature multiple bedrooms and bathrooms, allowing for comfortable accommodation for larger parties. Many of the rentals come equipped with modern amenities such as fully stocked kitchens, private pools, and outdoor areas for relaxation and barbecuing.
How much does it cost to rent a holiday home in Crestwynd Bay?
Prices for holiday 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 holiday 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 holiday rentals with parking?
Vrbo offers a wide selection of holiday 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 holiday rentals in Crestwynd Bay?
A long-stay holiday 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 holiday rental?
The best time to visit Crestwynd Bay for a holiday rental is during the peak season from February to April. This period attracts many travellers looking to escape colder climates and enjoy the warm, inviting weather of Florida. With temperatures typically ranging from 20 to 29 degrees Celsius, it's superb for outdoor activities such as beach days, water sports, and exploring the nearby attractions.

July is also a popular month, drawing travellers. Expect a vibrant atmosphere filled with exciting events and plenty of opportunities to relax by the beach or take part in local festivities. However, be prepared for warmer temperatures and potential humidity.

For those seeking a more budget-friendly experience, consider visiting in October. This month often presents a delightful balance of pleasant weather and fewer crowds, allowing for a more relaxed exploration of the area's stunning beaches and natural parks. The warm temperatures (around 25 degrees Celsius) still make it a great time for outdoor activities, such as hiking in the nearby nature reserves or enjoying a leisurely stroll along the shoreline.
Are there any remote work holiday rentals in Crestwynd Bay?
In Crestwynd Bay, Florida, there are plenty of remote work-friendly holiday rentals available, with around 45 options to choose from. This vibrant community near the popular attractions of Orlando offers a great environment for those looking to blend work and leisure. Many of the properties come equipped with essential amenities for remote work, including Wi-Fi, dedicated desk spaces, and comfortable office chairs. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Crestwynd Bay holiday rental?
Book your Crestwynd Bay holiday 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 holiday 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 holiday 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 cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Crestwynd Bay holiday 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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