Compare Winter Springs Villas

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Villas in Winter Springs

Walk to Lake: Stunning Central Florida Home!

Walk to Lake: Stunning Central Florida Home!

Guests staying at this villa enjoy an outdoor pool, a sauna, and free WiFi in public areas. Onsite parking is available for a fee. Other amenities at this family-friendly villa include a hot tub, laundry facilities, and barbecue grills.
Pool
Hot Tub
Resort style family friendly vacation villa

Resort style family friendly vacation villa

$362 nightly
The price is $402 total per night
$402 total
May 20 - May 21
Total includes taxes and fees
Guests of this villa enjoy features like an outdoor pool, a gym, and an arcade/game room. Additional amenities include laundry facilities and barbecue grills.
Vista Cay Modern

Vista Cay Modern

4 out of 5
4846 Tidecrest Ave #192, Orlando, FL
Guests of this villa enjoy features like an outdoor pool, a gym, and an ATM. If you decide to drive, there's free offsite parking.
Pool
Kitchen
6B/5B Estate on 2+ Acres W/Pool, Guesthouse, Theater & More

6B/5B Estate on 2+ Acres W/Pool, Guesthouse, Theater & More

Guests staying at this villa have access to laundry facilities, barbecue grills, and a garden. Transportation is made easy with limo/town car service. Helpful staff is there to provide concierge services, as well as offer insight about the area.
Enchanted 2 Bedroom Home near Downtown Winter Garden

Enchanted 2 Bedroom Home near Downtown Winter Garden

Guests staying at this villa have access to laundry facilities, barbecue grills, and a garden.
Renovated Condo by Convention Center & I-drive

Renovated Condo by Convention Center & I-drive

4 out of 5
4114 Breakview Drive #109, Orlando, FL
At this villa, guests enjoy an outdoor pool, a gym, and free WiFi in public areas. A stay here includes free parking. Friendly staff can provide concierge services, and also offer advice about sightseeing. Other amenities at this family-friendly villa include an arcade/game room and barbecue grills.
Elegant and Spacious 3BD Town Home With CDC Standards - Close to Convention Center #3vc007

Elegant and Spacious 3BD Town Home With CDC Standards - Close to Convention Center #3vc007

3.5 out of 5
5014 Tideview Circle, Orlando, FL
An outdoor pool and free WiFi in public areas are features at this villa. Free parking is available if you drive.
4,800 sf Estate | Pool, Lake, Weddings and Events

4,800 sf Estate | Pool, Lake, Weddings and Events

$851 nightly
The price is $942 total per night
$942 total
May 13 - May 14
Total includes taxes and fees
Guests staying at this villa enjoy a water park, a hot tub, and laundry facilities. Other amenities at this family-friendly villa include a garden and barbecue grills.
Majestic Dreams

Majestic Dreams

4 out of 5
4845 Tidecrest Avenue #145, Orlando, FL
Guests of this villa enjoy features like an outdoor pool, a gym, and an arcade/game room. If you decide to drive, there's free parking. Other amenities at this family-friendly villa include an ATM and barbecue grills.
Pool
Kitchen
Don't see what you're looking for?
See all available properties in Winter Springs
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotel Options in Winter Springs

    DoubleTree by Hilton at the Entrance to Universal Orlando

    DoubleTree by Hilton at the Entrance to Universal Orlando

    5780 Major Blvd, Orlando, FL
    $93 nightly
    The price is $104 total per night from May 22 to May 23
    $104 total
    May 22 - May 23
    Total includes taxes and fees
    8.2/10 Very Good! (6,246 reviews)
    Hyatt Regency Orlando International Airport

    Hyatt Regency Orlando International Airport

    9300 Jeff Fuqua Boulevard, Orlando, FL
    $179 nightly
    The price is $201 total per night from May 19 to May 20
    $201 total
    May 19 - May 20
    Total includes taxes and fees
    9.2/10 Wonderful! (3,238 reviews)
    Universal's Cabana Bay Beach Resort

    Universal's Cabana Bay Beach Resort

    6550 Adventure Way, Orlando, FL
    $205 nightly
    The price is $231 total per night from May 28 to May 29
    $231 total
    May 28 - May 29
    Total includes taxes and fees
    8.8/10 Excellent! (5,192 reviews)

Luxury Villas

Book luxury villas in Winter Springs
There are plenty of ways to up your vacation game, but one of the best is by staying in a luxury villa in Winter Springs. Villas, with their thoughtful layout and elegant décor, let you travel in style. They come in a variety of sizes and offer a great experience, whether you’re traveling on your own or with a group of friends. Orbitz has fantastic deals on villas in Winter Springs, so book one now. You’ll feel like a million bucks before you even check in.

Spacious luxury villas in Winter Springs
You won’t have a problem finding your own space in Winter Springs. If you’re traveling in a group, go for a three-bedroom or larger villa; separate bedrooms can make it that much easier to keep the peace, especially when you’re all staying in one house. You can also explore Winter Springs on your own and use a one-bedroom villa as your home base.

A top-end villa experience in Winter Springs rivals that of a luxury resort. Float in a swimming pool with an elaborate mosaic bottom, work out in your own gym, and let the daily housekeeping staff clean up after you while a private chef whips up one delicious meal after another. This is the life!

Winter Springs Villas essential information

Accommodation
74 Villas
Lowest Price
$104 total
Highest Price
$942 total
Popular accommodation
Walk to Lake: Stunning Central Florida Home!, Resort style family friendly vacation villa, Vista Cay Modern, 6B/5B Estate on 2+ Acres W/Pool, Guesthouse, Theater & More, Enchanted 2 Bedroom Home near Downtown Winter Garden, Renovated Condo by Convention Center & I-drive, Elegant and Spacious 3BD Town Home With CDC Standards - Close to Convention Center #3vc007, 4,800 sf Estate | Pool, Lake, Weddings and Events, Majestic Dreams

Villas in Winter Springs

Most Popular

More Places To Stay in Winter Springs