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

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1740 Best Oceanfront 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 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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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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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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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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Windsor Hills 402B No Resort Fees! New Water-Park! Close to Pool and Lakeview
Windsor Hills 402B No Resort Fees! New Water-Park! Close to Pool and Lakeview
Condo
Kissimmee, FL, 34747, United States
0.2k from Crestwynd Bay center

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

2 Bedrooms6 Guests
9.0

Fabulous

55 reviews

$152
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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Updated Windsor Hills Largest Condo - Family Water Park Fun & Near Disney Parks
Updated Windsor Hills Largest Condo - Family Water Park Fun & Near Disney Parks
Condo
Kissimmee, FL, 34747, United States
0.2k from Crestwynd Bay center

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

3 Bedrooms7 Guests
9.4

Superb

122 reviews

$187
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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Magical Moments Await: Delight in a One-of-a-Kind Windsor Hills Condo!
Magical Moments Await: Delight in a One-of-a-Kind Windsor Hills Condo!
Condo
Kissimmee, FL, 34747, United States
0.2k from Crestwynd Bay center

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

3 Bedrooms6 Guests
9.4

Superb

33 reviews

$203
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 Condo w/all things Mickey. Pool/Waterpark and minutes from Disney!
Windsor Hills Condo w/all things Mickey. Pool/Waterpark and minutes from Disney!
Condo
Kissimmee, FL, 34747, United States
0.2k from Crestwynd Bay center

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

2 Bedrooms6 Guests
9.6

Exceptional

32 reviews

$157
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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Newly Renovated! Your Disney Getaway! Water slides, pool arcade and more!
Newly Renovated! Your Disney Getaway! Water slides, pool arcade and more!
Condo
Kissimmee, FL, 34747, United States
0.2k from Crestwynd Bay center

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

3 Bedrooms7 Guests
9.6

Exceptional

155 reviews

$200
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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Magical Residence Resort, 5 min Disney
Magical Residence Resort, 5 min Disney
House
Kissimmee, FL, 34747, United States
0.3k from Crestwynd Bay center

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

4 Bedrooms10 Guests
10.0

Exceptional

35 reviews

$531
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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Stay in this wonderful home just 3 miles from Disney World!
Stay in this wonderful home just 3 miles from Disney World!
House
Kissimmee, FL, 34747, United States
0.4k from Crestwynd Bay center

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

6 Bedrooms12 Guests
9.8

Exceptional

13 reviews

$463
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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Minutes Away from Theme Parks! 3-Bed Townhome, 6 minutes to Disney World!
Minutes Away from Theme Parks! 3-Bed Townhome, 6 minutes to Disney World!
House
Kissimmee, FL, 34747, United States
0.4k from Crestwynd Bay center

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

3 Bedrooms6 Guests
10.0

Exceptional

201 reviews

$238
Average price / night
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DLuxx Top Vacay 4 Miles from Disney 5 suites 7599
DLuxx Top Vacay 4 Miles from Disney 5 suites 7599
House
Orlando, FL, USA
0.2k from Crestwynd Bay center

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

5 Bedrooms13 Guests
9.4

Superb

5 reviews

$294
Average price / night
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☆ Location matters! Private palm paradise view from pool - 1 block to waterpark
☆ Location matters! Private palm paradise view from pool - 1 block to waterpark
Villa
Kissimmee, FL, 34747, United States
0.4k from Crestwynd Bay center

AC, Arcade, Barbecue, Breakfast Available, Crib, Dryer, Fitness Equipment, Free Parking, Heater

5 Bedrooms10 Guests
10.0

Exceptional

24 reviews

$326
Average price / night
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2 Miles to Disney - 20 sec Walk to Clubhouse - Private Pool - Free Water Park
2 Miles to Disney - 20 sec Walk to Clubhouse - Private Pool - Free Water Park
House
Kissimmee, FL, 34747, United States
0.5k from Crestwynd Bay center

AC, Arcade, Barbecue, Dryer, Extra Bed, Fitness Equipment, Free Parking, Heater, Hot Tub

3 Bedrooms8 Guests
9.6

Exceptional

214 reviews

$231
Average price / night
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Vacation in the Sun! Spacious 3 Bedroom, 6 minutes from Disney World!
Vacation in the Sun! Spacious 3 Bedroom, 6 minutes from Disney World!
House
Kissimmee, FL, 34747, United States
0.5k from Crestwynd Bay center

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

3 Bedrooms6 Guests
10.0

Exceptional

111 reviews

$254
Average price / night
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Amazing Lakeview Windsor Hills resort, 6BR, 2 massage chairs
Amazing Lakeview Windsor Hills resort, 6BR, 2 massage chairs
Villa
Kissimmee, FL, 34747, United States
0.5k from Crestwynd Bay center

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

6 Bedrooms14 Guests
10.0

Exceptional

58 reviews

$664
Average price / night
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Lakefront Windsor Hills - 6 Bed 4 Bath Home with Custom Mickey Mouse Heated Pool
Lakefront Windsor Hills - 6 Bed 4 Bath Home with Custom Mickey Mouse Heated Pool
House
Kissimmee, FL, 34747, United States
0.5k from Crestwynd Bay center

AC, Arcade, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

6 Bedrooms12 Guests
10.0

Exceptional

29 reviews

$422
Average price / night
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Massive Windsor Hills Private Pool Home! 2638 Daulby- Don't Miss This!
Massive Windsor Hills Private Pool Home! 2638 Daulby- Don't Miss This!
House
Kissimmee, FL, 34747, United States
0.5k from Crestwynd Bay center

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

6 Bedrooms14 Guests
9.6

Exceptional

19 reviews

$217
Average price / night
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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 Oceanfront 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 Oceanfront Rentals on the Map

Frequently Asked Questions

You can explore 1740 verified oceanfront rentals in Crestwynd Bay. These properties are located directly along the shoreline, offering uninterrupted access to the beach and ocean views.

Oceanfront rental prices in Crestwynd Bay vary depending on the property size, exact beachfront location, and season. Rates typically start from around $116 per night, with higher prices for larger homes or peak travel periods. Properties located directly on popular stretches of coastline tend to command premium rates.

Many oceanfront rentals in Crestwynd Bay offer direct access to the beach, often through private walkways or dedicated entry paths. Some properties may share access points, so it’s helpful to review the listing details to understand the type of beach access provided.

Yes, some oceanfront rentals in Crestwynd Bay welcome pets. Currently, 11 listings allow pets, although policies can vary by property. It’s recommended to check specific house rules for details such as size limits or additional fees.

Oceanfront properties are often in high demand, especially during peak travel seasons, so booking 90 to 120 days in advance is recommended for the best selection. During quieter periods, you may still find availability closer to your travel dates.

Oceanfront rentals in Crestwynd Bay often include features designed for a comfortable coastal stay, such as Child Friendly, Pool, and Ocean View. These amenities help guests make the most of their time by the water.

Yes, there is a clear difference. "Oceanfront" means the property is located directly on the beach with no obstructions between the home and the water. "Ocean View" typically means the ocean is visible from certain angles or rooms, but the property may not be right on the shoreline.