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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
Air Conditioner
Internet
Child Friendly
Laundry
US $225/Night
7 Nights - US $1,577
House
4 Bedrooms
3 Baths
8 Guests
1948.27 ft²
Parking
Pool- Air Conditioner
- Internet
US $102/Night
7 Nights - US $715
House
10.0(11 Reviews)
1 Bedroom
1 Bath
- Parking
Balcony/Terrace
Kitchen- Air Conditioner
US $301/Night
7 Nights - US $2,107
Condo
10.0(5 Reviews)
3 Bedrooms
3 Baths
8 Guests
1444 ft²
Hot Tub- Parking
- Pool
Ocean View
US $438/Night
7 Nights - US $3,068
House
10.0(24 Reviews)
6 Bedrooms
6 Baths
15 Guests
3756.6 ft²
- Parking
- Pool
Spa- Air Conditioner
US $509/Night
7 Nights - US $3,564
New
House
10.0(3 Reviews)
5 Bedrooms
3 Baths
10 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $345/Night
7 Nights - US $2,418
Condo
10.0(3 Reviews)
3 Bedrooms
2 Baths
8 Guests
1400 ft²
Private Pool- Hot Tub
- Parking
- Pool
US $182/Night
7 Nights - US $1,276
House
9.6(28 Reviews)
8 Bedrooms
6 Baths
26 Guests
4391 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $443/Night
7 Nights - US $3,104
New
Condo
9.6(24 Reviews)
3 Bedrooms
2 Baths
6 Guests
1600 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- Kitchen
US $234/Night
7 Nights - US $1,638
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
9.8(50 Reviews)
8 Bedrooms
11 Baths
20 Guests
8000 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $4,403/Night
7 Nights - US $30,820
House
10.0(1 Review)
11 Bedrooms
13 Baths
32 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $3,122/Night
7 Nights - US $21,853
House
9.0(7 Reviews)
14 Bedrooms
15 Baths
32 Guests
12160 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $2,999/Night
7 Nights - US $20,990
Villa
10.0(3 Reviews)
8 Bedrooms
9 Baths
21 Guests
7445 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $2,716/Night
7 Nights - US $19,013
House
10.0(1 Review)
10 Bedrooms
13 Baths
20 Guests
8407 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $2,702/Night
7 Nights - US $18,915
Villa
10.0(5 Reviews)
12 Bedrooms
12 Baths
32 Guests
12987 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $2,647/Night
7 Nights - US $18,526
House
9 Bedrooms
15 Baths
16 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Air Conditioner
US $2,575/Night
7 Nights - US $18,022
House
10.0(3 Reviews)
9 Bedrooms
9 Baths
26 Guests
8379 ft²
- Private Pool
Oceanfront- Hot Tub
- Parking
US $2,546/Night
7 Nights - US $17,823
House
12 Bedrooms
14 Baths
32 Guests
6816 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $2,170/Night
7 Nights - US $15,192
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(330 Reviews)
4 Bedrooms
3 Baths
8 Guests
1450 ft²
- Hot Tub
- Parking
- Pool
- Spa
US $222/Night
7 Nights - US $1,556
House
10.0(241 Reviews)
7 Bedrooms
6 Baths
16 Guests
3650 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $634/Night
7 Nights - US $4,439
House
10.0(176 Reviews)
4 Bedrooms
3 Baths
8 Guests
1853 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $276/Night
7 Nights - US $1,933
Condo
10.0(159 Reviews)
3 Bedrooms
2 Baths
8 Guests
1462 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $304/Night
7 Nights - US $2,130
Condo
10.0(148 Reviews)
3 Bedrooms
2 Baths
8 Guests
1450 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $418/Night
7 Nights - US $2,929
House
10.0(131 Reviews)
4 Bedrooms
3 Baths
10 Guests
1875 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $272/Night
7 Nights - US $1,904
House
10.0(127 Reviews)
8 Bedrooms
4 Baths
16 Guests
3000 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $435/Night
7 Nights - US $3,045
Villa
10.0(125 Reviews)
4 Bedrooms
3 Baths
10 Guests
1874 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $460/Night
7 Nights - US $3,222
House
10.0(124 Reviews)
3 Bedrooms
3 Baths
8 Guests
1440 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $320/Night
7 Nights - US $2,241
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.
New
Villa
9.0(2 Reviews)
5 Bedrooms
6 Baths
10 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $718/Night
7 Nights - US $5,026
Villa
10.0(8 Reviews)
8 Bedrooms
5 Baths
21 Guests
4305.56 ft²
- Parking
- Pool
- Air Conditioner
- Internet
US $528/Night
7 Nights - US $3,696
US $623/Night
7 Nights - US $4,362
New
Condo
3 Bedrooms
3 Baths
8 Guests
1686 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $481/Night
7 Nights - US $3,366
House
10.0(7 Reviews)
5 Bedrooms
4 Baths
10 Guests
2185.07 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $224/Night
7 Nights - US $1,567
House
10.0(1 Review)
6 Bedrooms
4 Baths
18 Guests
2550 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $493/Night
7 Nights - US $3,454
House
2 Bedrooms
2 Baths
4 Guests
- Air Conditioner
- Internet
Pet Friendly- Laundry
US $130/Night
7 Nights - US $911
House
10.0(111 Reviews)
6 Bedrooms
4 Baths
16 Guests
3500 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $676/Night
7 Nights - US $4,734
Villa
10.0(98 Reviews)
9 Bedrooms
7 Baths
18 Guests
3784 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $903/Night
7 Nights - US $6,319
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.
