Crestwynd Bay vacation rentals

We found 2,082 vacation rentals — enter your dates for availability

Discover a selection of 8 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:Jun 19 - Jun 26

Image gallery for Villa Sonrisa - 5 Bedroom/5 Bath Luxury, Minutes To Disney In Windsor Hills

Air Conditioned Game Room - Billiards, Pinball, Multi-Arcade, Bubble Hockey
10 out of 10, Exceptional, (229 reviews)
Exceptional
(229 reviews)

Villa Sonrisa - 5 Bedroom/5 Bath Luxury, Minutes To Disney In Windsor Hills

Kissimmee

8% off
Price is $341
$2,385 for 7 nights
All fees included
Villa Sonrisa - 5 Bedroom/5 Bath Luxury, Minutes To Disney In Windsor Hills

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Find out more about Crestwynd Bay

Why visit Crestwynd Bay

  • Family-friendly activities: Crestwynd Bay offers a variety of attractions perfect for families, ensuring fun for all ages.
  • Outdoor recreation: Enjoy serene lakefronts and nearby golf courses for a relaxing day in nature.
  • Proximity to Disney: Experience magical adventures just a short drive away in the famous Disney area.
  • Unique shopping: Explore local shops for one-of-a-kind finds and souvenirs.
  • Diverse accommodations: Choose from a range of vacation rentals, including luxurious villas and cozy condos.

Popular types of accommodation around Crestwynd Bay

Planning your getaway to Crestwynd Bay? Discover the perfect stay with our fantastic selection of vacation rentals. From houses and luxurious villas to cozy condos, Crestwynd Bay offers a variety of accommodations to suit every traveler’s needs. Enjoy top-notch amenities and a welcoming atmosphere as you explore this beautiful resort area. Start your search for the ideal cottage today and make your vacation unforgettable.

  • Houses: The top choice for visitors to Crestwynd Bay, offering spacious comfort for families and groups, perfect for a relaxing getaway.
  • Villas: These luxurious accommodations come with upscale amenities, ideal for those seeking a touch of elegance during their stay.
  • Condos: A popular option for travelers looking for convenience and community, usually featuring shared facilities and a home-like atmosphere.
  • Apartments: Great for solo travelers or couples, offering all the essentials for a comfortable and enjoyable stay.
  • Cottages: Quaint and charming, these cozy retreats provide a peaceful escape for those wanting a more intimate experience.**

Top attractions near Crestwynd Bay

Crestwynd Bay offers a perfect blend of family-friendly activities, outdoor adventures, and entertainment options. Visitors can enjoy attractions like theme parks, serene lakes, and golf courses, making it an ideal destination for families and outdoor enthusiasts alike. Whether you're exploring local points of interest or seeking thrilling experiences, Crestwynd Bay promises a memorable vacation filled with fun and relaxation.

  • Walt Disney World® Resort: A magical theme park offering thrilling rides, enchanting attractions, and beloved characters. Perfect for families, it provides an unforgettable experience filled with entertainment and excitement, just 6 miles from Crestwynd Bay.
  • Orange County Convention Center: This vibrant arts center hosts a variety of cultural events and exhibitions. It's a hub for creativity and innovation, located 10 miles from Crestwynd Bay, where you can immerse yourself in the local arts scene.
  • ChampionsGate Golf Club: A welcoming golf course and accommodation, ideal for families and excursions. With friendly staff and stunning greens, it's just 4 miles from Crestwynd Bay, making it a perfect spot for golf enthusiasts.

Things to do recommended for couples

For a romantic getaway in Crestwynd Bay, enjoy a round of mini-golf at Disney's Winter Summerland, just 2 miles away. Indulge in dinner at Pirate's Dinner Adventure, 12 miles from you, or unwind at the luxurious Ridgewood Lakes Golf and Country Club, 9 miles away.

Things to do recommended for families

Your family will love the excitement at ESPN Wide World of Sports Complex, just 2 miles away. Enjoy thrilling water adventures at Disney's Typhoon Lagoon Water Park, 5 miles away, or unwind at Northeast Regional Park, located 4 miles from Crestwynd Bay, perfect for relaxation and wellness.

Things to do recommended for groups

Explore the vibrant Disney Springs™ for shopping and dining, just 6 miles from Crestwynd Bay. Enjoy the entertainment and family-friendly atmosphere at Old Town, 5 miles away. For outdoor fun, visit Mystic Dunes Golf Club, located just 1 mile from your base for a round of golf.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

Whether you're traveling with friends, family, pets, or planning an extended stay, it's important to prioritize your preferences when searching. Here are some helpful Vrbo booking tips for you.

  • Traveling to Crestwynd Bay with a group: Think about how many bedrooms you'll require, as well as any amenities like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for all of these options, and many others, on Vrbo.
  • Traveling to Crestwynd Bay with young kids: Traveling with young kids can be quite demanding. 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 how close you are to family-friendly attractions.
  • Taking your pets with you to Crestwynd Bay: For many families, a vacation feels incomplete without their furry companions. If you can relate, explore Vrbo listings that welcome pets. Most of these pet-friendly properties come equipped with 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 with great rates for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Crestwynd Bay

Crestwynd Bay offers a delightful blend of family-friendly activities and picturesque surroundings, making it a perfect vacation spot. Explore the nearby Disney area for magical experiences, enjoy outdoor recreation by serene lakefronts, and indulge in area shopping for unique finds. With friendly locals and a welcoming atmosphere, Crestwynd Bay is an ideal base for memorable excursions in Orlando, Florida, ensuring a relaxing and entertaining getaway for all ages.

  • Orlando: Orlando is a bustling metropolis known as the Theme Park Capital of the World. Situated close to Crestwynd Bay, it offers a plethora of family-friendly entertainment options. Visitors can explore world-renowned attractions such as Walt Disney World, Universal Studios, and SeaWorld. Beyond the theme parks, Orlando boasts vibrant shopping districts like International Drive and The Mall at Millenia, an array of dining choices, and cultural venues such as the Dr. Phillips Center for the Performing Arts. Outdoor enthusiasts can enjoy lush parks and beautiful lakes, making Orlando a perfect blend of adventure and relaxation.
  • Four Corners: Four Corners is a charming village that provides a more laid-back atmosphere while still being in proximity to many attractions. It’s an ideal spot for families seeking entertainment and outdoor activities. Golf enthusiasts will appreciate the nearby golf courses, while resorts in the area offer leisure and relaxation. Four Corners is also conveniently located near major theme parks and entertainment hubs, ensuring that guests have easy access to thrilling adventures while enjoying a peaceful retreat after a day of fun.
  • Windsor Hills: Windsor Hills is a delightful neighborhood located just 0.3 miles from Crestwynd Bay, making it an easy visit for tourists. This community is perfect for families looking for an entertainment-themed vacation. Windsor Hills features access to resorts, shopping areas, and golf facilities, catering to a variety of interests. The neighborhood is also close to popular attractions like theme parks and stadiums, allowing guests to experience the excitement of nearby Orlando while enjoying the comforts of a welcoming community atmosphere.

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 SunnyAverageSlightly High
May77.2°F (25.1°C)Light RainMostly SunnyAverageAverage
June81.1°F (27.3°C)Light RainMostly SunnyAverageAverage
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 looking to save on your next vacation? Being flexible with your travel dates can help, as prices can vary. Additionally, booking a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan new adventures, pick up right where you left off, or manage and organize your travel itinerary. You can easily access properties you've saved and booked, now categorized under Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.vrbo.com/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 type of accommodation, with about 41 available throughout the area. These homes typically feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups. Many also include outdoor spaces such as patios or private gardens, great for enjoying the warm Florida climate. Additionally, there are several apartments, condos, and cottages available, which offer a variety of amenities and settings for travelers seeking a comfortable stay in this charming neighborhood.
Are there any beach house rentals in Crestwynd Bay?
In Crestwynd Bay, there are several beach house rentals available, primarily suiting families and groups looking for spacious rooms. These vacation homes typically feature multiple bedrooms, fully equipped kitchens, and living areas designed for relaxation. Many properties also include outdoor spaces such as patios or decks, great for enjoying the warm Florida weather.
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, popular rental amenities include fully equipped kitchens, allowing guests to prepare their own meals. Many rentals also feature coffee and tea makers for a convenient morning routine. Onsite parking is commonly available, making it easy for travelers with vehicles. A shared pool is a highlight, providing a refreshing spot for relaxation and leisure, while many properties also offer decks or patios where guests can enjoy the Florida sunshine and outdoor living.
Can I find family house rentals in Crestwynd Bay?
In Crestwynd Bay, Florida, there are numerous family-friendly house rentals available, with around 43 options to choose from. This charming community is conveniently located near popular attractions such as Walt Disney World®, making it an ideal base for families visiting the theme parks. Many of these homes feature spacious living areas, fully equipped kitchens for preparing family meals, and private pools for relaxation after a day of adventure.

Additionally, visitors can enjoy amenities like game rooms, outdoor patios, and laundry facilities, enhancing the comfort of their stay. The nearby neighborhoods also offer easy access to shopping and dining options, ensuring that all the necessities and fun experiences are within reach.
Can I rent a vacation home with a pool or hot tub in Crestwynd Bay?
In Crestwynd Bay, Florida, there are plenty of vacation homes available for rent that feature both pools and hot tubs, with around 45 options to choose from. This charming community, located near the attractions of Orlando, provides a great backdrop for family getaways and relaxation. Many of these rentals come with private pools, spacious outdoor areas for sunbathing, and hot tubs, great for unwinding after a day of adventures.

Travelers can expect amenities such as fully equipped kitchens, comfortable living spaces, and often game rooms or entertainment areas, making them ideal for larger groups or families. The proximity to local attractions and the vibrant Orlando area enhances the appeal, allowing guests to easily explore theme parks and shopping while enjoying the comforts of their vacation home.
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.
Can I book pet-friendly vacation rentals in Crestwynd Bay?
Yes, you can book pet-friendly vacation rentals in Crestwynd Bay. This area offers a variety of homes that welcome pets, making it an excellent choice for travelers looking to bring their furry companions along. With 19 pet-friendly options available, you can expect amenities such as fenced yards, pet beds, and easy access to nearby parks or walking trails. Many of these rentals are well-equipped with modern kitchens, spacious living areas, and outdoor spaces for relaxation.
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 best time to visit Crestwynd Bay is during the peak season from February to April, when the weather is pleasantly warm, averaging between the mid-70s to low 80s Fahrenheit. This period attracts travelers, as the region comes alive with activities and events, making it an ideal time for those looking to enjoy the beautiful beaches and outdoor attractions.

The month of July is particularly popular, offering vibrant summer vibes with plenty of opportunities for water sports, beach days, and local festivals. Expect a bustling atmosphere as visitors flock to the area, eager to soak up the sun and experience the excitement that Crestwynd Bay has to offer.

For travelers seeking a more budget-friendly option, October presents a wonderful opportunity to explore the area at a quieter pace. The weather remains warm, and you can enjoy the stunning fall scenery without the crowds. This month is superb for leisurely strolls along the beach or visits to local attractions with fewer tourists around.
Are there any remote work vacation rentals in Crestwynd Bay?
In Crestwynd Bay, Florida, there are numerous options for remote work vacation rentals, with around 47 properties available. This area is known for its family-friendly atmosphere and proximity to popular attractions like Walt Disney World® and other theme parks. Many of these rentals come equipped with essential remote work amenities, including high-speed internet and free Wi-Fi, which are crucial for those needing to stay connected during their stay.

Travelers can expect a variety of accommodations, from spacious townhomes to cozy condos, often featuring dedicated workspaces, comfortable seating areas, and fully equipped kitchens for convenience. Additionally, many properties boast amenities such as pools, fitness centers, and outdoor spaces, providing a superb balance of work and relaxation after a productive day. 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, Florida, United States of America?
Crestwynd Bay is a charming community located near the popular attractions of Kissimmee and Orlando. One of the top draws of the area is its proximity to Walt Disney World® Resort, making it an ideal base for families looking to explore the theme parks. Visitors can easily access the parks from Crestwynd Bay, enjoying the convenience of returning to their vacation rentals after a day of fun.

Another attraction nearby is the beautiful Lake Tohopekaliga, which offers opportunities for fishing, boating, and enjoying scenic views. The surrounding area features several shopping and dining options, particularly along the bustling Highway 192 corridor, where travelers can find a variety of restaurants and shops to suit all tastes.

Additionally, the community is just a short drive from the vibrant attractions of Orlando, including Universal Studios and the International Drive area, which is filled with entertainment, dining, and shopping options. For those seeking outdoor activities, the nearby Kissimmee State Park provides trails for hiking and biking, as well as chances for wildlife viewing in a natural setting.
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 cabin or a beach condo, 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 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.
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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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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