Crestwynd Bay holiday rentals
We found 2,111 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:22 Jan - 29 Jan
Exceptional
(175 reviews)
Welcome to The Windsor Dream!
Kissimmee
S$3,239
for 7 nights, 1 villa
S$463 per night
includes taxes & fees
Exceptional
(5 reviews)
Stunning 4BR/4BA Villa in Windsor Hills | Near Disney
Kissimmee
S$2,570
for 7 nights, 1 villa
S$367 per night
includes taxes & fees
Exceptional
(6 reviews)
Mickey’s Vacation Villa-Premium- Minutes from Disney World with private pool!
Kissimmee
S$5,345
for 7 nights, 1 home
S$764 per night
includes taxes & fees
Exceptional
(107 reviews)
6BR Family Retreat Near Disney | Pool + Arcade + Resort Access
Kissimmee
S$3,245
for 7 nights, 1 home
S$464 per night
includes taxes & fees
Exceptional
(19 reviews)
Luxary villa close to disney
Kissimmee
S$1,890
for 7 nights, 1 villa
S$270 per night
includes taxes & fees
Exceptional
(35 reviews)
Fully Renovated w Heated pool, 3 miles from Disney
Kissimmee
S$5,644
for 7 nights, 1 home
S$806 per night
includes taxes & fees
Exceptional
(151 reviews)
Getaway with Mickey in Windsor Hills!
Kissimmee
S$1,571
for 7 nights, 1 apartment
S$224 per night
includes taxes & fees
Exceptional
(204 reviews)
Welcome to The Windsor Magic with Professional Arcade Room! Brand New 2024!
Kissimmee
S$3,547
for 7 nights, 1 home
S$507 per night
includes taxes & fees
Exceptional
(37 reviews)
Paradise Villa, No rear neighbors, Minutes from Disney
Kissimmee
S$2,354
for 7 nights, 1 home
S$336 per night
includes taxes & fees
Exceptional
(125 reviews)
Star Wars Villa - 10 Mins to Disney
Kissimmee
S$2,755
for 7 nights, 1 villa
S$394 per night
includes taxes & fees
Exceptional
(133 reviews)
Amazing Private Theater and Game Room! Pool/Spa & Star Wars room! Free Pool Heat
Kissimmee
S$3,083
for 7 nights, 1 home
S$440 per night
includes taxes & fees
Exceptional
(218 reviews)
3 BR Condo with Beautiful Pool & Water Park Minutes to Disney Worlds Front Gate
Kissimmee
S$1,746
for 7 nights, 1 apartment
S$249 per night
includes taxes & fees
Exceptional
(75 reviews)
Extrended Pool Deck/No Rear Neighbors/Windsor Hills Resort, 3 Miles to Disney®!
Kissimmee
S$4,051
for 7 nights, 1 home
S$579 per night
includes taxes & fees
Exceptional
(57 reviews)
NEW Immersive Luxury Experience- 2 miles from Disney. Game Room, 3 en-suites
Kissimmee
S$2,419
for 7 nights, 1 home
S$346 per night
includes taxes & fees
Wonderful
(236 reviews)
Vacation Rental near Disney, Univeral Studios, Epic, w/free parking and Wi-Fi.
Kissimmee
S$1,458
for 7 nights, 1 apartment
S$208 per night
includes taxes & fees
Exceptional
(34 reviews)
Windsor Orlando Arcade Room, Movie Theater, Pool & Hot Tub, King Bed, Bunk Bed
Kissimmee
S$3,406
for 7 nights, 1 home
S$487 per night
includes taxes & fees
Exceptional
(138 reviews)
Cinderella Pool Villa - 10 minutes from Disney
Kissimmee
S$2,633
for 7 nights, 1 villa
S$376 per night
includes taxes & fees
Exceptional
(134 reviews)
Renovations Kitchen & Bath. "Be Our Guest" in Windsor Hills-pool heat included
Kissimmee
S$2,369
for 7 nights, 1 home
S$338 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
Tito's Beachy Townhouse, 1.5 miles from Disney
Sleeps 8 · 3 bedrooms · 2+ bathrooms
Top Rated Windsor Hills First Floor -INSTANT BOOK- Known for Extra Cleanliness.
Sleeps 6 · 2 bedrooms · 2 bathrooms
My Disney Oasis - 3bd/3ba 2.5 miles to Disney!
Sleeps 8 · 3 bedrooms · 3 bathrooms
ALL NEW fully remodeled and updated! One of Closest community near Disneyworld
Sleeps 8 · 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
What is the most popular type of holiday rental accommodation in Crestwynd Bay?
The most desirable types of holiday rentals in Crestwynd Bay are townhomes. Want something different? Vrbo has many options to match the needs of our guests, so you'll see properties in all shapes and sizes, and for all budgets. The perfect home away from home is waiting for you — get hold of yours today.
How much does it cost to rent a holiday rental in Crestwynd Bay?
A number of factors determine what you'll pay for a holiday rental in Crestwynd Bay, such as the time of year, property type and length of stay. But, all our holiday homes have one thing in common — amazing value. Just enter your travel dates to find your home away from home.
How much does it cost to rent a beach house in Crestwynd Bay?
When you travel and the style and size of the property will influence the cost of your beachside stay. Click on your Crestwynd Bay travel dates to view your options on Vrbo. Did someone just say "private pool"? Use our filters to select the features and amenities you want in your beach house.
Are there pet-friendly holiday rentals in Crestwynd Bay?
Good news. There are. You'll find 48 stays that welcome pets in Crestwynd Bay on Vrbo. Our furry kids deserve a getaway too, so simply use our search function for pet-friendly holiday rentals to find a pad where your pup can be near his favourite humans.
Can I rent a house with a pool in Crestwynd Bay?
Pack your swimming gear and inflatable flamingo, because there are 45 houses with a private pool in Crestwynd Bay. Book one of these popular holiday rentals and make every day a pool day. Simply enter your travel dates into Vrbo, then check the "pool" filter to find a place to make a splash!
What are popular rental amenities in Crestwynd Bay?
When it comes to rental amenities that people prefer in Crestwynd Bay, a barbecue grill, a fireplace and nearby museums rank the highest. With Vrbo holiday homes, you'll discover options to match your taste and style, whether you're holidaying with family members, friends or even pets.
Are there large group holiday rentals in Crestwynd Bay?
You'll find 38 holiday rentals in Crestwynd Bay that can sleep five or more people. From family getaways to events like birthday parties, these stays have ample space to gather with the people that matter the most.
Are there holiday rentals in Crestwynd Bay that welcome kids?
Bring the whole family together for fun-filled adventures in Crestwynd Bay at one of our 48 family-friendly holiday properties. A lot of these stays provide conveniences that are ideal for getaways with the kids, including kitchens, bunk beds and entertainment units. Just check the "Properties good for families" filter and pick out your favourite.
What are the top attractions for families in Crestwynd Bay?
Keeping the kids amused during your Crestwynd Bay holiday is easy with these awesome family-friendly attractions:
- Fun Spot America
- Island H2O Live!
- Surfari Water Park
Are there holiday rentals with WiFi in Crestwynd Bay?
You'll find 34 holiday rentals with WiFi in Crestwynd Bay. If you'd like to disconnect from daily life during your escape, but still want to be connected to the internet, these getaways are just what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find holiday rentals with air conditioning in Crestwynd Bay?
Crestwynd Bay has 48 holiday rentals where you'll be able to kick back in air-conditioned comfort. To locate a property on Vrbo that provides this perk, enter your preferred travel dates and use the filter tool to select the "air conditioning" box.
How old do you have to be to rent a holiday rental in Crestwynd Bay?
It's a good idea to check with the Crestwynd Bay holiday rental you want on Vrbo as the minimum age differs. However, normally it's 16, 18 or 21.
How long can I rent a holiday rental in Crestwynd Bay for?
How long you can rent a holiday rental in Crestwynd Bay is down to the property. Simply enter your chosen travel dates to look at a list of options offering extended stays. With loads of amenities like laundries and air conditioning, as well as some offering weekly or monthly discounts, you're sure to find somewhere perfect to call your home away from home in Crestwynd Bay.