Search Hotels in Countryside, Kissimmee

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30 Dec - 31 Dec
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31 Dec - 1 Jan
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2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

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Our top choices for Countryside hotels

4 outdoor pools, open 5:30 AM to midnight, pool cabanas (surcharge)
Rosen Shingle Creek

Rosen Shingle Creek

Rosen Shingle Creek
4.5 star property
26.8 km from Countryside
9.4 out of 10, Exceptional, (4371)
"Great place to stay. Definitely will stay here again.."
United States
Donnell
The price is ฿3,773
฿4,244 total
includes taxes & fees
23 Jan - 24 Jan 2026
Rosen Shingle Creek
Property grounds
Seasons Florida Resort

Seasons Florida Resort

Seasons Florida Resort
2.0 star property
15.3 km from Countryside
8.8 out of 10, Excellent, (3321)
"A great place to stay for the price"
United States
Jennie
The price is ฿1,994
฿2,263 total
includes taxes & fees
5 Jan - 6 Jan 2026
Seasons Florida Resort
Lobby lounge
Aloft Orlando Lake Buena Vista

Aloft Orlando Lake Buena Vista

Aloft Orlando Lake Buena Vista
3.0 star property
23.2 km from Countryside
8.8 out of 10, Excellent, (1926)
"Good place to stay "
United States
victor
The price is ฿2,469
฿2,777 total
includes taxes & fees
4 Jan - 5 Jan 2026
Aloft Orlando Lake Buena Vista
Outdoor pool, pool umbrellas, pool loungers
Wyndham I-Drive Avanti Resort & Conference Center

Wyndham I-Drive Avanti Resort & Conference Center

Wyndham I-Drive Avanti Resort & Conference Center
3.5 star property
30.3 km from Countryside
7.4 out of 10, Good, (3970)
"Great location "
United States
Mark
The price is ฿1,972
฿2,860 total
includes taxes & fees
5 Jan - 6 Jan 2026
Wyndham I-Drive Avanti Resort & Conference Center
Outdoor pool, pool cabanas (surcharge), pool umbrellas
Hyatt Regency Orlando

Hyatt Regency Orlando

Hyatt Regency Orlando
4.5 star property
26.8 km from Countryside
9.2 out of 10, Wonderful, (1911)
"Great stay, cleanliness, staff"
United States
wathik
The price is ฿4,249
฿6,537 total
includes taxes & fees
2 Jan - 3 Jan 2026
Hyatt Regency Orlando
6 outdoor pools, free pool cabanas, pool umbrellas
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
4.0 star property
20.7 km from Countryside
9.4 out of 10, Exceptional, (4202)
"Enjoyed our stay. "
United States
WILLIAM
The price is ฿3,451
฿3,882 total
includes taxes & fees
28 Jan - 29 Jan 2026
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
In-room safe, laptop workspace, blackout curtains, iron/ironing board
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

Palazzo Lakeside Hotel
3.0 star property
16.4 km from Countryside
8.2 out of 10, Very good, (5144)
"Beautiful place to stay."
United States
Mohammad
The price is ฿892
฿2,089 total
includes taxes & fees
8 Jan - 9 Jan 2026
Palazzo Lakeside Hotel
Outdoor pool, pool loungers
Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area
3.0 star property
21.9 km from Countryside
9.8 out of 10, Exceptional, (5483)
"Great stay!"
United States
Kiran
The price is ฿5,111
฿5,750 total
includes taxes & fees
4 Jan - 5 Jan 2026
Drury Plaza Hotel Orlando - Disney Springs Area
Lobby
Holiday Inn Resort Orlando - Lake Buena Vista by IHG

Holiday Inn Resort Orlando - Lake Buena Vista by IHG

Holiday Inn Resort Orlando - Lake Buena Vista by IHG
3.5 star property
21.1 km from Countryside
8.4 out of 10, Very good, (3602)
"Very convenient and liked the hotel"
United States
Melanie
The price is ฿2,089
฿3,418 total
includes taxes & fees
25 Jan - 26 Jan 2026
Holiday Inn Resort Orlando - Lake Buena Vista by IHG
Exterior
Ramada by Wyndham Kissimmee Gateway

Ramada by Wyndham Kissimmee Gateway

Ramada by Wyndham Kissimmee Gateway
3.0 star property
20.3 km from Countryside
8.0 out of 10, Very good, (3916)
"Phenomenal hotel for the price point as well as the children. "
United States
Destiny
The price is ฿1,595
฿2,457 total
includes taxes & fees
20 Jan - 21 Jan 2026
Ramada by Wyndham Kissimmee Gateway
Premium bedding, desk, laptop workspace, blackout curtains
Candlewood Suites Orlando - Lake Buena Vista by IHG

Candlewood Suites Orlando - Lake Buena Vista by IHG

Candlewood Suites Orlando - Lake Buena Vista by IHG
2.5 star property
22.8 km from Countryside
9.0 out of 10, Wonderful, (2320)
"Loved the experience "
United States
Deana
The price is ฿2,089
฿2,706 total
includes taxes & fees
5 Jan - 6 Jan 2026
Candlewood Suites Orlando - Lake Buena Vista by IHG
View from room
Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista
3.5 star property
22.6 km from Countryside
8.6 out of 10, Excellent, (5618)
"Great property to stay"
United States
Deepankar
The price is ฿2,592
฿2,916 total
includes taxes & fees
23 Jan - 24 Jan 2026
Rosen Inn Lake Buena Vista
Bar (on property)
SpringHill Suites by Marriott Orlando Theme Parks/Lake Buena Vista

SpringHill Suites by Marriott Orlando Theme Parks/Lake Buena Vista

SpringHill Suites by Marriott Orlando Theme Parks/Lake Buena Vista
3.0 star property
23.3 km from Countryside
8.6 out of 10, Excellent, (3503)
"Clean room, comfortable bed and great breakfast "
United States
Jena
The price is ฿3,007
฿3,383 total
includes taxes & fees
25 Jan - 26 Jan 2026
SpringHill Suites by Marriott Orlando Theme Parks/Lake Buena Vista
View from room
Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando
3.0 star property
27.6 km from Countryside
8.6 out of 10, Excellent, (5480)
"Great stay"
United States
Stephanie
The price is ฿2,489
฿2,800 total
includes taxes & fees
28 Jan - 29 Jan 2026
Rosen Inn at Pointe Orlando
Exterior
Holiday Inn Resort Kissimmee by the Parks by IHG

Holiday Inn Resort Kissimmee by the Parks by IHG

Holiday Inn Resort Kissimmee by the Parks by IHG
3.5 star property
20.8 km from Countryside
8.4 out of 10, Very good, (1120)
"Great hotel"
United States
Steven
The price is ฿2,247
฿3,179 total
includes taxes & fees
13 Jan - 14 Jan 2026
Holiday Inn Resort Kissimmee by the Parks by IHG
Courtyard
Nobile Hotel Parkway at Celebration Orlando

Nobile Hotel Parkway at Celebration Orlando

Nobile Hotel Parkway at Celebration Orlando
2.5 star property
18.8 km from Countryside
8.0 out of 10, Very good, (1015)
"Excellent front desk and stay, fe"
United States
Kariem
The price is ฿1,436
฿2,599 total
includes taxes & fees
5 Jan - 6 Jan 2026
Nobile Hotel Parkway at Celebration Orlando
Exterior
Caribe Royale Orlando

Caribe Royale Orlando

Caribe Royale Orlando
4.5 star property
19.3 km from Countryside
9.2 out of 10, Wonderful, (4556)
"excellent place to stay. "
United States
Arshad
The price is ฿6,140
฿8,261 total
includes taxes & fees
2 Jan - 3 Jan 2026
Caribe Royale Orlando
Outdoor pool, open 9 AM to 10 PM, pool loungers
Orlando Palms Hotel

Orlando Palms Hotel

Orlando Palms Hotel
2.5 star property
28.8 km from Countryside
7.6 out of 10, Good, (2258)
"Accommodation was great , clean and not too expensive "
United States
Jossy
The price is ฿1,861
฿2,471 total
includes taxes & fees
12 Jan - 13 Jan 2026
Orlando Palms Hotel
Property amenity
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel
3.0 star property
29.8 km from Countryside
8.6 out of 10, Excellent, (763)
"What a wonderful stay! "
United States
Lucia
The price is ฿2,663
฿2,996 total
includes taxes & fees
26 Jan - 27 Jan 2026
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel
Outdoor pool, pool umbrellas, pool loungers
Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks
3.0 star property
20.5 km from Countryside
9.4 out of 10, Exceptional, (2137)
"Great accommodation close to everything "
United States
VICTOR
The price is ฿2,185
฿3,737 total
includes taxes & fees
4 Jan - 5 Jan 2026
Kompose Boutique Resort at Theme Parks
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Where to stay in Countryside

Find the best Countryside areas for the activities you enjoy most.

Reunion

The top golf courses and fun-filled water parks are top of the list for many visitors to Reunion. A stop by Reunion Resort Golf Course or Jack Nicklaus Course might round out your trip.

Windsor Hills

While there might not be top attractions in Windsor Hills, you can explore the larger area and discover places like Mystic Dunes Golf Club and Island H2O Live!.

Orange Lake

If you're spending some time in Orange Lake, Walt Disney World® Resort and Orange Lake Golf are top sights worth seeing.

Lake Berkley

While Lake Berkley may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Medieval Times and Give Kids the World Village.

Buena Ventura Lakes

The golf courses and sporting events are a few reasons travellers visit Buena Ventura Lakes. Want to see more of the surrounding area? Silver Spurs Arena and Osceola Heritage Park are a few top sights nearby.

Top Countryside Hotel Reviews

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

10/10 Excellent
"Room was nice, spacious & very clean. Hotel staff were very polite & it was a quick check-in process. The amenities were a plus. Location was quick to everything. Will be staying here again☺️"
chardonnay 4-night trip
Posted 1 day ago
The Grove Resort & Water Park Orlando

Frequently asked questions

What's it like in Countryside?
You'll be sure to have fun exploring Kissimmee's Countryside neighbourhood.
If I need to cancel my hotel reservation in Countryside, will I receive a refund?
Yes, the majority of hotel room reservations are fully refundable if you cancel prior to the hotel's cancellation deadline, which often is within 24-48 hours of your arrival date. If you have a reservation that's non-refundable, you might still have the option to cancel and receive a refund within a 24-hour period of booking. Enter dates in and click on "Search", then you can filter by "fully refundable" to get top deals in Countryside.
What is there to do in this Kissimmee neighbourhood?
Popular attractions in the larger Kissimmee area include Walt Disney World® Resort, Disney's Animal Kingdom® Theme Park and Old Town. While you're out sightseeing, Silver Spurs Arena and Osceola Heritage Park are a couple of sights to visit in the city.