Winter Springs holiday rentals

We found 18,024 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:13 Nov - 20 Nov

Private kitchen
Community house 2 lazy river
Bar / restaurant area
Dining
Excellent
(43 reviews)

Resort style, pool home within minutes to Disney

Kissimmee

7% off
AU$2,155
for 7 nights, 1 home
AU$308 per night
includes taxes & fees
Resort style, pool home within minutes to Disney
Bedroom 1 - Romantic Retreat Master Bedroom with king bed and ensuite
Bronson Clubhouse lazy river, community pool, and children's pirate playscape
Bronson Gym open to guest 9a to 9pm
Fully equipped kitchen
Exceptional
(51 reviews)

NEW 9Bdrm Themed w Arcade near Disney & Universal

Kissimmee

7% off
AU$5,406
for 7 nights, 1 home
AU$772 per night
includes taxes & fees
NEW 9Bdrm Themed w Arcade near Disney & Universal
Dining
Private kitchen
Interior
Room
Exceptional
(149 reviews)

JUST REMODELED!! 3BR/2BR Chic Villa Near Disney UNIT A

Kissimmee

7% off
AU$1,534
for 7 nights, 1 villa
AU$219 per night
includes taxes & fees
JUST REMODELED!! 3BR/2BR Chic Villa Near Disney UNIT A
Private kitchen
Marina
Interior
Exterior
Exceptional
(33 reviews)

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

Sanford

8% off
AU$1,547
for 7 nights, 1 houseboat
AU$221 per night
includes taxes & fees
Luxury Floating House - Boat Tree Marina on St. John’s River, Sanford
Private kitchen
Room
Dining
Living area
Exceptional
(19 reviews)

Sanford Group Getaway- 4BR/Sleeps 10, Pet Friendly

Lake Mary

8% off
AU$3,553
for 7 nights, 1 home
AU$508 per night
includes taxes & fees
Sanford Group Getaway- 4BR/Sleeps 10, Pet Friendly
Interior
Water park with giant water slide, kids' pools, lazy river
Bar (on property)
Interior
Exceptional
(84 reviews)

Once Upon A Time@Storey Lake-9 Bedroom Disney Haven w/ Game Room & Private Pool!

Kissimmee

7% off
AU$4,191
for 7 nights, 1 villa
AU$599 per night
includes taxes & fees
Once Upon A Time@Storey Lake-9 Bedroom Disney Haven w/ Game Room & Private Pool!
Pool Patio
Living Room
Dining Room
Hallway
Excellent
(15 reviews)

CHARMING VILLA AT SONOMA RESORT AT TAPESTRY

Kissimmee

7% off
AU$3,436
for 7 nights, 1 villa
AU$491 per night
includes taxes & fees
CHARMING VILLA AT SONOMA RESORT AT TAPESTRY
Interior
Pool
Private kitchen
Living area
Wonderful
(23 reviews)

Magical charm couple miles away from Disney

Kissimmee

7% off
AU$2,238
for 7 nights, 1 home
AU$320 per night
includes taxes & fees
Magical charm couple miles away from Disney
Luxurious Bedroom Featuring A King-Sized Bed And Elegant Modern Design
Spacious Group Friendly Design
Poolside Dining Area with Wall Mounted TVs
Private Jacuzzi Hot Tub
Wonderful
(20 reviews)

Upstay: 15BR Villa w Games Room, Pool & Cinema

Kissimmee

7% off
AU$9,664
for 7 nights, 1 home
AU$1,381 per night
includes taxes & fees
Upstay: 15BR Villa w Games Room, Pool & Cinema
Fully Equipped Kitchen
Your private poolside dining area  - perfect for BBQ meals cooked on your grill after a swim!
Kitchen Island with Bar Seating
Spacious Group Friendly Layout
Very good
(10 reviews)

Upstay | Disney Luxury Pool Game Room Cinema

Kissimmee

7% off
AU$7,514
for 7 nights, 1 home
AU$1,073 per night
includes taxes & fees
Upstay | Disney Luxury Pool Game Room Cinema
Poolside Dining Option with BBQ Grill
Bella Vida Resort Hot Tub Jacuzzi
Bella Vida Resort Clubhouse
Additional Kitchen Island Seating for 4
Excellent
(19 reviews)

Upstay: Resort-Style 12BR Villa—Bella Vida Resort

Kissimmee

7% off
AU$6,701
for 7 nights, 1 home
AU$957 per night
includes taxes & fees
Upstay: Resort-Style 12BR Villa—Bella Vida Resort
Living area
Luxury Villa
Dining Area
2021- New Kitchen Appliances (dishwasher)
Wonderful
(202 reviews)

Luxury Villa - Pool, LCD TVs , Free Internet On Disney's Doorstep !!

Kissimmee

7% off
AU$1,634
for 7 nights, 1 home
AU$233 per night
includes taxes & fees
Luxury Villa - Pool, LCD TVs , Free Internet On Disney's Doorstep !!
Fully Equipped Kitchen with Stainless Steel Appliances
Located at the Veranda Palms Resort
Large capacity dining table
Located at the Veranda Palms Resort
Exceptional
(7 reviews)

Upstay Sleeps 26 w Private Pool, Hot Tub, Games

Kissimmee

7% off
AU$5,847
for 7 nights, 1 home
AU$835 per night
includes taxes & fees
Upstay Sleeps 26 w Private Pool, Hot Tub, Games
Large Dining Table with Seating for up to 10
Relax In The Scenic Pool Area With Comfortable Loungers
Spacious Open Concept Design
Fully Equipped Chef's Kitchen
Wonderful
(36 reviews)

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

Kissimmee

7% off
AU$4,297
for 7 nights, 1 home
AU$614 per night
includes taxes & fees
Upstay: Modern Home w Pool, Games & BBQ—Sleeps 18
Contemporary design living area smart TV
Contemporary design living area
Contemporary design living area
Large kitchen island with bar seating
Wonderful
(18 reviews)

Upstay: Family Home w Pool, Cinema & Games Room

Kissimmee

7% off
AU$4,595
for 7 nights, 1 home
AU$656 per night
includes taxes & fees
Upstay: Family Home w Pool, Cinema & Games Room
Room
Pool
Dining
Living area
Exceptional
(24 reviews)

17 mins to Theme Parks, Your All in One Stay with Heated Pool

Kissimmee

7% off
AU$2,124
for 7 nights, 1 home
AU$303 per night
includes taxes & fees
17 mins to Theme Parks, Your All in One Stay with Heated Pool
Kitchen with Granite Counters and Stainless Steel Aplliances
Large Dining Table that can seat 8
Interior
Interior
Exceptional
(113 reviews)

FREE Early Check-In When Available!

Kissimmee

7% off
AU$2,041
for 7 nights, 1 home
AU$292 per night
includes taxes & fees
FREE Early Check-In When Available!
Comfortable Furnishings
Bella Vida Resort Community Pool
6 Bedroom Home at the Bella Vida Resort
Bar Seating at the Kitchen Island
Very good
(35 reviews)

Family Home with Pool, BBQ & Cinema Near Disney

Kissimmee

7% off
AU$2,974
for 7 nights, 1 home
AU$425 per night
includes taxes & fees
Family Home with Pool, BBQ & Cinema Near Disney
Lobby
Pool
Meeting facility
Outdoor dining
Exceptional
(135 reviews)

Luxury Pool Home Steps to Disney, 2 Master Suites, Gated, Game Rm, BBQ Free WiFi

Kissimmee

6% off
AU$2,466
for 7 nights, 1 home
AU$352 per night
includes taxes & fees
Luxury Pool Home Steps to Disney, 2 Master Suites, Gated, Game Rm, BBQ Free WiFi
20 Guest Capacity Home at Bella Vida
Refreshing Pool Area with Outdoor Seating at Bella Vida Resort
Large Capacity Dining Space
Fully Equipped Kitchen with Island Bar Seating
Excellent
(19 reviews)

Upstay—Vibrant Home w Themed Rooms, Pool & Games

Kissimmee

7% off
AU$3,538
for 7 nights, 1 home
AU$505 per night
includes taxes & fees
Upstay—Vibrant Home w Themed Rooms, Pool & Games
Alternate View Of The Dining Room Highlighting Its Modern Style
Relaxing Covered Jacuzzi Hot Tub Overlooking The Resort Pool
Spacious Living Room With Plush Seating And 43" Smart TV
Stunning Exterior With Manicured Lawn And Ample Parking Space
Very good
(18 reviews)

Bella Vida House with Pool and Games - Near Disney!

Kissimmee

7% off
AU$2,780
for 7 nights, 1 home
AU$397 per night
includes taxes & fees
Bella Vida House with Pool and Games - Near Disney!
Private kitchen
Living area
Living area
Room
Exceptional
(56 reviews)

Clear Lake Front home near Orlando / Sanford SFB Boombah

Sanford

7% off
AU$2,171
for 7 nights, 1 home
AU$310 per night
includes taxes & fees
Clear Lake Front home near Orlando / Sanford SFB Boombah
Dining
Pool
Inviting open concept family room
Interior
Wonderful
(20 reviews)

Near Disney & Universal Pool + Spa Family 4BR Private Pool, Spa Fenced Yard

Kissimmee

5% off
AU$2,081
for 7 nights, 1 home
AU$297 per night
includes taxes & fees
Near Disney & Universal Pool + Spa Family 4BR Private Pool, Spa Fenced Yard
Windsor Hills has some fabulous sports courts for guests to enjoy.
Access to the community pool and waterslide are included free of charge with your rental. The community pool is a 15 minute walk from the house and has free onsite parking.
The Marketplace at Windsor Hills is a great place for snacks, drinks and souvenirs!
Be our guests!
Exceptional
(142 reviews)

Mickey Pool Villa - 10 minutes to Disney

Kissimmee

7% off
AU$3,114
for 7 nights, 1 villa
AU$445 per night
includes taxes & fees
Mickey Pool Villa - 10 minutes to 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)
  • Cranes Roost Park (5.2 mi / 8.4 km)
  • Lake Jesup (5.7 mi / 9.2 km)
  • Kraft Azalea Gardens (6.5 mi / 10.4 km)
  • Sylvan Lake Park (8.5 mi / 13.7 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.

More holiday ideas