Seasons holiday lettings

We found 390 holiday rentals — enter your dates for availability

Discover a selection of 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:15 May - 22 May

Image gallery for 8BR/5BA pool home,Near Disney,SeaWorld,Convention Center

8br/5ba 3680sqft pool villa
9.0 out of 10, Wonderful, (15 reviews)
Wonderful
(15 reviews)

8BR/5BA pool home,Near Disney,SeaWorld,Convention Center

Kissimmee

22% off
Price is £1,397
for 7 nights, 1 home
£200 per night
includes taxes & fees
8BR/5BA pool home,Near Disney,SeaWorld,Convention Center

Find spaces that suit your style

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  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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.

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.

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

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.

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

How much does it cost to rent a holiday home in Seasons?
Prices for holiday 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 holiday 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.
Are there any Seasons holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Seasons 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 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 find long-stay holiday rentals in Seasons?
A long-stay holiday rental in Seasons 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Seasons for a holiday rental?
The best time to book a holiday rental in Seasons, Florida, is during the peak season from June to August. This vibrant period attracts families and sun-seekers eager to enjoy the warm weather, sandy beaches, and a multitude of outdoor activities. July, in particular, stands out as the most popular month, where the lively option is palpable, making it ideal for those who revel in a bustling environment filled with fellow holidaymakers.

During these summer months, you can expect pleasant temperatures averaging between 25 to 32 degrees Celsius, superb for sunbathing, swimming, and exploring local attractions. Whether you're lounging by the pool, enjoying water sports, or visiting nearby theme parks, the options for fun are plentiful.

For those seeking a more budget-friendly experience, October presents a fantastic alternative. As the tourist crowds thin out, you can relish in a quieter atmosphere while still enjoying the warm climate. With temperatures remaining relatively mild, you'll have the opportunity to explore the area's natural beauty and take part in outdoor activities without the hustle and bustle of peak season.

Ultimately, your choice of when to visit Seasons will depend on whether you prefer the energetic vibe of summer or the tranquil charm of autumn.
How early should I book a Seasons holiday rental?
Book your Seasons holiday 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 holiday 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 variety of attractions that capture the essence of the area. The neighbourhood is known for its proximity to the beautiful beaches of the Gulf Coast, where activities such as sunbathing, swimming, and water sports are popular. Nearby, the scenic Fort Myers Beach offers a vibrant setting with beachside dining, shops, and entertainment options.

For those interested in nature, the Lovers Key State Park is an excellent spot, providing opportunities for hiking, kayaking, and wildlife viewing in a stunning natural setting. The area is also close to the Estero Bay Preserve State Park, which features diverse ecosystems and numerous trails for exploring.

In terms of family-friendly attractions, the nearby Sun Splash Family Waterpark offers a fun day out with water slides and pools suitable for all ages.
Can I change or cancel my Seasons home rental booking on Vrbo?
To find Seasons holiday 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 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 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, Vrbo 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 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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