House holiday rentals in Osceola County
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Top-rated house rentals in Osceola County
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Holiday rentals for every style
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Popular amenities for house rentals in Osceola County
House rentals with a pool
Home in Osceola County
4.86 out of 5 average rating, 138 reviewsOpen dates for May - Near Disney
5–12 Aug
Home in Kissimmee
4.79 out of 5 average rating, 109 reviews4 Bedroom Kissimmee Vacation Home
12–19 Jan
Home in Kissimmee
4.88 out of 5 average rating, 108 reviewsNo Airbnb Fee! Thematic Rooms w/ Pvt Pool °o° Area
24–29 Sep
Home in Haines City
4.82 out of 5 average rating, 106 reviewsSouthern Dunes Golf Vacation Villa
7–14 Oct
Home in Kissimmee
4.97 out of 5 average rating, 262 reviewsUpscale Contemporary Waterfront 3/2 Heated Pool
17–24 Oct
Home in Saint Cloud
5.0 out of 5 average rating, 10 reviewsHarmony Golf Villa
27 May – 3 Jun
Home in Kissimmee
5.0 out of 5 average rating, 3 reviewsCarpe-D Lake Marion Resort Vacation Villa
12–19 Aug
Home in St. Cloud
5.0 out of 5 average rating, 19 reviewsUpdated Pool Home 25 Mins To Theme Parks!
11–18 May
Weekly house rentals
Home in St. Cloud
5.0 out of 5 average rating, 4 reviewsPet friendly + in Dwtn + 20mi to Disney & Parks!
10–17 Sep
Home in Kissimmee
4.82 out of 5 average rating, 38 reviewsNewly Renovated Kissimmee Duplex
10–17 May
Home in Kissimmee
5.0 out of 5 average rating, 66 reviewsVilla by the Lakes
8–15 Jan
Home in Lake Wales
4.96 out of 5 average rating, 28 reviewsLa Casita Redonda
21–28 Feb
Home in Davenport
5.0 out of 5 average rating, 13 reviewsSpacious House Near Attractions
13–20 Oct
Home in Kissimmee
4.95 out of 5 average rating, 22 reviewsCheerful, 3 bedroom home with pool
29 Nov – 6 Dec
Home in Lake Wales
4.91 out of 5 average rating, 78 reviews"Cutty Shack" Waterfront Kissimmee River House 3/3
25 Aug – 1 Sep
Home in Lake Wales
4.92 out of 5 average rating, 88 reviewsLake house 3/2 Fish 4 Monster Bass! Kayak & Canoe
14–21 Aug
Private house rentals
Home in Kissimmee
4.96 out of 5 average rating, 25 reviewsLakeside Boho Bliss: The BohoBay
2–9 Sep
Home in Lake Wales
4.92 out of 5 average rating, 66 reviews*This must be THE PLACE FL*
17–24 Jul
Home in Kissimmee
4.87 out of 5 average rating, 71 reviewsGreat home near Disney World for affordable rentals
10–17 Sep
Home in Kissimmee
4.97 out of 5 average rating, 37 reviewsNewly renovated Resort themed home near Disney
24 Sep – 1 Oct
Home in Frostproof
5.0 out of 5 average rating, 77 reviewsRIVER RANCH Country Retreat- ATVing!
24 Sep – 1 Oct
Home in Kissimmee
4.93 out of 5 average rating, 41 reviewsNew Listing! Casita Bonita Pool House
4–11 Jan
Home in Osceola County
4.89 out of 5 average rating, 19 reviewsLarge Private Home on Golf course by Disney
2–9 Feb
Home in Kissimmee
5.0 out of 5 average rating, 3 reviewsFlip Flop Getaway at Runaway Beach Club *Disney*
8–15 Apr
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