House holiday rentals in Osceola County
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Top-rated house rentals in Osceola County
Guests agree: These houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Osceola County house rentals
House rentals with a pool
Home in Kissimmee
4.97 out of 5 average rating, 262 reviewsUpscale Contemporary Waterfront 3/2 Heated Pool
7–14 Oct
Home in Kissimmee
4.79 out of 5 average rating, 109 reviews4 Bedroom Kissimmee Vacation Home
11–18 May
Home in Haines City
4.82 out of 5 average rating, 106 reviewsSouthern Dunes Golf Vacation Villa
7–14 Oct
Home in Kissimmee
4.92 out of 5 average rating, 150 reviewsHome Away From Home
9–16 May
Home in Kissimmee
5.0 out of 5 average rating, 3 reviewsCarpe-D Lake Marion Resort Vacation Villa
14–21 Aug
Home in Kissimmee
5.0 out of 5 average rating, 8 reviewsUniquely Chic home near Disney!
23–30 Oct
Home in Davenport
4.93 out of 5 average rating, 60 reviewsSweet vacation home.
15–22 May
Home in Kissimmee
5.0 out of 5 average rating, 11 reviewsQuiet 2bd Oasis with King bed and Pool
31 Dec – 7 Jan
Weekly house rentals
Home in Kissimmee
4.82 out of 5 average rating, 39 reviewsNewly Renovated Kissimmee Duplex
12–17 May
Home in Haines City
4.81 out of 5 average rating, 16 reviewsVilla Blanca Villa Villa
2–9 Mar
Home in Kissimmee
5.0 out of 5 average rating, 66 reviewsVilla by the Lakes
23–30 Sep
Home in Kissimmee
4.94 out of 5 average rating, 52 reviewsSpacious 4/2 getaway! Near Theme Parks!
27 Jul – 3 Aug
Home in Lake Wales
4.96 out of 5 average rating, 28 reviewsLa Casita Redonda
22–29 Dec
Home in Lake Wales
4.92 out of 5 average rating, 66 reviews*This must be THE PLACE FL*
16–23 Aug
Home in Lake Wales
4.92 out of 5 average rating, 88 reviewsLake house 3/2 Fish 4 Monster Bass! Kayak & Canoe
19–26 Sep
Home in Kissimmee
4.97 out of 5 average rating, 30 reviewsKissimmee cottage *15mi to WDW*
24–31 Jan
Private house rentals
Home in Osceola County
4.9 out of 5 average rating, 20 reviewsLarge Private Home on Golf course by Disney
26 Oct – 2 Nov
Home in Lake Wales
4.94 out of 5 average rating, 17 reviewsLake Rosalie Getaway
18–25 Dec
Home in Kissimmee
4.96 out of 5 average rating, 25 reviewsLakeside Boho Bliss: The BohoBay
19–26 Oct
Home in Kissimmee
4.87 out of 5 average rating, 71 reviewsGreat place to stay near Disney World for reasonable rentals
10–17 Sep
Home in Lake Wales
4.93 out of 5 average rating, 15 reviewsCozy House near to Legoland FL
14–21 Jun
Home in Haines City
5.0 out of 5 average rating, 3 reviewsGolf Course Retreat
14–21 Jul
Home in Frostproof
5.0 out of 5 average rating, 77 reviewsRIVER RANCH Country Retreat- ATVing!
19–26 Jul
Home in Kissimmee
5.0 out of 5 average rating, 11 reviewsTwist of Lime Cottage in Margaritaville nr Disney
16–23 May
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