Orlando and Kissimmee Vacation Rentals Homes, condos, and townhomes for a magical vacation in Orlando or Kissimmee Where Florida Kissimmee Paradise Palm Resort - People 1 + 2 + 3 + 4 + 5 + 6 + 7 + 8 + 9 + 10 + 11 + 12 + 13 + 14 + 15 + 16 + 17 + 18 + 19 + 20 + 21 + 22 + 23 + 24 + 25 + 26 + 27 + 28 + 29 + 30 + Search View all Orlando and Kissimmee Area Properties USA > Florida > Orlando Visit Orlando Of course Walt Disney World and Universal Theme Parks draw people from around the world, but this central Florida hotspot has not only the parks’ fantasy playground but also a buzzing downtown scene, fantastic dining options, and a vibe that’s as diverse as its visitors. Catch an Orlando Magic game for a different sort of enchantment. Blend time in nature with the arts when you stroll around Lake Eola and then see a performance at the adjacent Walt Disney Amphitheater. The arts don’t stop there. Creativity abounds in the Mills 50 district–and the food scene! Quick bites from food trucks to upscale cuisine tempt any palate. Equal parts fantasy and reality, Orlando charts an exciting course for adventure. Find Your Orlando Rental Search while moving Featured Orlando Vacation Rentals Your Local TeamLocally Owned and Operated In OrlandoRemember, when you rent with SkyRun, you can expect superior, prompt, and personalized service that’s hard to find in a top-down rental corporation. Enjoy a personal relationship with your property manager, who can answer any questions and address all concerns promptly. Have a question about local activities, amenities, or services? Our local staff can provide recommendations for getting the most out of your stay. Our property managers are just a stone’s throw away from most of our rentals. That means they’re available to step in to help with any situation. Meet the dynamic team of Chris and Stephanie, a blend of Florida and Long Island roots. Chris, a proud University of Florida alum, ventured from Orlando’s Muzak to the helm of Commercial Systems Group. With a successful 15-year ownership, Chris and his partner propelled CSG to $20M in revenue and 100+ employees, culminating in its 2019 sale. Now, he embarks on a fresh journey with SkyRun, alongside by his wife Stephanie. Hailing from Long Island, Stephanie’s path led from Vermont University’s Lacrosse fields to Florida’s education sector, and eventually into insurance sales. Balancing motherhood since 2015 and with a new addition on the horizon, Stephanie’s eagerness to contribute to their new business venture knows no bounds. Chris & Stephanie InmanOrlando, FLOwner Of SkyRun OrlandoLet's Talk! Things to Do Theme Parks and Attractions What To Expect Check-In Instructions Property Damage Waiver Travel Insurance ShoppingBargain hunters and luxury lovers, Orlando has you covered. Malls and designer outlets host national retailers for the latest season’s goods. Smaller boutiques mean you can source unique goods to remind you of your Florida stay. The best part? Many of Orlando’s shops are embedded with the city’s entertainment options, which means you don’t have to choose between retail therapy and fun for the whole gang. Dining and NightlifeThe flavors of this city are out of this world and take you around the world. Of course the theme parks attract visitors with their world-class fare and casual bites, but Orlando’s dining scene also serves up upscale wine bars, breweries, eateries serving up quick bites to Michelin-starred menus. Eat your way along International Drive’s haunts piling on the American, Latin and other world flavors. Devour Asian delicacies at Universal CityWalk and then cap off the night with live music. In short, the parks aren’t the only stops in town that will dazzle all of your senses. Water AdventuresEven though the ocean might not border Orlando, that doesn’t mean that you can’t get on the water. The city brims with ecotourism outings, kayaking, and boating excursions that blend learning with fun. Different outfitters offer airboat rides of the rivers, marshes, and swamps dotting the area. Sailing Orlando offers the only sailing outing in the area–who says you need the Atlantic? Rent a kayak or book a tour to explore the waterways in the Orlando area. GolfingThe Sunshine State means year-round golfing (but pack the sunscreen). Here you’ll find options for every golfer, including mini-golf, Topgolf, and world-class courses like Arrnold Palmer’s Bay Hill Club and Lodge, Grand Cypress Golf Club, and Grand Vista Golf Club. Multiple public courses like Dubsdread Golf Course, Falcon’s Fire Golf Club, Shingle Creek Golf Club, MetroWest Golf Club, and more demand that you pack your clubs and perfect your game under the Florida sun. GolfingThe Sunshine State means year-round golfing (but pack the sunscreen). Here you’ll find options for every golfer, including mini-golf, Topgolf, and world-class courses like Arrnold Palmer’s Bay Hill Club and Lodge, Grand Cypress Golf Club, and Grand Vista Golf Club. Multiple public courses like Dubsdread Golf Course, Falcon’s Fire Golf Club, Shingle Creek Golf Club, MetroWest Golf Club, and more demand that you pack your clubs and perfect your game under the Florida sun. Spas and WellnessPamper yourself at one of Orlando’s wellness spots. Indulge in full-body massages, facials, and other treatments to have you glowing from the inside out. World-class resorts like the Waldorf Astoria Spa and The Ritz-Carlton Spa provide a total sensory feast. Others, like the Woodhouse Day Spa and The Spa at Bella Collina, provide a serene escape with tranquil environments and personalized services. After the hustle and pizzazz of Orlando’s attractions, time blissing out is a must. Walt Disney World ResortEnchantment awaits at this iconic wonderland. Four theme parks—Magic Kingdom, Epcot, Disney’s Hollywood Studios, and Disney’s Animal Kingdom—immerse guests in worlds of fantasy. Come for rides like the Haunted Mansion and Guardians of the Galaxy: Cosmic Rewind and stroll EPCOT–it’s like visiting Europe in one stop. Beloved characters, the attention to detail, and the dining bounty make this Disney stop nothing short of extraordinary. Don’t forget the nightly fireworks! Universal Orlando ResortSpend the morning exploding through Diagon Alley, dodging Gringotts goblins, and downing butterbeer –it’s Harry Potter come to life. Then go back in time for the afternoon at Jurassic World. Universal Orlando Resort’s Hollywood’s thrills meet the heart-racing thunder of world-class rides. Sprint down the Mummy roller coaster or, sing along with Shrek during a boat ride. Beat the Florida heat at Volcano Bay, a water park teeming with colossal slides and coastal vibes. SeaWorld OrlandoGrab your poncho–Shamu’s powerful performance might get you wet! Don’t miss this Orlando mainstay named the Best Theme Park in Florida by USA Today Readers in 2023. Marine habitats put up close and personal with penguins, tropical fish, and dolphins (and you can even feed them). And the roller coasters! Mako, Kraken, and Manta will have you screaming. Attractions like Antarctica: Empire of the Penguin, the Dolphin Nursery, Turtle Trek, and Shark Encounter blend entertainment with education about conservation. LEGOLAND FloridaBuild the perfect excursion at LEGOLAND Florida! Conquer dragon-breath blasts on The Dragon coaster, zoom through a magical underwater kingdom on LEGO NINJAGO, and find the world’ first Peppa Pig theme park. The smallest imaginations have no limits at LEGO City, where young builders can earn their driver’s license or pilot a LEGO plane. Live shows, interactive play zones, the chance to meet LEGO characters, and the Fall 2024 opening of SEA LIFE Aquarium make LEGOLAND an Orlando destination to build into any itinerary. GatorlandGet up close and personal (but not too close!) with the reptilian stars at Gatorland. The new Croc Rock Adventure lets you climb, traverse a bridge, then zipline through the air. If you want your gator-watching a little lower key, a swamp cruise lets you ride through their wild habitats. Maybe a healthy distance from these prehistoric creatures is on the agenda. Watch the professional trainers and crocs put on a jaw-dropping show where you’ll learn about Florida’s fascinating ecosystem, and even feed these prehistoric creatures. Don’t miss the Capybara Encounter for maximum cuteness. Titanic: The Artifact ExhibitionFeel the grandeur, the excitement, and the heartache. More than a museum, the Titanic Artifact Exhibition features the liner’s grand staircase replica, audio recordings from survivors and witnesses, and an iceberg wall replicating the frigid temperatures that awaited the doomed passengers. Come aboard your journey with a boarding pass detailing a passenger’s story and fate. You’ll even explore the engine room and steerage quarters, gaining a deeper understanding of life on all decks of the “unsinkable” ship. Even if you’ve seen the movie, this hands-on experience will amaze and move you. Madame Tussauds OrlandoAre we in Hollywood? You might think so when you walk the red carpet at Madame Tussauds Orlando. Channing Tatum, Beyoncé, and Tiger Woods dazzle–in wax, of course. History lovers can see Obama at work in the Oval Office and Civil Rights leader Martin Luther King Jr. New “inhabitants” like Awkafina and Bad Bunny add even more sparkle. Bundle your tickets with other ICON Park attractions for even more savings. WonderWorks OrlandoScience meets serious fun at WonderWorks, an amusement park that entertains and educates–all in an upside-down building! More than 100 exhibits will bend your mind as you explore space, physics, art and technology. The Anti-Gravity Chamber, the Bed of Nails, and the Hurricane Shack demands a hands-on and gravity-defying experience. Magic fans, don’t miss the evening’s The Outta Control Magic Comedy Dinner Show. Kennedy Space CenterBlast out of this world and peek into the future worlds at the Kennedy Space Center. The towering Saturn V rocket, the launch simulators, and the Space Shuttle Atlantis will have you marveling at how far we’ve come and wondering what’s next. Shoppers, head to the “World’s Largest Space Shop” set up by NASA for all the space-themed gear you can envision. Orlando ICON ParkICON Park has earned the name “Orlando’s Ultimate Entertainment Destination” with good reason. The Park hosts sites like Madame Tussauds, The Wheel (an enormous ferris wheel), SeaLife Orlando Aquarium, the Museum of Illusion, and more. All that entertainment means appetites roar and you can please the whole group with more than 20 eateries serving up Gordon Ramsay fare to quick bites like wings. Stay into the night for live music. This is one-stop entertainment shopping. Museum of IllusionsBend your mind in a space where nothing is what it seems. The Museum of Illusions’ optical illusions, mind games, and interactive exhibits tha challenge every sense.Rooms will make you shrink or grow, adventures turn you upside-down, and puzzles will frustrate you in the best possible way. Tickets can be purchased alone or as part of ICON Park’s bundle options. What To Expect What is included As local residents, SkyRun staff are available to help you make the most of your trip to Orlando. We strive to have your property ready with everything you need and to provide you with all the information you will need even before you have to ask for it. But if you DO need something, our staff are here to help daily (and on call 24/7 for emergencies). We communicate with you the way YOU want to communicate. That can be using our webchat or simply giving us a call. We’ll also be sending you a few emails before and during your stay wth important information. You can also text us via our industry exclusive 2-way text messaging system. Included Services Pre-arrival quality inspection Hot tub maintenance (as applicable) Most properties have free parking (check each property listing for possible charges) Luxury linens & towels Fully equipped kitchens Wi-Fi and TV’s Departure cleaning and trash removal Starter Supplies Salt, pepper and cooking oil Coffee and coffee filters Garbage bags Dish/Dishwasher and laundrty detergent (as applicable) Hand soap and lotion Shampoo and conditioner TP, paper towels and tissue Hairdryer Check-In Instructions Check-In | Check-Out Check-in is 4:00pm ET and check-out is 10:00am ET. A check-in instructions email will be distributed to guests 7 days prior to arrival date containing directions and access information for the property. In most cases guests will access a property via a lockbox or smart lock using the given access code. Early check-ins can only be confirmed on the day of arrival. Guests must depart the property by the check-out time unless a late checkout has been coordinated and confirmed with the SkyRun office. Late check-outs must be coordinated directly with the SkyRun office no later than 9am on the day of departure; please note that if we have an incoming guest we will not be able to accommodate a late checkout. We ask that guests remove major trash from the unit, return the furniture to it’s original location, and load and run the dishwasher. Parking Parking may be limited. The check-in instructions email will contain information regarding parking at your property. Any parking fines assessed to your vehicles during your stay will be billed to you if they are billed to us. Parking fines can be significant. Property Damage Waiver Enjoy peace-of-mind with our incidental damage protection. SkyRun includes a property damage protection waiver on each reservation. The damage waiver covers damage to the property up to $1,500 so long as the damage is accidental and reported to SkyRun prior to your departure. It does not cover damage that is willful, the result of negligence, or damaged caused by the misuse of household items. It also doesn’t cover unreported damage. SkyRun doesn’t charge our guests a refundable damage deposit in lieu of the waiver. Unlike a refundable damage deposit, the damage protection waiver is non-refundable. If during your rental of our property, you damage the real or personal property assigned to that property, SkyRun will cover the cost of repairs or the cost to replace the property up to an amount not to exceed $1,500. Should the cost of the damage exceed $1,500 or does not meet the criteria for a “covered loss”, and the property owner’s insurance policy also does not cover the loss, then you shall be responsible for the full amount of the damage which will be charged to the credit card on file. Coverage is provided to you and all travelling companions that are staying in the home overnight during your stay. Coverage is not provided for loss due to: Your intentional acts or gross negligence. Any damage that occurs if you are in violation of the terms and conditions (including but not limited to having more than maximum occupancy or having a party). Loss, theft or damage to any personal effects owned by you or brought on the covered stay by you. Loss, theft or damage caused by any person other than you or your traveling companions with whom you share the property reservation unless substantiated by a police report. Your duties in the event of damage. You must: Take all reasonable, necessary steps to protect the property and prevent further damage to it. Report the loss in writing (email ok) prior to check-out to the SkyRun staff. Provide us documentation such as pictures to substantiate the claim. Travel Insurance Nationwide® Travel Insurance protects your vacation investment against unforeseen events like a hurricane, sickness, injury, flight cancellation, job loss and much more. Group coverage protects everyone in your traveling party for one low price. To learn more, email us at OrlandoPremium@SkyRun.com. Property Management You Can Trust Owning a vacation rental shouldn’t be stressful. Let SkyRun ease your worries and increase your revenue with our vacation rental management solutions. Why choose SkyRun? As a locally owned & operated business, our homeowners are not just a number to us, they’re our neighbors. But as a franchise, we have access to tools and tech that help you stay ahead of the game. That’s why thousands of second homeowners trust us with their properties. Learn More “My property’s income has doubled in the last year! SkyRun is a great business partner to me and their willingness to listen and grow revenue has been stellar.” Kay JohnsonDestin, FL SkyRun has done an amazing job with my beach condo. They pay attention to every detail and provide incredible service. They are super responsive and go way above and beyond. In just a very short time they have secured a large number of bookings for my unit. Exceptional company to work with and I highly recommend them. Nan S.Sarasota, FL SkyRun has been wonderful to work with. They are very forthcoming and professional. The team does an outstanding job taking care of both property owners and guests alike. UliSarasota, FL Orlando Blog Do I Need Short-Term Rental Insurance for My Vacation Property? Read More How to Turn Your House into an Airbnb: A Complete Guide from Vacation Rental Experts Read More SkyRun Selects PriceLabs’ Revenue Management Platform to Maximize Vacation Rental Revenue Read More SkyRun Named Among Top New & Emerging and Fastest Growing Franchises Read More View All Explore Nearby Areas St Augustine Orlando Frequently Asked Questions How do I know I’m getting a good vacation rental? SkyRun provides photos, virtual tours, maps, amenity details and reviews about the property you will be renting. Our staff has first-hand knowledge of each property, so don't hesitate to call us if you have any questions. What’s included? Our rentals come fully furnished including TVs, high-speed internet, linens and towels, a microwave, dishes, pots, pans, and other kitchen essentials. We sweat the details and provide supplies like shampoo, conditioner, tissues, paper towels, dishwasher detergent, soaps, trash bags, etc. We provide everything you expect from a fine hotel, and then some. Refer to individual listings to see more amenity information, and please contact us directly if you still have questions. Am I getting a good deal? When you book direct with SkyRun you avoid paying service fees that traditional listing sites like Airbnb and Vrbo charge. Our prices are also competitive with rent-from-owner rates, but we offer professional service, optional travel insurance, and immediate on-site assistance should the need arise. In addition, we offer exclusive discounts from local businesses, available only to SkyRun guests. SkyRun can help you plan and save on your entire vacation experience, not only the rental itself. We also offer a fantastic value on lodging booked within 30 - 60 days of arrival with our dynamically adjusted rates. How do I rent a property? What are the deposit and payment terms? You can rent any of our properties by booking directly on this website using a credit card or you can call to book a reservation if you would like to speak with a vacation planner. When you book, 1/3 of your total reservation cost or a minimum of $300 is charged as a non-refundable deposit to secure your rental. 30 days before your arrival, the remaining amount is due and becomes non-refundable if you need to cancel for any reason (see travel insurance above for exceptions). At this time, the credit card we have on file will be automatically charged for the balance. How do I check-in? For most properties, SkyRun utilizes a convenient keypad lock system which allows you to enter your vacation rental using a personalized access code, as opposed to having to pick up a key and worrying about keeping track of it during your stay. This also saves you the trouble of coming to a check-in center beforehand. Your welcome packet will be in your rental upon arrival, and our staff is always only a phone call away if any questions arise. What are the house rules? No smoking and no pets (unless specifically designated as a pet-friendly property) are allowed in the rentals. House parties and exceeding the maximum occupancy at any time are prohibited. As in your own home, renters are of course subject to citations for noise violations, etc, handed down by public officials. Remember you are staying as a guest in someone's home, where much investment has been made to make your stay enjoyable; please treat all private property with the respect it deserves. Sign up for emails Trip inspiration, special offers, and vacation planning tips. Name(Required) First Last Email By submitting this form, I agree to SkyRun’s Privacy Policy Δ