Seasons vacation rentals

We found 390 vacation rentals — enter your dates for availability

Discover a selection of vacation rentals in Seasons that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, vacation rentals have the best amenities for hanging out with the people that matter most, which might include parking and a fireplace. No matter what you're looking for, you'll be sure to find a rental to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Seasons

Showing deals for:May 29 - Jun 5

Image gallery for Large 6 bed, top level comfort, pool, close to the parks & superb lake view!

Exterior
9.6 out of 10, Exceptional, (141 reviews)
Exceptional
(141 reviews)

Large 6 bed, top level comfort, pool, close to the parks & superb lake view!

Kissimmee

8% off
Price is $314
$2,200 for 7 nights
All fees included
Large 6 bed, top level comfort, pool, close to the parks & superb lake view!

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Find out more about Seasons

Why visit Seasons

  • Proximity to Theme Parks: Seasons is just minutes away from Disney and other major attractions, making it a prime location for family fun.
  • Diverse Accommodation Options: Choose from private vacation homes, villas, and condos to suit every traveler's needs.
  • Outdoor Adventures: Enjoy nearby lakes and parks for outdoor activities and relaxation amidst nature.
  • Family-Friendly Atmosphere: Experience a vibrant setting perfect for creating unforgettable memories with loved ones.
  • Cultural Experiences: Explore a variety of entertainment-themed activities and local attractions in the area.

Popular types of accommodation around Seasons

Seasons offers a variety of vacation rentals that cater to every traveler's needs. Whether you're looking for Houses, Villas, or Condos, you'll find the perfect fit for your stay. Located near popular attractions, our accommodations in Seasons, Florida, provide easy access to Kissimmee hotels and convenient parking options. Enjoy transparency, savings, and reassurance as you plan your getaway in this vibrant area.

  • Houses: The top choice for visitors in Seasons, offering spacious accommodations perfect for families or groups.
  • Villas: A popular alternative, these elegant properties provide luxury and ample amenities for a relaxing getaway.
  • Condos: These convenient units offer a blend of comfort and communal amenities, ideal for couples or small families.
  • Apartments: A practical option for travelers seeking home-like comforts in a central location.
  • Cottages: Quaint and cozy, these charming retreats provide a unique and intimate vacation experience.**

Top attractions near Seasons

Seasons in Kissimmee, Florida, is ideal for family vacations and business trips alike, offering a variety of attractions to explore. Popular points of interest include theme parks, lakes, and amusement parks, ensuring there’s something for everyone. Whether you're seeking outdoor adventures or cultural experiences, Seasons provides a perfect backdrop for an unforgettable getaway with family or friends.

  • Walt Disney World® Resort: A magical theme park offering enchanting experiences for the whole family, with thrilling rides, beloved characters, and immersive attractions, all set in a beautifully themed environment located 10 miles from Seasons.
  • Orange County Convention Center: A vibrant arts center showcasing diverse cultural events, exhibitions, and conventions, making it a hub of creativity and community, just 8 miles away from Seasons.
  • Fun Spot America: An exciting amusement park filled with outdoor adventures, rides, and games for all ages, perfect for family fun, located merely 3 miles from Seasons.

Things to do recommended for couples

For a romantic getaway in Kissimmee, enjoy a fun round at Pirate's Island Adventure Golf, just 0.8 miles away. Savor a memorable dining experience at Pirate's Dinner Adventure, 11 miles from Seasons, and unwind with wine at True Blue Winery, located 13 miles from your stay.

Things to do recommended for families

Your family will have a blast at ESPN Wide World of Sports Complex, just 6 miles away, soaking in the sports atmosphere. Aquatica, an exciting waterpark 8 miles from Seasons, offers fun for all ages. Don't miss Wonderworks, a thrilling arcade adventure zone located 9 miles away.

Things to do recommended for groups

Experience the magic of Disney Springs™ for shopping and dining, just 6 miles from Seasons. Explore Old Town for entertainment and local fun, only 4 miles away. Don't miss Medieval Times, a captivating theater showcasing culture and romance, a mere 0.4 miles from your stay.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Seasons

If you're traveling with a group, family, or pets, or if you're planning an extended stay, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Seasons with a group: Think about how many bedrooms you'll require, as well as features like a complete kitchen or outdoor areas for group activities. Luckily, you can easily filter for these options and much more on Vrbo.
  • Traveling to Seasons with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, think about how close you are to family-friendly activities.
  • Taking your pets with you to Seasons: For many families, a vacation isn’t truly complete without their furry companion. If that resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Seasons: If you're seeking vacation rentals with discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay near Seasons

Seasons in Kissimmee, Florida, is the perfect family getaway, just minutes from Disney and all the excitement Orlando has to offer. Enjoy a relaxing vacation retreat surrounded by friendly people and a vibrant atmosphere. Explore nearby attractions, indulge in entertainment-themed activities, and create unforgettable memories with loved ones. Whether you're seeking adventure or relaxation, Seasons provides the ideal base for your Florida vacation.

  • Orlando: Orlando is a bustling metropolis known for its family-friendly attractions and entertainment-themed experiences. Situated just a short drive from Seasons, this vibrant city is famous for its world-renowned theme parks, including Walt Disney World and Universal Studios. Visitors can indulge in a variety of outdoor activities, from exploring beautiful parks to shopping at premier retail centers. The city also features a thriving arts scene, boasting museums and theatres that cater to diverse tastes. Orlando's convenient location makes it an ideal base for exploring nearby beaches and film studios, ensuring an exciting vacation for all ages.
  • Kissimmee: Kissimmee is a charming city that offers a rich blend of family fun, entertainment, and business experiences. Located near Seasons, Kissimmee is perfect for those looking to immerse themselves in the magic of Florida's theme parks, such as the iconic attractions just minutes away. The city boasts a variety of shopping areas and malls, making it easy for visitors to find souvenirs and enjoy local dining. With its welcoming atmosphere and proximity to resorts, Kissimmee serves as a fantastic hub for both leisure travelers and business guests, making it a versatile destination.
  • Crystal Cove: Located only 0.3 miles from Seasons, Crystal Cove is a delightful neighborhood that attracts visitors seeking family-oriented and outdoor experiences. This picturesque area features beautiful resorts and shopping venues, alongside a well-maintained golf course for those looking to tee off. Crystal Cove’s close proximity to major theme parks and a film studio makes it an attractive spot for entertainment seekers. Whether you’re exploring local dining options or enjoying recreational activities, this neighborhood provides a relaxing yet engaging atmosphere for your vacation.

Best time to go to Seasons

If you're planning a trip to Seasons, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs in February to March and July, while off-peak times, like September to November tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January60.6°F (15.9°C)Light RainMostly SunnyAverageAverage
February64.4°F (18.0°C)Light RainMostly SunnySlightly HighSlightly Low
March67.6°F (19.8°C)Light RainMostly SunnySlightly HighAverage
April72.7°F (22.6°C)Light RainMostly SunnyAverageAverage
May77.2°F (25.1°C)Light RainMostly SunnyAverageAverage
June81.1°F (27.3°C)Light RainMostly SunnyAverageSlightly High
July82.4°F (28.0°C)Moderate RainMostly SunnySlightly HighSlightly High
August82.6°F (28.1°C)Moderate RainMostly SunnyAverageAverage
September80.4°F (26.9°C)Moderate RainMostly SunnySlightly LowSlightly Low
October75.2°F (24.0°C)Light RainMostly SunnySlightly LowSlightly Low
November68.5°F (20.3°C)Light RainMostly SunnySlightly LowAverage
December64.4°F (18.0°C)No Rain (Dry)Mostly SunnyAverageSlightly High

Booking with Vrbo is a breeze

Are you eager to save on your next getaway? Being flexible with your travel dates can really help, as prices tend to vary. Additionally, booking a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, utilize our filters to sort by price, location, and type of vacation rental. We're here to help you find the best options for your trip.

Save more with One Key

Reserve an eligible Vrbo for your group getaway and earn OneKeyCash on the total booking amount. Being the planner truly has its rewards. When you join our travel rewards program, One Key, you’ll gain access to exclusive discounts and earn OneKeyCash on qualifying reservations. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers a user-friendly platform for planning your travels. You can easily create new trips, continue planning from where you paused, or review and organize your itineraries. Your saved or booked properties will be neatly organized under the categories of Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Seasons?
In Seasons, Florida, vacation houses are the most common type of rental accommodation, with about 27 available throughout the area. These houses typically offer spacious living areas, fully equipped kitchens, and outdoor spaces where guests can relax and enjoy the warm Florida weather. Additionally, there are several villas and cottages that provide unique stays, often featuring private pools and garden areas, making them suitable for families or groups looking for a comfortable getaway.
How much does it cost to rent a vacation home in Seasons?
Prices for vacation rentals in Seasons 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Seasons to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Seasons vacation house rentals?
You can find great discounts on house rentals in Seasons on Vrbo, 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.
What are popular rental amenities in Seasons?
In Seasons, Florida, travelers can expect a variety of popular rental amenities that enhance their stay. Most vacation rentals feature fully equipped kitchens, allowing guests to prepare their own meals conveniently. Many properties come with private pools, superb for relaxing and enjoying the Florida sunshine. Additionally, rentals often include coffee and tea makers for a quick caffeine fix and travel cribs for families traveling with young children. Some accommodations also provide entertainment options, such as arcade game rooms, adding an extra layer of fun for guests of all ages.
Can I find family house rentals in Seasons?
In Seasons, Florida, there are plenty of family-friendly house rentals available—specifically, around 27 options for visitors to choose from. This area is known for its spacious properties that cater to families, featuring amenities such as full kitchens for preparing meals, comfortable living areas for relaxation, and often private outdoor spaces where children can play.

Visitors can expect to find homes equipped with conveniences like laundry facilities, Wi-Fi, and sometimes even game rooms for entertainment. The location is conveniently situated near various attractions, including theme parks and recreational areas, making it an ideal base for family adventures.
Can I rent a vacation home with a pool or hot tub in Seasons?
In Seasons, Florida, there are plenty of vacation homes available for rent that feature both pools and hot tubs, with around 30 options for homes with pools and 17 with hot tubs. This area is known for its sunny climate and family-friendly atmosphere, making it an excellent choice for travelers looking to relax and enjoy outdoor activities.

Many of these rentals come equipped with private pools, inviting hot tubs, and spacious outdoor living areas great for soaking up the sun. Travelers can also expect amenities such as fully equipped kitchens, comfortable living spaces, and often, access to nearby recreational facilities or parks.
Are there any Seasons vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Seasons with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo 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.
Can I book pet-friendly vacation rentals in Seasons?
In Seasons, Florida, there are several pet-friendly vacation rentals available, with around 18 options to choose from. These properties often feature amenities such as private pools, well-equipped kitchens, and spacious living areas, suiting families and groups looking for comfort during their stay. Many rentals also provide outdoor spaces like fenced yards or patios, which are ideal for pets to enjoy.

The neighborhood itself is known for its tranquil atmosphere and proximity to various parks and recreational areas, making it a suitable destination for pet owners. Local parks often offer walking trails and open spaces for pets to roam freely, enhancing the overall experience for travelers with furry companions.
Can I find long-stay vacation rentals in Seasons?
A long-stay vacation rental in Seasons is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit Seasons for a vacation rental?
The best time to visit Seasons for a vacation rental is during the summer months, particularly July, when the area comes alive with vibrant energy and warm weather. This peak season, spanning from June to August, attracts many travelers looking to enjoy outdoor activities, beach outings, and local events in this beautiful part of Florida.

July offers the warmest temperatures, typically ranging from the mid-70s to the low 90s Fahrenheit, creating an ideal environment for sunbathing, swimming, and exploring the coastline. Whether you're lounging on the beach or engaging in water sports, the pleasant climate enhances every experience.

For those who prefer a quieter atmosphere and more budget-friendly options, consider planning your visit in October. This month often features lower rental rates and fewer crowds, while still providing comfortable temperatures ideal for outdoor exploration. You can enjoy the local attractions at a more leisurely pace, allowing you to fully soak in the natural beauty of the area without the hustle and bustle of peak season.

Ultimately, your choice of timing will depend on whether you're seeking the lively summer vibe with all its festivities or the peaceful charm of the fall.
Are there any remote work vacation rentals in Seasons?
In Seasons, Florida, there are several remote work vacation rentals available, with around 33 options to choose from. Travelers can expect amenities that cater to their work-from-home needs, including free Wi-Fi and internet access in the rentals, ensuring a seamless connection for remote work. Many properties offer comfortable workspaces, such as dedicated desks or cozy nooks, allowing for productivity amidst a relaxing environment.

The area itself is known for its pleasant weather and proximity to various attractions, providing a balance of work and leisure. Guests can enjoy easy access to nearby parks and recreational areas, superb for unwinding after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Seasons vacation rental?
Book your Seasons vacation rental 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 Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Seasons, Florida, United States of America?
In Seasons, Florida, visitors can enjoy a range of attractions that highlight the area's natural beauty and recreational opportunities. The nearby Walt Disney World® Resort is a major draw, offering a variety of theme parks and entertainment options suitable for all ages. Families often find vacation rentals in the surrounding areas of Kissimmee and Lake Buena Vista, providing convenient access to the parks.

Additionally, the area boasts numerous golf courses, such as the ChampionsGate Golf Club, which attracts golf enthusiasts looking for a round in the sunny Florida weather. For those seeking outdoor activities, Lake Tohopekaliga in nearby Kissimmee offers opportunities for fishing, boating, and birdwatching, while the scenic parks and nature trails in the vicinity provide great spots for walking and picnicking.

Local shopping and dining can be found at various plazas and markets, ideal for visitors who wish to enjoy a taste of Florida's culinary scene.
Can I change or cancel my Seasons home rental booking on Vrbo?
To find Seasons vacation rentals with free cancellation, just use Vrbo'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". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers 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, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Seasons vacation rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing 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 favorites, and build the perfect itinerary together.

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