Short-Term Rentals in Crestwynd Bay, FL: Compare 10+ Sites & Save

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21691 Best Short-Term Rentals in Crestwynd Bay (Starting from $125)

2813 Almaton #403
2813 Almaton #403
House
Orlando, FL, USA
0.1k from Crestwynd Bay center

Accommodations, Pools, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Vacation rentals

3 Bedrooms6 Guests
New to Booking
$154
Average price / night
Check Availability
NEW amazing upscale dream house just 5 Minutes to Disney Parks
NEW amazing upscale dream house just 5 Minutes to Disney Parks
House
Kissimmee, FL, 34747, United States
0.0k from Crestwynd Bay center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen

4 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$256
Average price / night
Check Availability
7650 Comrow #204
7650 Comrow #204
House
Orlando, FL, USA
0.1k from Crestwynd Bay center

Accommodations, Pools, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Vacation rentals

3 Bedrooms8 Guests
New to Booking
$236
Average price / night
Check Availability
Serenity - Family & Pet Friendly, 10 Minutes to Disney & Attractions
Serenity - Family & Pet Friendly, 10 Minutes to Disney & Attractions
House
Kissimmee, FL, 34747, United States
0.1k from Crestwynd Bay center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
New to Booking
$396
Average price / night
Check Availability
WH205B 3 BR Windsor Hills Condo!
WH205B 3 BR Windsor Hills Condo!
House
Orlando, FL, USA
0.1k from Crestwynd Bay center

Cheap, Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$177
Average price / night
Check Availability
Spacious 4-bedroom townhome only 5 minutes from Disney World
Spacious 4-bedroom townhome only 5 minutes from Disney World
House
Kissimmee, FL, 34747, United States
0.1k from Crestwynd Bay center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms10 Guests
New to Booking
$313
Average price / night
Check Availability
Sun-Kissed in Kissimmee
Sun-Kissed in Kissimmee
House
Orlando, FL, USA
0.1k from Crestwynd Bay center

Cheap, Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Accessible hotels

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$150
Average price / night
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Windsor Hills  Charming 3BR Condo, Pool, By Disney
Windsor Hills Charming 3BR Condo, Pool, By Disney
Condo
Kissimmee, FL, 34747, United States
0.1k from Crestwynd Bay center

AC, Arcade, Balcony, Crib, Dryer, Elevator, Fitness Equipment, Free Parking, Heater

3 Bedrooms6 Guests
New to Booking
$210
Average price / night
Check Availability
Wonderful Life at Windsor Hills
Wonderful Life at Windsor Hills
Apartment
Orlando, FL, USA
0.1k from Crestwynd Bay center

Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay, Self-catering

3 Bedrooms6 Guests
9.4

Superb

5 reviews

$195
Average price / night
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Family Friendly Townhome Near Attractions
Family Friendly Townhome Near Attractions
House
Kissimmee, FL, 34747-1807, United States
0.1k from Crestwynd Bay center

AC, Balcony, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
New to Booking
$372
Average price / night
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2 Bed 2 Bath Condo First Floor Windsor Hills
2 Bed 2 Bath Condo First Floor Windsor Hills
Apartment
Orlando, FL, USA
0.1k from Crestwynd Bay center

Apartments, Accommodations, Parking, Lodgings, Places to stay, Accessible hotels, Condos

1 Bedroom6 Guests
1.0

Review score

1 reviews

$125
Average price / night
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Quiet Corner Gem in Gated Crestwynd Bay
Quiet Corner Gem in Gated Crestwynd Bay
House
Kissimmee, FL, 34747, United States
0.1k from Crestwynd Bay center

AC, Balcony, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
New to Booking
$406
Average price / night
Check Availability
Cozy Apartment at Windsor Hills WH28131
Cozy Apartment at Windsor Hills WH28131
Apartment
Orlando, FL, USA
0.1k from Crestwynd Bay center

Apartments, Accommodations, Lodgings, Places to stay

3 Bedrooms6 Guests
5.0

Review score

3 reviews

$160
Average price / night
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Windsor Hill Fun Condo Starwars, Moana, Pool, Spa
Windsor Hill Fun Condo Starwars, Moana, Pool, Spa
Condo
Kissimmee, FL, 34747, United States
0.1k from Crestwynd Bay center

AC, Arcade, Balcony, Crib, Dryer, Elevator, Fitness Equipment, Free Parking, Heater

3 Bedrooms6 Guests
New to Booking
$271
Average price / night
Check Availability
Disney-area 4br Retreat Relax & Swim By The Pool
Disney-area 4br Retreat Relax & Swim By The Pool
House
Orlando, FL, USA
0.1k from Crestwynd Bay center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom8 Guests
New to Booking
$280
Average price / night
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Cozy 3BDR House near Disney - AL
Cozy 3BDR House near Disney - AL
House
Kissimmee, FL, 34747, United States
0.1k from Crestwynd Bay center

AC, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking, TV

3 Bedrooms6 Guests
New to Booking
$154
Average price / night
Check Availability
Windsor Hills Spacious Condo,Pool,Slides,By Disney
Windsor Hills Spacious Condo,Pool,Slides,By Disney
House
Orlando, FL, USA
0.1k from Crestwynd Bay center

Cheap, Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$380
Average price / night
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Minutes to Magic! Walt Disney World Awaits
Minutes to Magic! Walt Disney World Awaits
House
Kissimmee, FL, 34747, United States
0.1k from Crestwynd Bay center

AC, Arcade, Balcony, Crib, Dryer, Free Parking, Heater, Hot Tub, Internet

3 Bedrooms6 Guests
New to Booking
$163
Average price / night
Check Availability
Windsor Hills Cozy 3 BR Condo, Starwars, By Disney
Windsor Hills Cozy 3 BR Condo, Starwars, By Disney
House
Orlando, FL, USA
0.1k from Crestwynd Bay center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Hot tubs, Places to stay, Family

3 Bedrooms6 Guests
New to Booking
$447
Average price / night
Check Availability
Relax in a Charming 3BD Home BBQ
Relax in a Charming 3BD Home BBQ
House
Kissimmee, FL, 34747, United States
0.1k from Crestwynd Bay center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms7 Guests
New to Booking
$224
Average price / night
Check Availability
ALM2813-403
ALM2813-403
House
Orlando, FL, USA
0.1k from Crestwynd Bay center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom6 Guests
New to Booking
$222
Average price / night
Check Availability
5 Min to Disney | 4 Suites | Hot tub & BBQ
5 Min to Disney | 4 Suites | Hot tub & BBQ
House
Kissimmee, FL, 34747, United States
0.1k from Crestwynd Bay center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Hot Tub, Internet

4 Bedrooms8 Guests
New to Booking
$306
Average price / night
Check Availability
Home Near Disney Private Pool & Playground
Home Near Disney Private Pool & Playground
House
Howey in the Hills, FL, USA
0.1k from Crestwynd Bay center

Accommodations, Pools, Parking, Villas, Vacation homes, Spa, Cottages, Pet-friendly, Lodgings

3 Bedrooms6 Guests
New to Booking
$147
Average price / night
Check Availability
Comfy Townhome Minutes from Disney
Comfy Townhome Minutes from Disney
House
Kissimmee, FL, 34747, United States
0.1k from Crestwynd Bay center

AC, Balcony, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms7 Guests
New to Booking
$377
Average price / night
Check Availability
Rumi Vacation Stays-  Just 2 miles  from Disney .
Rumi Vacation Stays- Just 2 miles from Disney .
House
Kissimmee, FL, 34747, United States
0.1k from Crestwynd Bay center

AC, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

3 Bedrooms8 Guests
New to Booking
$241
Average price / night
Check Availability
Charming 3-Bedroom Modern Townhome near Disney
Charming 3-Bedroom Modern Townhome near Disney
House
Kissimmee, FL, 34747, United States
0.1k from Crestwynd Bay center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

3 Bedrooms7 Guests
New to Booking
$241
Average price / night
Check Availability
Serenity - Family & Pet Friendly, Amazing Location
Serenity - Family & Pet Friendly, Amazing Location
Cottage
2706 Andros Lane,, Kissimmee, FL, 34747, United States
0.1k from Crestwynd Bay center

AC, Barbecue, Crib, Free Parking, Heater, Internet, Kitchen, No Smoking, Outdoor Space

New to Booking
$461
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Short-Term Rentals in Crestwynd Bay.

Stay Near Crestwynd Bay's Top Attractions

VacationByOwnerRentals can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.

Crestwynd Bay Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 21691 verified short-term rentals in Crestwynd Bay, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Crestwynd Bay vary depending on location, property size, and travel dates. Rates typically start from around $125 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Crestwynd Bay include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Crestwynd Bay, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Crestwynd Bay often include amenities such as Fireplace/Heating, Wellness Facilities, and Child Friendly, providing a comfortable and convenient stay.

Short-term rentals in Crestwynd Bay are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.