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Kissimmee Vacation Rentals

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4282 rentals in Kissimmee.
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Belle's Cove, Family-Friendly Villa with Gameroom and Hot Tub
4 bedrooms
4 bathrooms
Sleeps 8
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Family-Friendly Large Villa with a Pool, Jacuzzi,
5 bedrooms
4 bathrooms
Sleeps 10
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BRUSONS RETREAT, 5 Bed Villa, South Facing Pool & Terrace.
5 bedrooms
4 bathrooms
Sleeps 10
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Debbie's Florida Retreat a Luxury Vacation Home
4 bedrooms
3 bathrooms
Sleeps 8
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villanirvana
4 bedrooms
3 bathrooms
Sleeps 8
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SUPER Close To Disney, Gameroom, Private Backyard, Lake, Free WiFi, Pool, Spa
7 bedrooms
5 bathrooms
Sleeps 17
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Free Pool and Spa Heat Offering Total Privacy, 10 Minutes from Disney!
3 bedrooms
3 bathrooms
Sleeps 6
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New rates
3 bedrooms
3 bathrooms
Sleeps 8
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Seasons Villa,5 Bedrooms, Pool with Spa, Gameroom Sleeps 10
5 bedrooms
4 bathrooms
Sleeps 10
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New 9Br/6Ba luxurious Pool House from $300/nt, Close To Disney
9 bedrooms
6 bathrooms
Sleeps 18
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Sonshines Florida Villa, Peaceful Getaway and Pool
3 bedrooms
2 bathrooms
Sleeps 6
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Oakhill Disney Villa
4 bedrooms
2 bathrooms
Sleeps 8
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Luxury 4 Bedroom Villa with Private Pool, 2 Miles from Disney
4 bedrooms
3 bathrooms
Sleeps 8
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A stunning pool home in Kissimmee, Disney Paradi
4 bedrooms
3 bathrooms
Sleeps 9
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Bella Vida New Phase 6 bedroom Modern Home
6 bedrooms
7 bathrooms
Sleeps 12
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Family Resort - 14BR Mansion - Private Pool and More!
14 bedrooms
11 bathrooms
Sleeps 31
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Alberto Circle, Fun Vacation House with Pool
3 bedrooms
3 bathrooms
Sleeps 6
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KENNEDY#1 PRIVATE POOL AND SPA! AHHHH!! EAGLE POINTE IN KISSIMMEE
4 bedrooms
2 bathrooms
Sleeps 8
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Magical Manor, Beautiful Emerald Island Lake View Villa
6 bedrooms
5 bathrooms
Sleeps 14
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Superb 4 Bedroom Home, just 3 minutes from Disney
4 bedrooms
3 bathrooms
Sleeps 8
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Lake Star Villa
5 bedrooms
4 bathrooms
Sleeps 10
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The Seasons Villa, lake view and 4 master bedrooms
6 bedrooms
6 bathrooms
Sleeps 13
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The Retreat - Explore Disney & Florida in style
4 bedrooms
4 bathrooms
Sleeps 10
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Family Friendly Four Bedroom w/ Pool 4896
4 bedrooms
3 bathrooms
Sleeps 12
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Disney 5 Star Vacations / The Osprey Villa
5 bedrooms
4 bathrooms
Sleeps 10
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Located in Emerald Island Resort Beautiful 7 Bed 4.5 Bath Villa Close 2 Disney
7 bedrooms
7 bathrooms
Sleeps 16
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Amazing Disney Condo, Pool & Hot tub Onsite
3 bedrooms
2 bathrooms
Sleeps 6
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Spacious 4-bed lakeside pool villa near Disney
4 bedrooms
2 bathrooms
Sleeps 10
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Completely remodelled 2020. Luxury 4 Bed 3 Bath Villa with own pool. Near Disney
4 bedrooms
3 bathrooms
Sleeps 10
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Disney Orlando House w/Private Pool
3 bedrooms
3 bathrooms
Sleeps 6
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Beautiful 5 bed/3.5 bath-2 En-suites, Free SPA Heat, WiFi, Disney/Universal.
5 bedrooms
4 bathrooms
Sleeps 10
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Bass Lake Beauty with a Pool, WiFi and Air Conditioning
3 bedrooms
2 bathrooms
Sleeps 6
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Disney Vacation Rental, Private Townhouse in gated community
4 bedrooms
3 bathrooms
Sleeps 10
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Luxury Modern Villa 13Beds- Sleep 25+ -Disney Near
5 bedrooms
5 bathrooms
Sleeps 25
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A 3 bed/3 bath townhouse with a south facing pool and Toystory Kid's room
3 bedrooms
3 bathrooms
Sleeps 8
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Villa Journey - 3 miles from Disney, 2 Masters and a Private Pool & Spa!
4 bedrooms
3 bathrooms
Sleeps 8
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CW2- 1 mile from Disney, nice town home in Gated Community
3 bedrooms
3 bathrooms
Sleeps 8
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4 br, Very close to Disney. Luxury furnished, Gated Resort, Private Pool. WIFI
4 bedrooms
2 bathrooms
Sleeps 10
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4BR Private Pool/Spa, WiFi, ROKU TVs, BBQ-Pets Considered-Clean and Spacious
4 bedrooms
3 bathrooms
Sleeps 10
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The Charming Mickey's Tree House,
4 bedrooms
2 bathrooms
Sleeps 9
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GORGEOUS 2609 Luxury Home-Near all parks & EVERYTHING!
9 bedrooms
9 bathrooms
Sleeps 18
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AMAZING POOL HOME,GAME ROOM, 10 MIN. FROM DISNEY!!
4 bedrooms
3 bathrooms
Sleeps 10
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Stunning Lake Berkley Villa with a Pool
3 bedrooms
2 bathrooms
Sleeps 6
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Private Villa on Eagle Pointe, in Disney area, Pool and Spa, Yard, WiFi, BBQ, Direct TY, Toys
3 bedrooms
2 bathrooms
Sleeps 8
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Amazing 5 Bed Villa with Private Pool and Spa up to 12 Guests - 4839 LL
5 bedrooms
4 bathrooms
Sleeps 12
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Disney World is 4 Miles away and Close to area water parks.
3 bedrooms
2 bathrooms
Sleeps 10
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Villa di Lusso
6 bedrooms
10 bathrooms
Sleeps 14
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Deluxe 5 bedrooms villa - Storey Lake
5 bedrooms
4 bathrooms
Sleeps 14
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V5018
5 bedrooms
4 bathrooms
Sleeps 10
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Stunning 6 Bed Pool Home Close to Disney Parks.
6 bedrooms
4 bathrooms
Sleeps 12
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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.
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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.