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5 Bedroom Vacation Homes In Kissimmee Fl

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Cumbrian Lakes 5 Bedroom Rental 407-966-4144 Kissimmee Orlando Vacation Homes 360

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Experience Kissimmee With Your Pet In A Vacation Rental

If you’re looking for pet-friendly rentals while you vacation in Florida, Kissimmee is a great option. Located in central Florida, Kissimmee is close enough to all the attractions but far enough away from Orlando that you can find great pet-friendly rentals at cheaper prices. There are plenty of things to do in Kissimmee, whether you’re looking for daytime activities or nighttime entertainment. Within 30 minutes, you can be at Walt Disney World Resort. With fun for kids and adults alike, Kissimmee really is an optimal place to stay.

What Is The Best Area To Stay When Traveling To Kissimmee

Whether you’re 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.

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Vacation Homeremington Golf Club 5 Bedroom Pool Home Near Disney

1031 Berkeley Drive, Kissimmee, 34744, United States of AmericaShow map

The 10 score is from guests who booked this property on other travel websites we trust. There arent any reviews from guests yet, so this score can tell you more about the propertys quality.

Kissimmee Fl 5 Bedroom Homes For Sale

Upmarket family villas in Orlando
  • Brokered byRoad House Realty Inc.New
  • Brokered byLa Rosa Realty LlcFor Sale
  • Brokered byMacera Realty Group IncPending
  • Brokered byEXP Realty, LLCPending
  • Brokered byLA ROSA REALTY KISSIMMEENew – 15 hours ago
  • Brokered byEXP Realty, LLCPending
  • Brokered byEXP Realty, LLCNewOpen House TODAY
  • Brokered byWEICHERT, REALTORS – HallmarkNew
  • Brokered byOrlando Regional RealtyPending
  • Brokered byWJH BROKERAGE FL LLCNew Construction
  • Brokered byAmg International RealtyPending
  • Brokered byAmeriteam Realty Inc.Pending
  • Built byD.R. Horton – Orlando East CityNewNew Construction
  • Brokered byPremier Sotheby’s International RealtyPending
  • Brokered byAGENT PLUS REALTYFor Sale
  • Built byD.R. Horton – Orlando East CityNew Construction
  • Built byD.R. Horton – Orlando East CityNew Construction
  • Brokered byTrue Oak RealtyPending
  • Built byD.R. Horton – Orlando East CityTo Be Built
  • Brokered byMark Spain Real EstateNew
  • Built byD.R. Horton – Orlando East CityTo Be Built
  • Built byD.R. Horton – Orlando East CityNew Construction
  • Brokered byLegacy Plus RealtyPending
  • Built byD.R. Horton – Orlando East CityTo Be Built
  • Built byD.R. Horton – Orlando East CityNewNew Construction
  • Brokered byKeller Williams RealtyPending
  • Built byD.R. Horton – Orlando East CityNewNew Construction
  • Brokered byBARDELL REAL ESTATEPending
  • Brokered byKeller Williams Realty Of WhNew
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    Activities Near Kissimmee Vacation Homes

    Kissimmee’s 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 you’ll take in the surrounding wetland wilderness. Eco-tours via horseback, zipline, or airboat are just a few of your options. You’ll 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 region’s theme park lights twinkle below.

    Orlando Vacation Home Rentals

    Here at Homes of America Rentals we understand what makes a luxury vacation home right for you. We make it our business to find a vacation rental that meets all of your needs and goes above and beyond your expectations. By providing the finest in vacation rentals we can ensure that your vacation is a success no matter where you decide to stay.

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    Luxury 5 Bed Villa With South

    Indian Creek 5 Bedroom Rental 407-966-4144 Kissimmee Orlando
    • Minimum Stay: 5 nights
    • Living Area: 2216 sq. ft.

    A luxurious 5 bedroom 4 bath villa with south-facing pool situated in luxury Emerald Island Resort Orlando. Located a short distance from the popular destinations such as Disney World, Sea World and Universal Studios and accommodates 10-12 guests. This tastefully-decorated 5 bedroom/4 bath vacation rental is in a great location: 3 miles or 5 minutes from Disney World, close to the famous Formosa Gardens Shopping area and will surely create many memories on your next vacation. Lilo’s Magic villa in Emerald Island Resort Villa Features:3 Miles to Disney in Emerald Island Resort 5 bedrooms, 4 bathrooms Towels and linens provided Fully air-conditioned Fully equipped kitchen Full-size washer and dryerDVD Players Free WIFI, just bring your laptop Surround sound system Full size clothes washer and dryer Pack ‘n play/High chair

    Unique Benefits

    Direct from owners with no booking fees and commissions 3 miles or 5 minutes from Disney World Gated resort community

    Themed bedrooms

    Area Information

    Emerald Island Resort is a gated resort community with community features accessible to all guests. The community is close to Disney World and many restaurants, shops and grocery stores.

    Favorite Places To Eat

    So many to choose from


    No booking or service fees

    Save up to 15% over other websites

    Florida’s #1 vacation rental site

    We’re the experts


    Pool heat per night: $30

    Tax Rate: 13.5%



    Nearest Airport

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    Among The Features That You Can Enjoy Here Are:

    • 3 signature golf courses. This is the golfers choice!
    • Reunion Golf Academy
    • On-property shuttle service
    • Restaurants and bars

    With regards to 5 bedroom vacation rentals in Orlando Florida, Reunion Resort does have plenty of options to offer you. There are several vacation homes in Reunion that can comfortably sleep up to 10 people and unlike when staying in a hotel, you wont feel crowded or cramped in these homes as they are spacious, lavishly decorated and are fully furnished to welcome you.

    These houses come with a fully equipped kitchen with stainless steel appliances, wooden cabinets, and granite countertop that will make you want to whip up a snack or a light bite for the gang while on vacation.

    Youll love the open-plan design in the living area where you will also have a dining area that will seat up to six guests. The flat-screen TV in the living room is accompanied by comfortable seating for you to relax. And if you want to avoid the community pool, you can take a dip in your own private pool instead. The large pool typically comes with a child safety fence, with lounge chairs offering you a chance to sit back and relax under the Florida sun or enjoy an alfresco meal.

    Can I Rent Villas In Calabria

    Yes, of course. Vrbo has 43 Villas in Calabria. Our other popular types of vacation rentals in Calabria include:

    • Houses: 220 rentals available
    • Townhouses: 65 rentals available
    • Condos/Apartments: 3 rentals available

    But you can also enjoy a great stay in one of our other vacation rentals including Studios and more.

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    Our Commitment To Safety

    As part of our commitment to the health and safety of our Guests, and the larger community, we have high standards for sanitation and employ robust cleaning procedures. Some of these steps include:

    • All bookings have a minimum of 30 hours between departure and next arrival
    • Extra cleaning and sanitization with special attention to disinfection of high touch areas before every arrival
    • Safety recommendations and procedures posted throughout the villa
    • All housekeeping staff wear protective gloves and masks
    • Adequate time between the home inspectors visit and your check in time.
    • All staff wear masks and practice social distancing should you need assistance during your stay.
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    Historic Sites Near Kissimmee Vacation Homes

    2636TW Veranda Palms Community 6 Bedrooms 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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    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!

    What To Expect From Orlando House Rentals With Private Pools

    When you rent one of the 5-bed Orlando house rentals with private pools with Magical Vacation Homes, you are getting attention to detail, a home everyone will love, and the confidence that comes from working with experts in Florida resort homes. Here are just a few of the unique amenities our smoke-free and pet-free vacation homes have to offer you.

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    Br/55bath/4miles To Disneyak/$149 Specials/freespa/lanai

    • Minimum Stay: 4 – 5 nights
    • Living Area: 2881 sq. ft.


    John Beck

    Year Purchased: 2004

    About the owner: I am the father of 7 and grandfather of 10. Disney trips started in 1976 and continue to this day. It’s hard to find a place with more vacation options than the Orlando area. We saw this development being built in 2000 and decided this was the ideal place to own a short-term rental house our children and grandchildren could use while renting it out in between. The Financial Crisis of 2007-8 brought much grief to this community. As Treasurer and President of the Homeowners Association, I was able to keep the associations cash flow at a healthy level and thereby preserved the vital landscaping services. The location is almost perfect at 3 miles from Disney and the landscaping is outstanding. Animal Kingdom is 10 minutes away, Disney Hollywood Studios is 15 minutes and the Magic Kingdom is 20 minutes away. Some say the landscaping at the resort is like an extension of the Disney landscaping. The house provides everything imaginable to have a great vacation experience.

    Calendar last updated: February 23, 2022

    Links to more information:

    Best Time To Travel To Kissimmee Vacation Homes

    5 Bedroom Orlando Vacation Home | Family Rental House | Florida

    You don’t 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 it’s also the height of hurricane season, so check local forecasts.

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    Orlando Vacation Home Location And Key Resort Features

    • Minutes from Disney
    • Complimentary Transportation to Disney, Universal, and SeaWorld
    • Complimentary Resort Transportation throughout the Property and Reunion
    • 2 Full-Service Restaurants and 2 Full-Service Bars On-premises as well as Dining Delivery
    • Concierge Services Available
    • 24-hour Onsite Service and Maintenance Team
    • Amazing Pools, Cabanas and Water Activities
    • Sports and Recreational Courts/Fields including Basketball, Soccer, Volleyball, and Tennis
    • Water Park with Six Premier Slides, Kids Splash Zone, Adult Pool, and Private Cabanas
    • Spa Services Available in Homes and in Cabanas
    • Hang 10 Hideaway Kids Club
    • Activities for the Entire Family
    • Fitness Center
    • Additional Home Amenities Available for Delivery

    Who Should Rent 4 To 5 Bedroom Vacation Rentals In Orlando

    If you are going to travel with 4 people or more, such as two families traveling together, or a group such as a bachelorette party or golf outing, renting a vacation home is recommended. Who else are these homes good for?

    • Small family reunions
    • Christmas, Easter or other holidays
    • Golf trips
    • Small weddings or birthday parties
    • Business trips

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    When Is The Best Time To Stay In A Vacation Rental In Kissimmee

    Kissimmees busy season runs from March to August, with peak visitation periods taking place during U.S. Thanksgiving, Christmas, and Spring Break . During these times, Orlandos theme parks are teeming with fans of every age, and the states heat and humidity are at their peak. To avoid the worst of the heat, consider visiting between October and March, when temperatures are a bit milder and the crowds have eased up slightly. Pack a light jacket or sweater to wear after the sun sets. The months of July through September are the rainy season in central Florida. Temperatures can often rise above 30 degrees Celsius, and afternoon thundershowers are a common occurrence, so be sure to have protective gear on hand.

    What Are The Vacation Rentals Near Disney World Like

    Kissimmee, Florida: $325,000

    Houses of this size boast extra amenities. They include all the standard comforts that make you feel at home, such as fully-stocked kitchens, Wi-Fi, and plenty of TVs so everyone can relax in their preferred ways. But, they often include special perks, such as their own game rooms, grills, and/or and Jacuzzis. A few of these properties lie within resort communities, granting you access to additional amenities such as fitness rooms and tennis courts.

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    Couple’s 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.

    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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    Stay Cool & Comfortable

    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.

    Places To Visit Near Kissimmee Vacation Rentals

    Orlando Vacation Home Rental | Luxury Family House | 5 Bedroom | Florida

    Don’t list the attractions in Kissimmee out loud to your kids. The excitement might be too much for them. Luckily, the amusements on offer are fun for grown-ups, too. Green Meadows Farm is a peaceful countryside getaway where you can pet the animals, milk a cow, and have a picnic on the grass. Gatorland is a theme park with a playful, vintage feel. There are live animal shows and plenty of alligators in its breeding marsh, and you can buy hot dogs to feed them. Fun Spot America features old-time carnival rides and go-kart tracks.

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