Resorts in Crestwynd Bay, FL: Compare 10+ Sites & Save

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601 Best Resorts in Crestwynd Bay (Starting from $79)

Orlando Disney -Windsor hills Resort Condo
Orlando Disney -Windsor hills Resort Condo
Resort
Orlando, FL, USA
0.2k from Crestwynd Bay center

Hot Tub, Pool, Air Conditioner, Security/Safety, Internet, View, Sports/Activities

6.5

Good

2 reviews

$142
Average price / night
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2BR Villa, Beautiful heated pool & Jacuzzi!  Just minutes from all attractions.
2BR Villa, Beautiful heated pool & Jacuzzi! Just minutes from all attractions.
Resort
Kissimmee, FL, 34747, United States
0.1k from Crestwynd Bay center

AC, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

10.0

Exceptional

2 reviews

$329
Average price / night
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Summerville Vacation Resort
Summerville Vacation Resort
Resort
Orlando, FL, USA
0.2k from Crestwynd Bay center

Accommodations, Pools, Resorts, Parking, Pet-friendly, Lodgings, Hot tubs, Places to stay, Family

7.3

Good

32 reviews

$365
Average price / night
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5 BR 6 BA Villa 5min to Disney!
5 BR 6 BA Villa 5min to Disney!
Resort
Kissimmee, FL, 34747, United States
0.2k from Crestwynd Bay center

AC, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

8.4

Very Good

6 reviews

$328
Average price / night
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Magical 4BR Escape - Pet-Friendly, 9 Min to Disney
Magical 4BR Escape - Pet-Friendly, 9 Min to Disney
Resort
Orlando, FL, USA
0.3k from Crestwynd Bay center

Accommodations, Pools, Parking, Resort villages, Lodgings, Jacuzzis, Places to stay, Family

New to Booking
$165
Average price / night
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Disney 2 miles w/Heated Pool, water park, basketball tennis courts,  game room
Disney 2 miles w/Heated Pool, water park, basketball tennis courts, game room
Resort
Kissimmee, FL, 34747, United States
0.2k from Crestwynd Bay center

AC, Balcony, Crib, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Hot Tub

9.0

Fabulous

28 reviews

$179
Average price / night
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Westgate Grand Villa
Westgate Grand Villa
Resort
Orlando, FL, USA
0.5k from Crestwynd Bay center

Accommodations, Resorts, Lodgings, Jacuzzis, Places to stay, Family

New to Booking
$191
Average price / night
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*Pixie Dust Penthouse*  Totally Remodeled, Luxury 4th floor Condo
*Pixie Dust Penthouse* Totally Remodeled, Luxury 4th floor Condo
Resort
KISSIMMEE, FL, 34747, United States
0.2k from Crestwynd Bay center

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

10.0

Exceptional

7 reviews

$246
Average price / night
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Westgate Town Center Resort
Westgate Town Center Resort
Resort
Crestwynd Bay, Kissimmee, Florida, USA
0.6k from Crestwynd Bay center

Cheap, Accommodations, Pools, Resorts, Parking, Romantic, Pet-friendly, 3-star, Lodgings

8.3

Very Good

437 reviews

$99
Average price / night
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Grand 1 BR with jacuzzi tub. Fourteen pools, minigolf, bike rentals and more.
Grand 1 BR with jacuzzi tub. Fourteen pools, minigolf, bike rentals and more.
Resort
Kissimmee, FL, 34747, United States
0.3k from Crestwynd Bay center

AC, Balcony, Dryer, Fitness Equipment, Heater, Internet, Kitchen, Laundry, No Smoking

New to Booking
$307
Average price / night
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Westgate Vacation Villas Resort
Westgate Vacation Villas Resort
Resort
Crestwynd Bay, Kissimmee, Florida, USA
0.7k from Crestwynd Bay center

Cheap, Accommodations, Pools, Resorts, Parking, Romantic, Pet-friendly, 3-star, Lodgings

8.7

Fabulous

54 reviews

$114
Average price / night
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Rent/Own 2 Bedroom Unit at Westgate Vacation Villas
Rent/Own 2 Bedroom Unit at Westgate Vacation Villas
Resort
Kissimmee, FL, 34747, United States
0.3k from Crestwynd Bay center

AC, Arcade, Balcony, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Hot Tub

8.0

Good

1 reviews

$282
Average price / night
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Hilton Vacation Club Mystic Dunes Orlando
Hilton Vacation Club Mystic Dunes Orlando
Resort
Orlando, FL, USA
0.8k from Crestwynd Bay center

Cheap, Accommodations, Pools, Resorts, Parking, Golf, Romantic, Hilton , 3-star

8.9

Fabulous

2486 reviews

$128
Average price / night
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Spacious 4-Bedroom Resort Condo, Minutes from Disney, with Waterpark and more
Spacious 4-Bedroom Resort Condo, Minutes from Disney, with Waterpark and more
Resort
Kissimmee, FL, 34747, United States
0.4k from Crestwynd Bay center

AC, Balcony, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

New to Booking
$510
Average price / night
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Charming 2-bedroom resort in wonderful Kissimmee with AC, WiFi,
Charming 2-bedroom resort in wonderful Kissimmee with AC, WiFi,
Resort
Kissimmee, FL, 34747, United States
0.4k from Crestwynd Bay center

AC, Balcony, Dryer, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

New to Booking
$340
Average price / night
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Charming 2 bedroom 2 bathroom resort with amenities.
Charming 2 bedroom 2 bathroom resort with amenities.
Resort
Kissimmee, FL, 34747, United States
0.4k from Crestwynd Bay center

AC, Dryer, Extra Bed, Fitness Equipment, Free Parking, Heater, Internet, Laundry, Microwave

New to Booking
$486
Average price / night
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Westgate Towers Resort
Westgate Towers Resort
Resort
Crestwynd Bay, Kissimmee, Florida, USA
1.1k from Crestwynd Bay center

Cheap, Accommodations, Pools, Resorts, Parking, Romantic, Pet-friendly, 3-star, Lodgings

8.2

Very Good

86 reviews

$79
Average price / night
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Grand 1 Bedroom Lock Off   sleep 4  every thing inside,washer dryer full kitchen
Grand 1 Bedroom Lock Off sleep 4 every thing inside,washer dryer full kitchen
Resort
Kissimmee, FL, 34747, United States
0.4k from Crestwynd Bay center

AC, Arcade, Balcony, Breakfast Available, Dryer, Elevator, Extra Bed, Fireplace, Fitness Equipment

New to Booking
$172
Average price / night
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Kompose Boutique Resort @ Theme Parks
Kompose Boutique Resort @ Theme Parks
Resort
Orlando, FL, USA
1.2k from Crestwynd Bay center

Cheap, Accommodations, Pools, Resorts, Parking, Pet-friendly, Lodgings, Hot tubs, Places to stay

9.2

Superb

1455 reviews

$120
Average price / night
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BEAUTIFUL RESORT STUDIO NEAR DISNEY
BEAUTIFUL RESORT STUDIO NEAR DISNEY
Resort
Kissimmee, FL, 34747, United States
0.4k from Crestwynd Bay center

AC, Dryer, Extra Bed, Internet, Laundry, No Smoking, Pool, Washer

New to Booking
$277
Average price / night
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Orbit One Vacation Villas
Orbit One Vacation Villas
Resort
Orlando, FL, USA
1.3k from Crestwynd Bay center

Cheap, Accommodations, Pools, Resorts, Parking, 3-star, Lodgings, Hot tubs, Places to stay

9.2

Superb

518 reviews

$126
Average price / night
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Grand 2 Bedroom Combo \nGrand 1 Bedroom Lock-Off\nTraditional 1 Bedroom Lock-Off
Grand 2 Bedroom Combo \nGrand 1 Bedroom Lock-Off\nTraditional 1 Bedroom Lock-Off
Resort
Kissimmee, FL, 34747, United States
0.5k from Crestwynd Bay center

AC, Dryer, Fitness Equipment, Internet, Laundry, No Smoking, Washer

New to Booking
$328
Average price / night
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Magic Village Yards Trademark Collection by Wyndham
Magic Village Yards Trademark Collection by Wyndham
Resort
Orlando, FL, USA
1.4k from Crestwynd Bay center

Accommodations, Pools, Resorts, Parking, Romantic, 4-star, Lodgings, Hot tubs, Places to stay

8.7

Fabulous

317 reviews

$253
Average price / night
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Cozy 1-bedroom resort with fitness room, WiFi in welcoming Kissimmee
Cozy 1-bedroom resort with fitness room, WiFi in welcoming Kissimmee
Resort
Kissimmee, FL, 34747, United States
0.5k from Crestwynd Bay center

New to Booking
$181
Average price / night
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Holiday Inn Resort Kissimmee by the Parks by IHG
Holiday Inn Resort Kissimmee by the Parks by IHG
Resort
Orlando, FL, USA
1.5k from Crestwynd Bay center

Accommodations, Pools, Resorts, Parking, Holiday inn , Pet-friendly, 3-star, Lodgings, Places to stay

7.5

Good

3104 reviews

$89
Average price / night
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Cozy Resort in Kissimmee near Disney
Cozy Resort in Kissimmee near Disney
Resort
Kissimmee, FL, 34747, United States
0.5k from Crestwynd Bay center

AC, Dryer, Fitness Equipment, Heater, Internet, Laundry, No Smoking, Washer

New to Booking
$147
Average price / night
Check Availability
12 person family friendly- Book from Jan- Dec.2026.  Block your dates.
12 person family friendly- Book from Jan- Dec.2026. Block your dates.
Resort
Kissimmee, FL, 34747, United States
0.5k from Crestwynd Bay center

AC, Balcony, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

10.0

Exceptional

1 reviews

$366
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 Resorts in Crestwynd Bay.

Stay Near Crestwynd Bay's Top Attractions

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Crestwynd Bay Resorts on the Map

Frequently Asked Questions

You can explore 601 verified resorts in Crestwynd Bay. These include a range of options such as beachfront resorts, mountain retreats, and all-inclusive stays designed for a more immersive vacation experience.

Resort prices in Crestwynd Bay vary depending on the season, property type, and included experiences. Rates typically start from around $79 per night, with higher prices for all-inclusive packages or premium resort properties.

Many resorts in Crestwynd Bay offer on-site activities such as Pool, Laundry, and Child Friendly. These features allow guests to enjoy dining, entertainment, and recreation without needing to leave the property.

Yes, some resorts in Crestwynd Bay offer all-inclusive packages where meals, drinks, and select activities are included in the rate. This option can simplify planning and provide a more predictable overall cost for your stay.

For popular travel periods such as holidays or peak seasons, booking 90 to 120 days in advance is recommended to secure the best options. During quieter periods, you may find more availability closer to your travel dates.

Yes, some resorts in Crestwynd Bay welcome pets. Currently, 16 listings allow pets, although policies may vary. It’s helpful to review property details to understand any restrictions or additional fees.

A hotel typically focuses on accommodation, while a resort offers a wider range of on-site amenities such as dining, entertainment, and recreational activities. Resorts are often designed to provide a more complete, stay-on-property experience.