Luxury Vacation Rentals in Kissimmee

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 1,014 vacation rentals – enter your dates for availability.

Top-rated vacation rentals in Kissimmee

Property in Kissimmee

15 bedrooms•14.5 baths

New

Home in Kissimmee

12 bedrooms•11.5 baths

•

~$180 less than other sites

Home in Kissimmee

4 bedrooms•3 baths

•

~$35 less than other sites

Home in Kissimmee

8 bedrooms•6 baths

Home in Poinciana

4 bedrooms•3 baths

New

Home

15 bedrooms•14 baths

•

New

~$380 less than other sites

Home in Kissimmee

15 bedrooms•14.5 baths

•

New

~$380 less than other sites

Townhome in Kissimmee

4 bedrooms•3 baths

•

~$60 less than other sites

Welcome to Kissimmee

Make your next Central Florida stay effortless with Wander’s collection of luxury vacation rentals in Kissimmee. Choose from resort-style homes with private pools, expansive living areas, multiple suites, and flexible spaces suited for groups or extended stays.

Every home looks exactly like the photos, is pristinely cleaned, and is supported by 24/7 concierge. Hotel-grade touches include ultra fast WiFi, dedicated workstations, chef-ready kitchens, and options for gyms or pools, so you can balance downtime and productivity with ease. Settle into a private residence that runs with hotel precision and feels like home.

Destinations near Kissimmee

Available soon in Kissimmee

Property in Kissimmee

15 bedrooms•14.5 baths

•

New

~$145 less than other sites

Home in Kissimmee

4 bedrooms•3 baths

•

~$35 less than other sites

Home in Kissimmee

8 bedrooms•6 baths

•

~$75 less than other sites

Home in Poinciana

4 bedrooms•3 baths

•

New

~$55 less than other sites

Townhome in Kissimmee

4 bedrooms•3 baths

•

~$60 less than other sites

Home in Kissimmee

12 bedrooms•11.5 baths

•

~$180 less than other sites

Home in Kissimmee

5 bedrooms•5 baths

•

~$80 less than other sites

Home in Poinciana

4 bedrooms•3 baths

•

New

~$55 less than other sites

Featured vacation rentals in Kissimmee

Luxury

Home in Kissimmee

10 bedrooms•11 baths

New

Home in Four Corners

10 bedrooms•10 baths

New

Home in Four Corners

9 bedrooms•9.5 baths

New

Luxury

Home in Kissimmee

9 bedrooms•10.5 baths

•

~$760 less than other sites

Luxury

Home in Kissimmee

9 bedrooms•12 baths

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New

~$660 less than other sites

Home in Kissimmee

11 bedrooms•15 baths

•

~$875 less than other sites

Home in Kissimmee

11 bedrooms•10 baths

•

New

~$460 less than other sites

Luxury

Home in Kissimmee

14 bedrooms•14 baths

•

New

~$690 less than other sites

Highlights in Kissimmee

Discover world-famous theme parks, thrilling airboat rides, and classic family entertainment in this central Florida hub of fun and excitement.

Walt Disney World Resort

Universal Orlando Resort

Old Town Kissimmee

Fun Spot America Kissimmee

Gatorland

Wild Florida Airboats, Gator Park & Drive-thru Safari

Celebration Town Center

Kissimmee Lakefront Park

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.

Only the best homes

We’ll never not look like the pictures. Every Wander is beautiful and expertly operated, so you can leave any stress at the door.

Hotel-grade amenities

We’ll never leave you with nothing to do. From ultra fast WiFi to gyms and pools, our homes make it easy to blend work and play.

24/7 concierge service

We’ll never leave you hanging. Our chat-based Concierge is always available to help – from trip questions to special requests.

Inspiring and stunning views

We’ll never leave you uninspired. Every Wander has stunning views to refresh and inspire your soul. Adventure awaits.

Meticulous cleaning

We’ll never have you check in to a dirty house. Our cleaning teams are meticulous, and there are no chores at checkout.

Safety and security

We’ll never pass you off to a stranger. Every Wander location meets our industry-leading safety standards to give you peace of mind.

All homes in Kissimmee

Property in Kissimmee

15 bedrooms•14.5 baths

New

Home in Kissimmee

12 bedrooms•11.5 baths

•

~$180 less than other sites

Home in Kissimmee

4 bedrooms•3 baths

•

~$35 less than other sites

Home in Kissimmee

8 bedrooms•6 baths

Home in Poinciana

4 bedrooms•3 baths

New

Home

15 bedrooms•14 baths

•

New

~$380 less than other sites

Home in Kissimmee

15 bedrooms•14.5 baths

•

New

~$380 less than other sites

Townhome in Kissimmee

4 bedrooms•3 baths

•

~$60 less than other sites

View all homes

Most popular amenities for vacation rentals in Kissimmee

Basketball court (26)

Other popular amenities & vacation types in Kissimmee

Family vacation rentals in Kissimmee

Large group vacation rentals in Kissimmee

Hot tub vacation rentals in Kissimmee

Private pool vacation rentals in Kissimmee

Discover more of Kissimmee

Kissimmee places you at the center of Central Florida, pairing easy access to world famous theme parks with the calm of lakes and protected wetlands. Paddle Shingle Creek, spot wildlife along the Everglades headwaters, or watch sunset light up Lake Tohopekaliga from the shore.

Beyond the water, tee off at top local courses, browse Old Town’s classic Americana, and explore entertainment districts across greater Orlando. Day trips to springs or the Space Coast are within easy reach, giving you variety without the hassle. This is why Wander’s luxury vacation rentals in Kissimmee are the perfect choice, whether you’re traveling for work or leisure.

FAQs: Vacation Rentals in Kissimmee

Why should I book a Wander in Kissimmee over other vacation rentals?

Wander offers a level of consistency and quality you won’t find with most vacation rentals.

Every home in Kissimmee 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 Kissimmee?

Some of our most popular vacation rentals in Kissimmee include Luxurious 15-Bedroom Villa with Pool & Games Room, 4473 Monado, and Heated Pool~Game Room~Modern~Resort~Disney Magic. 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 Kissimmee?

Wander offers 1014 vacation rentals in Kissimmee, 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 Kissimmee?

You can check-in to Wander vacation rentals in Kissimmee after 4.00pm and check-out before 10.00am.

Do Wander’s vacation rentals in Kissimmee have WiFi access?

Yes. Every Wander home in Kissimmee 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.