Luxury Lakefront Vacation Rentals in Kissimmee

Luxury Lakefront 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 13 lakefront vacation rentals – enter your dates for availability.
Welcome to the lakeside at Kissimmee

Welcome to the lakeside at Kissimmee

Find your waterside escape with Wander’s luxury lakefront vacation rentals in Kissimmee. Our handpicked homes deliver the polish of a five-star stay with the comfort of a private residence, set right on the tranquil shores of Kissimmee’s celebrated lakes.
Expect inspiring water views from sunrise to twilight, sunlit living spaces, chef-worthy kitchens, and plush primary suites. Outdoor areas invite downtime with screened lanais, waterfront pools, and spacious patios, while select homes add private docks or boat lifts. Every stay includes hotel-grade amenities, ultra fast WiFi, pristine cleaning, and 24/7 concierge support so you can blend work and leisure with ease.

Highlights in Kissimmee

Discover a world of thrilling theme parks, outdoor adventures, and family-friendly entertainment in the heart of Central Florida.
Old Town
Gatorland
Shingle Creek Regional Park
Medieval Times Dinner & Tournament
Fun Spot America - Kissimmee
Lake Tohopekaliga

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 Kissimmee

Townhome in Kissimmee property photo 1

Townhome in Kissimmee

5 bedrooms4 baths
931 US dollars for 4 nights
Home in Davenport property photo 1

Home in Davenport

11 bedrooms12 baths
New
Home in Davenport property photo 1

Home in Davenport

11 bedrooms12 baths
New
Condo in Kissimmee property photo 1

Condo in Kissimmee

2 bedrooms2 baths
504 US dollars for 3 nights
Home in Davenport property photo 1

Home in Davenport

12 bedrooms13 baths
New
Townhome in Kissimmee property photo 1

Townhome in Kissimmee

5 bedrooms4 baths
784 US dollars for 4 nights
Condo in Kissimmee property photo 1

Condo in Kissimmee

3 bedrooms2 baths
583 US dollars for 3 nights
Condo in Kissimmee property photo 1

Condo in Kissimmee

2 bedrooms2 baths
View all homes
Discover more lakeside charm in Kissimmee

Discover more lakeside charm in Kissimmee

Framed by the Kissimmee Chain of Lakes, this Florida haven is defined by glassy waters, moss-draped cypress, and vibrant sunsets. Lake Tohopekaliga and East Lake Toho are prized for trophy bass, broad shorelines, and wildlife from ospreys to sandhill cranes, giving the area a peaceful, distinctly Floridian character year-round.
Kissimmee sits minutes from Walt Disney World Resort, Universal Orlando, and championship golf, with easy access via Orlando International Airport. Warm winters and breezy evenings make it ideal for family time, romantic escapes, and working vacations. This is why Wander’s luxury lakefront vacation rentals in Kissimmee are the perfect choice, whether you are traveling for work or leisure.

FAQs: Vacation Rentals in Kissimmee

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

Wander offers a level of consistency and quality you won’t find with most lakefront 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 lakefront vacation rentals in Kissimmee?

Some of our most popular lakefront vacation rentals in Kissimmee include Wander Kissimmee Celebration, 1676OB - 11 Bed - Stunning Speakeasy - ST034, and 1660OB - 11 Bed - Wizards' Wonder - ST030. 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 lakefront vacation rentals does Wander have available in Kissimmee?

Wander offers 13 lakefront 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 lakefront vacation rentals in Kissimmee?

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

Do Wander’s lakefront 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.