Seasons holiday homes

We found 424 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.

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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

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    More space, more privacy, more amenities — more value

Why visit Seasons

  • Family-Friendly Attractions: Seasons is perfect for families, with easy access to nearby theme parks and amusement parks, ensuring fun-filled days for all ages.
  • Outdoor Activities: The serene lakes and green spaces in Seasons offer excellent opportunities for leisurely strolls, picnics, and outdoor adventures.
  • Welcoming Atmosphere: The friendly locals create a vibrant and welcoming vibe, making visitors feel right at home.
  • Romantic Getaways: Couples can enjoy romantic experiences amidst the beautiful scenery and tranquil surroundings.
  • Central Location: Seasons serves as a fantastic base for exploring Central Florida's enchanting attractions, including the magical Disney experiences.

Top attractions near Seasons

Seasons in Kissimmee, Florida, is an ideal destination for families, couples, and anyone seeking entertainment. The area boasts a variety of attractions, including theme parks and amusement parks, perfect for those looking for fun-filled days. Visitors can also enjoy the serene lakes and outdoor experiences available within Seasons, making it a great spot for cultural exploration and relaxation. Whether you're here for romance or adventure, Seasons has something for everyone.

  • Walt Disney World® Resort: A world-renowned theme park offering enchanting experiences, thrilling rides, and magical entertainment for families and visitors of all ages, creating unforgettable memories.
  • Lake Bryan: A picturesque lake featuring sandy beaches and stunning scenery, perfect for outdoor activities like boating, picnicking, and romantic strolls, making it an ideal escape into nature.
  • Universal CityWalk: A vibrant tourist precinct filled with diverse dining options, shops, and entertainment, providing a lively atmosphere for families and friends to enjoy together.

Things to do recommended for couples

For a romantic getaway in Kissimmee, explore the enchanting streets of Old Town, take a sunset airboat ride through the Everglades, or indulge in a candlelit dinner at a local winery. Don't miss a leisurely stroll around Lake Tohopekaliga for stunning views and tranquillity.

Things to do recommended for families

Families will enjoy engaging local experiences around Seasons in Kissimmee, with a plethora of fun attractions and kid-friendly activities that promise memorable adventures for all ages.

Things to do recommended for groups

Explore the vibrant local culture by visiting the nearby Old Town amusement park or enjoy a thrilling day at the Kissimmee Lakefront Park, where you can picnic, paddle, or enjoy scenic walks with your mates.

*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

Whether you're journeying with a group, as a family, with your furry mates or planning an extended stay, be sure to set the right filters. Here are some Vrbo booking tips for you.

  • Traveling to Seasons with a group: Think about the number of bedrooms you'll require, along with features like a fully equipped kitchen or an outdoor area for group gatherings. Thankfully, you can easily filter for these options and many more on Vrbo.
  • Traveling to Seasons with young kids: Traveling with little ones can be a challenge. You must prioritise their comfort and safety, along with ensuring there are age-suitable facilities like a private swimming pool. It’s also wise to think about how close you are to attractions that are family-friendly.
  • Taking your pets with you to Seasons: For many, a family getaway isn’t truly fulfilled without their furry companion along for the adventure. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Seasons: If you’re after holiday rentals with special rates for month-long stays, you’ve come to the right spot. Use the appropriate filter to easily discover and save on monthly options. You might also want to consider including extras like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near Seasons

Seasons, Kissimmee, Florida, is a delightful neighbourhood perfect for family-friendly adventures and romantic getaways. You'll find a vibrant atmosphere with easy access to attractions like the magical Disney World and the lively Disney Springs. Enjoy relaxing strolls through the area, where friendly locals create a welcoming vibe. With its ideal location in Central Florida, Seasons is an excellent base to explore the enchanting experiences this region has to offer.

  • Orlando: Nestled in the heart of central Florida, Orlando is a vibrant metropolis offering a blend of family fun, entertainment, and business opportunities. The city boasts a variety of attractions, from expansive theme parks and renowned film studios to pristine beaches that invite relaxation. With a lively arts centre and bustling shopping areas, Orlando delivers an engaging travel experience that caters to diverse interests. Its strategic location ensures travellers can easily explore a wealth of local venues and attractions, making it an exciting stop on any itinerary.
  • Kissimmee: Just a short drive from Seasons, Kissimmee presents itself as a dynamic city with a rich offering of family-friendly and entertainment-themed experiences. This destination is celebrated for its range of leisure activities, including access to expansive shopping malls and vibrant resort areas. Travellers can immerse themselves in local culture by visiting nearby theme parks and film studios, or unwind at the beach. Kissimmee provides a well-rounded travel experience that perfectly balances relaxation with excitement.
  • Lake Buena Vista: A city situated 13km from Seasons, Lake Buena Vista is known for its excellent mix of family-oriented, entertainment, and business attractions. Visitors are drawn to its appealing combination of modern shopping centres and leisure venues. The area is home to notable landmarks including a world-class theme park, a dynamic film studio and a sports facility stadium, offering a variety of engaging experiences. Its proximity to key attractions makes Lake Buena Vista a compelling destination for travellers seeking both adventure and comfort.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January60.6°F (15.9°C)Light RainMostly Sunny
February64.4°F (18.0°C)Light RainMostly Sunny
March67.6°F (19.8°C)Light RainMostly Sunny
April72.7°F (22.6°C)Light RainMostly Sunny
May77.2°F (25.1°C)Light RainMostly Sunny
June81.1°F (27.3°C)Light RainMostly Sunny
July82.4°F (28.0°C)Moderate RainMostly Sunny
August82.6°F (28.1°C)Moderate RainMostly Sunny
September80.4°F (26.9°C)Moderate RainMostly Sunny
October75.2°F (24.0°C)Light RainMostly Sunny
November68.5°F (20.3°C)Light RainMostly Sunny
December64.4°F (18.0°C)No Rain (Dry)Mostly Sunny

Booking with Vrbo is a breeze

Are you keen to save some dollars on your next adventure? Being flexible with your travel dates can really help, as prices can vary. Additionally, if you opt for a longer stay, you often unlock significant savings. To discover the perfect Vrbo property that suits your budget, be sure to utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers an easy-to-use space where you can create new journeys, pick up right where you left off, or review and organise your plans. Your saved or booked properties are neatly sorted into categories such as Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

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.
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.
Are all fees included in the Seasons holiday homes prices shown on Bookabach?
Bookabach 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 Seasons holiday homes with parking?
Bookabach offers a wide selection of holiday homes 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 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 Seasons holiday homes?
You can find great discounts on holiday homes in Seasons on Bookabach, 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 Seasons holiday home booking on Bookabach?
To find Seasons holiday rentals with free cancellation, just use Bookabach'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, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Seasons?
A long-stay holiday home 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 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 Bookabach?
Bookabach'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 Seasons holiday home?
Book your Seasons 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 Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Seasons?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Seasons to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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 Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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 Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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