Seasons vacation rentals

We found 382 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.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

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, vacation houses are the most popular type of rental accommodation, with around 33 available throughout the area. These properties typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces such as patios or balconies to enjoy the pleasant Florida weather. Additionally, there are several villas and cottages, which offer more unique and intimate settings for travelers. Villas often come with luxurious amenities such as private pools and landscaped gardens, while cottages provide a cozy atmosphere for those looking for a quaint getaway.
Are there any beach house rentals in Seasons?
In Seasons, Florida, there are about 10 beach house rentals available, offering travelers a comfortable and spacious option for their stay. These beach houses typically feature multiple bedrooms and bathrooms, fully equipped kitchens, and open living areas that are ideal for family gatherings or groups. Many properties also include outdoor spaces such as patios or balconies, allowing guests to enjoy the pleasant Florida weather.
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, popular vacation rental amenities typically include private pools, fully equipped kitchens, and outdoor pools, including heated options. Travelers can expect to find properties with outdoor seating areas for relaxation and dining, making the most of the pleasant Florida weather. Many rentals are designed for comfort, offering spacious living areas and easy access to outdoor spaces, superb for family gatherings or leisurely vacations.
Are there any family house rentals in Seasons?
In Seasons, Florida, there are several family-friendly house rentals available, with around 29 options to choose from. This vibrant community offers a range of homes that are superb for families, featuring spacious living areas and ample bedrooms to accommodate everyone. Many of these properties come equipped with full kitchens, allowing for convenient meal preparations, and outdoor spaces where children can play or families can gather for barbecues.

The locale is ideally situated near attractions that appeal to visitors of all ages. Families can enjoy nearby parks, playgrounds, and recreational facilities that promote outdoor activities.
Can I rent a vacation home with a pool or hot tub in Seasons?
In Seasons, Florida, travelers can find a variety of vacation homes available for rent that include pools and hot tubs, with around 36 options featuring pools and 11 with hot tubs. This area is known for its sunny climate and family-friendly atmosphere, making it an ideal destination for relaxation and leisure. Many properties come equipped with inviting outdoor spaces, great for enjoying the warm weather, along with amenities such as fully equipped kitchens, spacious living areas, and often outdoor dining setups. These rentals are great for hosting gatherings or simply unwinding after a day of exploring the local attractions.
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.
Are there pet-friendly vacation rentals in Seasons?
In Seasons, Florida, there are several pet-friendly vacation rentals available, providing an inviting space for travelers with pets. Many of these rentals come equipped with modern amenities such as spacious kitchens, private pools, and outdoor living areas, superb for enjoying the warm Florida weather.

The area itself is known for its family-friendly atmosphere, and you'll find nearby parks where pets can roam freely. Additionally, the proximity to local attractions and beaches adds to the appeal, making it easy to explore the beautiful surroundings.
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 peak summer months of June to August. This vibrant season is great for travelers eager to soak up the sun and enjoy a variety of outdoor activities. With temperatures typically ranging from the mid-70s to low 90s Fahrenheit, you can comfortably explore the beautiful beaches, partake in water sports, or simply relax by the poolside.

July stands out as the most popular month, attracting both families and adventure seekers. During this time, the atmosphere is lively, with numerous local festivals and events that showcase the region's culture and community spirit. Whether you're looking to indulge in fresh seafood at waterfront restaurants or enjoy a scenic sunset cruise, there's something for everyone.

If you're considering a more budget-friendly option, October is an excellent month to visit. The weather remains pleasant, with milder temperatures in the low to mid-80s Fahrenheit, making it ideal for sightseeing and outdoor activities without the summer crowds. This shoulder season allows for a more relaxed experience while still providing access to stunning natural beauty and local attractions.

Ultimately, the best time to book a vacation rental in Seasons depends on your travel preferences.
Are there any remote work vacation rentals in Seasons?
In Seasons, Florida, there are numerous options for remote work vacation rentals, with around 38 properties available. The area provides a tranquil environment, ideal for those looking to balance work and leisure. Travelers can expect rentals equipped with essential amenities such as high-speed Wi-Fi, dedicated workspaces, and safes for security. Many properties also feature well-appointed living areas that create a comfortable atmosphere for both productivity and relaxation.

The surroundings offer opportunities for outdoor activities, with easy access to beaches, parks, and local attractions. This makes it feasible for remote workers to unwind 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.
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.

More Vacation Ideas