Family-friendly holiday rentals in Osceola County
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Top-rated family-friendly rentals in Osceola County
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Osceola County family-friendly rentals
Family-friendly home rentals with a hot tub
Townhouse in Kissimmee
4.85 out of 5 average rating, 138 reviewsPeaceful & Clean Family Home near Disney & Airport
3 – 10 Nov
Condo in Kissimmee
4.83 out of 5 average rating, 170 reviewsDisney Adorable Condo in the heart of it ALL! 1/1
17 – 24 Aug
Villa in Kissimmee
4.81 out of 5 average rating, 213 reviewsVeranda Palms Luxurious Home w/Pool & NEAR DISNEY
15 – 22 May
Condo in Kissimmee
4.8 out of 5 average rating, 115 reviewsStunning view, near Disney. 2 pools
2 – 9 Nov
Townhouse in Kissimmee
4.95 out of 5 average rating, 251 reviewsDisney/Universal Home Away from Home!
7 – 14 Oct
Townhouse in Kissimmee
4.95 out of 5 average rating, 161 reviewsBeautiful family home near all attractions.
21 – 28 June
Villa in Kissimmee
4.96 out of 5 average rating, 167 reviews4 bed villa w/private pool near Disney, sleeps 6+
22 – 29 Aug
Townhouse in Kissimmee
4.95 out of 5 average rating, 153 reviewsAmazing, luxe 3BD/2BA home mins to Parks! 5 Stars!
24 – 31 Aug
Family- and pet-friendly home rentals
Villa in Kissimmee
4.87 out of 5 average rating, 142 reviewsMinutes from Disney Gated LakeView Pvt Heated Pool
4 – 11 Oct
Home in Kissimmee
4.89 out of 5 average rating, 176 reviewsPrivateJacuzzi-BBQ-ResortPool-Gym-7mlsDisney
31 Mar – 7 Apr
Home in Kissimmee
4.89 out of 5 average rating, 145 reviewsLuxury Disney Vacation Home on Reunion Golf Resort
3 – 10 Sept
Condo in Champions Gate
4.85 out of 5 average rating, 262 reviewsMagical Champions Gate 3/2 Tuscan Penthouse
15 – 22 Aug
Villa in Kissimmee
4.85 out of 5 average rating, 370 reviewsAmazing Cozy 4Bed/3Bath, Disney Area, Private Pool
5 – 12 Dec
Home in Kissimmee
4.82 out of 5 average rating, 456 reviewsWelcome to your house in Orlando and Disney Area!
25 Jan – 1 Feb
Villa in Kissimmee
4.92 out of 5 average rating, 179 reviewsMad Men Magic Kingdom House*FAB POOL*OutdoorMOVIE
28 Mar – 4 Apr
Condo in Kissimmee
4.74 out of 5 average rating, 197 reviewsOrlando's Affordable Luxury
11 – 18 Nov
Family-friendly home rentals with a pool
Tiny home in Kissimmee
4.85 out of 5 average rating, 246 reviewsSmall World near Disney sleeps 4-5
26 Oct – 2 Nov
Townhouse in Kissimmee
4.78 out of 5 average rating, 273 reviewsDisney on a Budget Townhome
14 – 21 July
Townhouse in Kissimmee
4.87 out of 5 average rating, 316 reviewsSplendid house 5 min from Disney
6 – 13 Mar
Townhouse in Kissimmee
4.8 out of 5 average rating, 211 reviewsBeautiful Hollywood Style home next to Disney
29 Aug – 5 Sept
Apartment in Kissimmee
4.9 out of 5 average rating, 145 reviewsYour cozy spot
9 – 16 Sept
Apartment in Kissimmee
4.89 out of 5 average rating, 121 reviews1-103 Heated Pool, Gated Resort, Gym, free Wi-Fi
3 – 10 Dec
Apartment in Kissimmee
4.92 out of 5 average rating, 319 reviewsGreat Full Apartment. Just 5' from Disney Orlando
6 – 13 Oct
Townhouse in Kissimmee
4.94 out of 5 average rating, 180 reviewsNew Resort near Orlando Disney Private Hot Tub
2 – 9 Jan
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