Vacation rentals · Florida

Kissimmee vacation rentals you can book direct

735 homes from independent hosts and managers · every one bookable on the host's own site

CielStay lists 735 homes for rent in Kissimmee, run by independent hosts and property managers. All of them can be booked on the host's or manager's own website, across 56 booking sites. Some are also listed on Airbnb, Vrbo and Booking.com; each listing shows every place it can be booked.

They include 333 houses, 58 condos and 46 resort suites. The most common size is five or more bedrooms (343 homes). 451 homes sleep 10 or more.

Kissimmee rentals at a glance

Counted from what hosts list. Check the listing before you book.

By size
Studio or 1 bedroom30
2 bedrooms67
3 bedrooms129
4 bedrooms166
5 or more bedrooms343
Sleeps 10 or more451
Homes that list
Air conditioning649
Pool638
Hot tub239
Pets allowed59
EV charger24
Fireplace15

Planning a trip? Read our guide: Kissimmee & the Orlando Theme Park Area, Florida

Homes in Kissimmee for 6 or more

8 of the 681. Search them with your dates →

Resort Home, Private Pool and Spa, Outdoor Theater

Resort Home, Private Pool and Spa, Outdoor Theater

Unforgettable Orlando vacation home for 14, just 8 miles from Disney! This professionally designed retreat features a private pool & spa, three themed game rooms, and a tropical outdoor lounge. Your stay includes full access to the Windsor At Westside Resort waterpark, lazy river, bar and grill, and slides.

📍 Kissimmee, FL
👥 14🛏️ 6🚿 5
$353 / night
5br/5ba/5mi Disney • Heated Pool/SPA • Free rides!

5br/5ba/5mi Disney • Heated Pool/SPA • Free rides!

5BR 1 bath in Kissimmee

📍 Kissimmee, FL
👥 14🛏️ 5🚿 1
~$473 / night
estimate
Themed family home w/kids playroom & pool

Themed family home w/kids playroom & pool

Welcome to a family-friendly Disney themed home designed for easy days and relaxed evenings together, just right for your Orlando getaway.

📍 Kissimmee, FL
👥 7🛏️ 3🚿 3
$151 / night
Private Pool, Themed Rooms & Arcade Near Disney

Private Pool, Themed Rooms & Arcade Near Disney

This Kissimmee home features four themed bedrooms — Avatar, Disney Princess, Toy Story, Star Wars — plus an arcade game room and private screened pool. Walk to Storey Lake Resort's lazy river, waterslides, mini-golf, and tiki bar. 10 minutes from Disney World, 20 minutes from Universal Studios.

📍 Kissimmee, FL
👥 19🛏️ 9🚿 5
$389 / night
2472 Toy Barn Slide Bed & Game Room! Private Pool

2472 Toy Barn Slide Bed & Game Room! Private Pool

Your kids will lose their minds! This 5BR/4BA pool home in Windsor at Westside has a Toy Barn bunk room with a slide, a Mickey room, a Wizard room, a game room with pool table, foosball and gaming stations, plus a private pool – all about 15 minutes from Disney.

📍 Kissimmee, FL
👥 12🛏️ 5🚿 4
$335 / night
Upstay | Disney Luxury Pool Game Room Cinema

Upstay | Disney Luxury Pool Game Room Cinema

Upstay presents this family-friendly 33-guest capacity home, located at the Veranda Palms Resort, just a short drive from Disney. This 15-bedroom home includes a private outdoor swimming pool, jacuzzi hot tub, poolside dining area and BBQ grill.

📍 Kissimmee, FL
👥 33🛏️ 15🚿 16
$918 / night
Upstay—Vibrant Home w Themed Rooms, Pool & Games

Upstay—Vibrant Home w Themed Rooms, Pool & Games

Upstay presents this vibrant 8-bedroom, 20-guest capacity, family-friendly home, that's sure to keep you entertained. Kids will love the cool theme bedrooms! Plus the home features a beautiful, garden-facing back patio with an swimming pool, hot tub, and BBQ grill.

📍 Kissimmee, FL
👥 20🛏️ 8🚿 5
$413 / night
Stunning Villa w/ Updated Decor and Gameroom

Stunning Villa w/ Updated Decor and Gameroom

This villa has it all. You'll love the luxurious upscale touches with fantastic decor for adults, a brand new state of the art graffiti-inspired game room and whimsical themed rooms ! Your kiddos will love the Harry Potter Room and climbing on the bunk bed in their very own jungle!

📍 Kissimmee, FL
👥 12🛏️ 6🚿 5
$297 / night

Homes in Kissimmee with a pool

8 of the 638. Search them with your dates →

Game On! Orlando Board Game House near Disney

Game On! Orlando Board Game House near Disney

🎲 Welcome to Game On! Orlando, a 9BR/5BA board-game-themed mansion in ChampionsGate near Disney for up to 29 guests. Discover five immersive bunk rooms, four King retreats, two game areas, a private screened pool with waterslide and spa, and a giant outdoor movie screen.

📍 Kissimmee, FL
👥 16🛏️ 9🚿 5
$399 / night
excl. host's fees
9BR Fairytale Kingdom Sleeps 24 Pool Near Disney

9BR Fairytale Kingdom Sleeps 24 Pool Near Disney

✨ Welcome to Fairytale Kingdom — a one-of-a-kind 9BR luxury lakefront villa that sleeps up to 24 guests inside ChampionsGate Resort, just minutes from Disney. Every room tells a different story, from Avatar, Mario Kart, Guardians of the Galaxy, Princess Castle, Coco, Moana, Tangled, Disney Castle, and more.

📍 Kissimmee, FL
👥 16🛏️ 9🚿 5
$399 / night
excl. host's fees
Spacious 4Bd Disney w Resort Access at Lucaya 3210

Spacious 4Bd Disney w Resort Access at Lucaya 3210

Perfect for a special family or group getaway, this stylish 4-bedroom, 2-bath townhome at Lucaya Village Resort comfortably hosts up to 10 guests. Enjoy a spacious open-concept layout, fully equipped kitchen, and relaxing bedrooms across two floors.

📍 Kissimmee, FL
👥 10🛏️ 4🚿 3
~$181 / night
estimate
Epic Princess and Villains Hideaway- Private Pool Themed Rooms Near Disney

Epic Princess and Villains Hideaway- Private Pool Themed Rooms Near Disney

Private pool, princess & villain themed rooms, and no rear neighbors — all just minutes from Disney. Epic Storybook Hideaway is a 4BR family retreat tucked on a quiet cul-de-sac in Tuscany at Westside, featuring two master suites, a conservation view, and a Toy Story & Mario inspired game room.

📍 Kissimmee, FL
👥 10🛏️ 4🚿 3
$195 / night
excl. host's fees
5br/5ba/5mi Disney • Heated Pool/SPA • Free rides!

5br/5ba/5mi Disney • Heated Pool/SPA • Free rides!

5BR 1 bath in Kissimmee

📍 Kissimmee, FL
👥 14🛏️ 5🚿 1
~$473 / night
estimate
Upstay: Themed Family Home w Pool & Games Room

Upstay: Themed Family Home w Pool & Games Room

Upstay presents a fun-filled 12-bedroom resort home for up to 30 guests—perfect for large families or group getaways! With epic themed kids' rooms like Star Wars, Jurassic Park, and Frozen, bedtime is part of the adventure. Enjoy a private putting green, billiards table, and free resort access.

📍 Kissimmee, FL
👥 30🛏️ 12🚿 11.5
$673 / night
Spiderman studio near Disney & Universal

Spiderman studio near Disney & Universal

Step into an immersive Spiderman-themed studio at Legacy Grand - designed with neon lighting, skyline artwork, and superhero-inspired décor for an unforgettable Orlando escape.

📍 Kissimmee, FL
👥 40🚿 1
$150 / night
excl. host's fees
A Magical World of Luxury & Fun Near Disney

A Magical World of Luxury & Fun Near Disney

Experience Orlando's ultimate luxury 9BR themed villa at Storey Lake! Enjoy elegant interiors, spacious living areas, a private pool and an Avengers game room with Iron Man, pool table, and video games. Enter a magical Harry Potter-themed second floor with home theater!

📍 Kissimmee, FL
👥 28🛏️ 9🚿 5
$800 / night
excl. host's fees

Homes in Kissimmee

Homes with the host's own booking site first. Prices can change and may not be exact; the asterisk shows what each one includes.

Game On! Orlando Board Game House near Disney

Game On! Orlando Board Game House near Disney

🎲 Welcome to Game On! Orlando, a 9BR/5BA board-game-themed mansion in ChampionsGate near Disney for up to 29 guests. Discover five immersive bunk rooms, four King retreats, two game areas, a private screened pool with waterslide and spa, and a giant outdoor movie screen.

📍 Kissimmee, FL
👥 16🛏️ 9🚿 5
$399 / night
excl. host's fees
9BR Fairytale Kingdom Sleeps 24 Pool Near Disney

9BR Fairytale Kingdom Sleeps 24 Pool Near Disney

✨ Welcome to Fairytale Kingdom — a one-of-a-kind 9BR luxury lakefront villa that sleeps up to 24 guests inside ChampionsGate Resort, just minutes from Disney. Every room tells a different story, from Avatar, Mario Kart, Guardians of the Galaxy, Princess Castle, Coco, Moana, Tangled, Disney Castle, and more.

📍 Kissimmee, FL
👥 16🛏️ 9🚿 5
$399 / night
excl. host's fees
Spacious 4Bd Disney w Resort Access at Lucaya 3210

Spacious 4Bd Disney w Resort Access at Lucaya 3210

Perfect for a special family or group getaway, this stylish 4-bedroom, 2-bath townhome at Lucaya Village Resort comfortably hosts up to 10 guests. Enjoy a spacious open-concept layout, fully equipped kitchen, and relaxing bedrooms across two floors.

📍 Kissimmee, FL
👥 10🛏️ 4🚿 3
~$181 / night
estimate
Resort Home, Private Pool and Spa, Outdoor Theater

Resort Home, Private Pool and Spa, Outdoor Theater

Unforgettable Orlando vacation home for 14, just 8 miles from Disney! This professionally designed retreat features a private pool & spa, three themed game rooms, and a tropical outdoor lounge. Your stay includes full access to the Windsor At Westside Resort waterpark, lazy river, bar and grill, and slides.

📍 Kissimmee, FL
👥 14🛏️ 6🚿 5
$353 / night
Epic Princess and Villains Hideaway- Private Pool Themed Rooms Near Disney

Epic Princess and Villains Hideaway- Private Pool Themed Rooms Near Disney

Private pool, princess & villain themed rooms, and no rear neighbors — all just minutes from Disney. Epic Storybook Hideaway is a 4BR family retreat tucked on a quiet cul-de-sac in Tuscany at Westside, featuring two master suites, a conservation view, and a Toy Story & Mario inspired game room.

📍 Kissimmee, FL
👥 10🛏️ 4🚿 3
$195 / night
excl. host's fees
5br/5ba/5mi Disney • Heated Pool/SPA • Free rides!

5br/5ba/5mi Disney • Heated Pool/SPA • Free rides!

5BR 1 bath in Kissimmee

📍 Kissimmee, FL
👥 14🛏️ 5🚿 1
~$473 / night
estimate
Upstay: Themed Family Home w Pool & Games Room

Upstay: Themed Family Home w Pool & Games Room

Upstay presents a fun-filled 12-bedroom resort home for up to 30 guests—perfect for large families or group getaways! With epic themed kids' rooms like Star Wars, Jurassic Park, and Frozen, bedtime is part of the adventure. Enjoy a private putting green, billiards table, and free resort access.

📍 Kissimmee, FL
👥 30🛏️ 12🚿 11.5
$673 / night
Spiderman studio near Disney & Universal

Spiderman studio near Disney & Universal

Step into an immersive Spiderman-themed studio at Legacy Grand - designed with neon lighting, skyline artwork, and superhero-inspired décor for an unforgettable Orlando escape.

📍 Kissimmee, FL
👥 40🚿 1
$150 / night
excl. host's fees
A Magical World of Luxury & Fun Near Disney

A Magical World of Luxury & Fun Near Disney

Experience Orlando's ultimate luxury 9BR themed villa at Storey Lake! Enjoy elegant interiors, spacious living areas, a private pool and an Avengers game room with Iron Man, pool table, and video games. Enter a magical Harry Potter-themed second floor with home theater!

📍 Kissimmee, FL
👥 28🛏️ 9🚿 5
$800 / night
excl. host's fees
Themed family home w/kids playroom & pool

Themed family home w/kids playroom & pool

Welcome to a family-friendly Disney themed home designed for easy days and relaxed evenings together, just right for your Orlando getaway.

📍 Kissimmee, FL
👥 7🛏️ 3🚿 3
$151 / night
Star Wars | Pool + Hot Tub | Theater | Near Disney

Star Wars | Pool + Hot Tub | Theater | Near Disney

Our 8-bedroom, 6-bath Star Wars-inspired retreat makes group stays feel easy and fun. Book your Orlando stay and enjoy plenty of space to spread out and relax.

📍 Kissimmee, FL
👥 16🛏️ 8🚿 6
$449 / night
excl. host's fees
Star Wars Loft·5 En-Suite·Disney & Epic·Free Pool

Star Wars Loft·5 En-Suite·Disney & Epic·Free Pool

🛁 5 bedrooms, every one en-suite — no sharing, no morning lineup for the parks 🚀 Custom Millennium Falcon cargo bay loft — a hit with kids & teens 🏊 Heated pool & 🍖 BBQ grill INCLUDED · resort hot tub & lazy river nearby 🎢 4 mi to Disney · 15 min to Epic Universe · 🐾 pets stay free 💬 Real hosts, ~1-hour replies…

📍 Kissimmee, FL
👥 10🛏️ 5🚿 6
~$309 / night
estimate
Kissimmee Villa: 9BR Retreat, Sleeps 18

Kissimmee Villa: 9BR Retreat, Sleeps 18

Discover an oasis of relaxation at our luxurious 9-bedroom villa, accommodating up to 18 guests in the heart of Kissimmee. Just 6 miles from Orlando's premier attractions, this spacious retreat offers a perfect blend of comfort and convenience.

📍 Kissimmee, FL
👥 18🛏️ 9🚿 8
$395 / night
excl. host's fees
Once Upon a Minion 15BR Resort Mansion Near Disney

Once Upon a Minion 15BR Resort Mansion Near Disney

✨ Welcome to Once Upon a Minion, an extraordinary 15BR resort mansion at Veranda Palms near Disney, designed for up to 39 guests.

📍 Kissimmee, FL
👥 16🛏️ 15🚿 17
$977 / night
excl. host's fees
New Epic Solara Playhouse Custom Bunks and Slides Arcade & Theater

New Epic Solara Playhouse Custom Bunks and Slides Arcade & Theater

Epic Solara Playhouse is a standout family vacation home featuring two incredible custom kids’ bunk rooms, including a mirror maze with black lighting and a superhero room with a slide into a foam pit, plus a private movie room, arcade, screened pool, and walkable access to Solara Resort’s clubhouse and amenities near…

📍 Kissimmee, FL
👥 18🛏️ 7🚿 6.5
$320 / night
excl. host's fees
Rapunzel themed studio w/ pool & workspace

Rapunzel themed studio w/ pool & workspace

Step into the magic of this Tangled-inspired studio in Kissimmee - designed for guests who want their stay to feel as memorable as the trip itself.

📍 Kissimmee, FL
👥 40🚿 1
$150 / night
excl. host's fees
*New* Fun Retreat w/ Arcade, Pool & Balcony Views

*New* Fun Retreat w/ Arcade, Pool & Balcony Views

The Skyview Sanctuary is a three-story family retreat in Reunion Resort, packed with incredible entertainment and unforgettable spaces. Kids have their own magical worlds with two custom themed bunk rooms—one designed as a whimsical winter haven and the other styled like an enchanted boarding-school dormitory.

📍 Kissimmee, FL
👥 14🛏️ 5🚿 5
$220 / night
excl. host's fees
7BR Disney Escape Pool, Spa, Theater & Arcade

7BR Disney Escape Pool, Spa, Theater & Arcade

The magic doesn’t stop when you leave the parks. This unforgettable 7-bedroom, 5.5-bath Windsor at Westside escape sleeps up to 16 guests with an Avengers arcade, private Mickey cinema, immersive character bedrooms and a Moana-inspired pool deck.

📍 Kissimmee, FL
👥 16🛏️ 7🚿 5
$400 / night
excl. host's fees
5BR Fantastic Villa Pool & Game Room Near Disney

5BR Fantastic Villa Pool & Game Room Near Disney

🎮✨ Welcome to your family-friendly 5BR themed villa near Disney! This beautifully updated home features a private pool, an amazing Super Mario game room with arcade games, movie area, and an additional full-size bed, plus immersive themed bedrooms including Beauty & The Beast and Transformers.

📍 Kissimmee, FL
👥 12🛏️ 5🚿 4
$157 / night
excl. host's fees
Themed pool home near Disney w/ game room

Themed pool home near Disney w/ game room

Welcome to an immersive Solara Resort vacation home built for big groups!

📍 Kissimmee, FL
👥 22🛏️ 9🚿 7
$500 / night
excl. host's fees
Private Pool, Themed Rooms & Arcade Near Disney

Private Pool, Themed Rooms & Arcade Near Disney

This Kissimmee home features four themed bedrooms — Avatar, Disney Princess, Toy Story, Star Wars — plus an arcade game room and private screened pool. Walk to Storey Lake Resort's lazy river, waterslides, mini-golf, and tiki bar. 10 minutes from Disney World, 20 minutes from Universal Studios.

📍 Kissimmee, FL
👥 19🛏️ 9🚿 5
$389 / night
Relaxed 5BR home w/ pool & BBQ grill

Relaxed 5BR home w/ pool & BBQ grill

Step into a five-bedroom Kissimmee retreat with a screened private pool, heated spa & water views - just 20 mins from Walt Disney World.

📍 Kissimmee, FL
👥 10🛏️ 5🚿 3.5
$180 / night
excl. host's fees
Villains Themed | Pool + Hot Tub | Near Disney!

Villains Themed | Pool + Hot Tub | Near Disney!

Welcome to our Villian Themed 8-bedroom, 6-bath Windsor at Westside retreat, where bold villain-themed rooms and roomy group spaces set the scene. Gather your crew and enjoy a stay with space, character, and plenty of ways to unwind.

📍 Kissimmee, FL
👥 16🛏️ 8🚿 6
$396 / night
excl. host's fees
Happiest Home on Earth - Custom Pirate & Nature Bunks, 8 King Suites, Theater & Pool

Happiest Home on Earth - Custom Pirate & Nature Bunks, 8 King Suites, Theater & Pool

Welcome to Happiest Home on Earth, an unforgettable Central Florida escape designed for large families and groups who want it all.

📍 Kissimmee, FL
👥 25🛏️ 10🚿 12.5
$890 / night
excl. host's fees

400 of the 735 homes in Kissimmee

Questions about renting in Kissimmee

How many vacation rentals are there in Kissimmee?

CielStay lists 735 homes in Kissimmee, counted from the homes live today. By type: 333 houses, 58 condos and 46 resort suites.

Can I book a vacation rental in Kissimmee directly with the host?

Yes. Every home here can be booked on the host's or manager's own website. Each listing links to it, along with any other place the home is listed.

How do I book a Kissimmee vacation rental directly with the owner?

Open a home and choose Book direct: it takes you to the host's or manager's own booking site, where you see their price and terms. You can also message the host first. CielStay doesn't take the booking or the payment. Booking direct often costs less, because no platform fee or commission is added; compare the final totals before you pay.

Where can I rent a house in Kissimmee for 6 people?

681 homes here sleep 6 or more; 325 are houses, the rest condos or resort suites. Add your dates and group size in the search to see which are free.

Are there vacation rentals in Kissimmee with a pool?

638 homes list a pool, and 239 homes a hot tub. Some pools are shared, in a resort or community, so check the listing if you want a private one.

Are there pet-friendly rentals in Kissimmee?

59 homes list pets as allowed. Pet fees and limits vary by host, so check the house rules on the listing.

Are there rentals in Kissimmee for large groups?

451 homes sleep 10 or more, and 343 homes have five or more bedrooms.

How are prices shown?

Each home shows one price with a note on what it includes; the asterisk explains how we work it out. Prices can change and may not be exact. If a host hasn't shared a fee with us, we can't include it. The host's site or booking channel has the final total; taxes are extra.

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