Title: Kissimmee Luxury Vacations 2026 | Expedia.com ![](https://images.trvl-media.com/place/553248635976468613/a4b39294-97b5-4944-b58a-f1bdb34b53cf.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Kissimmee Luxury Vacations ## Book a Luxury Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## Top Luxury vacation packages in Kissimmee Price found within the past 48 hours. Click for updated prices. ![Westgate Town Center Resort](https://images.trvl-media.com/lodging/1000000/430000/426900/426819/62319b88_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Westgate Town Center Resort $152 per person May 30 - Jun 2 found 1 day ago Roundtrip flight included Atlanta (ATL) to Orlando (MCO) 8/10 Very Good! (1,510 reviews) Enjoyed our stay here but they really push selling their time-shares. Here are the things that should be noted: -no shuttle to Disney -no place to really find breakfast. I got an egg sandwich bagel at the cafe (ten dollars and the top of the bagel was rock hard). Cafe has line up since only place. -you pay extra for the pirate ship cove Reviewed on Mar 29, 2026 ![Westgate Vacation Villas Resort](https://images.trvl-media.com/lodging/1000000/100000/99000/98920/b8afec09_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Westgate Vacation Villas Resort Save 100% on your flight $172 per person May 30 - Jun 2 found 1 hour ago Roundtrip flight included Atlanta (ATL) to Orlando (MCO) 8/10 Very Good! (1,820 reviews) Average resort but worth trying out. Reviewed on Mar 29, 2026 ![Reunion Resort & Golf Club](https://images.trvl-media.com/lodging/1000000/1000000/992500/992499/45af642e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Reunion Resort & Golf Club Reunion Save 100% on your flight $389 per person Apr 29 - May 2 found 24 hours ago Roundtrip flight included Houston (HOU) to Orlando (MCO) 8.8/10 Excellent! (1,484 reviews) Beautiful resort, awesome staff and convenient location Reviewed on Mar 29, 2026 ![Magic Village Yards, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/10000000/9050000/9046300/9046290/979646d6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Magic Village Yards, Trademark Collection by Wyndham Save 100% on your flight $421 per person May 30 - Jun 2 found 1 hour ago Roundtrip flight included Atlanta (ATL) to Orlando (MCO) 9.2/10 Wonderful! (1,174 reviews) Good place, spacious units but a little dated. Great proximity to Disney World parks. Reviewed on Mar 28, 2026 ![FantasyWorld Resort](https://images.trvl-media.com/lodging/1000000/90000/84900/84866/76e24bdf_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### FantasyWorld Resort Save 100% on your flight $256 per person Apr 29 - May 2 found 10 hours ago Roundtrip flight included Atlanta (ATL) to Orlando (MCO) 8.6/10 Excellent! (1,009 reviews) The resort had lots to offer and was overall a nice stay. The villa needed a bit of repair and needed to be cleaned better in certain areas. Not enough toilet paper in the bathrooms, had to go to front office to get some more. The cost of the activities was a bit high (bingo for $5 a card) and there was an issue with the shuttle to Epcot. It was late both for pick up to get there and upon return we waited over 30 mins and eventually another shuttle driver took us to our resort but it wasn’t his run. The pool was great and having the small convenience store in the lobby was very handy. Reviewed on Mar 24, 2026 Don't see what you're looking for? See all available trips from Columbus to Kissimmee [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-30/2026-05-07/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=ORL&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Luxury vacations in Kissimmee Price found within the past 48 hours. Click for updated prices. ![Reunion Resort & Golf Club](https://images.trvl-media.com/lodging/1000000/1000000/992500/992499/45af642e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Reunion Resort & Golf Club Reunion Save 100% on your flight $389 per person Apr 29 - May 2 found 24 hours ago Roundtrip flight included Houston (HOU) to Orlando (MCO) 8.8/10 Excellent! (1,484 reviews) Beautiful resort, awesome staff and convenient location Reviewed on Mar 29, 2026 Don't see what you're looking for? See all available trips from Columbus to Kissimmee [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-30/2026-05-07/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=ORL&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Luxury vacations in Kissimmee Price found within the past 48 hours. Click for updated prices. ![Westgate Town Center Resort](https://images.trvl-media.com/lodging/1000000/430000/426900/426819/62319b88_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Westgate Town Center Resort $152 per person May 30 - Jun 2 found 1 day ago Roundtrip flight included Atlanta (ATL) to Orlando (MCO) 8/10 Very Good! (1,510 reviews) Enjoyed our stay here but they really push selling their time-shares. Here are the things that should be noted: -no shuttle to Disney -no place to really find breakfast. I got an egg sandwich bagel at the cafe (ten dollars and the top of the bagel was rock hard). Cafe has line up since only place. -you pay extra for the pirate ship cove Reviewed on Mar 29, 2026 ![Westgate Vacation Villas Resort](https://images.trvl-media.com/lodging/1000000/100000/99000/98920/b8afec09_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Westgate Vacation Villas Resort Save 100% on your flight $172 per person May 30 - Jun 2 found 1 hour ago Roundtrip flight included Atlanta (ATL) to Orlando (MCO) 8/10 Very Good! (1,820 reviews) Average resort but worth trying out. Reviewed on Mar 29, 2026 ![FantasyWorld Resort](https://images.trvl-media.com/lodging/1000000/90000/84900/84866/76e24bdf_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### FantasyWorld Resort Save 100% on your flight $234 per person May 30 - Jun 2 found 1 day ago Roundtrip flight included Atlanta (ATL) to Orlando (MCO) 8.6/10 Excellent! (1,009 reviews) The resort had lots to offer and was overall a nice stay. The villa needed a bit of repair and needed to be cleaned better in certain areas. Not enough toilet paper in the bathrooms, had to go to front office to get some more. The cost of the activities was a bit high (bingo for $5 a card) and there was an issue with the shuttle to Epcot. It was late both for pick up to get there and upon return we waited over 30 mins and eventually another shuttle driver took us to our resort but it wasn’t his run. The pool was great and having the small convenience store in the lobby was very handy. Reviewed on Mar 24, 2026 Don't see what you're looking for? See all available trips from Columbus to Kissimmee [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-30/2026-05-07/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=ORL&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Luxury vacations in Kissimmee Price found within the past 48 hours. Click for updated prices. ![Seasons Florida Resort](https://images.trvl-media.com/lodging/2000000/1820000/1813900/1813900/c5ff34ca_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Seasons Florida Resort Save 100% on your flight $279 per person Apr 29 - May 3 found 1 day ago Roundtrip flight included Baltimore (BWI) to Orlando (MCO) 9/10 Wonderful! (3,493 reviews) Everything was great 😁 Reviewed on Mar 29, 2026 ![Westgate Vacation Villas Resort](https://images.trvl-media.com/lodging/1000000/100000/99000/98920/b8afec09_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Westgate Vacation Villas Resort $601 per person Jun 4 - Jun 8 found 1 hour ago Roundtrip flight included Pittsburgh (PIT) to Orlando (MCO) 8/10 Very Good! (1,820 reviews) Average resort but worth trying out. Reviewed on Mar 29, 2026 ![Westgate Town Center Resort](https://images.trvl-media.com/lodging/1000000/430000/426900/426819/62319b88_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Westgate Town Center Resort Save 100% on your flight $375 per person Apr 30 - May 4 found 10 hours ago Roundtrip flight included Detroit (DTW) to Orlando (MCO) 8/10 Very Good! (1,510 reviews) Enjoyed our stay here but they really push selling their time-shares. Here are the things that should be noted: -no shuttle to Disney -no place to really find breakfast. I got an egg sandwich bagel at the cafe (ten dollars and the top of the bagel was rock hard). Cafe has line up since only place. -you pay extra for the pirate ship cove Reviewed on Mar 29, 2026 Don't see what you're looking for? See all available trips from Columbus to Kissimmee [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-30/2026-05-07/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=ORL&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## All you need to know about luxury vacations in Kissimmee #### What can I expect from a luxury Kissimmee vacation? Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury Kissimmee vacation. Sip handcrafted cocktails by an infinity pool, sink into bliss at a full-service spa with a massage cabana on the beach, and chat, cheers, and laugh through exquisite breakfasts, lunches, and dinners with spectacular views. #### How can I find all-inclusive luxury vacation packages in Kissimmee? By refining your filters, the most opulent all-inclusive vacation packages will appear before your eyes. Check the 5\* filter to find truly sensational stays. You barely need to lift a finger. #### Can I book a cheap Kissimmee luxury vacation? Affordable luxury is only ever a few clicks away. Enter your travel dates and sort the grandiose getaways on offer by price to see the most fiscally friendly retreats first. Filter by budget, too, to find your perfect balance of luxury. Right now, luxury vacations start at $152\. Prices and availability are subject to change. Additional terms may apply. #### How can I book a luxury family vacation in Kissimmee? Tailor your luxury family escape by checking the filters that set the whole family’s hearts a-flutter. Whether that’s wet and wild water parks, heavenly hot tubs, or the kid-quieting magic of free Wi-Fi. #### Can I book a package in Kissimmee with a luxury vacation home? A private paradise is true luxury! Filter by property type for houses, villas, and apartments. For an amazingly affordable all-in-one luxury experience, book your accommodation, airfare, and car rental as a package. #### How can I find the best luxury vacation deals in Kissimmee? Find absolute delight in the dropdown! Simply sort your tempting search results by deals to find that lean-budget luxury. For a budget conscious stay, consider booking a stay away from big cities or outside the peak months. #### Can I book a luxury holiday in Kissimmee with free cancellation and/or flexible dates? Freedom and flexibility are the greatest luxuries of all. Get both when you filter by payment option and book a trip with free cancellation or on a buy now, pay later plan. #### Why should I book my luxury trip to Kissimmee with Expedia? A luxurious trip follows a stress-free booking experience. Find, build, and book the most glorious of getaways in seconds—with ATOL protection for added peace of mind. ## Top Luxury Kissimmee Hotels ![Reunion Resort & Golf Club](https://images.trvl-media.com/lodging/1000000/1000000/992500/992499/45af642e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Reunion Resort & Golf Club 7593 Gathering Drive Kissimmee FL - 16 min drive from Old Town Stay at Reunion Resort & Golf Club if you're ready for a luxe getaway. Popular amenities include a golf course, 2 poolside bars, and 11 outdoor pools. 8.8/10 Excellent! (1,503 reviews) Beautiful resort, awesome staff and convenient location Reviewed on Mar 29, 2026 [](https://expedia.com/Orlando-Hotels-Reunion-Resort-Golf-Club.h992499.Hotel-Information) ![Magic Village Yards, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/10000000/9050000/9046300/9046290/979646d6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Magic Village Yards, Trademark Collection by Wyndham 3151 Pantanal Lane Kissimmee FL - 13 min drive from Old Town Be treated to deluxe lodging at Magic Village Yards, Trademark Collection by Wyndham, where you'll find deep soaking bathtubs and a champagne service. Deluxe ... 9.2/10 Wonderful! (1,179 reviews) Good place, spacious units but a little dated. Great proximity to Disney World parks. Reviewed on Mar 28, 2026 [](https://expedia.com/Orlando-Hotels-Magic-Village-Yards.h9046290.Hotel-Information) ![Celebration Suites](https://images.trvl-media.com/lodging/1000000/20000/10200/10102/b6f51cd0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Celebration Suites 5820 W Irlo Bronson Memorial Hwy Kissimmee FL - 4 min walk from Old Town Celebration Suites delivers luxe lodging where you'll enjoy premium bedding and more. Deluxe amenities at this resort include 3 outdoor pools, a 24-hour fitness ... 8.8/10 Excellent! (1,001 reviews) El área de la cocina estuvo súper equipada y en excelentes condiciones. Muy limpio el cuarto Reviewed on Mar 28, 2026 [](https://expedia.com/Orlando-Hotels-Celebration-Suites.h10102.Hotel-Information) [See all 27,438 properties in Kissimmee](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=7927) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. 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Kissimmee ](https://expedia.com/Car-Rentals-In-Kissimmee.d7927.Car-Rental-Guide)[ Kissimmee Vacations ](https://expedia.com/Kissimmee.d7927.Destination-Travel-Guides)[ Things to do in Kissimmee ](https://expedia.com/Things-To-Do-In-Kissimmee.d7927.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.