Luxury Vacation Rentals with a Private Pool in Osceola County

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 950 private pool vacation rentals – enter your dates for availability.

Top-rated private pool vacation rentals in Osceola County

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

Lakeview, South-Facing Pool, Resort, Disney 227

5 bedrooms•4 baths

•

New

~$80 less than other sites

Townhome in Kissimmee

4 bedrooms•3 baths

•

~$60 less than other sites

Welcome to private poolside luxury in Osceola County

Make your next Florida escape feel effortless with Wander's luxury private pool vacation rentals in Osceola County. Our approach blends the polish of a five-star hotel with the privacy of a beautiful home, so every arrival is stress free and every detail is intentional.

Choose from contemporary villas and spacious estates featuring screened, heated pools for year-round enjoyment and expansive sun terraces made for lingering days outside. Expect ultra fast WiFi, plush linens, pristine cleaning, and 24/7 concierge support that anticipates what you need. Whether you are planning a family retreat or a productive workcation, Wander delivers a rare balance of resort refinement and residential ease.

Available soon in Osceola County

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

Lakeview, South-Facing Pool, Resort, Disney 227

5 bedrooms•4 baths

•

New

~$80 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 Osceola County

Luxury

NM501L Legends Palazzo

9 bedrooms•10.5 baths

•

~$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

•

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

•

New

~$660 less than other sites

Orlando Oasis

11 bedrooms•15 baths

•

~$555 less than other sites

Harry Potter, Toy Story, Game Room, Disney 2505

15 bedrooms•14 baths

•

New

~$415 less than other sites

Highlights in Osceola County

Discover a vibrant mix of world-class theme park thrills, historic charm, and pristine Florida wilderness in Osceola County.

Old Town Kissimmee

Wild Florida Airboats & Gator Park

Celebration Town Center

Shingle Creek Regional Park

Kissimmee Lakefront Park

ESPN Wide World of Sports Complex

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 Osceola County

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

Lakeview, South-Facing Pool, Resort, Disney 227

5 bedrooms•4 baths

•

New

~$80 less than other sites

Townhome in Kissimmee

4 bedrooms•3 baths

•

~$60 less than other sites

View all homes

Most popular amenities for private pool vacation rentals in Osceola County

Basketball court (26)

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Discover more beyond the pool in Osceola County

Framed by shimmering lakes and cypress wetlands, Osceola County sits at the headwaters of the Everglades with a landscape that is uniquely Central Florida. Think sunrise colors on Lake Tohopekaliga, quiet bends along Shingle Creek, and broad conservation corridors that keep the horizon feeling open.

Connectivity is simple without sacrificing breathing room. Orlando International Airport is close, and the Florida Turnpike and US 192 place shopping, golf, and marquee entertainment within easy reach. Local festivals and the storied Silver Spurs Rodeo infuse the calendar with authentic Florida culture.

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

FAQs: Vacation Rentals in Osceola County

Why should I book a Wander in Osceola County 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 Osceola County 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 Osceola County?

Some of our most popular private pool vacation rentals in Osceola County include 4473 Monado, 226, and Large 8BR Home | Prime Location Orlando. 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 Osceola County?

Wander offers 950 private pool vacation rentals in Osceola County, 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 Osceola County?

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

Do Wander’s private pool vacation rentals in Osceola County have WiFi access?

Yes. Every Wander home in Osceola County 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.