Beach Home Rentals in Crestwynd Bay, FL: Compare 10+ Sites & Save

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892 Beach Home Rentals in Crestwynd Bay (Starting from $116)

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
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Windsor Hills Magical Retreat, Cinderella. Toy Story, Star Wars, 2mis to Disney!
Windsor Hills Magical Retreat, Cinderella. Toy Story, Star Wars, 2mis to Disney!
Condo
Kissimmee, FL, 34747, United States
0.1k from Crestwynd Bay center

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

3 Bedrooms8 Guests
10.0

Exceptional

4 reviews

$369
Average price / night
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Rumi Haven-Homey&Spacious Stay
Rumi Haven-Homey&Spacious Stay
House
Orlando, FL, USA
0.1k from Crestwynd Bay center

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

3 Bedrooms7 Guests
10.0

Exceptional

1 reviews

$121
Average price / night
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Windsor Hills 205! No Resort Fees! New Water-Park! Great Value!
Windsor Hills 205! No Resort Fees! New Water-Park! Great Value!
Condo
Kissimmee, FL, 34747, United States
0.1k from Crestwynd Bay center

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

3 Bedrooms8 Guests
8.8

Fabulous

45 reviews

$121
Average price / night
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Magical Adventure Condo w Waterpark near Disney No Resort Fees
Magical Adventure Condo w Waterpark near Disney No Resort Fees
Apartment
Orlando, FL, USA
0.1k from Crestwynd Bay center

Apartments, Cheap, Accommodations, Pools, Parking, Serviced apartments, Lodgings, Vacation rentals, Hot tubs

3 Bedrooms8 Guests
9.2

Superb

80 reviews

$212
Average price / night
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New Water Park! Huge Pool, 5 Minutes to Disney World!🏝
New Water Park! Huge Pool, 5 Minutes to Disney World!🏝
Condo
Kissimmee, FL, 34747, United States
0.1k from Crestwynd Bay center

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

2 Bedrooms5 Guests
9.8

Exceptional

280 reviews

$193
Average price / night
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Mickey's Welcome Inn - Closest Resort To Disney
Mickey's Welcome Inn - Closest Resort To Disney
House
Orlando, FL, USA
0.1k from Crestwynd Bay center

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

1 Bedroom6 Guests
9.1

Superb

18 reviews

$164
Average price / night
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Mickey Mouse Condo. Kid friendly Condo in Windsor Hills Resort.2 miles to Disney
Mickey Mouse Condo. Kid friendly Condo in Windsor Hills Resort.2 miles to Disney
Condo
Kissimmee, FL, 34747, United States
0.1k from Crestwynd Bay center

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

2 Bedrooms6 Guests
9.8

Exceptional

173 reviews

$184
Average price / night
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NEW awesome dream house, 5 Min to Disney
NEW awesome dream house, 5 Min to Disney
House
Orlando, FL, USA
0.2k from Crestwynd Bay center

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

4 Bedrooms10 Guests
9.4

Superb

12 reviews

$215
Average price / night
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Getaway with Mickey in Windsor Hills!
Getaway with Mickey in Windsor Hills!
Condo
Kissimmee, FL, 34747, United States
0.1k from Crestwynd Bay center

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

3 Bedrooms6 Guests
9.8

Exceptional

151 reviews

$168
Average price / night
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7671 Comrow Unit 205
7671 Comrow Unit 205
House
Orlando, FL, USA
0.2k from Crestwynd Bay center

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

3 Bedrooms8 Guests
9.0

Fabulous

1 reviews

$116
Average price / night
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Windsor Hills Resort 3 Bedroom 1st Floor Condo with Resort  Access
Windsor Hills Resort 3 Bedroom 1st Floor Condo with Resort Access
Condo
Kissimmee, FL, 34747, United States
0.1k from Crestwynd Bay center

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

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$185
Average price / night
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2785 Almaton #304
2785 Almaton #304
House
Orlando, FL, USA
0.2k from Crestwynd Bay center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Jacuzzis

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$116
Average price / night
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NEW AMAZING vacation home only 5 min.  from Disney
NEW AMAZING vacation home only 5 min. from Disney
House
Kissimmee, FL, 34747, United States
0.1k from Crestwynd Bay center

AC, Arcade, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Hot Tub, Internet

4 Bedrooms10 Guests
9.8

Exceptional

8 reviews

$281
Average price / night
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Magical Wizards Castle
Magical Wizards Castle
Villa
Orlando, FL, USA
0.2k from Crestwynd Bay center

Security/Safety, Ev Charge Station, Oceanfront, Internet, Sports/Activities, Pool, Ocean View

4 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$209
Average price / night
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Tito's Beachy Townhouse, 1.5 miles from Disney
Tito's Beachy Townhouse, 1.5 miles from Disney
House
Kissimmee, FL, 34747, United States
0.1k from Crestwynd Bay center

AC, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$196
Average price / night
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POOL VIEW 3 Bedroom Condo at Windsor Hills 'The Lido Deck'
POOL VIEW 3 Bedroom Condo at Windsor Hills 'The Lido Deck'
Apartment
Orlando, FL, USA
0.2k from Crestwynd Bay center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Jacuzzis, Places to stay, Family

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$153
Average price / night
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☆✴2 miles to Disney, W/Free WaterPark, Heated Pool, Hot tub, Game Room🕹 Mickey☆
☆✴2 miles to Disney, W/Free WaterPark, Heated Pool, Hot tub, Game Room🕹 Mickey☆
Condo
Kissimmee, FL, 34747, United States
0.1k from Crestwynd Bay center

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

3 Bedrooms7 Guests
9.8

Exceptional

34 reviews

$394
Average price / night
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DLuxx Vacay Disney 5 Suite House with Hot Tub 2633
DLuxx Vacay Disney 5 Suite House with Hot Tub 2633
House
Orlando, FL, USA
0.2k from Crestwynd Bay center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Hot tubs

5 Bedrooms12 Guests
9.2

Superb

8 reviews

$298
Average price / night
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Sunny Rays Escape in Windsor Hills Resort
Sunny Rays Escape in Windsor Hills Resort
Apartment
Kissimmee, FL, 34747, United States
0.1k from Crestwynd Bay center

AC, Arcade, Balcony, Dryer, Elevator, Fitness Equipment, Heater, Internet, Kitchen

3 Bedrooms6 Guests
9.6

Exceptional

104 reviews

$189
Average price / night
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Incredibles Hideaway in Windsor Hills Resort
Incredibles Hideaway in Windsor Hills Resort
Apartment
Four Corners, FL, 34747, United States
0.2k from Crestwynd Bay center

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

3 Bedrooms8 Guests
9.4

Superb

134 reviews

$171
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

3 Bedrooms8 Guests
9.0

Fabulous

28 reviews

$179
Average price / night
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🌞🌞 Your Perfect Stay for Sun, Fun and Everything Relaxation Retreat!!! 🌞🌞
🌞🌞 Your Perfect Stay for Sun, Fun and Everything Relaxation Retreat!!! 🌞🌞
Condo
Kissimmee, FL, 34747, United States
0.2k from Crestwynd Bay center

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

3 Bedrooms7 Guests
10.0

Exceptional

1 reviews

$202
Average price / night
Check Availability
Harry Potter\\Star Wars\\Toy Story\\Mickey Mouse\\Waterpark Condo 3 Miles to Disney
Harry Potter\\Star Wars\\Toy Story\\Mickey Mouse\\Waterpark Condo 3 Miles to Disney
Condo
Kissimmee, FL, 34747, United States
0.2k from Crestwynd Bay center

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

3 Bedrooms8 Guests
New to Booking
$229
Average price / night
Check Availability
Windsor Hills 3BR Condo — Near Disney
Windsor Hills 3BR Condo — Near Disney
Villa
Kissimmee, FL, 34747, United States
0.2k from Crestwynd Bay center

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

4 Bedrooms6 Guests
New to Booking
$199
Average price / night
Check Availability
Galaxy and Ears Getaway ★ Star Wars Themed 2BR ★ 2 Mi to Disney ★ Free Waterpark
Galaxy and Ears Getaway ★ Star Wars Themed 2BR ★ 2 Mi to Disney ★ Free Waterpark
Condo
Kissimmee, FL, 34747, United States
0.2k from Crestwynd Bay center

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

2 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$221
Average price / night
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Windsor Hills 3BR Condo — Near Disney Parks
Windsor Hills 3BR Condo — Near Disney Parks
Villa
Kissimmee, FL, 34747, United States
0.2k from Crestwynd Bay center

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

4 Bedrooms6 Guests
New to Booking
$204
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 Beach 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 Beach Rentals on the Map

Frequently Asked Questions

You can explore 892 verified beach rentals in Crestwynd Bay. Our listings are sourced from trusted booking providers, giving you access to a wide selection of oceanfront homes, seaside condos, and coastal stays—all in one place.

Beach rental prices in Crestwynd Bay vary depending on the season, property size, and distance from the shoreline. Rates typically start from around $116 per night, with beachfront properties and peak summer dates often priced higher. Comparing available options can help you find the best fit for your budget.

Many beach rentals in Crestwynd Bay offer direct access to the sand or are located within a short walking distance of the shoreline. You can use filters to find properties with beachfront locations, private walkways, or unobstructed ocean views.

Yes, many beach rentals in Crestwynd Bay welcome pets. Currently, 6 listings allow pets, although policies may vary by property. It’s also a good idea to check local beach regulations for any restrictions on pets during your stay.

For peak travel periods such as summer holidays or spring break, it’s recommended to book your beach rental 90 to 120 days in advance to secure the best options. During off-peak seasons, you may find more flexibility and availability closer to your travel dates.

Beach rentals in Crestwynd Bay often include amenities designed for coastal living, such as Ocean View, View, and Child Friendly. These features help enhance comfort and make it easier to enjoy time by the water.

Some beach rentals provide extras like chairs, umbrellas, or beach gear, but this can vary by property. It’s best to review the amenities section of each listing to confirm what is included and plan accordingly.