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8 Bedroom Vacation Homes In Kissimmee Florida

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8 bedroom Windsor Westside 407-966-4144 Vacation Rental Orlando – Kissimmee

With prices that start at $165 per night for 5-bed rentals, ranging up to a maximum of $410 per night, we have vacation houses in Orlando that fit everyones budget! Tile floors, vaulted ceilings, and ceiling fans in every room ensure that every member of your family will remain cool and comfortable, even during the hottest days of summer. Velvet sofas sit lightly upon plush carpeting in the living areas, while youll find granite countertops, stainless steel appliances, and custom cabinetry in the kitchens.

Couples Retreat In Kissimmee Vacation Homes

Couples will find plenty of romantic experiences and locations in Kissimmee. Vacation homes are available near places like Lake Tohopekaliga, a huge fishing lake with wildlife viewing, airboat rides, and swimming, and Kissimmee Lakefront Park, a waterside park with walking paths and fishing areas. Youll also enjoy Main Gate Flea Market, an indoor flea market with booths selling clothing, accessories, and other goods.

Reason 3 Safety For Your Family Peace Of Mind For You

A vacation is your time to unwind and escape the pressures of your workaday life.

But if youre a parent, a family vacation can just feel like another job, one where the stakes are higher than any youll find in your professional life.

But while theres no getting around the big job of parenting, with ILoveVH, your familys safety is one less thing you have to worry about on your vacation.

With our selection of 8-bedroom Orlando vacation rentals, your family can enjoy the safety of a gated, guarded entrance, private yards and garages, and Ring doorbell cameras, while you enjoy the peace of mind you deserve.

Because from getting everyone out the door on time, to getting everyone to bed on time, to ensuring Laura that no, Lindas half of the cookie is not bigger than hers, youve got enough on your plate.

But with ILoveVH, safety is in the bag.

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What Is The Best Area To Stay When Traveling To Kissimmee

Whether youre traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Kissimmee:

  • Bellavida: 841 vacation rentals
  • Eagle Pointe South: 356 vacation rentals
  • Cumbrian Lakes: 135 vacation rentals
  • Historic Downtown Kissimmee: 282 vacation rentals
  • Venetian Bay Villages: 266 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

Choose From 8 Properties

8 bedroom Kissimmee Vacation Home


Sitting on the luxury gated community of Windsor at Westside, one of Kissimmees best resorts, is this beautifully decorated, 8 bedroom vacation villa with lake views from the west-facing pool deck and an air-conditioned games room. Situated close to Disney World and other Orlando attractions.

  • 5 x Double Beds
  • 6 x Single Beds
  • 6 x Bathrooms

This 8 bedroom privately owned rental villa is on the luxury gated resort of Windsor at Westside, one of Kissimmees best and most popular communities. Situated close to Disney World, this villa has a southeast-facing private pool and spa and an air-conditioned games room area within the house.

  • 6 x Double Beds
  • 4 x Single Beds
  • 6 x Bathrooms

Pool HeatingIncluded

This 8 bedroom privately owned villa has fun, themed bedrooms for the kids, a fantastic games room and a southeast-facing private pool and spa. It is located on the highly recommended gated community of Emerald Island in Kissimmee, close to Disney and all other Orlando attractions and theme parks.

  • 7 x Double Beds
  • 4 x Single Beds
  • 4.5 x Bathrooms

This large 8 bedroom vacation villa is on the famous ChampionsGate resort, a gated community in Davenport, close to Disney World and many other popular Orlando attractions. Features include a games room, a home cinema room, themed kids bedrooms and a private pool and spa with outdoor dining area.

  • 6 x Double Beds
  • 4 x Single Beds
  • 5 x Bathrooms

Pool HeatingIncluded

  • 5 x Double Beds
  • 8 x Single Beds
  • 5 x Bathrooms

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Best Time To Travel To Kissimmee Vacation Homes

You dont have to worry about the cold in Kissimmee, even in winter. January temperatures average in the 70s, and skies are typically sunny. The city is crowded during the Christmas holiday but otherwise peaceful, and you might score a Kissimmee vacation rental at a low rate. Spring weather is mild, with highs between the 60s and 80s, and rental prices are still low. Summer is the busy season and also the hottest, so look for lodging with air-conditioning. Temperature-wise, autumn is as lovely as spring, but its also the height of hurricane season, so check local forecasts.

Activities Near Kissimmee Vacation Homes

Kissimmees historic downtown is the center of commercial life and offers a mix of family-owned businesses, shops, and restaurants. Consider a Kissimmee vacation rental within walking distance of Main Street, where you can enjoy breakfast at an outdoor cafe before deciding how youll take in the surrounding wetland wilderness. Eco-tours via horseback, zipline, or airboat are just a few of your options. Youll likely have the chance to spot alligators, black bears, and dozens of bird species. Nighttime helicopter tours over the city provide a unique thrill, as the regions theme park lights twinkle below.

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Refinished/painted S Facing Pool/spa Updated Decor Near Disney Sleeps 8

  • Sleeps: 8
  • Minimum Stay: 3 nights
  • Living Area: 1800 sq. ft.

Unique Benefits

4 Miles from Disney Theme Parks/Disney Springs. Centrally located and close to all attractions, dining, grocery, fast-food, and golf. 30 mins from the Airport. 80 mins from Clearwater Beach, which was rated the most beautiful beach in the U.S. and 50 mins from Coco Beach. Both well within reach of an amazing day trip to the beach. We also have a stroller, highchair and pack n play available. Grill is available upon request. Each Room is very spacious with lots of dresser drawers and closet space for clothes and empty luggage. There are two different areas for seating so that the adults and children and gather together for group fun and entertainment.

Why Kids Love It

Quiet and relaxing after a long day at the parks. Inground heated pool.

Area Information

Favorite Places To Eat

Who Should Rent 8 To 10 Bedroom Vacation Rentals Orlando Florida

8 Bedroom Luxury Vacation Home in Orlando, FL

Are you wondering if renting an 8 bedroom vacation rental in Orlando Florida is good for you? How about 9 or 10 bedrooms? This depends entirely on how many guests are in your party. These homes make a great choice for many kinds of larger groups.

  • Multiple families traveling together
  • Holiday vacations such as Christmas or Passover
  • Reunions
  • Business related events or incentives
  • Bachelor or bachelorette parties
  • Golf or girlfriend getaways

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Outdoor Adventures In Kissimmee Fl

If you’re looking for an outdoor adventure or hoping for a bit of an adrenaline rush during your stay, you’re in luck! Tee off at Kissimmee golf courses, including the Remington Golf Club, or view the city by sky in a hot air balloon with Thompson Aire. Discover the Florida Everglades and alligators on an airboat ride with Boggy Creek Airboat Rides, an unforgettable experience that is guaranteed to amaze guests of all ages!

Invite your friends, pack your bags, and leave your worries behind when you come to one of our Kissimmee vacation homes. This charming town promises an exciting getaway full of adventure and family-friendly fun that you’ll remember for years to come.

Make Kissimmee Your Next Getawaychoose From 309 Great Vacation Rentals

With geography unlike any other, the Sunshine State combines emerald-green waters, swamplands, and inland cities. If youre looking for a blend of both world-class tourist attractions and small-town charm, our Kissimmee vacation rentals are the perfect choice for you! Whether you’re planning a relaxing retreat or an adventure-filled experience, our vacation homes serve as the perfect home base as you explore all that the eventful Central Florida region has to offer.

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Bookingcom Guest Review Guidelines

To keep the rating score and review content relevant for your upcoming trip, we archive reviews older than 36 months.

Only a customer who has booked through and stayed at the property in question can write a review. This allows us to verify that our reviews come from real guests like you. Who better to tell others about the free breakfast, friendly staff, or their comfortable room than someone whos stayed at the property?

We want you to share your story, with both the good and the not-so-good. All we ask is that you follow a few simple guidelines.

Modern 10 Bedroom 8 Bath Home Only Minutes From Disney

8 Bedroom Vacation Homes In Kissimmee Florida
  • Minimum Stay: 4 nights
  • Living Area: 4300 sq. ft.

Located in popular Sonoma Resort, our home is the perfect place to stay for a care and stress-free holiday away. Whether you are looking to spend long days lounging by the pool, exploring the parks or stretching your legs on one of the surrounding golf courses, this is the perfect location. Guests benefit from access to all the excellent facilities including clubhouse, swimming pool, and the fitness area, so there truly is something for everyone, with all you need on your doorstep!

Area Information

Private, gated vacation home community with clubhouse, pool, and fitness center within walking distance! Around 10+ minutes driving to restaurants, shopping and any place you need during stay!


No booking or service fees

Save up to 15% over other websites

Florida’s #1 vacation rental site

We’re the experts


Calendar last updated: July 22, 2022

Guestbook comments from the owner:

This place was great. Chunning was very helpful and responded immediately to our needs. I definitely recommend it!

Very large and spacious home that 15 people are able to enjoy. Many bathrooms for all and plenty of closet space to spread out. Extremely comfortable heated pool with jacuzzi was super pleasant even at 9pm. Property manager very responsive and considerate. Will use again if need arises. 1/20/2022 at 12:54 AM

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See All 8 Bedroom Vacation Rental Home Types That You Can Rent

With a vacation rental, choosing your accommodations becomes another part of the vacation fun.

Gather the whole family around the computer to enjoy the thrill of the hunt, as you single out the 8-bedroom homes that make everyone happiest.

Looking for lakefront rentals?

Weve got the best deals on the best views in Orlando.

Want to include your four-legged family members on your family vacation?

We have a great selection of pet-friendly rentals to choose from.

Looking for something besides 8-bedroom houses?

ILoveVH has Orlandos most diverse selection of rentals, from condos to mega-mansions.

In short, whatever kind of vacation rental best suits your familys needs, youll find it in our inventory.

So what are you waiting for the vacation fun starts now with the home-finding process.

Explore these great options today:

Historic Sites Near Kissimmee Vacation Homes

Kissimmee has numerous historic sites and museums to explore during your trip. Vacation rentals are available near fascinating places like the Museum of Military History, a museum with military relics, photographs, and personal stories, and Osceola County Welcome Center and History Museum, a local history museum with dioramas and interactive exhibits of the countys history. You can also visit the Monument of the States, a mid-century monument with stones sourced from the 50 states to celebrate American unity.

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Reason 2 Give Your Family The Privacy Everyone Deserves

A family vacation is your chance to do something you love with the people you love most.

But as much as we love our families, everyone needs a little me-time every now and then, especially after a long day at the parks.

And thats where we come in.

With an 8-bedroom vacation home rental from ILoveVH, everyone in your family can find the space to refill their social fuel tank at night, for more comity during the day.

Not to mention, with a better nights sleep, you can enjoy more stamina for more activities, and really take your vacation by the horns.

So if youre ready to seize every day on your next Orlando, FL vacation, ILoveVH can help you book the 8-bedroom vacation rental of your dreams for less.

Rent Your Vacation Home By Amount Of Bedrooms

Full POV Review Legacy Vacation Resorts Kissimmee Florida 2 bedroom

Want to get back to the basics?

While choosing your home type is part of the vacation fun, how much fun you have during your vacation depends largely on how much sleep you get.

And how much sleep you get depends largely on how many bedrooms you choose.

With ILoveVH, you can find the right number of bedrooms, for restful nights that let you enjoy fun-filled days.

Looking for one bedroom for you and your partner?

Our selection of condos are ideal for empty-nesters and retirees.

How about a multi-family home for your multi-family vacation?

ILoveVH has rentals with up to 14 bedrooms!

In short, however many bedrooms you need to have the best vacation ever, youll them with ILoveVH.

Weve even made it easy.

Use our convenient bedroom filter to rent by number of rooms and get the best sleep youve ever had on vacation!

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Why Choose Tropical Escape For Your Vacation Rentals Near Disney World

Our mission here at Tropical Escape Vacation Homes is to make sure your vacation is a long string of happy memories. We do that by offering the finest properties and taking care of them to keep them in top condition. Cleaning? Well have it practically sparkling? Maintenance? Every appliance will work better than new. Well make sure everything is taken care of, so you can have a stress-free vacation in your dream home.

Use the sites search bar to see our available options and find the perfect Vacation Rentals near Disney World for you. If were open right now, you can also hit the Chat Live bar on the right side of your screen to talk to an agent. If you have questions, call us at 1-866-409-8598. Your vacation should be full of happy memorieslet our homes be one of them!

Access To Resort Amenities

Remember, when you book a stay in one of the 9 bedroom vacation rentals in Orlando Florida or one of the other larger homes, you have access to the community resort amenities that your community offers. Whether you book your stay in Solterra Resort, Solara Resort or Reunion, youll be able to enjoy their community pool, spa, childrens play area, parks, hot tub and many other amenities too.

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See All Vacation Homes For Rent In Orlando Fl

Still just browsing?

Why not browse Orlandos best, most diverse selection of vacation home rentals!

Because while popular booking sites and apps, and even many smaller booking agencies, simply re-list whatevers on the market, ILoveVH is different.

We curate our collection to include only the best vacation home rentals in Orlando.

In order to make our exclusive inventory, a home needs to have a prime location, quality design and construction by a trusted builder, and luxury amenities both private and shared.

Therefore, you can browse our selection of vacation home rentals with the peace of mind that anything you choose, youre going to love!

Meant To Be Lived & Enjoyed

1810SAWYER: Kissimmee FL 8 Bedroom Vacation Villa Rental (137227 ...

Once inside, cool tile floors invite you to take off your shoes and explore the kitchens that are the heart of the Orlando vacation home rental. Stainless steel appliances, granite countertops, and custom cabinetry make meal preparation in these fully equipped kitchens a joy. Game rooms with comfy couches, bathrooms with both walk-in showers and deep soaking tubs, living areas with state of the art electronics, bedrooms with premium mattresses, and views of the beauty that is an Orlando landscape-these homes are meant to be lived in and enjoyed!

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Bed Pool Homes Rates Starting At: $18500 A Night

When staying in a Florida Vacation Homes five-bedroom vacation house in Orlando, you can count on being spoiled against any other vacation accommodations. We cherish our guests, and it shows in the details that most hotels and other vacation property management companies overlook. Elegant, classy, and stocked with only the best in furnishings, appliances, and electronics, your Orlando vacation promises to be an unforgettable one when you stay in one of our stunning vacation houses in Orlando FL. When you come back home tanned, relaxed, and smiling, youll know you made the right decision! Five bedrooms, five bathrooms, and a pool to frolic in during long and lazy vacation days were not bragging when we say your Florida vacation home is guaranteed to be the highlight of an already fantastic getaway!

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Want To Write A Review

If you stayed at this property through, you can write a review.

  • Awesome: 9+

You’re eligible for a Genius discount at 8 Bedroom Vacation Home with Pool 1914! To save at this property, all you have to do is .

Located in Kissimmee, 12 miles from Kissimmee Value Outlet Shops and 13 miles from 192 Flea Market, 8 Bedroom Vacation Home with Pool 1914 offers free WiFi, an outdoor swimming pool and air conditioning. Guests might go for a swim in the private pool.

The vacation home features 8 bedrooms, 6 bathrooms, bed linen, towels, a flat-screen TV with cable channels, a dining area, a fully equipped kitchen, and a patio with pool views.

A car rental service is available at the vacation home.

Kissimmee Sports Arena & Rodeo is 14 miles from 8 Bedroom Vacation Home with Pool, while Plaza del Sol Kissimmee is 14 miles away. The nearest airport is Orlando International Airport, 27 miles from the accommodation.

8 Bedroom Vacation Home with Pool 1914 has been welcoming guests since Jun 14, 2019

Top Location: Highly rated by recent guests

Free Parking Available On Site

Get instant confirmation with FREE cancellation on most rooms!

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