Luxury Vacation Rentals with a Private Pool 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 952 private pool vacation rentals – enter your dates for availability.

Top-rated private pool vacation rentals in Kissimee

Luxurious Villa with Pool & Games Room

15 bedrooms•14.5 baths

•

New

~$230 less than other sites

4473 Monado

12 bedrooms•11.5 baths

•

~$175 less than other sites

Home in Kissimmee

8 bedrooms•6 baths

•

~$50 less than other sites

Large Home, Prime Location Orlando

8 bedrooms•5 baths

New

Retreat, Pool, Close to Disney

4 bedrooms•3 baths

•

New

~$55 less than other sites

Heated Pool Game Room Modern Resort Disney Magic

4 bedrooms•3 baths

•

~$35 less than other sites

Star Wars, Princess, Arcade Games, Disney 5334

4 bedrooms•3 baths

•

New

~$90 less than other sites

Harry Potter, Toy Story, Game Room, Disney 2505

15 bedrooms•14 baths

•

New

~$415 less than other sites

Welcome to private poolside luxury in Kissimee

Make a splash with our luxury private-pool vacation rentals in Kissimmee, where every stay feels like your own boutique resort. Wander handpicks exceptional homes featuring screened-in pools and spillover spas for all-day lounging and starry-night swims.

Expect resort-caliber decks with sun shelves, integrated spas, and cushioned loungers, paired with hotel-grade linens, pristine cleaning, and 24/7 concierge service. Many pools are heated and equipped with safety features for peace of mind.

Ultra fast WiFi and thoughtful work zones come standard, so blending work and play is effortless. With Wander, the home looks exactly like the photos and everything simply works from check-in to checkout.

Available soon in Kissimee

Luxurious Villa with Pool & Games Room

15 bedrooms•14.5 baths

•

New

~$230 less than other sites

Home in Kissimmee

8 bedrooms•6 baths

•

~$50 less than other sites

Retreat, Pool, Close to Disney

4 bedrooms•3 baths

•

New

~$55 less than other sites

Heated Pool Game Room Modern Resort Disney Magic

4 bedrooms•3 baths

•

~$35 less than other sites

Star Wars, Princess, Arcade Games, Disney 5334

4 bedrooms•3 baths

•

New

~$90 less than other sites

Townhome in Kissimmee

4 bedrooms•3 baths

•

~$60 less than other sites

Home in Kissimmee

12 bedrooms•11.5 baths

•

~$145 less than other sites

Home in Kissimmee

5 bedrooms•5 baths

•

~$80 less than other sites

Featured private pool vacation rentals in Kissimee

Harry Potter, Toy Story, Game Room, Disney 2505

15 bedrooms•14 baths

•

New

~$415 less than other sites

Luxury

NM501L Legends Palazzo

9 bedrooms•10.5 baths

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~$970 less than other sites

Luxury

500ML - 10 Bed - Michael's Manor - W001

10 bedrooms•11 baths

•

New

~$405 less than other sites

1200GT - 10 Bed - Alyssa's Abode - W261

10 bedrooms•10 baths

•

New

~$345 less than other sites

Luxury

W402E - The Eclectic Colonial Estate

14 bedrooms•14 baths

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New

~$680 less than other sites

Luxury

BD012E - The Luxurious Bear's Den Oasis

6 bedrooms•6 baths

New

Luxury

W320E - The Entertainment Mansion

9 bedrooms•12 baths

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New

~$660 less than other sites

Orlando Oasis

11 bedrooms•15 baths

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~$555 less than other sites

Highlights in Kissimee

Discover a world of thrilling theme parks, outdoor adventures, and classic Florida charm in the heart of Kissimmee.

Old Town Kissimmee

Shingle Creek Regional Park

Fun Spot America - Kissimmee

Kissimmee Lakefront 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.

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 Kissimee

Luxurious Villa with Pool & Games Room

15 bedrooms•14.5 baths

•

New

~$230 less than other sites

4473 Monado

12 bedrooms•11.5 baths

•

~$175 less than other sites

Home in Kissimmee

8 bedrooms•6 baths

•

~$50 less than other sites

Large Home, Prime Location Orlando

8 bedrooms•5 baths

New

Retreat, Pool, Close to Disney

4 bedrooms•3 baths

•

New

~$55 less than other sites

Heated Pool Game Room Modern Resort Disney Magic

4 bedrooms•3 baths

•

~$35 less than other sites

Star Wars, Princess, Arcade Games, Disney 5334

4 bedrooms•3 baths

•

New

~$90 less than other sites

Harry Potter, Toy Story, Game Room, Disney 2505

15 bedrooms•14 baths

•

New

~$415 less than other sites

View all homes

Most popular amenities for private pool vacation rentals in Kissimee

Basketball court (26)

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Discover more beyond the pool in Kissimee

Central Florida’s lake country sets the scene in Kissimmee, marrying blue-sky days with effortless proximity to Orlando’s headline attractions. The pace is relaxed yet refined, ideal for quick escapes or extended stays with the whole crew.

Fill your days with championship golf at Reunion and ChampionsGate, sunrise strolls along Lake Tohopekaliga, and boutique shopping and live entertainment at Promenade at Sunset Walk. Evenings bring warm breezes and fireworks glittering on the horizon.

This is why Wander’s luxury private-pool vacation rentals in Kissimmee are the perfect choice, whether you’re traveling for work or leisure.

FAQs: Vacation Rentals in Kissimee

Why should I book a Wander in Kissimee over other private pool vacation rentals?

Wander offers a level of consistency and quality you won’t find with most private pool 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 private pool vacation rentals in Kissimee?

Some of our most popular private pool vacation rentals in Kissimee include Luxurious 15-Bedroom Villa with Pool & Games Room, 4473 Monado, and 226. 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 private pool vacation rentals does Wander have available in Kissimee?

Wander offers 952 private pool 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 private pool vacation rentals in Kissimee?

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

Do Wander’s private pool 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.