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Osceola County long stay rentals
Stay a week, a month or longer in a comfortable place all your own
Featured long stay living spaces - Osceola County
Properties highly-rated for stays of 28 nights or longer, with space to feel right at home
Showing deals for:26 Jan - 23 Feb
Image gallery for 10min To Disney, Private Pool, Security Gated, Luxury stay in Kissimmee Orlando
9.49.4 out of 10, Exceptional, (98 reviews)
Exceptional
(98 reviews)
10min To Disney, Private Pool, Security Gated, Luxury stay in Kissimmee Orlando
Kissimmee, FL
12% off
Price is AU$9,388
AU$9,388
for 28 nights, 1 home
AU$335 per night
includes taxes & fees
Image gallery for Special Fall Discount -Gated -Lakeside Villa w/ Pool & HotTub, Near Disney
9.89.8 out of 10, Exceptional, (32 reviews)
Exceptional
(32 reviews)
Special Fall Discount -Gated -Lakeside Villa w/ Pool & HotTub, Near Disney
Kissimmee, FL
16% off
Price is AU$14,354
AU$14,354
for 28 nights, 1 villa
AU$513 per night
includes taxes & fees
Image gallery for Beautiful Pool Family House 4/2 in Kissimmee near to Disney/Universal.
9.09.0 out of 10, Wonderful, (4 reviews)
Wonderful
(4 reviews)
Beautiful Pool Family House 4/2 in Kissimmee near to Disney/Universal.
Kissimmee, FL
9% off
Price is AU$8,130
AU$8,130
for 28 nights, 1 home
AU$290 per night
includes taxes & fees
Image gallery for Home Away from Home
9.89.8 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)
Home Away from Home
Kissimmee, FL
21% off
Price is AU$8,521
AU$8,521
for 28 nights, 1 home
AU$304 per night
includes taxes & fees
Image gallery for Stylish and Cozy Pool Home near Disney in a Gated Community
9.69.6 out of 10, Exceptional, (15 reviews)
Exceptional
(15 reviews)
Stylish and Cozy Pool Home near Disney in a Gated Community
Kissimmee, FL
8% off
Price is AU$17,558
AU$17,558
for 28 nights, 1 villa
AU$627 per night
includes taxes & fees
Image gallery for Beautiful villa, 7 bedroom, 6 bath home with private pool and game room.
9.09.0 out of 10, Wonderful, (4 reviews)
Wonderful
(4 reviews)
Beautiful villa, 7 bedroom, 6 bath home with private pool and game room.
Kissimmee, FL
8% off
Price is AU$12,584
AU$12,584
for 28 nights, 1 villa
AU$449 per night
includes taxes & fees
Image gallery for Modern Luxury Villa with Everything
9.89.8 out of 10, Exceptional, (447 reviews)
Exceptional
(447 reviews)
Modern Luxury Villa with Everything
Kissimmee, FL
18% off
Price is AU$17,270
AU$17,270
for 28 nights, 1 villa
AU$617 per night
includes taxes & fees
Image gallery for Our Retro Mod Pod-Disney & Old Town Minutes Away!
9.49.4 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)
Our Retro Mod Pod-Disney & Old Town Minutes Away!
Kissimmee, FL
8% off
Price is AU$4,425
AU$4,425
for 28 nights, 1 cottage
AU$158 per night
includes taxes & fees
Image gallery for South facing Lakeside Retreat at Cumbrian Lakes
9.69.6 out of 10, Exceptional, (25 reviews)
Exceptional
(25 reviews)
South facing Lakeside Retreat at Cumbrian Lakes
Kissimmee, FL
8% off
Price is AU$8,324
AU$8,324
for 28 nights, 1 villa
AU$297 per night
includes taxes & fees
Image gallery for Lazy River!!! 8br/6ba pool villa from $270/NT, Close to Disney
9.29.2 out of 10, Wonderful, (17 reviews)
Wonderful
(17 reviews)
Lazy River!!! 8br/6ba pool villa from $270/NT, Close to Disney
Kissimmee, FL
32% off
Price is AU$15,233
AU$15,233
for 28 nights, 1 home
AU$544 per night
includes taxes & fees
Image gallery for Luxury Home in Champions' Gate with Private Pool & Game Room!
9.29.2 out of 10, Wonderful, (24 reviews)
Wonderful
(24 reviews)
Luxury Home in Champions' Gate with Private Pool & Game Room!
Davenport, FL
16% off
Price is AU$9,100
AU$9,100
for 28 nights, 1 home
AU$325 per night
includes taxes & fees
Image gallery for (IN296) Home 4/3 Private Pool & Free Waterpark
8.28.2 out of 10, Very good, (21 reviews)
Very good
(21 reviews)
(IN296) Home 4/3 Private Pool & Free Waterpark
Davenport, FL
16% off
Price is AU$7,026
AU$7,026
for 28 nights, 1 home
AU$251 per night
includes taxes & fees
Image gallery for Dream Vacation Getaway next to Disney with Private Pool --10BD/5BA
9.89.8 out of 10, Exceptional, (64 reviews)
Exceptional
(64 reviews)
Dream Vacation Getaway next to Disney with Private Pool --10BD/5BA
Kissimmee, FL
6% off
Price is AU$20,303
AU$20,303
for 28 nights, 1 home
AU$725 per night
includes taxes & fees
Image gallery for Spectacular big house, 4 Bedrooms, private pool
9.09.0 out of 10, Wonderful, (10 reviews)
Wonderful
(10 reviews)
Spectacular big house, 4 Bedrooms, private pool
Kissimmee, FL
12% off
Price is AU$8,646
AU$8,646
for 28 nights, 1 home
AU$309 per night
includes taxes & fees
Image gallery for Luxury Lake Resort ✨
1010 out of 10, Exceptional, (42 reviews)
Exceptional
(42 reviews)
Luxury Lake Resort ✨
Kissimmee, FL
7% off
Price is AU$15,819
AU$15,819
for 28 nights, 1 home
AU$565 per night
includes taxes & fees
Image gallery for Unforgettable Escape: Private Pool, Smart TV, Dreamy Resort, Moments from Disney
1010 out of 10, Exceptional, (39 reviews)
Exceptional
(39 reviews)
Unforgettable Escape: Private Pool, Smart TV, Dreamy Resort, Moments from Disney
Kissimmee, FL
12% off
Price is AU$10,102
AU$10,102
for 28 nights, 1 home
AU$361 per night
includes taxes & fees
Image gallery for Modern Luxury Villa in Storey Lake
9.29.2 out of 10, Wonderful, (49 reviews)
Wonderful
(49 reviews)
Modern Luxury Villa in Storey Lake
Kissimmee, FL
20% off
Price is AU$15,569
AU$15,569
for 28 nights, 1 villa
AU$556 per night
includes taxes & fees
Image gallery for New Villa Magic – Full House Comfort/ 5miDisney
9.69.6 out of 10, Exceptional, (5 reviews)
Exceptional
(5 reviews)
New Villa Magic – Full House Comfort/ 5miDisney
Kissimmee, FL
8% off
Price is AU$9,118
AU$9,118
for 28 nights, 1 villa
AU$326 per night
includes taxes & fees
Image gallery for PRIVATE Heated Pool |FREE Waterpark w/ Lazy River!
7.67.6 out of 10, Good, (5 reviews)
Good
(5 reviews)
PRIVATE Heated Pool |FREE Waterpark w/ Lazy River!
Davenport, FL
16% off
Price is AU$14,946
AU$14,946
for 28 nights, 1 villa
AU$534 per night
includes taxes & fees
Image gallery for 24 HOUR FLASH SALE - 5 STAR DISNEY VACATION HOME
9.49.4 out of 10, Exceptional, (57 reviews)
Exceptional
(57 reviews)
24 HOUR FLASH SALE - 5 STAR DISNEY VACATION HOME
Kissimmee, FL
8% off
Price is AU$14,460
AU$14,460
for 28 nights, 1 home
AU$516 per night
includes taxes & fees
Image gallery for CHARMING VILLA AT SONOMA RESORT AT TAPESTRY
8.28.2 out of 10, Very good, (11 reviews)
Very good
(11 reviews)
CHARMING VILLA AT SONOMA RESORT AT TAPESTRY
Kissimmee, FL
8% off
Price is AU$14,730
AU$14,730
for 28 nights, 1 villa
AU$526 per night
includes taxes & fees
Image gallery for 19-104 Two Master Suites, gated resort with heated pool, playground, lakes. gym
9.69.6 out of 10, Exceptional, (84 reviews)
Exceptional
(84 reviews)
19-104 Two Master Suites, gated resort with heated pool, playground, lakes. gym
Kissimmee, FL
8% off
Price is AU$5,472
AU$5,472
for 28 nights, 1 apartment
AU$195 per night
includes taxes & fees
Image gallery for 14 Mi to Disney Parks: Spacious Kissimmee Home
8.48.4 out of 10, Very good, (45 reviews)
Very good
(45 reviews)
14 Mi to Disney Parks: Spacious Kissimmee Home
Kissimmee, FL
14% off
Price is AU$10,078
AU$10,078
for 28 nights, 1 home
AU$360 per night
includes taxes & fees
Image gallery for Closest House to Resort • Star Wars Adventure + Home Theater!
1010 out of 10, Exceptional, (29 reviews)
Exceptional
(29 reviews)
Closest House to Resort • Star Wars Adventure + Home Theater!
Kissimmee, FL
8% off
Price is AU$19,084
AU$19,084
for 28 nights, 1 home
AU$682 per night
includes taxes & fees
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value