Crestwynd Bay holiday rentals
We found 2,070 holiday rentals — enter your dates for availability
Discover a selection of 13 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:1 Jan - 8 Jan
Exceptional
(26 reviews)
Welcome to The Windsor Treasure with Professional Arcade Room! Brand New 2024!
Kissimmee
AU$6,228
for 7 nights, 1 villa
AU$890 per night
includes taxes & fees
Exceptional
(91 reviews)
😎RELAX at Windsor Hills🌴, minutes to Disney - 5 bed / 5 bath, Private Pool🌞
Kissimmee
AU$3,499
for 7 nights, 1 home
AU$500 per night
includes taxes & fees
Exceptional
(6 reviews)
Mickey’s Vacation Villa-Premium- Minutes from Disney World with private pool!
Kissimmee
AU$5,941
for 7 nights, 1 home
AU$849 per night
includes taxes & fees
Exceptional
(203 reviews)
Welcome to The Windsor Magic with Professional Arcade Room! Brand New 2024!
Kissimmee
AU$6,277
for 7 nights, 1 home
AU$897 per night
includes taxes & fees
Exceptional
(16 reviews)
Theme Parks, Heated Pool, Theater, Arcades, Mario Kart Bedroom
Kissimmee
AU$5,881
for 7 nights, 1 home
AU$840 per night
includes taxes & fees
Exceptional
(124 reviews)
Star Wars Villa - 10 Mins to Disney
Kissimmee
AU$4,584
for 7 nights, 1 villa
AU$655 per night
includes taxes & fees
Exceptional
(138 reviews)
Cinderella Pool Villa - 10 minutes from Disney
Kissimmee
AU$4,410
for 7 nights, 1 villa
AU$630 per night
includes taxes & fees
Exceptional
(19 reviews)
Luxary villa close to disney
Kissimmee
AU$2,558
for 7 nights, 1 villa
AU$365 per night
includes taxes & fees
Exceptional
(218 reviews)
3 BR Condo with Beautiful Pool & Water Park Minutes to Disney Worlds Front Gate
Kissimmee
AU$2,157
for 7 nights, 1 apartment
AU$308 per night
includes taxes & fees
Exceptional
(104 reviews)
Monorail Silver | Near Disney & ESPN | Private Pool | No Rear Neighbors
Kissimmee
AU$3,072
for 7 nights, 1 home
AU$439 per night
includes taxes & fees
Exceptional
(134 reviews)
Steps from clubhouse. "Be Our Guest" in Windsor Hills-pool heat included
Kissimmee
AU$3,264
for 7 nights, 1 home
AU$466 per night
includes taxes & fees
Exceptional
(151 reviews)
Getaway with Mickey in Windsor Hills!
Kissimmee
AU$1,784
for 7 nights, 1 apartment
AU$255 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Crestwynd Bay
GREAT LOCATION in My Home Away-3 bed townhouse SLEEPS 8 just 1.5 miles from WDW!
Sleeps 8 · 3 bedrooms · 3+ bathrooms
RLR2Disney #2! (3 Turns To Disney)
Sleeps 8 · 3 bedrooms · 2+ bathrooms
3BR/3BA Twin Kings CB
Sleeps 8 · 3 bedrooms · 3 bathrooms
Tito's Beachy Townhouse, 1.5 miles from Disney
Sleeps 8 · 3 bedrooms · 2+ bathrooms
Top 1% Windsor Hills Condo-Ground Floor-2 Miles to Disney's World Drive
Sleeps 6 · 2 bedrooms · 2 bathrooms
Family friendly, minutes to Disney! Newly updated condo.
Sleeps 6 · 3 bedrooms · 2 bathrooms
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
When is the best time to visit Crestwynd Bay for a holiday rental?
The most popular time to visit Crestwynd Bay is during the summer months, particularly in July, when families and adventure seekers flock to this charming destination. This period offers warm weather ideal for beach activities, water sports, and exploring the beautiful coastal scenery that Crestwynd Bay is known for.If you're considering outdoor activities and sightseeing, the climate during July typically hovers around 28 to 33 degrees Celsius, providing great conditions for sunbathing and swimming. The area buzzes with energy, and you'll find a range of local events, making it a vibrant time to experience the community spirit.For those looking to enjoy a quieter atmosphere while still appreciating the region's beauty, October is a fantastic option. This month sees fewer tourists, allowing for a more relaxed pace to explore the delightful coastal paths and indulge in the area's culinary offerings without the summer crowds.Ultimately, the best time to visit Crestwynd Bay for a holiday rental hinges on your preference for lively summer activities or a more tranquil experience in the fall.
What are the top attractions in Crestwynd Bay, Florida, United States of America?
Crestwynd Bay is a quiet and family-friendly neighbourhood located near the bustling Orlando area, making it a convenient base for exploring top attractions. Just a short drive away, visitors can easily access the world-famous Walt Disney World® Resort, which includes multiple theme parks such as Magic Kingdom and Epcot. The proximity to these attractions allows for quick day trips, ensuring a magical experience for families.In addition to Disney, the nearby area features various entertainment options such as Universal Studios and SeaWorld, both of which are within a reasonable distance for a fun-filled outing. For those looking to relax, the nearby Lake Buena Vista offers beautiful views and opportunities for outdoor activities.
Are all fees included in the Crestwynd Bay holiday homes prices shown on Stayz?
Stayz 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.
Are there any Crestwynd Bay holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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 any discounts for Crestwynd Bay holiday homes?
You can find great discounts on holiday homes in Crestwynd Bay on Stayz, 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.
Can I change or cancel my Crestwynd Bay holiday home booking on Stayz?
To find Crestwynd Bay holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Crestwynd Bay?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Crestwynd Bay holiday home?
Book your Crestwynd Bay holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Crestwynd Bay?
Prices for holiday homes 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. Stayz offers something for every taste and budget, from affordable homes in Crestwynd Bay to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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