Seasons holiday rentals

We found 415 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:27 Nov - 4 Dec

Property grounds
Club House Foyer
Mediterranean styled villa: you enjoy the entire home - no sharing with other vacationers
Club House Patio
Very good
(31 reviews)

Renovated 4BR Villa with Private Pool Spa in Bellavida Resort Near Disney

Kissimmee

5% off
AU$2,892
for 7 nights, 1 villa
AU$413 per night
includes taxes & fees
Renovated 4BR Villa with Private Pool Spa in Bellavida Resort Near Disney
Property grounds
Pool
Living area
Exterior
Wonderful
(40 reviews)

6-Bed Villa, Private Pool & Hot Tub! Game Room | Gated Resort near Disney

Kissimmee

6% off
AU$3,477
for 7 nights, 1 home
AU$497 per night
includes taxes & fees
6-Bed Villa, Private Pool & Hot Tub! Game Room | Gated Resort near Disney
Elegant Dining Room With Seating For Eight And Stylish Accents
Private Pool and Jacuzzi Hot Tub
Fully Equipped Games Room With Air Hockey, Foosball, And Big Screen TV
Spacious Living Room With Plush Seating And 43" Smart TV
Very good
(18 reviews)

Bella Vida House with Pool and Games - Near Disney!

Kissimmee

7% off
AU$3,274
for 7 nights, 1 home
AU$468 per night
includes taxes & fees
Bella Vida House with Pool and Games - Near Disney!
Indoor Family Dining Area
Private Swimming Pool with Sun Loungers
King bedroom with en-suite bathroom
Living Room with Smart TV and High Speed Internet
Wonderful
(7 reviews)

Spacious 4BR Family Townhouse—Private Pool & BBQ

Kissimmee

7% off
AU$2,399
for 7 nights, 1 home
AU$343 per night
includes taxes & fees
Spacious 4BR Family Townhouse—Private Pool & BBQ
Living area
Exterior
Pool
Dining
Exceptional
(28 reviews)

4BR Disney Oasis: Private Screened Pool + FREE Pool Heat! (20 Min to Parks)

Kissimmee

5% off
AU$2,517
for 7 nights, 1 home
AU$360 per night
includes taxes & fees
4BR Disney Oasis: Private Screened Pool + FREE Pool Heat! (20 Min to Parks)
Exterior
Pool
Living area
Private kitchen
Exceptional
(138 reviews)

South‑facing private pool/spa for all‑day sunshine. Equipped interior games room

Kissimmee

8% off
AU$3,263
for 7 nights, 1 home
AU$466 per night
includes taxes & fees
South‑facing private pool/spa for all‑day sunshine. Equipped interior games room

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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 Stayz?
Stayz 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?
Stayz 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 Stayz, 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 Stayz?
To find Seasons holiday rentals with free cancellation, just use Stayz'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, Stayz 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 Stayz?
Stayz'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 Stayz 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. Stayz offers something for every taste and budget, from affordable homes in Seasons to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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 StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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 Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz 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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