Winter Springs holiday rentals

We found 18,357 holiday rentals — enter your dates for availability
Discover a selection of 9 homes and other holiday rentals in Winter Springs that are perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday homes have the amenities that you need and want for your stay, including parking and a TV. At the end of the day, you'll find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Winter Springs

Showing deals for:1 Jan - 8 Jan

Interior
Terrace/patio
Pool
Room
Exceptional
(115 reviews)

Lake Front Suite -Close to all Attractions

Apopka

8% off
AU$1,010
for 7 nights, 1 home
AU$144 per night
includes taxes & fees
Lake Front Suite -Close to all Attractions
Living area
Living area
Interior
Private kitchen
Exceptional
(6 reviews)

A comfortable home close to the city, yet tucked away from the noise.

Orlando

7% off
AU$1,944
for 7 nights, 1 home
AU$278 per night
includes taxes & fees
A comfortable home close to the city, yet tucked away from the noise.
Property grounds
Marina
Marina
Interior
Exceptional
(73 reviews)

Downtown Floating Bungalow Historic Sanford Lake Monroe Marina

Sanford

8% off
AU$1,920
for 7 nights, 1 houseboat
AU$274 per night
includes taxes & fees
Downtown Floating Bungalow Historic Sanford Lake Monroe Marina
Marina
Marina
Private kitchen
Exterior
Exceptional
(35 reviews)

Luxury Floating House - Boat Tree Marina on St. John’s River, Sanford

Sanford

8% off
AU$1,600
for 7 nights, 1 houseboat
AU$229 per night
includes taxes & fees
Luxury Floating House - Boat Tree Marina on St. John’s River, Sanford
Pool
Pool
Exterior
Exterior
Exceptional
(128 reviews)

Last-minute special, NEW beds/AC/pool heater/laminate floor, park view!

Kissimmee

7% off
AU$2,063
for 7 nights, 1 villa
AU$295 per night
includes taxes & fees
Last-minute special, NEW beds/AC/pool heater/laminate floor, park view!
Private kitchen
Interior
Interior
Exterior
Wonderful
(19 reviews)

Family friendly home in Sanford

Sanford

7% off
AU$2,190
for 7 nights, 1 home
AU$313 per night
includes taxes & fees
Family friendly home in Sanford
Living area
Room
Living area
Private kitchen
Exceptional
(19 reviews)

Sanford's Sunset - Pet-friendly home, 4BR/sleeps 10

Lake Mary

8% off
AU$3,714
for 7 nights, 1 home
AU$531 per night
includes taxes & fees
Sanford's Sunset - Pet-friendly home, 4BR/sleeps 10
Additional Upstairs Lounge Area with Air Hockey Table
Lots of Lounge Space for Everyone!
Private Games Room with Pool Table
Private Swimming Pool and Hottub
Wonderful
(38 reviews)

Upstay: Modern Home w Pool, Games & BBQ—Sleeps 18

Kissimmee

7% off
AU$6,421
for 7 nights, 1 home
AU$917 per night
includes taxes & fees
Upstay: Modern Home w Pool, Games & BBQ—Sleeps 18
Expansive Living Room with Smart TV and High Speed WiFi
Large Swimming Pool, Hot Tub and Private Garden Facing Sundeck
In House Movie Theatre
Fun Games Room with Foosball, Table Tennis and Pool
Excellent
(19 reviews)

Upstay—Vibrant Home w Themed Rooms, Pool & Games

Kissimmee

7% off
AU$5,305
for 7 nights, 1 home
AU$758 per night
includes taxes & fees
Upstay—Vibrant Home w Themed Rooms, Pool & Games
No Quarters Needed!
Professional Arcade Room
Brand New in 2024
All Games Set to "Free-Play"
Exceptional
(26 reviews)

Welcome to The Windsor Treasure with Professional Arcade Room! Brand New 2024!

Kissimmee

10% off
AU$6,097
for 7 nights, 1 villa
AU$871 per night
includes taxes & fees
Welcome to The Windsor Treasure with Professional Arcade Room! Brand New 2024!
Indoor Family Dining Area
Private Swimming Pool with Sun Loungers
King bedroom with en-suite bathroom
Living Room with Smart TV and High Speed Internet
Wonderful
(7 reviews)

Spacious 4BR Family Townhouse—Private Pool & BBQ

Kissimmee

8% off
AU$3,737
for 7 nights, 1 home
AU$534 per night
includes taxes & fees
Spacious 4BR Family Townhouse—Private Pool & BBQ
Games room
Pool
Room
Games room
Very good
(10 reviews)

290 LF - BellaVida Cozy 6BR Pool Home

Kissimmee

11% off
AU$2,615
for 7 nights, 1 home
AU$374 per night
includes taxes & fees
290 LF - BellaVida Cozy 6BR Pool Home
Garage-turned-games-room with, foosball, game consoles and more!
Luxury Patio with Private Pool and Hot Tub, Games, Smart TVs, BBQ and more.
Large Capacity Living Area with 3 Big Screen TVs
Private Movie Theatre with giant projection screen and cinema style recliners
Excellent
(15 reviews)

Upstay Family Resort Mansion- Pool, Games, Theater

Kissimmee

8% off
AU$10,752
for 7 nights, 1 home
AU$1,536 per night
includes taxes & fees
Upstay Family Resort Mansion- Pool, Games, Theater
Immersive Luigi's Mansion
Brand New Professional Arcade Room
Skee-Ball and Basketball (All Free-Play)
Professional Air Hockey
Exceptional
(203 reviews)

Welcome to The Windsor Magic with Professional Arcade Room! Brand New 2024!

Kissimmee

10% off
AU$6,361
for 7 nights, 1 home
AU$909 per night
includes taxes & fees
Welcome to The Windsor Magic with Professional Arcade Room! Brand New 2024!
Property grounds
Pool
Exterior
Private kitchen
Exceptional
(19 reviews)

Luxary villa close to disney

Kissimmee

7% off
AU$2,593
for 7 nights, 1 villa
AU$370 per night
includes taxes & fees
Luxary villa close to disney
dinning
Great to find a way to cook while your stay
Private kitchen
Interior
Exceptional
(70 reviews)

Tiny Hidden Cottage

Longwood

8% off
AU$1,162
for 7 nights, 1 cottage
AU$166 per night
includes taxes & fees
Tiny Hidden Cottage
Covered spa/hot tub, patio grill available, view to fenced bach yard
Interior detail
full size kitchen to utilize everything included
private screened swimming pool with sundeck
Exceptional
(12 reviews)

Tropical Pool & Spa Home, 3/2, Near Disney, Universal, Sea World, Beaches

Altamonte Springs

7% off
AU$2,566
for 7 nights, 1 home
AU$367 per night
includes taxes & fees
Tropical Pool & Spa Home, 3/2, Near Disney, Universal, Sea World, Beaches
Room
Property grounds
Interior
Private kitchen
Exceptional
(8 reviews)

Trailhouse Retreat with Hot Tub, Firepit & Bikes

Sanford

7% off
AU$3,273
for 7 nights, 1 home
AU$468 per night
includes taxes & fees
Trailhouse Retreat with Hot Tub, Firepit & Bikes
The living room accent wall is of a galaxy far, far away.
Access to the community pool and waterslide are included free of charge with your rental. The community pool is a 5 minute walk from the house and has free onsite parking.
Front of house.
The Marketplace at Windsor Hills is a great place for snacks, drinks and souvenirs!
Exceptional
(124 reviews)

Star Wars Villa - 10 Mins to Disney

Kissimmee

7% off
AU$4,672
for 7 nights, 1 villa
AU$667 per night
includes taxes & fees
Star Wars Villa - 10 Mins to Disney
Living Room at Villa Ichabod
Storey Lake Resort Overview
Upstairs Master Bedroom at Villa Ichabod
TRON Game Room at Villa Ichabod
Exceptional
(27 reviews)

Walk to Clubhouse | Tron Game Room | Tiki Bar | Private Pool | 7BR Villa

Kissimmee

8% off
AU$6,196
for 7 nights, 1 villa
AU$885 per night
includes taxes & fees
Walk to Clubhouse | Tron Game Room | Tiki Bar | Private Pool | 7BR Villa
Spacious open concept design
Private Swimming Pool and Screened-in Patio
Garage-turned-games-room
Large Capacity Dining Area with Patio Access
Exceptional
(5 reviews)

Resort Home w Pool, Games, BBQ - Near Disney!

Kissimmee

7% off
AU$4,116
for 7 nights, 1 home
AU$588 per night
includes taxes & fees
Resort Home w Pool, Games, BBQ - Near Disney!
Room
Pool
Living area
Room
Wonderful
(12 reviews)

4826 LL - Storey Lake Dream 4BR Pool Home Near Disney

Kissimmee

11% off
AU$2,423
for 7 nights, 1 home
AU$346 per night
includes taxes & fees
4826 LL - Storey Lake Dream 4BR Pool Home Near Disney
Spacious Group Friendly Layout
Relax on a sunlounger on your private patio after taking a dip in your backyard swimming pool.
Billiards, foosball, air hockey and basketball are some of the games you'll find in the in-house games room!
Kick back and relax in the in-home superhero themed movie theatre.
Very good
(10 reviews)

Upstay | Disney Luxury Pool Game Room Cinema

Kissimmee

7% off
AU$8,609
for 7 nights, 1 home
AU$1,230 per night
includes taxes & fees
Upstay | Disney Luxury Pool Game Room Cinema
Upstairs TV Lounge
Private Sundeck with Swimming Pool
Comfortable Furnishings
Indoor Family Dining Area
Very good
(35 reviews)

Family Home with Pool, BBQ & Cinema Near Disney

Kissimmee

7% off
AU$4,417
for 7 nights, 1 home
AU$631 per night
includes taxes & fees
Family Home with Pool, BBQ & Cinema Near Disney

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

The scenic city of Winter Springs awaits you

Enjoy the temples and other features of Winter Springs. This scenic city is known for its baseball games, lake and parks. Universal Orlando Resort and Kia Center are just a couple of the must-see attractions in the area. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in and around Winter Springs

Are you hoping to find things to do in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Winter Springs a fun place to get away to. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Universal Orlando Resort (18.4 mi / 29.6 km)
  • Central Florida Zoo & Botanical Gardens (8.9 mi / 14.3 km)
  • Dubsdread Golf Course (9.4 mi / 15.1 km)
  • Rio Pinar Country Club (12.2 mi / 19.6 km)
  • King's Landing (12.8 mi / 20.6 km)
  • Ventura Country Club (13 mi / 20.9 km)

Exploring the natural landscape of Winter Springs

Whether you're an adventurous traveller or just want to spend some time taking in the scenery, Winter Springs is a great place to get out in nature. These are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Boombah-Soldiers Creek Park (1.5 mi / 2.4 km)
  • Central Winds Park (2.3 mi / 3.7 km)
  • Red Bug Lake Park (3.4 mi / 5.5 km)
  • Cranes Roost Park (5.2 mi / 8.4 km)
  • Sanlando Park (5.5 mi / 8.9 km)
  • Lake Jesup (5.7 mi / 9.2 km)

How to get to and around Winter Springs

The nearest airport is in Orlando, FL (SFB-Orlando Sanford Intl.), located 6.6 mi (10.6 km) from the city centre. If you can't find a flight that's convenient for your trip, you could book a flight to Orlando International Airport (MCO), which is 18.5 mi (29.8 km) away.

Frequently asked questions

What is the best area to stay in Winter Springs when booking a holiday rental?
When considering a holiday rental in Winter Springs, Florida, a popular area to stay is the charming neighbourhood near the picturesque Central Winds Park. This area offers a lovely blend of natural beauty and recreational facilities, making it ideal for families and outdoor enthusiasts. Central Winds Park itself is a top attraction, featuring walking trails, sports fields, and picnic areas, superb for a relaxing day out.Another appealing area is the vicinity of the Winter Springs Town Centre, which boasts a variety of shops, restaurants, and community events. Staying here gives you easy access to vibrant local culture and dining options. The properties in these areas tend to be quite popular, providing a range of choices from cosy townhouses to spacious family homes, all designed to make your stay comfortable and enjoyable.
What is the most popular type of holiday rental accomodation in Winter Springs?
In Winter Springs, holiday houses are the most popular type of holiday rental, with approximately 20 available throughout the area. These properties are generally situated in family-friendly neighbourhoods, providing a homely atmosphere ideal for both relaxation and social gatherings. Most holiday houses come equipped with multiple bedrooms, full kitchens, and spacious living areas, often featuring outdoor spaces such as patios or gardens for enjoying the pleasant Florida weather.
Are there any family house rentals in Winter Springs?
In Winter Springs, several family-friendly house rentals are available, providing ample options for those travelling with children. The neighbourhoods here offer spacious homes equipped with essential amenities like full kitchens, living areas for family gatherings, and often outdoor spaces for kids to enjoy. Many properties also feature conveniences such as Wi-Fi and laundry facilities, ensuring a comfortable stay for everyone.Visitors can explore nearby attractions like Central Winds Park, which has playgrounds, picnic areas, and sports fields, superb for family outings. Additionally, the area's proximity to the scenic shores of Lake Jessup offers opportunities for outdoor activities like fishing and nature walks.
Can I rent a holiday home with a pool or hot tub in Winter Springs?
In Winter Springs, there are several holiday homes available for rent that feature pools and hot tubs. This picturesque suburb, located just north of Orlando, offers a variety of options for travellers seeking relaxation and leisure. Many of these properties come equipped with private swimming pools, outdoor lounging areas, and hot tubs, great for unwinding after a day of exploring the local attractions.The neighbourhoods in Winter Springs provide a tranquil atmosphere, with easy access to parks and recreational areas. Amenities such as fully equipped kitchens, spacious living areas, and outdoor dining spaces are commonly found, making these rentals ideal for families or groups. Additionally, the proximity to Orlando means that guests can enjoy both the serene environment of Winter Springs and the vibrant entertainment options nearby.
Are there pet-friendly house rentals in Winter Springs?
In Winter Springs, there are several pet-friendly house rentals available, providing a comfortable environment for travellers with pets. Many of these properties feature amenities such as spacious backyards, fully equipped kitchens, and cosy living areas, making them ideal for families or groups.The area is known for its beautiful parks, including the expansive Central Winds Park, which offers walking trails, picnic areas, and playgrounds, superb for enjoying time outdoors with your furry friends. Additionally, the nearby Lake Jessup provides opportunities for outdoor activities like fishing and hiking, ensuring that both pets and their owners can enjoy a vibrant outdoor lifestyle.
Are there any remote work holiday rentals in Winter Springs?
In Winter Springs, Florida, there are around 20 remote work-friendly holiday rentals available, making it a great choice for those looking to blend work and leisure. Many of these properties are equipped with reliable high-speed internet and Wi-Fi, ensuring a smooth working experience. Most accommodations also feature comfortable living spaces, often with dedicated work areas, allowing for productivity during your stay.The area boasts a pleasant suburban environment, with nearby parks and recreational facilities providing opportunities for breaks and relaxation after work hours. Additionally, you can find local cafes and restaurants offering a variety of dining options, enhancing your experience in this charming part of Florida. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Winter Springs?
In Winter Springs, holiday rentals typically come equipped with a variety of popular amenities to enhance the guest experience. Most properties feature a well-equipped kitchen, allowing travellers to prepare their own meals. Additionally, many rentals include a porch or lanai, great for enjoying the pleasant Florida weather. Onsite parking is commonly available, offering convenience for those travelling by car. Other amenities often found in these rentals include a blender for making smoothies or other refreshments, as well as a deck or patio area for outdoor relaxation.
When is the best time to visit Winter Springs for a holiday rental?
September is one of the most popular months to visit Winter Springs, Florida, as the summer crowds begin to thin and the weather remains pleasantly warm. This transitional time offers a great opportunity for outdoor activities, including leisurely strolls through the scenic parks and enjoying the lush surroundings.The peak season runs from February to April, attracting visitors looking for comfortable temperatures (averaging between 15 to 25 degrees Celsius) and vibrant local festivals. During these months, the area buzzes with activity, making it ideal for those seeking a lively option filled with community events and outdoor fun.If you're looking for a more budget-friendly option, consider planning your visit in October. This month allows you to enjoy the tranquil beauty of Winter Springs without the hustle and bustle of peak tourist season. With fewer crowds, you can take your time to explore the local attractions and perhaps even catch the vibrant autumn colours.Ultimately, the best time to book a holiday rental in Winter Springs depends on your preferences for activities and atmosphere.
What are the top attractions in Winter Springs?
In Winter Springs, visitors can enjoy a variety of attractions that highlight the area's natural beauty and community spirit. Tuscawilla Park is a wonderful spot for outdoor activities, featuring walking trails, picnic areas, and playgrounds, making it superb for families. The nearby Winter Springs Town Centre offers shopping, dining, and entertainment options, ideal for those looking to explore local culture.For nature enthusiasts, the Cross Seminole Trail provides an excellent opportunity for walking, biking, and appreciating the scenic surroundings. Additionally, the city is close to the Central Florida Zoo & Botanical Gardens in nearby Sanford, which can be a delightful day trip for families and animal lovers alike.
Are all fees included in the Winter Springs holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Winter Springs holiday homes with parking?
Stayz offers a wide selection of holiday homes in Winter Springs with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Winter Springs holiday homes?
You can find great discounts on holiday homes in Winter Springs on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Winter Springs holiday home booking on Stayz?
To find Winter Springs holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Winter Springs?
A long-stay holiday home in Winter Springs is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Winter Springs holiday home?
Book your Winter Springs holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Winter Springs?
Prices for holiday homes in Winter Springs vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Winter Springs to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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