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 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
15–22 Jul
Home in Davenport
4.92 out of 5 average rating, 179 reviewsBeautiful 5BD/5BA & Pool 20 min to Disney Orlando
5–12 May
Home in Kissimmee
4.97 out of 5 average rating, 262 reviewsUpscale Contemporary Waterfront 3/2 Heated Pool
22–29 Jul
Home in Kissimmee
4.81 out of 5 average rating, 125 reviewsBeautiful private home with pool and lake
10–17 Jul
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 St. Cloud
5.0 out of 5 average rating, 20 reviewsUpdated Pool Home 25 Mins To Theme Parks!
10–17 Aug
Home in Kissimmee
5.0 out of 5 average rating, 8 reviewsUniquely Chic home near Disney!
5–12 Nov
Weekly house rentals
Home in Kissimmee
4.82 out of 5 average rating, 39 reviewsNewly Renovated Kissimmee Duplex
12–17 May
Home in Lake Wales
4.96 out of 5 average rating, 28 reviewsLa Casita Redonda
25 Jul – 1 Aug
Home in Kissimmee
5.0 out of 5 average rating, 66 reviewsVilla by the Lakes
24–31 Dec
Home in Lake Wales
4.91 out of 5 average rating, 78 reviews"Cutty Shack" Waterfront Kissimmee River House 3/3
26 Aug – 2 Sep
Home in Kissimmee
5.0 out of 5 average rating, 11 reviewsQuiet 2bd Oasis with King bed and Pool
24–31 May
Home in Lake Wales
5.0 out of 5 average rating, 45 reviewsLake access, Canal front Crooked Lake Gem
13–20 Apr
Home in Lake Wales
4.92 out of 5 average rating, 88 reviewsLake house 3/2 Fish 4 Monster Bass! Kayak & Canoe
11–18 Nov
Home in Kissimmee
4.97 out of 5 average rating, 30 reviewsKissimmee cottage *15mi to WDW*
21–28 Nov
Private house rentals
Home in Haines City
4.81 out of 5 average rating, 16 reviewsVilla Blanca Villa Villa
19–26 Nov
Home in Osceola County
4.9 out of 5 average rating, 21 reviewsLarge Private Home on Golf course by Disney
27 Sep – 4 Oct
Home in Kissimmee
4.98 out of 5 average rating, 63 reviewsCasita Disney! Cute and Boho Townhouse near Disney
1–8 Nov
Home in Davenport
5.0 out of 5 average rating, 14 reviewsSpacious House Near Attractions
9–16 Dec
Home in Frostproof
5.0 out of 5 average rating, 77 reviewsRIVER RANCH Country Retreat- ATVing!
26 Feb – 5 Mar
Home in Kissimmee
4.94 out of 5 average rating, 54 reviewsNice Vacation Home with Pool
16–23 Oct
Home in Davenport
5.0 out of 5 average rating, 7 reviewsHome near Disney
24–31 Jul
Home in Haines City
5.0 out of 5 average rating, 3 reviewsGolf Course Retreat
14–21 Jul
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