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Best Place to Stay in Kissimmee
Discover premium Place to Stay in Kissimmee, crafted for travelers seeking comfort, style, and privacy throughout their journey. Each Place to Stay features a thoughtfully designed interior and carefully chosen amenities that elevate the stay experience beyond the ordinary. Enjoy spacious layouts, refined design, and the flexibility of a private Place to Stay that offers both relaxation and independence, perfect for travelers who value quality, space, and a stay that feels truly special.
Resort
2 Baths
8 Guests
Fireplace/Heating
Air Conditioner
Internet
Child Friendly
US $225/Night
7 Nights - US $1,577
House
4 Bedrooms
3 Baths
8 Guests
1948.27 ft²
Pool
Pet Friendly
Parking- Air Conditioner
US $102/Night
7 Nights - US $715
House
9 Bedrooms
6 Baths
24 Guests
4391 ft²
Private Pool
Hot Tub- Fireplace/Heating
- Pool
US $709/Night
7 Nights - US $4,960
New
House
9 Bedrooms
5 Baths
22 Guests
4305 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $492/Night
7 Nights - US $3,443
House
10.0(24 Reviews)
6 Bedrooms
6 Baths
15 Guests
3756.6 ft²
Spa- Fireplace/Heating
- Pool
- Parking
US $509/Night
7 Nights - US $3,564
House
7 Bedrooms
6 Baths
16 Guests
2800 ft²
- Private Pool
- Hot Tub
- Spa
- Fireplace/Heating
US $329/Night
7 Nights - US $2,305
New
House
4 Bedrooms
3 Baths
12 Guests
1914 ft²
- Private Pool
- Fireplace/Heating
- Pool
Balcony/Terrace
US $256/Night
7 Nights - US $1,790
House
3 Bedrooms
2 Baths
6 Guests
1281 ft²
- Fireplace/Heating
- Pool
Kitchen- Parking
US $199/Night
7 Nights - US $1,390
House
10.0(1 Review)
6 Bedrooms
4 Baths
18 Guests
2550 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $363/Night
7 Nights - US $2,538
Luxury Places to Stay in Kissimmee
Discover exceptional places to stay in Kissimmee with PickleTrip, where comfort, privacy, and quality come together. From luxury private villas to thoughtfully designed holiday homes, each stay offers a refined and relaxing experience. Enjoy spacious interiors, premium amenities, and the freedom to travel your way. Your perfect PickleTrip stay starts here.
House
9 Bedrooms
15 Baths
16 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $4,491/Night
7 Nights - US $31,439
House
9.0(7 Reviews)
14 Bedrooms
15 Baths
32 Guests
12160 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $3,062/Night
7 Nights - US $21,436
House
11 Bedrooms
13 Baths
32 Guests
- Private Pool
- Hot Tub
- Spa
- Fireplace/Heating
US $3,036/Night
7 Nights - US $21,251
House
12 Bedrooms
14 Baths
32 Guests
6816 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $2,964/Night
7 Nights - US $20,747
Villa
10.0(5 Reviews)
12 Bedrooms
12 Baths
32 Guests
12987 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $2,646/Night
7 Nights - US $18,525
House
10.0(2 Reviews)
9 Bedrooms
9 Baths
26 Guests
8379 ft²
- Private Pool
Oceanfront- Hot Tub
- Fireplace/Heating
US $2,595/Night
7 Nights - US $18,164
House
9.8(50 Reviews)
8 Bedrooms
11 Baths
20 Guests
8000 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $2,456/Night
7 Nights - US $17,193
House
10.0(2 Reviews)
10 Bedrooms
13 Baths
32 Guests
6861 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $2,456/Night
7 Nights - US $17,189
House
10.0(1 Review)
10 Bedrooms
13 Baths
20 Guests
8407 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $2,368/Night
7 Nights - US $16,574
Top-Rated Villas with a Pool in Kissimmee
Explore top-rated private villas with pools in Kissimmee, carefully selected based on guest reviews and overall experience. These villas offer private pool access, elegant interiors, and inviting outdoor spaces designed for relaxation. Ideal for travelers seeking comfort, privacy, and memorable stays.
Villa
10.0(326 Reviews)
4 Bedrooms
3 Baths
8 Guests
1450 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $181/Night
7 Nights - US $1,265
Villa
10.0(260 Reviews)
5 Bedrooms
5 Baths
11 Guests
2500 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $314/Night
7 Nights - US $2,197
House
10.0(237 Reviews)
7 Bedrooms
6 Baths
16 Guests
3650 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $550/Night
7 Nights - US $3,849
Condo
10.0(180 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $128/Night
7 Nights - US $898
House
10.0(174 Reviews)
4 Bedrooms
3 Baths
8 Guests
1853 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $234/Night
7 Nights - US $1,640
Condo
10.0(155 Reviews)
3 Bedrooms
2 Baths
8 Guests
1462 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $252/Night
7 Nights - US $1,762
Villa
10.0(148 Reviews)
5 Bedrooms
3 Baths
10 Guests
2255 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $295/Night
7 Nights - US $2,065
Condo
10.0(140 Reviews)
3 Bedrooms
2 Baths
8 Guests
1450 ft²
- Hot Tub
- Fireplace/Heating
- Pool
Ocean View
US $222/Night
7 Nights - US $1,555
House
10.0(131 Reviews)
4 Bedrooms
3 Baths
10 Guests
1875 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $226/Night
7 Nights - US $1,583
Pet-Friendly Villas in Kissimmee
Find pet-friendly private villas in Kissimmee, perfect for travelers who want to bring their pets along without compromising comfort. These villas provide welcoming environments, spacious layouts, and thoughtful amenities for both guests and pets. Enjoy a stress-free getaway where everyone feels at home.
House
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $91/Night
7 Nights - US $639
House
10.0(9 Reviews)
1 Bedroom
6 Baths
14 Guests
3196.88 ft²
- Spa
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $321/Night
7 Nights - US $2,247
House
4 Bedrooms
3 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $494/Night
7 Nights - US $3,459
House
10.0(113 Reviews)
6 Bedrooms
3 Baths
12 Guests
2486 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $656/Night
7 Nights - US $4,595
Villa
10.0(8 Reviews)
1 Bedroom
5 Baths
21 Guests
4305.56 ft²
- Fireplace/Heating
- Pool
- Pet Friendly
- Parking
US $528/Night
7 Nights - US $3,696
House
10.0(107 Reviews)
6 Bedrooms
4 Baths
16 Guests
3500 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $691/Night
7 Nights - US $4,840
Villa
10.0(97 Reviews)
9 Bedrooms
7 Baths
18 Guests
3784 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $947/Night
7 Nights - US $6,627
House
10.0(94 Reviews)
6 Bedrooms
4 Baths
16 Guests
3500 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $352/Night
7 Nights - US $2,467
Condo
10.0(77 Reviews)
3 Bedrooms
2 Baths
6 Guests
1250 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- Pet Friendly
US $174/Night
7 Nights - US $1,219
Place to Stay FAQs
What is the most popular destination for a Place to Stay?
Kissimmee is a highly sought-after destination for Places to Stay, offering over 23823+ options. Visitors love this location for its variety, convenience, and unforgettable experiences.
How do I ensure the Place to Stay meets my needs?
Review the description, photos, and verified guest reviews carefully. For specific requirements, you can contact the provider directly to ensure the Place to Stay is right for you.
How can I communicate special requests for a Place to Stay?
Use the platform’s messaging system to reach out to the owner or provider. This allows you to ask questions and discuss any special requests before your trip.
What should I do if I need to modify or cancel my Place to Stay booking?
Modifications and cancellations are usually handled through our partners. Policies vary by listing or activity, so check the specific terms for your Place to Stay through our partners. Please visit the partner’s website with whom you booked.
Are there different price ranges available for Places to Stay?
Yes, Places to Stay are available for various budgets. Use the price filter to find options that match your financial preferences while still offering quality experiences.
