Property in Kissimmee
Luxury Vacation Rentals in Kissimee
Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.
We found 772 vacation rentals – enter your dates for availability.
Welcome to Kissimee
Find your place in our collection of luxury vacation rentals in Kissimmee, where resort-community villas and tranquil lake-view homes meet Wander’s five-star standards. It is the sweet spot between a luxury hotel and a private residence, consistently delivered and always photo-true.
Expect private screened pools, multiple king suites, chef-grade kitchens, game or cinema rooms, and airy outdoor dining. Ultra fast WiFi, purpose-built workspaces, pristine cleaning, and 24/7 concierge keep everything effortless.
From sleek pool homes for a workcation to expansive estates for a milestone gathering, every stay is beautifully operated so you can simply arrive and relax.
Destinations near Kissimee
Highlights in Kissimee
Discover Kissimmee's perfect blend of thrilling theme parks, classic Florida nature, and vibrant family-friendly entertainment.
Old Town Kissimmee
Fun Spot America - Kissimmee
Kissimmee Lakefront Park
Shingle Creek Regional Park
Gatorland
Medieval Times Dinner & Tournament
IT'S A VACATION HOME, BUT BETTER
The Wander difference
Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.
All homes in Kissimee
Property in Kissimmee
15 bedrooms•14.5 baths
2,552 US dollars for 3 nights•
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Property in Kissimmee
15 bedrooms•15 baths
2,552 US dollars for 3 nights•
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Home in Kissimmee
12 bedrooms•11.5 baths
2,050 US dollars for 4 nights•
Home in Kissimmee
2 bedrooms•3 baths
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Home in Kissimmee
6 bedrooms•6 baths
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Home in Kissimmee
3 bedrooms•5 baths
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Home in Kissimmee
4 bedrooms•2 baths
1,387 US dollars for 4 nights•
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Home in Kissimmee
5 bedrooms•3 baths
1,302 US dollars for 4 nights•
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Most popular amenities for vacation rentals in Kissimee
Other popular amenities & vacation types in Kissimee
Discover more of Kissimee
Set between shimmering lakes and Orlando’s marquee attractions, Kissimmee offers easy energy, sunshine, and variety in one destination. Start on Lake Tohopekaliga, stroll Old Town’s retro streets, then watch the sky glow over the water at dusk.
Access is simple via Orlando International Airport, and major highways place theme parks, championship golf, and the headwaters of the Everglades within easy reach. With family-friendly buzz, abundant outdoor space, and warm weather most of the year, it is a smart choice for groups and quick escapes. That is why Wander's luxury vacation rentals in Kissimmee are ideal, whether you are traveling for work or leisure.
FAQs: Vacation Rentals in Kissimee
Why should I book a Wander in Kissimee over other vacation rentals?
Wander offers a level of consistency and quality you won’t find with most vacation rentals.
Every home in Kissimee delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?
Which are Wander’s most popular vacation rentals in Kissimee?
Some of our most popular vacation rentals in Kissimee include Luxurious 15-Bedroom Villa with Pool & Games Room, Disney-Adjacent 15BD/15BA Oasis with Private Pool, and 4473 Monado. Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.
How many different vacation rentals does Wander have available in Kissimee?
Wander offers 772 vacation rentals in Kissimee, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.
What time is check-in and check-out at Wander’s vacation rentals in Kissimee?
You can check-in to Wander vacation rentals in Kissimee after 4.00pm and check-out before 10.00am.
Do Wander’s vacation rentals in Kissimee have WiFi access?
Yes. Every Wander home in Kissimee has ultra fast, reliable WiFi so you can stay connected throughout your stay.
What is Wander’s cancellation policy?
You can cancel your reservation within 24 hours of booking for a full refund.
For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.
For some homes, a 30-day deadline applies; this will be clearly shown before you book.