Luxury Pet-Friendly 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 28 pet-friendly vacation rentals – enter your dates for availability.

Top-rated pet-friendly vacation rentals in Kissimmee

Townhome in Orlando

4 bedrooms•3.5 baths

4.5

1628NP - 9 Bed - Whimsical Wonderland - SR015V

Home in Kissimmee

9 bedrooms•6.5 baths

New

1761CV - 8 Bed - Amazonian Abode - SR012V

Home in Kissimmee

8 bedrooms•6.5 baths

New

1742CV - 9 Bed - Champion's Chateau - SR011V

Home in Kissimmee

9 bedrooms•6.5 baths

New

Home in Kissimmee

9 bedrooms•6.5 baths

New

1600NP - 8 Bed - Memories Mansion - SR019V

Home in Kissimmee

8 bedrooms•6.5 baths

New

1766CV - 9 Bed - Outerspace Oasis - SR007V

Home in Kissimmee

9 bedrooms•6.5 baths

New

1640NP - 9 Bed - Mythical Manor - SR013V

Home in Kissimmee

9 bedrooms•6.5 baths

New

Welcome to pet-friendly Kissimmee

Explore our luxury pet-friendly vacation rentals in Kissimmee and upgrade your next getaway with the comfort of a private home and the polish of a luxury hotel. Each Wander is beautifully designed, professionally cleaned, and supported by 24/7 concierge, so you can settle in with zero stress.

Thoughtful for pets and people alike, our homes offer generous layouts, easy-care finishes, and secure outdoor areas. Enjoy ultra fast WiFi, hotel-grade linens, and elevated extras like private pools or fitness spaces. Bring the dog without compromise and experience the best of hotel-grade consistency in a private setting.

Available soon in Kissimmee

Home in Kissimmee

8 bedrooms•6 baths

$1,356 for 3 nights•

New

Featured pet-friendly vacation rentals in Kissimmee

Home in Kissimmee

11 bedrooms•15 baths

$10,994 for 3 nights•

4.8

Highlights in Kissimmee

Experience the thrill of world-famous theme parks, scenic airboat rides, and charming historic districts in this sunny Florida destination.

Walt Disney World Resort

Old Town

Gatorland

Fun Spot America Theme Parks

Boggy Creek Airboat Adventures

Shingle Creek Regional Park

Celebration Town Center

Island H2O Water 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

Townhome in Orlando

4 bedrooms•3.5 baths

4.5

Home in Kissimmee

9 bedrooms•6.5 baths

New

Home in Kissimmee

8 bedrooms•6.5 baths

New

Home in Kissimmee

9 bedrooms•6.5 baths

New

Home in Kissimmee

9 bedrooms•6.5 baths

New

Home in Kissimmee

8 bedrooms•6.5 baths

New

Home in Kissimmee

9 bedrooms•6.5 baths

New

Home in Kissimmee

9 bedrooms•6.5 baths

New

View all homes

Most popular amenities for pet-friendly vacation rentals in Kissimmee

Basketball Court (19)

Exercise Equipment (1)

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Other popular amenities & vacation types in Kissimmee

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Discover more pet-friendly spots in Kissimmee

Kissimmee delivers the best of Central Florida in one place, from the wide waters of Lake Tohopekaliga to lively entertainment districts. Start the day with a sunrise at Kissimmee Lakefront Park, then find world-class thrills minutes away at Walt Disney World Resort and other marquee attractions.

Glide beneath cypress canopies on Shingle Creek, catch classic car cruise nights at Old Town, or tee off at Falcon’s Fire. With year-round sunshine and Orlando International Airport a short drive away, getting here is easy. That blend of access and atmosphere is why Wander’s luxury pet-friendly 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 pet-friendly vacation rentals?

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

Some of our most popular pet-friendly vacation rentals in Kissimmee include 14506, 1628NP - 9 Bed - Whimsical Wonderland - SR015V, and 1761CV - 8 Bed - Amazonian Abode - SR012V. 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 pet-friendly vacation rentals does Wander have available in Kissimmee?

Wander offers 28 pet-friendly 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 pet-friendly vacation rentals in Kissimmee?

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

Do Wander’s pet-friendly 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.