Seasons holiday lettings

We found 387 holiday rentals — enter your dates for availability

Discover a selection of 39 homes and other holiday rentals in Seasons that are perfect for your trip. Whether you're travelling with your children and pets, with friends or just your children, holiday rentals have the amenities that you expect for your stay, which might include air conditioning and a pool. At the end of the day, you'll be sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts - Seasons

Showing deals for:3 Oct - 10 Oct
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Why visit Seasons

  • Proximity to Theme Parks: Seasons is just a stone's throw from iconic attractions like Disney World, making it perfect for family outings.
  • Diverse Accommodation Options: Choose from private holiday homes, charming villas, or stylish condos tailored to suit your needs.
  • Outdoor Adventures: Enjoy scenic lakes and parks, offering plenty of opportunities for fun and relaxation in nature.
  • Friendly Local Atmosphere: Experience the warmth of the local community, with welcoming residents and vibrant entertainment options.
  • Cultural Experiences: Explore nearby towns and immerse yourself in the rich culture and charm of the Kissimmee area.

Popular types of accommodation around Seasons

If you're not quite sure what type of accommodation to expect in Seasons, there's no need to worry—we've got you covered. Our most popular options include houses, charming villas, and stylish condos. Whether you're seeking a holiday apartment or a rental villa in Kissimmee, our selection of holiday homes in Kissimmee ensures you'll find the perfect place for your getaway.

  • Houses: The top choice for visitors to Seasons, offering spacious and comfortable accommodations perfect for families or groups.
  • Villas: The second most sought-after option, featuring luxurious living spaces with private amenities.
  • Condos: A popular third choice, providing convenient living with shared facilities in a vibrant community.
  • Apartments: Fourth in popularity, ideal for couples or solo travellers seeking a home-away-from-home experience.
  • Cottages: A charming fifth option, perfect for those wanting a quaint and cosy retreat.**

Top attractions near Seasons

Seasons in Kissimmee, Florida, is ideal for family, entertainment, and business-themed holidays. Visitors can enjoy a variety of attractions, including theme parks, amusement parks, and scenic lakes. The area offers a plethora of points of interest that cater to families seeking outdoor adventures and cultural experiences. Whether you're travelling with loved ones or on business, Seasons has something for everyone to enjoy.

  • Walt Disney World® Resort: A magical theme park offering enchanting attractions, thrilling rides, and immersive experiences for families. With its iconic Cinderella Castle, it's a haven for fun and entertainment, perfect for creating unforgettable memories.
  • Orange County Convention Center: A vibrant arts centre showcasing diverse cultural events, exhibitions, and conventions. It's a hub for creativity and innovation, allowing visitors to immerse themselves in the local arts scene.
  • Kissimmee Lakefront Park: A picturesque urban park featuring serene lake views, walking paths, and picnic areas. Ideal for families and outdoor enthusiasts, it offers a tranquil escape within the bustling city.

Things to do recommended for couples

For a delightful couple's getaway near Seasons, explore the enchanting Congo River Golf for a bit of fun, savour a romantic dinner at Pirate's Dinner Adventure, or indulge in exquisite wines at True Blue Winery. Each offers a unique experience to create lasting memories together.

Things to do recommended for families

Families will love the excitement of Kissimmee Go-Karts, only 621m from Seasons, and can enjoy the thrilling rides at Aquatica, 5.0km away. For sports enthusiasts, the ESPN Wide World of Sports Complex, located 3.7km away, offers a vibrant atmosphere for all ages.

Things to do recommended for groups

When visiting Seasons in Kissimmee, groups can enjoy a delightful shopping experience at Disney Springs™, just 3.7km away, or explore Old Town, 2.5km away, offering a mix of entertainment and family fun. Don't miss the enchanting Medieval Times theatre, a mere 0.2.5km from your accommodation.

Booking with Vrbo is simple

Are you hoping to cut costs on your upcoming getaway? Being flexible with your travel dates can be beneficial, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Where to stay near Seasons

Seasons in Kissimmee, Florida, is an ideal spot for a family-friendly holiday, offering proximity to renowned attractions such as Disney World. Visitors can immerse themselves in the vibrant atmosphere of the area, where friendly locals and ample entertainment options await. Explore nearby towns and experience the charm of Kissimmee, making it a perfect blend of relaxation and adventure for all ages.

  • Kissimmee: Located a mere 2.5km from Seasons, Kissimmee is a vibrant city renowned for its family-friendly atmosphere and entertainment options. Here, visitors can indulge in a variety of activities, from exploring expansive shopping areas and bustling mall centres to enjoying world-class resorts. Kissimmee serves as a gateway to thrilling attractions like theme parks and film studios, ensuring a delightful experience for all ages. With its proximity to picturesque beaches, it offers a perfect blend of leisure and excitement.
  • Crystal Cove: A charming neighbourhood just 186m away from Seasons, Crystal Cove is perfect for those seeking a family-oriented and outdoor experience. This area boasts a range of activities, including access to delightful resorts, shopping areas, and golf courses. Crystal Cove is close to significant landmarks such as theme parks and a convention centre, making it an ideal spot for both relaxation and adventure. The picturesque surroundings enhance its appeal, providing a serene escape amidst the action.
  • Bellavida: Also located 186m from Seasons, Bellavida is an inviting neighbourhood that caters to families and outdoor enthusiasts alike. Visitors can enjoy various activities, including access to luxurious resorts and well-maintained golf courses. The area is near popular attractions such as theme parks, film studios, and a tranquil lake, offering a delightful mix of fun and relaxation. With its beautiful landscapes and family-friendly amenities, Bellavida is a fantastic destination for a memorable holiday.

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

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

When travelling with a group, family, pets, or planning an extended stay, it's essential to prioritise your preferences. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Seasons with a group: Think about how many bedrooms you'll require, as well as features like a fully-equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Seasons with young kids: Travelling with young children can present its own set of challenges. It's important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it would be wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Seasons: For many, a family holiday isn’t truly fulfilled without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. The majority of pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortably at home.
  • Planning for a long term stay visiting Seasons: If you’re seeking holiday 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. You might also want to consider including features such as a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Vrbo Trips: Effortless planning

Vrbo's clever Trip Board offers you a dedicated space to plan new adventures, pick up from where you last left off, or easily view and organise your travel arrangements. Any properties you've previously saved or booked can now be accessed under Potential, Upcoming, or Current Trips. To make the most of Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of holiday rental accommodation in Seasons?
Houses are the most popular kind of holiday rental in Seasons, according to our data. Even if you've got something different in mind, Vrbo has holiday homes in a variety of shapes and sizes. Look over our options to find your ideal fit.
How much does it cost to rent a holiday rental in Seasons?
Length of stay, property type and season are some factors that can affect the price of a holiday home. Simply add your dates of travel to find your ideal fit. From cosy country cottages to sprawling luxury villas, all Vrbo holiday rentals offer terrific value.
How much does it cost to rent a beach house in Seasons?
The average price for a holiday rental close to the beach in Seasons depends on when you'll be there and the type and size of property you're looking for. You can find prices easily and quickly on Vrbo by entering your travel dates and destination. Then use our handy filter tool to select the number of bedrooms and amenities that you require, like WiFi, air conditioning and a pool.
Are there pet-friendly holiday rentals in Seasons?
With 28 properties that welcome four-legged guests, your furry little friend can join you on your Seasons getaway. Use our filter tool to browse our pet-friendly holiday rentals and find a stay that'll set tails wagging on Vrbo.
Can I rent a house with a pool in Seasons?
Grab your swimsuit and inflatable lounger, because there are 28 houses with a private pool in Seasons. Stay at one of these superb holiday rentals and let every day be a pool day. Simply enter your travel dates into Vrbo, then check the "pool" filter to find the perfect place to make a splash!
What are popular rental amenities in Seasons?
Some of the most popular rental amenities people are searching for in Seasons include a lake view, a barbecue grill and a chef. Whether you're hitting the road with family, your besties or even pets, Vrbo holiday rentals feature the best amenities for hanging out with the people you love.
Are there large group holiday rentals in Seasons?
With four properties that can host 10 or more guests in Seasons, you don't have to leave anyone off your invite list. From fun family get-togethers to special events like birthday and Christmas parties, Vrbo will help you find a large group rental that fits the occasion.
Are there holiday rentals in Seasons that welcome kids?
Bring the entire family together for the adventure of a lifetime in Seasons at one of our 28 family-friendly properties. A lot of these stays provide conveniences that are just perfect for getaways with the kids, including laundries, extra bedrooms and patios. Just click on the "Properties good for families" filter box and pick your favourite option.
What are the top attractions for families in Seasons?
Keep the kids amused at these top family-friendly attractions in Seasons:

  • Fun Spot America
  • Island H2O Live!
  • Kissimmee Go-Karts

Are there holiday rentals with WiFi in Seasons?
Take your pick of seven holiday rentals with WiFi in Seasons. If you'd like to disconnect from the world on your escape, but still want to be connected to the internet, these properties are for you. Narrow your search by applying the WiFi filter on Vrbo.
How can I find holiday rentals with air conditioning in Seasons?
Choose from 26 holiday rentals with air conditioning in Seasons offering that cool, cool breeze and extra element of comfort. Just enter your preferred travel dates and then make use of our filter tool to find stays with air conditioning.
How old do you have to be to rent a holiday rental in Seasons?
It's a good idea to check with the Seasons holiday property you want on Vrbo as age restrictions differ. However, it's generally 16, 18 or 21.
How long can I rent a holiday rental in Seasons for?
The length of time you can rent a holiday rental in Seasons varies according to the property. Simply enter your desired travel dates to see a list of options offering extended stays. With a range of amenities like washing machines and air conditioning, as well as some offering discounted weekly or monthly prices, you're sure to find somewhere perfect to call your home away from home in Seasons.

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