Luxury Vacation Rentals with a Private Pool in Kissimmee

Luxury Vacation Rentals with a Private Pool 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 847 private pool vacation rentals – enter your dates for availability.

Top-rated private pool vacation rentals in Kissimmee

Bella Vida Escape, Pool & Spa property photo 1

Bella Vida Escape, Pool & Spa

6 bedrooms•6 baths
1,278 US dollars for 4 nights•
New

~$110 less than other sites

BELLA VIDA (891MB) - Spacious HOME POOL/SPA property photo 1

BELLA VIDA (891MB) - Spacious HOME POOL/SPA

5 bedrooms•4 baths
843 US dollars for 3 nights•
New

~$70 less than other sites

Themed Rooms, Mario Kart, Private Pool, Disney property photo 1

Themed Rooms, Mario Kart, Private Pool, Disney

15 bedrooms•14.5 baths
4,989 US dollars for 4 nights•
New

~$390 less than other sites

Playset, Princess, Arcade Games, Disney 5334 property photo 1

Playset, Princess, Arcade Games, Disney 5334

4 bedrooms•3 baths
1,271 US dollars for 3 nights•
New

~$95 less than other sites

Luxurious Villa with Pool & Games Room property photo 1

Luxurious Villa with Pool & Games Room

15 bedrooms•15.5 baths
2,623 US dollars for 3 nights•
New

~$230 less than other sites

Home in Kissimmee property photo 1

Home in Kissimmee

5 bedrooms•5 baths
945 US dollars for 3 nights•

~$75 less than other sites

Bella Blue at Bella Vida Resort property photo 1

Bella Blue at Bella Vida Resort

6 bedrooms•5 baths
700 US dollars for 2 nights•

~$55 less than other sites

Home in Kissimmee property photo 1

Home in Kissimmee

12 bedrooms•11.5 baths
1,798 US dollars for 3 nights•

~$140 less than other sites

Welcome to private poolside luxury in Kissimmee

Welcome to private poolside luxury in Kissimmee

Slip into resort mode with luxury private-pool vacation rentals in Kissimmee, Florida. Each Wander home pairs the polish of a five-star stay with the privacy of your own poolside retreat. Expect hotel-grade amenities, ultra fast WiFi, dedicated workspaces, and flawless operations backed by 24/7 concierge.
Think sunlit great rooms that open to screened lanais, heated pools with spillover spas, and outdoor lounges built for all-day relaxation. Chef-ready kitchens, premium linens, and thoughtful smart-home touches come standard. Every property looks exactly like the photos and is maintained to the highest standard, so all you have to do is arrive.

Available soon in Kissimmee

Home in Kissimmee property photo 1

Home in Kissimmee

4 bedrooms•3 baths
803 US dollars for 3 nights•

~$60 less than other sites

1672OB - 12 Bed - Rock N' Roll Retreat - ST033 property photo 1
Luxury

1672OB - 12 Bed - Rock N' Roll Retreat - ST033

12 bedrooms•13 baths
2,634 US dollars for 3 nights•
New

~$205 less than other sites

2013OC - 6 Bed - Lofty Landing - ST089 property photo 1

2013OC - 6 Bed - Lofty Landing - ST089

6 bedrooms•6.5 baths
1,525 US dollars for 3 nights•
New

~$115 less than other sites

2025OC - 6 Bed - Cosmic Cavern - ST086 property photo 1

2025OC - 6 Bed - Cosmic Cavern - ST086

6 bedrooms•6.5 baths
1,547 US dollars for 3 nights•
New

~$115 less than other sites

2041OC - 6 Bed - Cozy Kingdom - ST083 property photo 1

2041OC - 6 Bed - Cozy Kingdom - ST083

6 bedrooms•6.5 baths
1,485 US dollars for 3 nights•
New

~$130 less than other sites

2045OC - 6 Bed - Adventure Abode - ST082 property photo 1

2045OC - 6 Bed - Adventure Abode - ST082

6 bedrooms•6.5 baths
1,540 US dollars for 3 nights•
New

~$120 less than other sites

MU Formosa property photo 1

MU Formosa

5 bedrooms•4 baths
800 US dollars for 3 nights•

~$60 less than other sites

1759OB - 11 Bed - Celebrity Chateau - ST073 property photo 1
Luxury

1759OB - 11 Bed - Celebrity Chateau - ST073

11 bedrooms•12 baths
2,698 US dollars for 3 nights•
New

~$210 less than other sites

Featured private pool vacation rentals in Kissimmee

W451E - The Glamorous Getaway property photo 1

W451E - The Glamorous Getaway

10 bedrooms•12 baths
3,946 US dollars for 3 nights•
New

~$325 less than other sites

RC069P Fairway Royal Cottage property photo 1

RC069P Fairway Royal Cottage

13 bedrooms•12.5 baths
6,034 US dollars for 4 nights•
New

~$470 less than other sites

NM501L Legends Palazzo property photo 1
Luxury

NM501L Legends Palazzo

9 bedrooms•10.5 baths
11,688 US dollars for 4 nights•

~$910 less than other sites

1200GT - 10 Bed - Alyssa's Abode - W261 property photo 1

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

10 bedrooms•10 baths
4,168 US dollars for 3 nights•
New

~$320 less than other sites

W320E - The Entertainment Mansion property photo 1
Luxury

W320E - The Entertainment Mansion

9 bedrooms•12 baths
7,449 US dollars for 3 nights•
New

~$620 less than other sites

NM430L Legends Palace property photo 1
Luxury

NM430L Legends Palace

13 bedrooms•16 baths
14,441 US dollars for 3 nights•

~$1,130 less than other sites

NM391L Legends Coastal Sanctuary property photo 1

NM391L Legends Coastal Sanctuary

10 bedrooms•12.5 baths
4,158 US dollars for 3 nights•
New

~$320 less than other sites

1148 Grand Traverse property photo 1
Luxury

1148 Grand Traverse

14 bedrooms•20 baths
5,545 US dollars for 4 nights•
New

~$435 less than other sites

Highlights in Kissimmee

Discover world-famous theme parks, thrilling airboat rides, and classic downtown charm in this central Florida family-fun destination.
Walt Disney World® Resort
Universal Orlando Resort
SeaWorld Orlando
Gatorland
Old Town Kissimmee
Kissimmee Lakefront Park
Fun Spot America Theme Parks - Kissimmee
Wild Florida Airboats, Gator Park & Drive-thru Safari

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

Bella Vida Escape, Pool & Spa property photo 1

Bella Vida Escape, Pool & Spa

6 bedrooms•6 baths
1,278 US dollars for 4 nights•
New

~$110 less than other sites

BELLA VIDA (891MB) - Spacious HOME POOL/SPA property photo 1

BELLA VIDA (891MB) - Spacious HOME POOL/SPA

5 bedrooms•4 baths
843 US dollars for 3 nights•
New

~$70 less than other sites

Themed Rooms, Mario Kart, Private Pool, Disney property photo 1

Themed Rooms, Mario Kart, Private Pool, Disney

15 bedrooms•14.5 baths
4,989 US dollars for 4 nights•
New

~$390 less than other sites

Playset, Princess, Arcade Games, Disney 5334 property photo 1

Playset, Princess, Arcade Games, Disney 5334

4 bedrooms•3 baths
1,271 US dollars for 3 nights•
New

~$95 less than other sites

Luxurious Villa with Pool & Games Room property photo 1

Luxurious Villa with Pool & Games Room

15 bedrooms•15.5 baths
2,623 US dollars for 3 nights•
New

~$230 less than other sites

Home in Kissimmee property photo 1

Home in Kissimmee

5 bedrooms•5 baths
945 US dollars for 3 nights•

~$75 less than other sites

Bella Blue at Bella Vida Resort property photo 1

Bella Blue at Bella Vida Resort

6 bedrooms•5 baths
700 US dollars for 2 nights•

~$55 less than other sites

Home in Kissimmee property photo 1

Home in Kissimmee

12 bedrooms•11.5 baths
1,798 US dollars for 3 nights•

~$140 less than other sites

View all homes

Most popular amenities for private pool vacation rentals in Kissimmee

Outdoor pool (846)
Jacuzzi (401)
Hot tub (401)
Private chef (30)
Heated pool (136)
Gym (457)
Ev charger (9)
Indoor pool (3)
Kayaks (81)
Club access (1)
Movie theater (2)
Basketball court (26)
Tennis court (16)
Lake access (148)
Sauna (6)
Bicycle (86)

More popular private pool destinations near Kissimmee

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Other popular amenities & vacation types in Kissimmee

Family vacation rentals in Kissimmee
Large group vacation rentals in Kissimmee
Hot tub vacation rentals in Kissimmee
Discover more beyond the pool in Kissimmee

Discover more beyond the pool in Kissimmee

Central Florida energy meets lakeside tranquility in Kissimmee. Here, blue-sky days stretch long and warm, setting the scene for boating on Lake Tohopekaliga, kayaking Shingle Creek, and airboat rides through the headwaters of the Everglades. Championship golf, family attractions, and year-round events keep the pace lively.
When you want a change of scenery, explore brick-lined streets in Celebration, classic car nights at Old Town, and open-air shopping and dining from Promenade at Sunset Walk to Disney Springs. With easy access to Orlando’s marquee parks and a calmer, residential feel at home base, Kissimmee makes vacation time feel effortless. This is why Wander’s luxury private-pool vacation rentals in Kissimmee, Florida 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 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 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 private pool vacation rentals in Kissimmee?

Some of our most popular private pool vacation rentals in Kissimmee include Bella Vida Escape | 6BR | Pool & Spa, BELLA VIDA (891MB) - Spacious 5BR 4BA HOME*POOL/SPA, and Themed Rooms | Mario Kart | Private Pool | Disney. 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 Kissimmee?

Wander offers 847 private pool 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 private pool vacation rentals in Kissimmee?

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

Do Wander’s private pool 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.