Lakeside Estates vacation rentals

We found 43 vacation rentals — enter your dates for availability

Discover a selection of 9 homes and other vacation rentals in Lakeside Estates that are perfect for your trip. Whether you're staying in a vacation rental with family, friends, or just your furry companion, you'll find the amenities you need and want, which might include a hot tub and garden. You'll be able to choose a rental that has what everyone needs, including options that are accessible or non-smoking.

Find spaces that suit your style

Find out more about Lakeside Estates

Why visit Lakeside Estates

  • Family-Friendly Activities: Lakeside Estates offers a range of outdoor and recreational activities perfect for families and friends.
  • Proximity to Theme Parks: Enjoy easy access to famous theme parks and amusement parks, providing endless entertainment.
  • Scenic Lakeside Living: Experience the beauty of tranquil bungalows and stunning waterfront views in a charming neighborhood.
  • Diverse Accommodation Options: Choose from private vacation homes, villas, and condos tailored to your group's needs.
  • Warm Local Community: Revel in a friendly atmosphere with welcoming locals, ensuring a memorable vacation experience.

Popular types of accommodation around Lakeside Estates

If you're wondering about the accommodation options available in Lakeside Estates, you’re in the right place. Our most sought-after choices include Houses, Villas, and Condos. Whether you're looking for spacious rental suites, cozy bedroom townhomes, adjoining homes for larger groups, or exceptional residences with additional parking, we have the perfect spot to make your getaway memorable. Enjoy the beauty of Lakeside Estates with the comfort and convenience you deserve.

  • Houses: The top choice for visitors in Lakeside Estates, offering spacious living and a home-like atmosphere, perfect for families or groups.
  • Villas: A popular second option, these upscale accommodations provide luxury and privacy, ideal for a relaxing getaway.
  • Condos: These versatile spaces are the third most sought-after, combining convenience with amenities for a comfortable stay.
  • Apartments: Offering a cozy and cost-effective option, apartments rank fourth for those seeking a homely feel.
  • Cottages: Charming and quaint, cottages are a delightful fifth choice, perfect for a peaceful retreat.**

Top attractions near Lakeside Estates

Lakeside Estates in Kissimmee, Florida, is perfect for family-oriented vacations, offering a blend of outdoor activities and entertainment. Visitors can enjoy nearby theme parks, amusement parks, and beautiful lakes, making it an ideal destination for cultural and recreational experiences. Whether you're travelling with family or friends, don't miss the chance to explore the scenic lake country and create lasting memories in this vibrant area.

  • Universal Orlando Resort: A thrilling theme park featuring world-class rides and attractions. Enjoy immersive experiences based on popular movies, perfect for families seeking adventure and entertainment. With a vibrant atmosphere, it promises unforgettable memories.
  • Orange County Convention Center: A hub of culture, this arts centre hosts diverse events, from conventions to exhibitions. Experience the local arts scene and community events, showcasing the rich cultural tapestry of the area.
  • Silver Spurs Arena: Just 1.6km away, this entertainment facility hosts family-friendly events, including rodeos and concerts. The lively atmosphere and variety of shows make it a must-visit for entertainment enthusiasts.

Things to do recommended for couples

For a romantic getaway near Lakeside Estates, indulge in a delightful dinner at Pirate's Dinner Adventure, only 19.3km away. Enjoy some fun at Pirate's Cove Adventure Golf, 17.7km away, and unwind with a wine tasting at True Blue Winery, situated 29.0km from your stay.

Things to do recommended for families

Your family will have a blast at Universal’s Volcano Bay, a thrilling waterpark just 19.3km from Lakeside Estates. Enjoy the excitement of the Houston Astros Spring Training, 1.6km away, or explore the adventures at Wonderworks, located 17.7km from your stay.

Things to do recommended for groups

Explore Disney Springs™ for shopping and dining, only 16.1km from Lakeside Estates. Enjoy a fun day at the Florida Mall, located 14.5km away, or immerse yourselves in medieval culture at Medieval Times, just 9.7km away, for an unforgettable evening filled with entertainment.

*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 Lakeside Estates

When you're planning a trip—whether it's with friends, family, pets, or for an extended stay—be sure to prioritize your preferences in the search filters. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Lakeside Estates with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Lakeside Estates with young kids: Traveling with little ones can be quite the adventure. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Lakeside Estates: For many families, a trip isn't truly fulfilling without their furry companions. If that resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Lakeside Estates: If you’re in search of vacation rentals that offer 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 features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Lakeside Estates

Explore the charm of Lakeside Estates, a delightful neighborhood perfect for family-friendly adventures and outdoor fun. Immerse yourself in the idyllic lakeside living, where tranquil bungalows meet stunning waterfront views. Nearby, you’ll find vibrant communities and excursions that cater to both romance and relaxation. Whether you're seeking a peaceful retreat or engaging entertainment, Lakeside Estates offers a warm atmosphere and friendly locals, making it an ideal vacation spot in Kissimmee, Florida.

  • Orlando: Orlando is a bustling metropolis known for its family-friendly attractions and vibrant entertainment scene. As the home of Lakeside Estates, it offers easy access to world-renowned theme parks and a plethora of outdoor activities. You'll find an array of resorts and shopping areas to explore, alongside cultural gems like the arts centre. The city's landmarks, including famous theme parks and film studios, make for unforgettable experiences. Whether you're seeking thrilling rides or leisurely beach days, Orlando has something for everyone.
  • Kissimmee: Kissimmee is a lively city that complements your stay in Lakeside Estates with its rich array of family-oriented and entertainment-themed experiences. The city boasts a range of resorts, shopping areas, and shopping mall centres that cater to all tastes. Kissimmee's proximity to iconic theme parks and film studios ensures that adventure awaits at every turn. Whether you’re looking to indulge in retail therapy or enjoy a day at the beach, Kissimmee delivers a perfect mix of leisure and excitement.
  • Morgan Point: Morgan Point is a charming neighbourhood located a mere 1.1km from Lakeside Estates, making it an ideal destination for families seeking outdoor activities and entertainment. This area features a variety of venues, including theatres and golf courses, providing ample opportunities for recreation. Explore local attractions such as the beach, history museum, and urban park, where you can relax and soak in the local culture. Morgan Point offers a delightful blend of relaxation and adventure, ensuring a memorable visit.

Best time to go to Lakeside Estates

If you're planning a trip to Lakeside Estates, 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 journey? One effective strategy is to remain flexible with your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often leads to substantial savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board provides you with a convenient area to plan new adventures, keep your existing plans on track, or review and organize your reservations. The properties you've saved or booked are conveniently categorized into Potential, Upcoming, or Current Trips. To check out Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Lakeside Estates?
In Lakeside Estates, vacation houses are the predominant type of rental, with around 35 available throughout the area. These properties typically feature spacious layouts with multiple bedrooms, fully equipped kitchens, and outdoor spaces for relaxation, making them ideal for families or groups. Additionally, there are several apartments, cottages, and villas available, each offering a unique charm and amenities suited for different preferences. Many of these rentals are located near local parks and recreational areas, providing easy access to outdoor activities.
Are there any beach house rentals in Lakeside Estates?
In Lakeside Estates, Florida, there are several beach house rentals available, providing a variety of options for visitors seeking a seaside escape. These properties typically feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or larger groups. Many beach houses also come with outdoor spaces such as patios or balconies, allowing guests to enjoy the warm Florida sun and scenic views. Located near local attractions and the beautiful coastline, these rentals offer a superb base for exploring the area while enjoying the comforts of home.
How much does it cost to rent a vacation home in Lakeside Estates?
Prices for vacation rentals in Lakeside Estates 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. Vrbo offers something for every taste and budget, from affordable rentals in Lakeside Estates to more spacious homes.
Are there any discounts for Lakeside Estates vacation house rentals?
You can find great discounts on house rentals in Lakeside Estates 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 Lakeside Estates?
In Lakeside Estates, popular vacation rental amenities include fully equipped kitchens, which are essential for those who prefer self-catering during their stay. Many properties also feature private pools, offering guests a great spot for relaxation and enjoyment in the Florida sun. Additional conveniences might include blenders for preparing smoothies or cocktails, as well as coffee and tea makers to start the day off right.
Are there any family house rentals in Lakeside Estates?
In Lakeside Estates, Florida, there are numerous family-friendly house rentals available, with around 25 options to choose from. This area is known for its spacious homes that cater to families, featuring amenities such as full kitchens, ample living spaces, and outdoor areas superb for children to play. Many properties also offer conveniences like Wi-Fi and air conditioning, ensuring a comfortable stay for everyone.
Can I rent a vacation home with a pool or hot tub in Lakeside Estates?
In Lakeside Estates, Florida, there are plenty of vacation homes available for rent that come with pools and hot tubs, with around 23 properties featuring pools alone. This charming area offers a relaxing environment, superb for families or groups looking to unwind. Many of these rentals include amenities such as spacious outdoor patios, barbecue areas, and well-equipped kitchens, making them ideal for entertaining and enjoying meals al fresco.
Are there any Lakeside Estates vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Lakeside Estates 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.
Are there pet-friendly vacation rentals in Lakeside Estates?
Yes, you can book pet-friendly vacation rentals in Lakeside Estates, Florida. This area offers a selection of properties that welcome pets, ensuring a comfortable stay for both you and your furry companions. Many of the available rentals typically feature amenities such as spacious backyards, patios for outdoor relaxation, and modern kitchens, making them ideal for families or groups.
Can I find long-stay vacation rentals in Lakeside Estates?
A long-stay vacation rental in Lakeside Estates 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 Lakeside Estates for a vacation rental?
The best time to visit Lakeside Estates for a vacation rental is during the peak season from June to August, with July being the most popular month. This summer period is superb for those seeking sun-soaked days and vibrant outdoor activities. The warm climate, typically reaching the low 30s Celsius, creates an inclusive setting for beachgoers and nature enthusiasts alike.

During these months, you can immerse yourself in various recreational activities, from boating and fishing on the serene lakes to exploring the lush landscapes that surround the area. The lively community events and festivals in Lakeside Estates also enhance the vacation experience, offering opportunities to connect with fellow travellers and locals.

For those looking for a more budget-friendly option, consider planning your visit in October. This month, while quieter, still boasts pleasant weather, ideal for leisurely strolls along the water's edge and enjoying the natural beauty of the region without the summer crowds.
Are there any remote work vacation rentals in Lakeside Estates?
In Lakeside Estates, Florida, there is a good selection of remote work vacation rentals, with approximately 32 options available. This area is particularly appealing for those looking to blend work and leisure, as many properties come equipped with essential amenities for remote work, including Wi-Fi, dedicated office spaces, and ergonomic furniture such as desk chairs and desks. Some rentals may even feature additional conveniences like computer monitors, enhancing the work-from-home experience. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Lakeside Estates vacation rental?
Book your Lakeside Estates 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 Lakeside Estates home rental booking on Vrbo?
To find Lakeside Estates 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 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 Lakeside Estates 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.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.

More Vacation Ideas