Estia Villas - Vacation Rentals in Osceola County
Villa
10.0
(
330 Reviews
)
4 Bedrooms
3 Bathrooms
8 Guests
1450 ft²
-
Hot Tub -
Spa -
Fireplace/Heating -
Pool
US $222
/Night
7 Nights - $1,556
Villa
8.0
(
12 Reviews
)
3 Bedrooms
3 Bathrooms
6 Guests
-
Parking -
Air Conditioner -
Internet -
Child Friendly
US $100
/Night
7 Nights - $700
10.0
(
2 Reviews
)
1 Bedroom
1 Bathroom
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace -
View
US $970
/Night
7 Nights - $6,792
Villa
10.0
(
222 Reviews
)
4 Bedrooms
3 Bathrooms
8 Guests
1750 ft²
-
Private Pool -
Hot Tub
-
Fireplace/Heating
-
Pool
US $250
/Night
7 Nights - $1,750
Villa
10.0
(
205 Reviews
)
6 Bedrooms
4 Bathrooms
12 Guests
2812 ft²
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $481
/Night
7 Nights - $3,370
Villa
10.0
(
168 Reviews
)
9 Bedrooms
5 Bathrooms
20 Guests
3200 ft²
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $640
/Night
7 Nights - $4,483
Villa
10.0
(
125 Reviews
)
4 Bedrooms
3 Bathrooms
10 Guests
1874 ft²
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $460
/Night
7 Nights - $3,222
Villa
10.0
(
46 Reviews
)
7 Bedrooms
4 Bathrooms
16 Guests
3300 ft²
-
Private Pool
-
Hot Tub
-
Spa
-
Fireplace/Heating
US $411
/Night
7 Nights - $2,877
See More Osceola County Vacation Rentals
Luxury Places to Stay in Osceola County
Over 10000+
Luxury Places to Stay in or Near Osceola County
Villa
8.0
(
2 Reviews
)
5 Bedrooms
5 Bathrooms
14 Guests
3000 ft²
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
Unlock the Best Price
House
8.8
(
11 Reviews
)
6 Bedrooms
5 Bathrooms
17 Guests
3100 ft²
-
Private Pool
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
Unlock the Best Price
House
8.8
(
3 Reviews
)
5 Bedrooms
5 Bathrooms
12 Guests
2400 ft²
-
Private Pool
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
Unlock the Best Price
House
5 Bedrooms
5 Bathrooms
12 Guests
-
Private Pool
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
Unlock the Best Price
House
5 Bedrooms
5 Bathrooms
12 Guests
-
Private Pool
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
Unlock the Best Price
Villa
10.0
(
58 Reviews
)
5 Bedrooms
5 Bathrooms
12 Guests
5201 ft²
-
Private Pool
-
Oceanfront -
Hot Tub
-
Fireplace/Heating
Unlock the Best Price
Resort
8.0
(
1 Review
)
2 Bathrooms
8 Guests
-
Hot Tub
-
Pool
-
Air Conditioner
-
Internet
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New
House
1 Bedroom
2 Bathrooms
6 Guests
-
Pool
-
Parking
-
Air Conditioner
-
Internet
US $8,499
/Night
7 Nights - $59,494
Find More Osceola County Villas, Resorts, & Rentals on BedroomVillas
Top-Rated Vacation Rentals with a Pool in Osceola County
Over 10000+
Top-Rated Vacation Rentals with a Pool in or Near Osceola County
House
10.0
(
382 Reviews
)
6 Bedrooms
4 Bathrooms
14 Guests
3534 ft²
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $581
/Night
7 Nights - $4,070
House
10.0
(
323 Reviews
)
4 Bedrooms
3 Bathrooms
8 Guests
1800 ft²
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $312
/Night
7 Nights - $2,183
Condo
10.0
(
316 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
-
Kitchen
US $218
/Night
7 Nights - $1,527
Villa
10.0
(
280 Reviews
)
3 Bedrooms
3 Bathrooms
6 Guests
2931 ft²
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $336
/Night
7 Nights - $2,353
House
10.0
(
269 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1797 ft²
-
Fireplace/Heating
-
Pool
-
Ocean View -
Balcony/Terrace
US $147
/Night
7 Nights - $1,028
House
10.0
(
244 Reviews
)
7 Bedrooms
6 Bathrooms
14 Guests
4000 ft²
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $508
/Night
7 Nights - $3,559
House
10.0
(
241 Reviews
)
7 Bedrooms
6 Bathrooms
16 Guests
3650 ft²
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $634
/Night
7 Nights - $4,439
House
10.0
(
240 Reviews
)
4 Bedrooms
3 Bathrooms
10 Guests
2146 ft²
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $230
/Night
7 Nights - $1,612
Pet-Friendly Vacation Rentals in Osceola County
Over 7235+
Pet-Friendly Vacation Rentals in or Near Osceola County
7.7
(
804 Reviews
)
12 Bedrooms
11 Bathrooms
34 Guests
1018.98 ft²
-
Hot Tub
-
Pool
-
Balcony/Terrace
-
Pet Friendly
US $99
/Night
7 Nights - $693
10.0
(
2 Reviews
)
1 Bedroom
1 Bathroom
-
Hot Tub
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
US $623
/Night
7 Nights - $4,362
House
10.0
(
197 Reviews
)
4 Bedrooms
3 Bathrooms
8 Guests
1600 ft²
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $230
/Night
7 Nights - $1,608
House
10.0
(
190 Reviews
)
4 Bedrooms
3 Bathrooms
9 Guests
2003 ft²
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $324
/Night
7 Nights - $2,269
Condo
9.6
(
211 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1200 ft²
-
Hot Tub
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
US $176
/Night
7 Nights - $1,229
Villa
9.6
(
133 Reviews
)
6 Bedrooms
4 Bathrooms
13 Guests
3511 ft²
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $369
/Night
7 Nights - $2,580
Condo
9.4
(
167 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1250 ft²
-
Hot Tub
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
US $172
/Night
7 Nights - $1,202
Condo
9.4
(
102 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1200 ft²
-
Hot Tub
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
US $162
/Night
7 Nights - $1,134
See More Pet-Friendly Vacation Rentals in Osceola County on PetFriendly.io
Large Vacation Homes & Villas in Osceola County
Over 28172+
Large Vacation Homes & Villas in or Near Osceola County
4 Bedrooms
3 Bathrooms
10 Guests
3476.74 ft²
-
Pool
-
Balcony/Terrace
-
Breakfast -
Parking
US $285
/Night
7 Nights - $1,995
10.0
(
2 Reviews
)
1 Bedroom
1 Bathroom
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
-
Kitchen
US $421
/Night
7 Nights - $2,944
House
10.0
(
110 Reviews
)
5 Bedrooms
5 Bathrooms
10 Guests
3000 ft²
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $451
/Night
7 Nights - $3,160
House
9.6
(
289 Reviews
)
4 Bedrooms
2 Bathrooms
10 Guests
1700 ft²
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $201
/Night
7 Nights - $1,409
House
9.6
(
241 Reviews
)
5 Bedrooms
3 Bathrooms
12 Guests
2632 ft²
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $302
/Night
7 Nights - $2,116
Villa
9.6
(
240 Reviews
)
4 Bedrooms
3 Bathrooms
10 Guests
1800 ft²
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $220
/Night
7 Nights - $1,537
Villa
9.6
(
192 Reviews
)
4 Bedrooms
4 Bathrooms
10 Guests
2794 ft²
-
Private Pool
-
Oceanfront
-
Hot Tub
-
Fireplace/Heating
US $247
/Night
7 Nights - $1,726
House
9.6
(
162 Reviews
)
5 Bedrooms
5 Bathrooms
14 Guests
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $397
/Night
7 Nights - $2,776
See More Family Vacation Rentals in Osceola County on FVR
Wheelchair Accessible Vacation Homes in Osceola County
Over 4177+
Wheelchair Accessible Vacation Homes in or Near Osceola County
8.9
(
13 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
1194.79 ft²
-
Pool
-
Parking
-
Air Conditioner
-
Internet
US $122
/Night
7 Nights - $854
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
-
Fireplace/Heating
-
Pool
-
Kitchen
-
Parking
US $606
/Night
7 Nights - $4,239
Condo
10.0
(
237 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1300 ft²
-
Hot Tub
-
Fireplace/Heating
-
Pool
-
Ocean View
US $186
/Night
7 Nights - $1,305
Condo
10.0
(
100 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
-
Hot Tub
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
US $243
/Night
7 Nights - $1,700
Condo
10.0
(
88 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1344 ft²
-
Oceanfront
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $154
/Night
7 Nights - $1,079
Condo
9.8
(
218 Reviews
)
3 Bedrooms
2 Bathrooms
7 Guests
1450 ft²
-
Hot Tub
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
US $209
/Night
7 Nights - $1,465
New
Condo
9.6
(
24 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1600 ft²
-
Hot Tub
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
US $234
/Night
7 Nights - $1,638
Condo
9.8
(
25 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1400 ft²
-
Hot Tub
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
US $221
/Night
7 Nights - $1,547
Osceola County Vacation Rentals and Airbnb Places to Stay Under $200
Over 10417+
Osceola County Vacation Rentals and Airbnb Places to Stay Under $200
3 Bedrooms
2 Bathrooms
6 Guests
107.64 ft²
-
Balcony/Terrace
-
Parking
-
Air Conditioner
-
Internet
US $100
/Night
7 Nights - $700
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $190
/Night
7 Nights - $1,333
House
10.0
(
50 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
2300 ft²
-
Private Pool
-
Fireplace/Heating
-
Pool
-
Ocean View
US $187
/Night
7 Nights - $1,308
House
9.8
(
170 Reviews
)
3 Bedrooms
3 Bathrooms
6 Guests
2038 ft²
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $192
/Night
7 Nights - $1,346
Condo
10.0
(
48 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
900 ft²
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
-
Kitchen
US $187
/Night
7 Nights - $1,309
Condo
9.8
(
293 Reviews
)
2 Bedrooms
2 Bathrooms
5 Guests
1100 ft²
-
Oceanfront
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $164
/Night
7 Nights - $1,145
Condo
9.8
(
132 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1100 ft²
-
Hot Tub
-
Fireplace/Heating
-
Pool
-
Ocean View
US $169
/Night
7 Nights - $1,181
House
9.8
(
86 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1595 ft²
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
-
Kitchen
US $161
/Night
7 Nights - $1,130
See More Osceola County Vacation Rental Deals
Instantly Bookable Vacation Homes in Osceola County
Over 30844+
Instantly Bookable Vacation Homes in or Near Osceola County
House
10.0
(
174 Reviews
)
4 Bedrooms
1 Bathroom
8 Guests
-
Private Pool
-
Pool
-
Ocean View
-
Balcony/Terrace
US $155
/Night
7 Nights - $1,085
House
10.0
(
202 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
1745 ft²
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $230
/Night
7 Nights - $1,609
House
10.0
(
121 Reviews
)
3 Bedrooms
3 Bathrooms
6 Guests
1487 ft²
-
Private Pool
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
US $202
/Night
7 Nights - $1,417
House
9.8
(
161 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
-
Private Pool
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
US $254
/Night
7 Nights - $1,776
House
9.8
(
104 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
2040 ft²
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $341
/Night
7 Nights - $2,384
House
9.8
(
104 Reviews
)
4 Bedrooms
3 Bathrooms
9 Guests
1640 ft²
-
Hot Tub
-
Spa
-
Fireplace/Heating
-
Pool
US $278
/Night
7 Nights - $1,943
House
9.8
(
98 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
-
Private Pool
-
Fireplace/Heating
-
Pool
-
Ocean View
US $227
/Night
7 Nights - $1,588
House
9.8
(
87 Reviews
)
4 Bedrooms
2 Bathrooms
9 Guests
2100 ft²
-
Private Pool
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
US $302
/Night
7 Nights - $2,114
About Osceola County Vacation Rentals
With more than 8443 Osceola County vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Estiavillas and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Osceola County.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Estiavillas Osceola County, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Osceola County. Places to stay near Osceola County are 2089.65 ft² on average, with prices averaging US $515 a night.
Estiavillas makes it easy and safe to find and compare vacation rentals in Osceola County with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Top Rental Accommodation Types in Osceola County
| Type | Count |
|---|---|
| Villas | 7683 |
| Vacation Homes | 671 |
| Holiday Apartments | 84 |
| Resorts | 3 |
| Hotels | 2 |
Use these Quick Filters to Find a Vacation Rental in Osceola County
★ Pro Tip: Estiavillas makes it easy to compare the best listings on Estiavillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Estiavillas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Osceola County.
Weather in Osceola County
View the weather forecast for Osceola County before booking your Osceola County Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Osceola County, FL
Estiavillas offers a large selection of top attractions around Osceola County. Research things to do on your vacation before you visit Osceola County.
Old Town
ESPN Wide World of Sports
Osceola Heritage Park
Silver Spurs Arena
Kissimmee Lakefront Park
Mystic Dunes Golf Club
Medieval Times
ChampionsGate Golf Club
Fun Spot America
Reunion Resort Golf Course
Lake Tohopekaliga
Give Kids the World Village
192 Flea Market
Braves Spring Training
Osceola Performing Arts Center
Kissimmee Civic Center
Boggy Creek Airboat Rides
Capone's Dinner Show
Osceola Regional Medical Center
Austin-Tindall Regional Park
Skate Reflections
Falcon's Fire Golf Club
Celebration Golf Club
Kissimmee Go-Karts
Houston Astros Spring Training
Alligator Lake
Kissimmee Bay Country Club
Tupperware Center
Disney Wilderness Preserve
Congo River Golf
Other Places to Stay Near Osceola County, FL
Kissimmee
24,524 Properties
Disney's Maingate West
17,633 Properties
Four Corners
16,625 Properties
West Kissimmee
14,824 Properties
Historic Downtown Kissimmee
7,212 Properties
Reunion
2,044 Properties
Windsor Hills
1,268 Properties
Disney's Maingate East
1,068 Properties
Windsor Palms
715 Properties
Bellavida
224 Properties
Lake Berkley
156 Properties
Buena Ventura Lakes
108 Properties
Complexes around Osceola County, FL
Kissimmee
309 Properties
Disney
40 Properties
Orlandos Sunshine Orlando
97 Properties
Corners
48 Properties
Paradise Townhome
26 Properties
Emerald Island Resort
46 Properties
Garden
34 Properties
Umco Clermont
29 Properties
Kissimmee
33 Properties
Solara Resort
11 Properties
Bella Vida Resort
10 Properties
Paradox Circle
16 Properties
Seasons
13 Properties
Retreat At Championsgate
13 Properties
Indian Creek
4 Properties
Osceola County Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Osceola County?
There are a lot of options in Osceola County. If you plan on staying in the Osceola County area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Osceola County:
- 4 Bedroom Villa 2 Miles from Disney Entrance Kissimmee off Us192
- Amazing villa close to Disney with 5* Reviews
- Mickeys Magical Villa Disney Five Star Pool Villa Home at Windsor Hills
- Delightful modern 4 bed, 3 bath villa with private pool/spa and lake view.
- Outstanding 6 Bed Villa, Pool & Spa, Superb Lakefront Setting, 5* Windsor Hills
- Hakuna Ma'Cottage - Minecraft Room, Southern Pool!
- VRBO STAYED! 6 Bedrms, Free Wifi, 2.5 Miles to Disney! Theater, Mickey Pool!
- Welcome to The Windsor Dream!
- BEST HOUSE! Harry Potter, CARS, Princesses, StarWars, Avengers. Disney 8-10 min!
- Welcome to The Windsor Fantasy!
How many vacation rentals have private pools in Osceola County?
There are 21630 vacation rentals with private pools near Osceola County. Top-rated homes that have access to a swimming pool include:
Which vacation homes in Osceola County are best for families?
If you are looking for a family-friendly vacation home in Osceola County, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Osceola County:
How many vacation rentals are available in Osceola County?
Currently, the total number of properties listed in 2026 is over 8443 in the Osceola County area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Osceola County.
