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Kissimmee Vacation Rentals

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3980 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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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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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 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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villanirvana, vacation rental in Kissimmee

villanirvana

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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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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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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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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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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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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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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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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(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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SUPER Close To Disney, Gameroom, Private Backyard, Lake, Free WiFi, Pool, Spa, vacation rental in Kissimmee

SUPER Close To Disney, Gameroom, Private Backyard, Lake, Free WiFi, Pool, Spa

7 bedrooms
5 bathrooms
Sleeps 17
Match: Sleeps
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Plenty of 2021 openings, vacation rental in Kissimmee

Plenty of 2021 openings

3 bedrooms
3 bathrooms
Sleeps 8
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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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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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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Roughtallys Villa, vacation rental in Kissimmee

Roughtallys Villa

7 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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New 6 Bedrooms, Special lighting ,4 miles - Disneys, CHECK THIS OUT!!, vacation rental in Kissimmee

New 6 Bedrooms, Special lighting ,4 miles - Disneys, CHECK THIS OUT!!

6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Luxury 6 bedroom villa ✦ 3 Miles or 5 min to Disney ✦ South pool ✦Movie Room, vacation rental in Kissimmee

Luxury 6 bedroom villa ✦ 3 Miles or 5 min to Disney ✦ South pool ✦Movie Room

6 bedrooms
6 bathrooms
Sleeps 14
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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Oakhill Disney Villa, vacation rental in Kissimmee

Oakhill Disney Villa

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Bella Vida New Phase 6 bedroom Modern Home, vacation rental in Kissimmee

Bella Vida New Phase 6 bedroom Modern Home

6 bedrooms
7 bathrooms
Sleeps 12
Match: Sleeps
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Hideaway Villa,Terra Verde Resort - Xbox,PS2,Games Room, Pool, vacation rental in Kissimmee

Hideaway Villa,Terra Verde Resort - Xbox,PS2,Games Room, Pool

5 bedrooms
4 bathrooms
Sleeps 12
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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Family Resort - 14BR Mansion - Private Pool and BBQ!, vacation rental in Kissimmee

Family Resort - 14BR Mansion - Private Pool and BBQ!

14 bedrooms
11 bathrooms
Sleeps 31
Match: Sleeps
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6 Bdr Vacation Home in Beautiful Resort, vacation rental in Kissimmee

6 Bdr Vacation Home in Beautiful Resort

6 bedrooms
7 bathrooms
Sleeps 17
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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6-bedroom house w/ private pool 10 min from Disney, vacation rental in Kissimmee

6-bedroom house w/ private pool 10 min from Disney

6 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
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Wow! 7 Bed Lakeside Villa Pool/Spa Nr Disney Fast Wifi, Gamerm. Guarded Resort!, vacation rental in Kissimmee

Wow! 7 Bed Lakeside Villa Pool/Spa Nr Disney Fast Wifi, Gamerm. Guarded Resort!

7 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Family Resort - 8BR Mansion - Private Pool, BBQ and Game Room!, vacation rental in Kissimmee

Family Resort - 8BR Mansion - Private Pool, BBQ and Game Room!

8 bedrooms
5 bathrooms
Sleeps 18
Match: Sleeps
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Unit 9- 3 Bedroom Home 7625, vacation rental in Kissimmee

Unit 9- 3 Bedroom Home 7625

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

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

8 bedrooms
6 bathrooms
Sleeps 18
Match: Sleeps
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The Seasons Villa, lake view and 4 master bedrooms, vacation rental in Kissimmee

The Seasons Villa, lake view and 4 master bedrooms

6 bedrooms
6 bathrooms
Sleeps 13
Match: Sleeps
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Exceptional 4 Bedroom/Pool Disney Vacation Home, vacation rental in Kissimmee

Exceptional 4 Bedroom/Pool Disney Vacation Home

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Family Friendly Four Bedroom w/ Pool 4896, vacation rental in Kissimmee

Family Friendly Four Bedroom w/ Pool 4896

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Villa Journey - 3 miles from Disney, 2 Masters and a Private Pool & Spa!, vacation rental in Kissimmee

Villa Journey - 3 miles from Disney, 2 Masters and a Private Pool & Spa!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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A stunning pool home in Kissimmee, Disney Paradi, vacation rental in Kissimmee

A stunning pool home in Kissimmee, Disney Paradi

4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Tranquil Holiday Home-Games Room, Private Pool, WiFi, Disney/Orlando, vacation rental in Kissimmee

Tranquil Holiday Home-Games Room, Private Pool, WiFi, Disney/Orlando

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Located in Emerald Island Resort  Beautiful 7 Bed 4.5 Bath Villa Close 2  Disney, vacation rental in Kissimmee

Located in Emerald Island Resort Beautiful 7 Bed 4.5 Bath Villa Close 2 Disney

7 bedrooms
7 bathrooms
Sleeps 16
Match: Sleeps
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Pat and Ron's Holiday Home, Relaxing Retreat, vacation rental in Kissimmee

Pat and Ron's Holiday Home, Relaxing Retreat

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Disney Dream Villa, vacation rental in Kissimmee

Disney Dream Villa

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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SPECIAL OFFER! - AMAZING NEW HOUSE with Lake View in Orlando, 5 MIN DISNEY, vacation rental in Kissimmee

SPECIAL OFFER! - AMAZING NEW HOUSE with Lake View in Orlando, 5 MIN DISNEY

6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Executive 4 Bedroom / 3 Bathroom Lake View Home in Gated Resort Community, vacation rental in Kissimmee

Executive 4 Bedroom / 3 Bathroom Lake View Home in Gated Resort Community

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Disney Orlando House w/Private Pool, vacation rental in Kissimmee

Disney Orlando House w/Private Pool

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Completely remodelled 2020. Luxury 4 Bed 3 Bath Villa with own pool. Near Disney, vacation rental in Kissimmee

Completely remodelled 2020. Luxury 4 Bed 3 Bath Villa with own pool. Near Disney

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Alberto Circle, Fun Vacation House with Pool, vacation rental in Kissimmee

Alberto Circle, Fun Vacation House with Pool

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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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.