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Kissimmee Vacation Rentals

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3428 rentals in Kissimmee.

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Belle's Cove, Family-Friendly Villa with Gameroom and Hot Tub, vacation rental in Kissimmee

Belle's Cove, Family-Friendly Villa with Gameroom and Hot Tub

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Disney 5 Star Vacations / The Osprey Villa, vacation rental in Kissimmee

Disney 5 Star Vacations / The Osprey Villa

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Themed rooms, lots of space no crowds!, vacation rental in Kissimmee

Themed rooms, lots of space no crowds!

6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Villa Linton - Beautiful Florida Home with Themed Bedrooms, vacation rental in Kissimmee

Villa Linton - Beautiful Florida Home with Themed Bedrooms

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Family-Friendly Large Villa with a Pool, Jacuzzi,, vacation rental in Kissimmee

Family-Friendly Large Villa with a Pool, Jacuzzi,

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Disney Family Villa pool/spa/games room, 5 bds 4 bathrooms, 15 Mins to Disney, vacation rental in Kissimmee

Disney Family Villa pool/spa/games room, 5 bds 4 bathrooms, 15 Mins to Disney

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Roughtallys Villa, vacation rental in Kissimmee

Roughtallys Villa

7 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Amazing Disney Condo, Pool & Hot tub Onsite, vacation rental in Kissimmee

Amazing Disney Condo, Pool & Hot tub Onsite

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Palm Tree Villa Florida, 5 Star Review Rating with Pool Lift & Wheel in Shower., vacation rental in Kissimmee

Palm Tree Villa Florida, 5 Star Review Rating with Pool Lift & Wheel in Shower.

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Debbie's Florida Retreat a Luxury Vacation Home, vacation rental in Kissimmee

Debbie's Florida Retreat a Luxury Vacation Home

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Superb 4 Bedroom Home, just 3 minutes from Disney, vacation rental in Kissimmee

Superb 4 Bedroom Home, just 3 minutes from Disney

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Disney Vacation Villa with Lake View, vacation rental in Kissimmee

Disney Vacation Villa with Lake View

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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DISNEY WORLD! LOW $'S!  ENTIRE NEW Home! Harry Potter Theme, Sleeps 8!, vacation rental in Kissimmee

DISNEY WORLD! LOW $'S! ENTIRE NEW Home! Harry Potter Theme, Sleeps 8!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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villanirvana, vacation rental in Kissimmee

villanirvana

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Star Lake Villa, close to Disney with pool, vacation rental in Kissimmee

Star Lake Villa, close to Disney with pool

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The Charming Mickey's Tree House,, vacation rental in Kissimmee

The Charming Mickey's Tree House,

4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Fantasy Pool Home, vacation rental in Kissimmee

Fantasy Pool Home

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Disney Dream Villa At CLC Encantada Resort, vacation rental in Kissimmee

Disney Dream Villa At CLC Encantada Resort

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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BRUSONS RETREAT, 5 Bed Villa, South Facing Pool & Terrace., vacation rental in Kissimmee

BRUSONS RETREAT, 5 Bed Villa, South Facing Pool & Terrace.

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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DISNEY DREAM LUXURY HOME PRIVATE WATERPARK POOL SPA, vacation rental in Kissimmee

DISNEY DREAM LUXURY HOME PRIVATE WATERPARK POOL SPA

6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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New Opening 9 Br/6 Ba luxurious Pool House from $300/nt, Close To Disney, vacation rental in Kissimmee

New Opening 9 Br/6 Ba luxurious Pool House from $300/nt, Close To Disney

9 bedrooms
6 bathrooms
Sleeps 18
Match: Sleeps
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Sonshines Florida Villa, Peaceful Getaway  and Pool, vacation rental in Kissimmee

Sonshines Florida Villa, Peaceful Getaway and Pool

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stunning 6 Bed Pool Home Close to Disney Parks., vacation rental in Kissimmee

Stunning 6 Bed Pool Home Close to Disney Parks.

6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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⭐Spacious 7 Bedrooms w/ Private Pool - Great Location!⭐, vacation rental in Kissimmee

⭐Spacious 7 Bedrooms w/ Private Pool - Great Location!⭐

7 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Luxury 4 Bedroom Villa with Private Pool, 2 Miles from Disney, vacation rental in Kissimmee

Luxury 4 Bedroom Villa with Private Pool, 2 Miles from Disney

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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New Upgraded Luxury Villa w/ Frozen & Star Wars Rooms at Encore!, vacation rental in Kissimmee

New Upgraded Luxury Villa w/ Frozen & Star Wars Rooms at Encore!

6 bedrooms
7 bathrooms
Sleeps 16
Match: Sleeps
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New 9br/6ba pool villa from $280/nt,Close to Disney, vacation rental in Kissimmee

New 9br/6ba pool villa from $280/nt,Close to Disney

9 bedrooms
6 bathrooms
Sleeps 20
Match: Sleeps
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Bargain Vacation Home near Disney, vacation rental in Kissimmee

Bargain Vacation Home near Disney

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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(9110-CAL) Calabria 5 Bed South Face Pool, GAMES ROOM, vacation rental in Kissimmee

(9110-CAL) Calabria 5 Bed South Face Pool, GAMES ROOM

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Charming Townhouse with Pool and Tennis Court in Gated Community, vacation rental in Kissimmee

Charming Townhouse with Pool and Tennis Court in Gated Community

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Villa di Lusso, vacation rental in Kissimmee

Villa di Lusso

6 bedrooms
10 bathrooms
Sleeps 14
Match: Sleeps
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Luxury Home with Exceptional Games Room. 610, vacation rental in Kissimmee

Luxury Home with Exceptional Games Room. 610

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Near Disney, 5 Star Princess Themed Home and Resort, vacation rental in Kissimmee

Near Disney, 5 Star Princess Themed Home and Resort

6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Magical Manor, Beautiful Emerald Island Lake View Villa, vacation rental in Kissimmee

Magical Manor, Beautiful Emerald Island Lake View Villa

6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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⭐Good Location for Theme Parks - Spacious 8 Bedrooms Villa w/ Private Pool⭐, vacation rental in Kissimmee

⭐Good Location for Theme Parks - Spacious 8 Bedrooms Villa w/ Private Pool⭐

8 bedrooms
6 bathrooms
Sleeps 20
Match: Sleeps
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A perfect Holiday House Waitting U at Windsor Palms Resort 10mins to Disney, vacation rental in Kissimmee

A perfect Holiday House Waitting U at Windsor Palms Resort 10mins to Disney

6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Stunning Lake View House 2mls to Disney,games room, vacation rental in Kissimmee

Stunning Lake View House 2mls to Disney,games room

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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SweetDreamsRUs - 4miles to Disney, Free WiFi, Free Pool Heat, South Facing Pool, vacation rental in Kissimmee

SweetDreamsRUs - 4miles to Disney, Free WiFi, Free Pool Heat, South Facing Pool

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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VP_1801R Veranda Jewel, vacation rental in Kissimmee

VP_1801R Veranda Jewel

13 bedrooms
11 bathrooms
Sleeps 25
Match: Sleeps
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Fantastic Orange Blossom Villa includes a Gameroom and Private Pool, vacation rental in Kissimmee

Fantastic Orange Blossom Villa includes a Gameroom and Private Pool

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Luxury Lakeside House with private solar heated pool & spa, vacation rental in Kissimmee

Luxury Lakeside House with private solar heated pool & spa

5 bedrooms
4 bathrooms
Sleeps 13
Match: Sleeps
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Kissimmee Windsor at Westside's 'The Second Star to the Right' vacation home, vacation rental in Kissimmee

Kissimmee Windsor at Westside's 'The Second Star to the Right' vacation home

7 bedrooms
6 bathrooms
Sleeps 17
Match: Sleeps
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New 9Br/6Ba luxurious Pool House from $300/nt, Close To Disney, vacation rental in Kissimmee

New 9Br/6Ba luxurious Pool House from $300/nt, Close To Disney

9 bedrooms
6 bathrooms
Sleeps 18
Match: Sleeps
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Ultimate luxury 15 bedroom suites for 30 guests, vacation rental in Kissimmee

Ultimate luxury 15 bedroom suites for 30 guests

15 bedrooms
15 bathrooms
Sleeps 30
Match: Sleeps
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Mickeys Clubhouse Windsor Palm Frozen & New Minion themed rooms, vacation rental in Kissimmee

Mickeys Clubhouse Windsor Palm Frozen & New Minion themed rooms

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Golden Palms Resort 8 Bedroom Vacation Home with Pool (1904), vacation rental in Kissimmee

Golden Palms Resort 8 Bedroom Vacation Home with Pool (1904)

8 bedrooms
7 bathrooms
Sleeps 18
Match: Sleeps
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New 8br/6ba pool villa from $260/nt , Close to Disney, vacation rental in Kissimmee

New 8br/6ba pool villa from $260/nt , Close to Disney

8 bedrooms
6 bathrooms
Sleeps 18
Match: Sleeps
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Florida Villa Dreams Come True, vacation rental in Kissimmee

Florida Villa Dreams Come True

3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Seasons Villa,5 Bedrooms, Pool with Spa, Gameroom Sleeps 10, vacation rental in Kissimmee

Seasons Villa,5 Bedrooms, Pool with Spa, Gameroom Sleeps 10

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Dis Oasis Villa at Windsor Palms Resort - Close to Disney!, vacation rental in Kissimmee

Dis Oasis Villa at Windsor Palms Resort - Close to Disney!

6 bedrooms
4 bathrooms
Sleeps 13
Match: Sleeps
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Frequently Asked Questions about Kissimmee

Kissimmee Vacation Rentals
Don’t automatically think you need to rent a vacation home in Orlando to be close to Walt Disney World. Smart vacationers know that searching for a vacation rental in Kissimmee, Florida often gets you space, luxury and a great rate—as well as a very short commute to the parks.
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Kissimmee Vacation Rentals
Don’t automatically think you need to rent a vacation home in Orlando to be close to Walt Disney World. Smart vacationers know that searching for a vacation rental in Kissimmee, Florida often gets you space, luxury and a great rate—as well as a very short commute to the parks.
Kissimmee Vacation Rentals for Families
More and more families are choosing to celebrate major events like birthdays and anniversaries with a multi-generational trip to Disney World. (It’s one of the few destinations where everyone from toddlers to seniors can have an equally great time.) And we can help you find a Kissimmee vacation rental that can handle any size family. Whether you’re interested in a one-bedroom condo rental in Kissimmee or a seven-bedroom luxury villa, our helpful vacation rental reviews make your selection easy.
Advantages of renting a vacation home in Kissimmee
Let’s be honest—while it’s great fun to spend a week visiting the Magic Kingdom, Epcot, Disney’s MGM Studios, Universal Studios and Islands of Adventure, for most of us, it’s a significant strain on our bank accounts. Staying in a hotel and eating in Orlando-area restaurants also adds up. However, we can help you find a great deal on a villa rental in Kissimmee… and even if you just take a few meals in your vacation home instead of in restaurants, your budget will thank you. You’ll even save money on baggage fees with a rental—when you’ve got your own washer and dryer, you can do a few loads of laundry and pack much less clothing.
Rent a vacation house with a pool in Kissimmee, Florida
How do you visit the Orlando theme parks and maintain your sanity? Escape the crowds in the mid-afternoon, when the heat peaks and everybody’s nerves are frazzled. By staying just a short distance away in Kissimmee, you can zip home for a refreshing dip in the pool. Little kids can nap in the comfortable A/C of your Kissimmee vacation rental. You’ll all return to WDW or Universal in a much better mood!
Rental deals in Kissimmee
Remember that Florida’s a year-round vacation destination—but it definitely has an off-season when you can snag a great deal on Kissimmee condo rentals. If you really want a bargain, plan to visit Kissimmee between Thanksgiving and Christmas. Your condo will be cheap, the parks will be less crowded, and if you’re coming from a northern climate, the weather in Kissimmee will still seem great compared to what you’d get at home.
Kissimmee and Orlando beyond Disney
Don’t forget, there’s more to this part of Florida than Mickey and Donald and friends. Animal lovers will want to spend a day at Sea World, or take a day trip to the Everglades. Shoppers should save time (and suitcase space) for bargain-hunting at outlets in Kissimmee and the nearby Orlando Premium Outlets. Just over an hour away, on Florida’s Space Coast, you’ll find the Kennedy Space Center and fantastic sandy beaches like Cocoa Beach. Taking a Disney Cruise departing from Port Canaveral? A vacation rental in Kissimmee is the perfect pre-cruise accommodation.