Regal Oaks holiday lettings

We found 89 holiday rentals — enter your dates for availability

Find spaces that suit your style

  • 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, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Why visit Regal Oaks

  • Family-Friendly Atmosphere: Regal Oaks offers a welcoming environment perfect for families, ensuring a delightful getaway.
  • Outdoor Adventures: Enjoy various activities around the picturesque lake and local parks, ideal for recreation and relaxation.
  • Charming Accommodations: Stay in spacious townhomes and villas equipped with pools and recreational facilities for added comfort.
  • Proximity to Local Attractions: Regal Oaks serves as a convenient base for exploring nearby shops and restaurants in Old Town.
  • Golfing Opportunities: Experience leisure time at the local country club, perfect for golf enthusiasts.

Popular types of accommodation around Regal Oaks

Discover the charm of Regal Oaks in Kissimmee, Florida, where a delightful selection of houses, villas, and condos awaits you. This premier destination offers spacious townhomes, perfect for families or groups seeking comfort and convenience. Enjoy amenities such as pools and recreational facilities, while being just moments away from local attractions. Regal Oaks promises a memorable stay, providing a perfect blend of relaxation and adventure for every traveller.

  • Houses: The top choice for visitors, offering spacious and comfortable living spaces ideal for families or groups.
  • Villas: Elegant and often luxurious, these properties provide a perfect blend of comfort and style for a memorable stay.
  • Condos: Conveniently located and often with shared amenities, these are great for those seeking a home-away-from-home experience.
  • Apartments: Practical and cosy, ideal for those wanting easy access to local attractions without the fuss.
  • Cottages: Charming and quaint, perfect for a relaxing getaway in a homely setting.**

Top attractions near Regal Oaks

Regal Oaks in Kissimmee, Florida, offers a delightful array of attractions for visitors, particularly families seeking outdoor adventures and cultural experiences. Within the area, you can explore charming theme parks, enjoy leisure time by the picturesque lake, or indulge in a round of golf at the local country club. Regal Oaks is an ideal base for those wanting to immerse themselves in fun-filled activities while soaking up the warm Floridian atmosphere.

  • Walt Disney World® Resort: This iconic theme park offers a magical experience with enchanting attractions, thrilling rides, and engaging entertainment for families. Immerse yourself in the whimsical worlds of beloved characters and enjoy unforgettable experiences.
  • Fun Spot America: Located nearby, this amusement park features exciting outdoor rides and games perfect for a day of adventure. With a variety of attractions suitable for all ages, it provides a lively atmosphere for families.
  • Lake Bryan: A picturesque lake offering serene views and a relaxing beach environment, ideal for romantic strolls or a peaceful day outdoors. It's a fantastic spot for picnics and enjoying nature.

Things to do recommended for couples

If you're seeking romance in Kissimmee, explore the enchanting Lake Tohopekaliga for a sunset boat ride or indulge in a candlelit dinner at a lakeside restaurant. Don’t miss the chance to stroll hand-in-hand through the charming Old Town, offering delightful shops and vibrant entertainment.

Things to do recommended for families

Families staying at Regal Oaks can delight in a day at the nearby Walt Disney World Resort, offering enchanting attractions and character encounters. Additionally, the interactive fun at the Orlando Science Center provides engaging exhibits, perfect for sparking curiosity in young minds.

Things to do recommended for groups

Groups visiting Regal Oaks can enjoy thrilling adventures at nearby theme parks like Walt Disney World and Universal Orlando. They can also explore the vibrant Old Town in Kissimmee, offering shopping, dining, and live entertainment, perfect for a memorable group outing.

*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 Regal Oaks

Regardless of whether you are travelling with a group, as a family, bringing your pets along, or seeking extended stays, it’s essential to apply the appropriate filters based on your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Regal Oaks with a group: Think about how many bedrooms you'll require, as well as additional features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily refine your search for all these options and more on Vrbo.
  • Traveling to Regal Oaks with young kids: Travelling with young children can present its challenges. It's important to prioritise their comfort and safety, along with suitable facilities 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 Regal Oaks: For many, a family getaway wouldn’t be the same without their furry companion by their side. If this resonates with you, explore 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 Regal Oaks: If you’re in search of holiday rentals that offer discounts for month-long stays, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodation. Don’t forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Regal Oaks

Regal Oaks in Kissimmee, Florida, offers a delightful family-friendly atmosphere, making it an ideal getaway. Visitors can enjoy the serene surroundings while exploring local attractions, including charming shops and restaurants in the nearby Old Town. With its great location, Regal Oaks serves as the perfect base for excursions, recreation, and relaxation, ensuring an unforgettable experience for families seeking adventure and leisure in the heart of Florida.

  • Orlando: As a bustling metropolis, Orlando is renowned for its family-friendly atmosphere and entertainment-centric offerings. Regal Oaks is conveniently located within this vibrant city. Visitors flock to Orlando for its myriad attractions, including world-famous theme parks, impressive shopping districts, and cultural arts centres. Must-visit landmarks include the iconic Walt Disney World, Universal Studios, and the beautiful beaches nearby. The city's well-connected transport network ensures a smooth travel experience, making it easy to explore these diverse attractions.
  • Kissimmee: Kissimmee is a charming city situated just a stone's throw from Regal Oaks. It draws families and thrill-seekers alike with its abundance of entertainment options. The city is famous for its welcoming resorts and expansive shopping areas, including popular shopping mall centres. Nearby attractions such as theme parks and film studios promise excitement and adventure. Kissimmee’s convenient location also provides easy access to scenic natural areas, making it an ideal base for exploring the surrounding attractions.
  • Lake Buena Vista: Located a mere 8km from Regal Oaks, Lake Buena Vista is a lively city that offers a wealth of family-oriented experiences. Known for its luxurious resorts and shopping venues, visitors can indulge in retail therapy or enjoy exquisite dining options. The area is home to prominent attractions like world-renowned theme parks and state-of-the-art sports facilities. The blend of entertainment and leisure makes Lake Buena Vista a delightful addition to your travel itinerary.

Best time to go to Regal Oaks

If you're planning a trip to Regal Oaks, 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 August to October tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 SunnySlightly LowAverage
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 SunnyAverageAverage
December64.4°F (18.0°C)No Rain (Dry)Mostly SunnyAverageSlightly High

Booking with Vrbo is a breeze

Are you aiming to save on your upcoming trip? Being flexible with your travel dates can be beneficial, as prices tend to vary. Additionally, booking an extended stay often allows for significant savings. To discover the perfect Vrbo property that aligns with your budget, make use of our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo's Trip Board offers a handy platform for you to plan new journeys, resume your previous arrangements, or manage your travel itinerary. You'll discover your saved or booked properties neatly organised under Potential, Upcoming, or Current Trips. To begin utilising Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What are the best holiday rentals near Regal Oaks?
The best holiday rentals near Regal Oaks are typically found in Kissimmee, Florida, offering convenient access to the area's attractions. You will find a wide array of options, including private holiday houses superb for a family stay and comfortable condos. If you are willing to drive a bit further, renting in nearby areas can be an affordable option for finding larger properties. You can choose from many great holiday rentals near Regal Oaks.

Many desirable properties boast excellent amenities such as shared pools or private pools for a refreshing dip, and fitness facilities for staying active. These homes are ideal for families or groups seeking a comfortable and convenient base for their adventures.
Are there any cheap holiday rentals near Regal Oaks?
There are several affordable holiday rentals near Regal Oaks, especially if you are flexible with location and travel dates. Budget-friendly stays are typically around £95 per night. Some stays even drop below this price point in September and January during the off-season, making it a great option for guests looking to experience the area without overspending. These holiday rentals often include amenities such as free WiFi, toiletries, and free self-parking, and can range from cosy studio properties to modest family homes, providing a clean, comfortable base for adventure.

To get the best value, consider staying slightly outside major hubs. If you're willing to drive a bit further, renting around nearby areas can be an affordable option. With a little planning, it is absolutely possible to find a comfortable stay near Regal Oaks so you can have a comfortable stay while keeping costs down.

*Pricing data are based on past 12 months data.
What are the best pet-friendly holiday rentals near Regal Oaks?
There are hundreds of pet-friendly holiday rentals near Regal Oaks, with over 590 properties available. These homes are predominantly private holiday houses and apartments located in Kissimmee, Florida. Many rentals offer specific amenities for pets, including designated dog exercise areas, and some even permit pets to stay free. Guests can also expect comfortable living spaces, well-equipped kitchens, and often private outdoor areas for relaxation.

When searching for the best pet-friendly holiday rentals near Regal Oaks, it is essential to review each property's specific pet policy regarding size restrictions or additional fees. While Regal Oaks itself welcomes service animals, pets are generally permitted in common outdoor areas on a lead.
What are the top holiday rentals with pools near Regal Oaks?
There are over 4,230 holiday rentals near Regal Oaks that include access to swimming pools, with both private and shared options available. Properties are concentrated in areas surrounding Regal Oaks and in Kissimmee, offering a variety of choices from private backyard pools to expansive community pools with waterslides. Many of these homes come fully equipped with amenities such as full kitchens, Wi-Fi, and multiple bedrooms, making them ideal for families or groups seeking comfort and convenience.

When selecting your rental, consider the benefits of each pool type. Private pools offer seclusion and are superb for families desiring a personal space, while shared pools often provide access to additional features like poolside bars or children's pools. For cooler months, look for heated or indoor options to ensure year-round enjoyment. Checking availability well in advance, especially for peak seasons, is advisable.
What are the best family holiday rentals near Regal Oaks?
There are over 3,475 family-friendly holiday homes available near Regal Oaks, primarily consisting of private holiday houses and condos. These properties offer ample space with multiple bedrooms and bathrooms, ensuring comfort for groups. Many come equipped with full kitchens for meal preparation, washer/dryers for convenience, and outdoor play areas like yards or patios. Entertainment options such as video games and access to playgrounds or water parks are also commonly found.

When selecting a home for your family stay, prioritise properties that offer separate living spaces for adults and children, and practical amenities like a fully equipped kitchen to simplify your trip. Staying close to Regal Oaks means less time travelling and more time enjoying the attractions.
Are there any luxury holiday rentals near Regal Oaks?
There are several luxury holiday rentals near Regal Oaks that combine scenic views with modern comfort. These properties often feature amenities such as private outdoor hot tubs, deep soaking bathtubs, private heated pools, and lake views. Guests can also find properties with golf onsite and premium bedding.

These homes are ideal for families or larger groups. Many of these top-tier stays are managed by highly rated Vrbo hosts, ensuring a professional and premium experience.
How much is a holiday rental near Regal Oaks?
Holiday rentals near Regal Oaks offer a wide range of options to suit different budgets, making it easy for guests to enjoy a memorable stay. Budget-friendly properties, such as simple apartments, typically start around £95 per night, providing an affordable option. Mid-range rentals, including private homes with standard amenities, are generally around £175 per night, offering more comfort and privacy. For those seeking a more luxurious experience, upscale options can cost £255 or more per night, especially during peak season.

Enter your destination, travel dates, and number of guests on search to see the best options. You can use filters to set a minimum and maximum nightly price range along with other preferences. Rates may vary based on the season and specific amenities, but with a little planning, guests can find a rental that perfectly balances convenience and value.

*Pricing data are based on past 12 months data.
Where should I stay when visiting Regal Oaks?
When visiting Regal Oaks, several areas offer excellent holiday rental options. The immediate vicinity of Old Town Kissimmee is highly recommended for its close proximity to Regal Oaks and its diverse range of entertainment and dining options. Properties here provide convenient access to local attractions.

Another excellent choice is the area around Celebration. This master-planned community offers a charming, pedestrian-friendly environment with beautiful homes and a delightful town centre, all just a short drive from Regal Oaks. Guests will appreciate the relaxed setting and accessible amenities.

For those seeking properties closer to the wider array of theme parks, the area along US Highway 192 (Irlo Bronson Memorial Highway) provides numerous holiday rental communities. These properties are a short drive from Regal Oaks and offer convenient access to many popular attractions.
What is the cheapest month to stay near Regal Oaks?
The cheapest time to find holiday rentals near Regal Oaks is typically during the late Summer to early Autumn (September) and the Winter (January), excluding any major local holiday periods. September is frequently the cheapest month, often providing lower rates on properties and homes. Guests can often find various savings during these months, with rates sometimes 10-20% less compared to peak season.
Are there any lakefront holiday rentals near Regal Oaks
Lakefront holiday rentals near Regal Oaks are available, primarily found on the many beautiful lakes in the Kissimmee area, such as Lake Toho or East Lake Toho. These properties are a short drive from Regal Oaks, offering convenient access to water activities such as kayaking, fishing, swimming, or relaxing by the shore.

These homes often feature spacious decks, fire pits, hot tubs, and full kitchens, making them ideal for families and larger groups. Guests can enjoy waterside views and unwind in peaceful surroundings.
Are there any monthly holiday rentals near Regal Oaks?
Vrbo offers excellent options for monthly holiday rentals near Regal Oaks, making it a great choice for those who want to combine work and adventure. Monthly rentals often feel like a true home away from home, with fully furnished properties equipped with essential amenities like high-speed Wi-Fi, full kitchens, and comfortable workspaces, perfect for remote work or a summer holiday with the family. With flexible monthly rental options, Vrbo is a convenient and comfortable choice for extended stays near Regal Oaks.
Are there any last-minute holiday rentals near Regal Oaks?
Vrbo makes it simple to find last-minute holiday rentals near Regal Oaks that blend comfort, style, and great value. Vrbo offers plenty of options for guests ready to pack up and go. Families and groups will find these deals especially appealing. Many spacious homes, complete with full kitchens, private pools, and multiple bedrooms, often become available when hosts want to fill open dates on their calendars.

Finding these stays is easy. Just enter your destination and travel dates, then use Vrbo's "Last Minute" or "Discounts" filter to uncover the best offers. You'll see reduced rates in the listings. Vrbo's last-minute rentals are a smart way to save while you explore. Whether you're planning a quick trip or a weekend getaway with friends, your last-minute escape is waiting, you just have to decide where to go next.
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 favourites, and build the perfect itinerary together.

More holiday ideas