Resort holiday rentals in Kissimmee
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Top-rated resort rentals in Kissimmee
Guests agree: these resort rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for resort rentals in Kissimmee
Family-friendly resort rentals
Resort in Celebration
Mystic Dunes Beautiful 2BR/2BA resort near Disney
15–22 Nov
Resort in Orlando
♥ Unforgettable vacations! Wonderful Resort! ✶ #1
12–19 May
Resort in Orlando
Amazing two-bedroom at Westgate Palace #12
1–8 May
Resort in Orlando
Book your next family vacation at Westgate Resorts
20–27 Sep
Resort in Kissimmee
Star Island Resort- 1 bedroom
8–15 May
Resort in Kissimmee
Orange Lake Country Club, Kissimmee, FLorida
15–22 May
Resort in Kissimmee
KING - SUITE STYLE - ORLANDO AREA VACATION GETAWAY
26 Apr – 3 May
Resort in Kissimmee
4.89 out of 5 average rating, 28 reviewsWestgate Town Center Resort & Spa
9–16 Jan
Resort rentals with a pool
Resort in Orange County
Club Wyndham Bonnet Creek, 1 BR Deluxe 174329
9–16 Sep
Resort in Kissimmee
4.75 out of 5 average rating, 4 reviewsStar Island Resort - 2 Bedroom Condo
14–21 Feb
Resort in Orlando
5.0 out of 5 average rating, 5 reviewsSpacious 3 Bedroom condo Lake Buena Vista area
27 Oct – 3 Nov
Resort in Kissimmee
4.6 out of 5 average rating, 5 reviewsTimeshare at Westgate town center
25 Feb – 4 Mar
Resort in Orlando
5.0 out of 5 average rating, 5 reviewsBest Resort for Family Vacation in the Nation
1–8 May
Resort in Davenport
4.86 out of 5 average rating, 7 reviews6bd Resort wt PrivatePool/ FreeWaterAmenities90
5–12 Oct
Resort in Lake Buena Vista
4.8 out of 5 average rating, 5 reviewsDisney Dreams Come True 1 Bedroom Condo, #2
27 Nov – 4 Dec
Resort in Osceola County
5.0 out of 5 average rating, 3 reviews3 Bedroom Deluxe Suite on Beautiful Florida Resort
26 Jun – 3 Jul
Resort rentals with a gym
Resort in Orlando
5.0 out of 5 average rating, 5 reviewsLas Palmeras Orlando - Studio
8–15 Nov
Resort in Orlando
5.0 out of 5 average rating, 4 reviewsDisney Florida Resorts
5–12 Oct
Resort in Celebration
5.0 out of 5 average rating, 3 reviewsSpecial Offers at Mystic Dunes Resort 2 Bedrooms
6–13 May
Resort in Orlando
4.67 out of 5 average rating, 3 reviewsWestgate lake resort & spa sleep up to 12 people
25 Dec – 1 Jan
Resort in Orlando
5.0 out of 5 average rating, 4 reviewsHarbour Lake - Studio
16–23 Apr
Resort in Kissimmee
New place to staySilver Lake Resort to Experience Orlando!
15–22 Jun
Resort in Lake Buena Vista
5.0 out of 5 average rating, 13 reviews1 Bedroom at Bonnet Creek Resort Near Disney!
1–8 Jun
Resort in Kissimmee
4.97 out of 5 average rating, 38 reviewsAmazing Townhome with Private Pool (SL4839)
1–8 Jan
Quick stats about resort rentals in Kissimmee
Total rentals
80 properties
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Rentals with a pool
80 properties have a pool
Family-friendly rentals
40 properties are a good fit for families
Total number of reviews
60 reviews
Nightly prices starting at
$55 SGD before taxes and fees
Destinations to explore
- St Petersburg Holiday rentals
- Anna Maria Island Holiday rentals
- Sarasota Holiday rentals
- Tampa Holiday rentals
- Key West Holiday rentals
- Naples Holiday rentals
- Miami Holiday rentals
- Miami Beach Holiday rentals
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- Resort rentals Orlando
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