Book Holiday Homes in Winter Springs

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Featured Holiday Homes in Winter Springs

Vista Cay Resort by Casiola Vacation Homes

Vista Cay Resort by Casiola Vacation Homes

3.5 out of 5
4874 Cayview Ave, Orlando, FL
The price is NZ$710 per night from 16 Jan to 17 Jan
NZ$710
includes taxes & fees
16 Jan - 17 Jan
Stay at this 3.5-star family-friendly vacation home in Orlando. Enjoy free WiFi, free parking, and 3 outdoor pools. Popular attractions Orlando International ...
Vista Cay Resort by Casiola Vacation Homes
Charming and Cozy  home in Altamonte Springs

Charming and Cozy home in Altamonte Springs

Altamonte Springs
The price is NZ$679 per night from 15 Jan to 16 Jan
NZ$679
includes taxes & fees
15 Jan - 16 Jan
Stay at this vacation home in Altamonte Springs. Enjoy free WiFi, private pools, and a garden. Popular attractions Altamonte Mall and Cranes Roost Park are located ...
Charming and Cozy home in Altamonte Springs
Sleeps 10 + Pool and Fully Fenced Yard plus enjoys 2 King Rooms

Sleeps 10 + Pool and Fully Fenced Yard plus enjoys 2 King Rooms

Orlando
Book a stay at this family-friendly vacation home in Orlando. Enjoy free WiFi, private pools, and a garden. Popular attractions Orlando International Premium ...
Sleeps 10 + Pool and Fully Fenced Yard plus enjoys 2 King Rooms
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Lake Vibes Only ~ Intimate Lake Cottage in Mount Dora

Lake Vibes Only ~ Intimate Lake Cottage in Mount Dora

Mount Dora
Book a stay at this family-friendly vacation home in Mount Dora. Enjoy free WiFi, a water park, and a garden. Popular attractions Trimble Park and Gilbert Park ...
Lake Vibes Only ~ Intimate Lake Cottage in Mount Dora
East Orlando Getaway - 3BR/2BTH * Private Pool

East Orlando Getaway - 3BR/2BTH * Private Pool

Orlando
The price is NZ$864 per night from 13 Jan to 14 Jan
NZ$864
includes taxes & fees
13 Jan - 14 Jan
Stay at this vacation home in Orlando. Enjoy free WiFi, private pools, and a water park. Popular attractions Rio Pinar Country Club and Boardwalk Bowl Entertainment ...
East Orlando Getaway - 3BR/2BTH * Private Pool
Beautiful home close to Parks

Beautiful home close to Parks

Orlando
Stay at this vacation home in Orlando. Enjoy free WiFi and air conditioning. Popular attractions Kia Center and Orlando International Premium Outlets are located ...
Beautiful home close to Parks
Private Luxury Pool / Smart-home

Private Luxury Pool / Smart-home

Orlando
Book a stay at this family-friendly vacation home in Orlando. Enjoy free WiFi, private pools, and a water park. Popular attractions Kia Center and Camping World ...
Private Luxury Pool / Smart-home
Full House with Big Fenced Backyard, Washer & Dryer / Pet-Friendly.

Full House with Big Fenced Backyard, Washer & Dryer / Pet-Friendly.

2 out of 5
Orlando
The price is NZ$513 per night from 14 Jan to 15 Jan
NZ$513
includes taxes & fees
14 Jan - 15 Jan
Book a stay at this family-friendly vacation home in Orlando. Enjoy a water park, a garden, and an in-room coffeemaker. Popular attractions Kia Center and Orlando ...
Full House with Big Fenced Backyard, Washer & Dryer / Pet-Friendly.
Large, beautiful, very comfortable one bedroom on small lake

Large, beautiful, very comfortable one bedroom on small lake

Orlando
The price is NZ$608 per night from 13 Jan to 14 Jan
NZ$608
includes taxes & fees
13 Jan - 14 Jan
Book a stay at this family-friendly vacation home in Orlando. Enjoy free WiFi, a water park, and a fitness center. Popular attractions Kia Center and Florida ...
Large, beautiful, very comfortable one bedroom on small lake
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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.

Winter Springs Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Winter Springs vacation homes are the perfect way for you to wing it.

Holiday houses in Winter Springs let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Winter Springs in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Winter Springs adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Winter Springs with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Winter Springs vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Winter Springs Holiday Homes essential information

Accommodation
1294 Holiday Homes
Lowest Price
NZ$188
Highest Price
NZ$864
Popular accommodation
Vista Cay Resort by Casiola Vacation Homes, Charming and Cozy home in Altamonte Springs, Sleeps 10 + Pool and Fully Fenced Yard plus enjoys 2 King Rooms, Lake Vibes Only ~ Intimate Lake Cottage in Mount Dora, East Orlando Getaway - 3BR/2BTH * Private Pool, Beautiful home close to Parks, Private Luxury Pool / Smart-home, Full House with Big Fenced Backyard, Washer & Dryer / Pet-Friendly., Large, beautiful, very comfortable one bedroom on small lake

Top trending hotels in Winter Springs

Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

4 out of 5
9300 Jeff Fuqua Boulevard, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is NZ$464 per night from 20 Jan to 21 Jan
NZ$464
includes taxes & fees
20 Jan - 21 Jan
Stay at this 4-star eco-certified hotel in Orlando. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the restaurant ...
Hyatt Regency Orlando International Airport
DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

4 out of 5
5780 Major Blvd, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is NZ$188 per night from 19 Jan to 20 Jan
NZ$188
includes taxes & fees
19 Jan - 20 Jan
Stay at this 4-star family-friendly hotel in Orlando. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the pool and the helpful staff in ...
DoubleTree by Hilton at the Entrance to Universal Orlando
Universal's Endless Summer Resort - Dockside Inn and Suites

Universal's Endless Summer Resort - Dockside Inn and Suites

3 out of 5
7125 Universal Boulevard, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is NZ$251 per night from 15 Jan to 16 Jan
NZ$251
includes taxes & fees
15 Jan - 16 Jan
Stay at this 3-star family-friendly hotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and 3 bars/lounges. Our guests praise the pool and the restaurant in ...
Universal's Endless Summer Resort - Dockside Inn and Suites
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Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

3.5 out of 5
6550 Adventure Way, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is NZ$375 per night from 16 Jan to 17 Jan
NZ$375
includes taxes & fees
16 Jan - 17 Jan
Stay at this 3.5-star family-friendly hotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
Universal's Cabana Bay Beach Resort
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.