Lakeside Estates vacation rentals

We found 42 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

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Lakeside Estates

Why visit Lakeside Estates

  • Family-friendly activities: Lakeside Estates offers a range of attractions suitable for all ages, making it perfect for family vacations.
  • Outdoor adventures: Enjoy various lake activities, including boat rentals and relaxing waterfront experiences.
  • Charming accommodations: Choose from private vacation homes, villas, and condos, many featuring stunning views and amenities.
  • Proximity to attractions: Explore nearby theme parks and amusement parks for thrilling entertainment options.
  • Picturesque surroundings: Experience beautiful landscapes and a warm atmosphere, ideal for both romantic getaways and family excursions.

Popular types of accommodation around Lakeside Estates

If you're looking for the ideal getaway in Lakeside Estates, you're in the right place. Our most popular vacation rental options include houses, villas, and condos. Whether you prefer a cozy cottage rental or a spacious house rental, we have something for everyone. Many of our properties feature fantastic amenities, including waterside decks for stunning views. Enjoy a relaxing retreat with all the comforts of home in beautiful Lakeside Estates.

  • Houses: These spacious rentals are the top choice for travelers seeking comfort and privacy, ideal for families or groups.
  • Villas: Luxurious and often featuring private pools, villas are perfect for those wanting an upscale getaway.
  • Condos: Offering amenities like pools and gyms, condos are a popular option for travelers seeking convenience and style.
  • Apartments: These versatile accommodations provide a home-like atmosphere, great for longer stays or budget travelers.
  • Cottages: Quaint and charming, cottages offer a cozy retreat for couples or small families looking for a peaceful escape.**

Top attractions near Lakeside Estates

Lakeside Estates in Kissimmee, Florida, is perfect for family vacations and outdoor adventures. With attractions like theme parks, lakes, and amusement parks, there's something for everyone. Enjoy a variety of lake activities, consider boat rentals, and explore vacation ideas that cater to families and culture enthusiasts. Whether you're looking for fun or relaxation, Lakeside Estates offers a memorable getaway for travelers of all ages.

  • Universal Orlando Resort: Experience thrilling rides and immersive attractions at this world-renowned theme park. With themed areas like The Wizarding World of Harry Potter, it offers fun for the whole family, making it a must-visit destination just 13 miles away.
  • Orange County Convention Center: This vibrant arts center, located 10 miles from Lakeside Estates, hosts a variety of cultural events and exhibitions, showcasing local and international talent in a dynamic setting.
  • Silver Spurs Arena: Just 1 mile away, this entertainment facility features family-friendly events, concerts, and rodeos, providing an exciting atmosphere for all ages.

Things to do recommended for couples

For a romantic getaway near Lakeside Estates, enjoy a lively dinner at Pirate's Dinner Adventure, just 12 miles away. For some playful competition, try Pirate's Cove Adventure Golf, 11 miles away, or soar through the skies with iFly Orlando, also 12 miles away, for an unforgettable experience.

Things to do recommended for families

Families staying at Lakeside Estates can splash around at Aquatica, just 9 miles away, enjoy a thrilling day at Wonderworks, located 11 miles away, or catch a Houston Astros Spring Training game, a short mile from their accommodation, for a fun-filled vacation experience.

Things to do recommended for groups

Experience the magic of Disney Springs™, just 10 miles from Lakeside Estates, with shopping and dining. Visit the Florida Mall, 9 miles away, for entertainment and family fun. Don't miss Medieval Times, 6 miles away, for a unique blend of culture and 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, your pets, or for an extended stay—be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Lakeside Estates with a group: Think about how many bedrooms you'll 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 young kids can be quite an adventure, but it does come with its challenges. It's important to prioritize their comfort and safety, and to seek out amenities that are suitable for their age, like a private swimming pool. Additionally, think about how close you'll be to family-friendly attractions to enhance your experience.
  • Taking your pets with you to Lakeside Estates: For many families, a vacation wouldn’t feel complete without their furry companion. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with 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 special rates for month-long stays, 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 consider additional features like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near Lakeside Estates

Exploring Lakeside Estates in Kissimmee, Florida, offers a delightful blend of family-friendly activities and stunning outdoor experiences. Nestled by beautiful waterfronts, this neighborhood is perfect for those seeking relaxing lake vacations. Nearby attractions provide a warm atmosphere, ideal for both romantic getaways and family excursions. From charming lakeside homes to vibrant local entertainment, Lakeside Estates promises an unforgettable getaway where friendly people and picturesque views await.

  • Orlando: As a bustling metropolis, Orlando is renowned for its family-friendly and entertainment-themed attractions. Lakeside Estates is conveniently located within Orlando, making it easy for visitors to explore the numerous resorts, shopping areas, and arts centers. The city is famous for its iconic theme parks, including Walt Disney World and Universal Studios, which offer thrilling experiences for all ages. Additionally, Orlando's vibrant arts scene is showcased in various theaters and galleries, while nearby beaches provide a perfect escape for sun-seekers.
  • Kissimmee: Kissimmee, a charming city close to Lakeside Estates, attracts travelers with its family-oriented and entertainment-focused atmosphere. Visitors can enjoy a variety of activities, including shopping at popular malls and relaxing at local resorts. The city is in close proximity to exciting theme parks, film studios, and beautiful beaches, making it a perfect base for exploring Central Florida. Kissimmee also offers a range of dining options, ensuring that every meal is an adventure in itself.
  • Morgan Point: Located just 0.7 miles from Lakeside Estates, Morgan Point is a delightful neighborhood ideal for families and outdoor enthusiasts. The area features a variety of recreational activities, including golf courses and theaters, catering to those seeking entertainment and relaxation. Additionally, Morgan Point is home to beautiful beaches, historical museums, and urban parks, providing ample opportunities for exploration and enjoyment. It's a great spot for tourists to unwind and soak in the local culture.

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 save on your upcoming trip? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, consider booking an extended stay, which can lead to substantial savings. To discover a Vrbo property that aligns with your budget, utilize our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Unlock savings with One Key

When you reserve a qualifying Vrbo for your group getaway, you'll earn OneKeyCash on the total booking amount. Being the organizer truly has its perks. Become a member of our One Key rewards program to unlock special savings and earn OneKeyCash on eligible stays. Sign up now and begin reaping the benefits.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a dedicated area to plan new trips, pick up right where you left off, and organize your travel plans with ease. You can now access properties you've previously saved or booked under the categories of Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/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 most common type of rental, with around 26 available in the area. These houses often feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups looking for a comfortable stay. Additionally, several apartments, villas, and cottages can be found, each offering unique amenities that cater to different preferences. Many of these properties include outdoor spaces such as patios or decks, great for enjoying the warm Florida weather.
Are there any beach house rentals in Lakeside Estates?
In Lakeside Estates, there are several beach house rentals available, providing a range of options for travelers. These properties typically feature spacious layouts with multiple bedrooms, fully equipped kitchens, and comfortable living areas, making them ideal for families or larger groups. Many beach houses also include outdoor amenities such as private patios or decks, where guests can relax and enjoy the warm Florida weather.
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 traveling 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. To get the best value, book early and take advantage of Vrbo's free rewards program.
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 rental amenities include fully equipped kitchens, which allow travelers to prepare their meals with ease. Many properties also feature private pools, providing a refreshing retreat right at home. Additional amenities often found are onsite parking for convenience, coffee and tea makers to start the day right, and blenders for making smoothies or cocktails.
Can I find family house rentals in Lakeside Estates?
In Lakeside Estates, Florida, there are approximately 21 family-friendly house rentals available. This charming community offers spacious homes ideal for families, featuring amenities such as well-equipped kitchens, multiple bedrooms, and comfortable living areas where everyone can gather. Many properties also include outdoor spaces, great for children to play and enjoy the Florida sunshine.

Visitors will appreciate the close proximity to local parks and recreational areas, which provide opportunities for outdoor activities and family fun. Additionally, nearby attractions enhance the experience, making it easy to explore local dining and shopping options.
Can I rent a vacation home with a pool or hot tub in Lakeside Estates?
In Lakeside Estates, Florida, there are several vacation homes available for rent that come equipped with pools and hot tubs, with around 21 options featuring pools. This charming area offers a relaxing atmosphere, superb for families or groups looking to unwind. Many of these rentals include amenities such as private swimming pools, hot tubs for soaking, spacious outdoor areas, and fully equipped kitchens to make your stay comfortable and enjoyable. Additionally, travelers can expect features like outdoor seating areas and barbecue grills, ideal for entertaining or enjoying meals outdoors.
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 travelers 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 book pet-friendly vacation rentals in Lakeside Estates?
In Lakeside Estates, travelers can find several pet-friendly vacation rentals that cater to their needs. Many of these properties are equipped with amenities such as spacious backyards, fully equipped kitchens, and comfortable living spaces, making them ideal for families or groups traveling with pets. The neighborhood itself offers a relaxed atmosphere, with easy access to local parks where pets can enjoy some outdoor time.
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. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
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. This vibrant period attracts families and sun-seekers eager to enjoy the warm Florida sunshine and indulge in a variety of outdoor activities. With average temperatures ranging from the mid-70s to the low 90s Fahrenheit, the summer months provide a great backdrop for swimming, boating, and relaxing on the beautiful beaches.

July stands out as the most popular month, offering a lively option filled with local events and opportunities for adventure. Visitors can partake in water sports, explore nature trails, or enjoy leisurely strolls along the picturesque waterfront. This time of year is also ideal for those looking to make the most of their vacation experience, as numerous attractions, dining options, and entertainment venues are at their best.

For travelers seeking a more budget-friendly option, consider visiting in October. This month allows for a quieter, more serene experience while still providing pleasant weather. With temperatures in the mid-70s, October is great for enjoying the natural beauty of the area, whether it's through scenic walks or exploring local parks.
Are there any remote work vacation rentals in Lakeside Estates?
In Lakeside Estates, Florida, there are 27 remote work-friendly vacation rentals available, making it a suitable destination for those looking to blend work and leisure. Many of these properties are equipped with essential amenities such as high-speed Wi-Fi and dedicated workspaces, including desks and comfortable chairs, ensuring a productive environment.

The area is peaceful and offers a suburban feel, ideal for remote work while still being close to local attractions. Travelers can expect modern accommodations featuring full kitchens for meal preparation, spacious living areas, and outdoor spaces for relaxation. 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.
What are the top attractions in Lakeside Estates, Florida, United States of America?
In Lakeside Estates, Florida, the primary attractions revolve around the beautiful natural landscapes and recreational activities available in the area. The nearby Lake Worth Lagoon offers opportunities for boating, fishing, and enjoying waterfront parks, which provide serene spots for picnicking and walking.

The community is also close to the vibrant city of Lake Worth Beach, where visitors can explore the local art scene, featuring galleries and murals, and enjoy the sandy beaches along the Atlantic Ocean.

For those interested in outdoor activities, the nearby John Prince Park provides walking trails, picnic areas, and sports facilities, making it a popular spot for both locals and visitors.
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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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