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

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5219 Best Villa Rentals in Crestwynd Bay (Starting from $119)

5 BR 6 BA Luxury Villa 5 min to Disneyworld 2169ft² BBQ
5 BR 6 BA Luxury Villa 5 min to Disneyworld 2169ft² BBQ
Villa
Orlando, FL, USA
0.1k from Crestwynd Bay center

Luxury, Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings

5 Bedrooms12 Guests
8.4

Very Good

22 reviews

$190
Average price / night
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♥ 5 BR 6 BA Villa 5min→Disneyworld | 2169ft² | BBQ
♥ 5 BR 6 BA Villa 5min→Disneyworld | 2169ft² | BBQ
Villa
Kissimmee, FL, 34747, United States
0.1k from Crestwynd Bay center

AC, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Microwave, No Smoking, Pool

5 Bedrooms12 Guests
New to Booking
$394
Average price / night
Check Availability
4 BR 4 BA Deluxe Villa 1804ft² 5min to Disney Parks
4 BR 4 BA Deluxe Villa 1804ft² 5min to Disney Parks
Villa
Orlando, FL, USA
0.1k from Crestwynd Bay center

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

4 Bedrooms10 Guests
8.9

Fabulous

13 reviews

$409
Average price / night
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★ 3 BR 3 BA Villa | 5min→Disneyworld | BBQ Grill ★
★ 3 BR 3 BA Villa | 5min→Disneyworld | BBQ Grill ★
Villa
Kissimmee, FL, 34747, United States
0.1k from Crestwynd Bay center

AC, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Microwave, No Smoking, Pool

3 Bedrooms10 Guests
New to Booking
$311
Average price / night
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3 BR 3 BA Villa 5min to Disneyworld BBQ Grill
3 BR 3 BA Villa 5min to Disneyworld BBQ Grill
Villa
Orlando, FL, USA
0.1k from Crestwynd Bay center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

4 Bedrooms8 Guests
New to Booking
$119
Average price / night
Check Availability
4 BR 4 BA Villa | 5min→Disneyworld |1804ft² | BBQ
4 BR 4 BA Villa | 5min→Disneyworld |1804ft² | BBQ
Villa
Kissimmee, FL, 34747, United States
0.1k from Crestwynd Bay center

AC, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Microwave, No Smoking

4 Bedrooms10 Guests
New to Booking
$335
Average price / night
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Summerville: 4BR3.5B Brand New Luxury Retreat
Summerville: 4BR3.5B Brand New Luxury Retreat
Villa
Orlando, FL, USA
0.2k from Crestwynd Bay center

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

5 Bedrooms10 Guests
8.5

Very Good

6 reviews

$189
Average price / night
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4BD All Suites Home with BBQ minutes from Disney
4BD All Suites Home with BBQ minutes from Disney
Villa
Kissimmee, FL, 34747, United States
0.2k from Crestwynd Bay center

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

4 Bedrooms8 Guests
New to Booking
$422
Average price / night
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5 BR 6 BA Luxury Villa 5min to Disneyworld SMV154
5 BR 6 BA Luxury Villa 5min to Disneyworld SMV154
Villa
Orlando, FL, USA
0.2k from Crestwynd Bay center

Luxury, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

5 Bedrooms12 Guests
New to Booking
$257
Average price / night
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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
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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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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
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Unwind at Orlando Condo 6419 - Ideal Family Getaway
Unwind at Orlando Condo 6419 - Ideal Family Getaway
Villa
Orlando, FL, USA
0.2k from Crestwynd Bay center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Accessible hotels, Condos

3 Bedrooms6 Guests
New to Booking
$366
Average price / night
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Orlando 4BR Townhome Summerville Resort
Orlando 4BR Townhome Summerville Resort
Villa
Kissimmee, FL, 34747, United States
0.2k from Crestwynd Bay center

AC, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave

4 Bedrooms8 Guests
New to Booking
$295
Average price / night
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Orlando Condo 6428: Your 5-Star Family Getaway
Orlando Condo 6428: Your 5-Star Family Getaway
Villa
Orlando, FL, USA
0.2k from Crestwynd Bay center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Accessible hotels, Condos

1 Bedroom8 Guests
New to Booking
$245
Average price / night
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4BR Disney-Themed Townhome
4BR Disney-Themed Townhome
Villa
kissimmee, FL, 34747, United States
0.2k from Crestwynd Bay center

AC, Crib, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

4 Bedrooms10 Guests
New to Booking
$290
Average price / night
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Serene 3 Bedroom Retreat in Orlando6494
Serene 3 Bedroom Retreat in Orlando6494
Villa
Orlando, FL, USA
0.2k from Crestwynd Bay center

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

1 Bedroom7 Guests
New to Booking
$219
Average price / night
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4BR Townhome 15min to Disney
4BR Townhome 15min to Disney
Villa
Kissimmee, FL, 34747, United States
0.2k from Crestwynd Bay center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Living Area

5 Bedrooms9 Guests
New to Booking
$293
Average price / night
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Stunning 2 Bedroom Retreat in Orlando6496
Stunning 2 Bedroom Retreat in Orlando6496
Villa
Orlando, FL, USA
0.2k from Crestwynd Bay center

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

1 Bedroom4 Guests
New to Booking
$201
Average price / night
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♥ 4 BR 4 BA Villa | 5min→Disneyworld |1804ft²| Gym
♥ 4 BR 4 BA Villa | 5min→Disneyworld |1804ft²| Gym
Villa
Kissimmee, FL, 34747, United States
0.2k from Crestwynd Bay center

AC, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Microwave, No Smoking, Pool

4 Bedrooms10 Guests
New to Booking
$367
Average price / night
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Orlando Paradise: 3 Bed Condo6505
Orlando Paradise: 3 Bed Condo6505
Villa
Orlando, FL, USA
0.2k from Crestwynd Bay center

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

3 Bedrooms6 Guests
New to Booking
$202
Average price / night
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☀ New 4 BR 4 BA Villa | Ground Zero to Theme Parks
☀ New 4 BR 4 BA Villa | Ground Zero to Theme Parks
Villa
Kissimmee, FL, 34747, United States
0.2k from Crestwynd Bay center

AC, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Microwave, No Smoking, Pool

4 Bedrooms8 Guests
New to Booking
$385
Average price / night
Check Availability
5 BR 6 BA Luxury Villa 5 min to Disneyworld Hot Tub & BBQ
5 BR 6 BA Luxury Villa 5 min to Disneyworld Hot Tub & BBQ
Villa
Orlando, FL, USA
0.2k from Crestwynd Bay center

Luxury, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

5 Bedrooms10 Guests
9.7

Exceptional

3 reviews

$158
Average price / night
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✧5min→Disneyworld✧Self Check-In✧BBQ✧Full Kitchen
✧5min→Disneyworld✧Self Check-In✧BBQ✧Full Kitchen
Villa
Kissimmee, FL, 34747, United States
0.2k from Crestwynd Bay center

AC, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Microwave, No Smoking, Pool

4 Bedrooms10 Guests
New to Booking
$392
Average price / night
Check Availability
♥ 4 BR 4 BA | Full Kitchen ♥A/C♥ 5min→Disneyworld
♥ 4 BR 4 BA | Full Kitchen ♥A/C♥ 5min→Disneyworld
Villa
Kissimmee, FL, 34747, United States
0.2k from Crestwynd Bay center

AC, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Microwave, No Smoking, Pool

4 Bedrooms8 Guests
New to Booking
$364
Average price / night
Check Availability
★ 3 BR 3BA Villa 5min→Disneyworld | Hot Tub | BBQ
★ 3 BR 3BA Villa 5min→Disneyworld | Hot Tub | BBQ
Villa
Kissimmee, FL, 34747, United States
0.2k from Crestwynd Bay center

AC, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Microwave, No Smoking

3 Bedrooms10 Guests
New to Booking
$320
Average price / night
Check Availability
★ 4 BR 4 BA Hidden Gem | Min ➡️ Disney | 1804ft² ❤
★ 4 BR 4 BA Hidden Gem | Min ➡️ Disney | 1804ft² ❤
Villa
Kissimmee, FL, 34747, United States
0.2k from Crestwynd Bay center

AC, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Microwave, No Smoking, Pool

4 Bedrooms9 Guests
New to Booking
$346
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 Villa Rentals in Crestwynd Bay.

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Crestwynd Bay Villa Rentals on the Map

Frequently Asked Questions

You can currently explore 5219 verified villa rentals in Crestwynd Bay. Our listings are sourced from multiple leading booking platforms, giving you a broad and up-to-date selection of luxury and private villas in one place.

Villa prices in Crestwynd Bay vary depending on the season, location, and amenities. Rates typically start from around $119 per night, with premium properties costing more during peak travel periods. Comparing options across different platforms can help you find the best value for your dates.

Many villas in Crestwynd Bay are designed for privacy and comfort, and a large number of them feature private pools. You can easily filter your search to find villas with pools, helping you choose the perfect stay for relaxation or group travel in Crestwynd Bay.

Yes, Crestwynd Bay offers a wide range of villas ideal for group stays. Many properties include 3 or more bedrooms, making them well-suited for family gatherings, events, or trips with friends. You can filter by bedroom count to quickly find options that match your group size.

For popular travel periods, it’s generally recommended to book your Crestwynd Bay villa around 60 to 90 days in advance to secure the best selection. However, since we compare 10+ sites, it’s still possible to find great last-minute options even 2 to 4 weeks before your trip.

Villas in Crestwynd Bay often include highly sought-after amenities such as Child Friendly, Fireplace/Heating, and Wellness Facilities. These features enhance comfort and convenience, making them especially popular among travelers visiting Crestwynd Bay.

To discover top-rated villas in Crestwynd Bay, you can sort listings by guest ratings and reviews. Our platform aggregates feedback from multiple trusted sources, helping you identify highly rated properties based on real guest experiences. Use the "Rating" filter above to start your search.