Holiday rentals in Kissimmee

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Top-rated holiday rentals in Kissimmee

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Guest suite in Kissimmee
Newly renovated near Disney and Universal Orlando
Entire suite , new ultra comfortable king size bed, free wifi, 64"TV with Netflix and Amazon Prime. Private bath, Living room and kitchen, shared laundry room, free parking 13 miles or 21 minutes from Disney World, Disney Springs shops and restaurants and Orlando Premium Outlets 16.6 miles or 23 minutes from Universal Orlando. 12.6 miles or 22 minutes from Aquatica and SeaWorld Orlando 11.6 miles or 22 minutes from Orlando International Airport 15 miles or 25 minutes from the Convention Center
22–29 Apr
₹5,235 per night
4.94 out of 5 average rating, 117 reviews
Guest favourite
Apartment in Kissimmee
First floor/your Disney escape
Our condo is located on the first Floor at resort-style community (with No Resort FEES and FREE parking) with a nice clubhouse featuring a game room, fitness center and outside, a tranquil free-form heated pool with plenty of deck chairs for all the vacationers. This resort also features a second pool, golf cage, tennis, basketball and volleyball courts, a playground, carwash area, picnic pavilions and grills, and scenic walking trails around landscaped wooded areas, fountains and ponds.
14–21 Sep
₹7,462 per night
4.92 out of 5 average rating, 110 reviews
Guest favourite
Flat in Kissimmee
Modern APT W/ Patio 15 mins from Theme Parks & MCO
Beautiful space where you can spend a beautiful vacation with your loved ones, the space is created with immense love and for you to feel at home. El acceso será autónomo, con llavín inteligente y una entrada completamente independiente y sin restricción de horario . Ofrecemos un patio exterior diseñado para tiempo de descanso,para compartir un café y también para fumar si fuera de su agrado El parqueo está concebido para dos autos y tenemos cámara de seguridad las24h Todo climatizado
2–9 Aug
₹9,037 per night
4.92 out of 5 average rating, 200 reviews

Popular amenities for Kissimmee holiday rentals

Stay near Kissimmee's top sights

Medieval Times Dinner & Tournament346 locals recommend
Silver Spurs Arena9 locals recommend
FantasyWorld Resort7 locals recommend
Give Kids The World Village7 locals recommend
Osceola Heritage Park12 locals recommend
Walmart Supercenter44 locals recommend

Other great holiday rentals in Kissimmee

Superhost
Apartment in Kissimmee
Beautiful Resort-Style Condo with Waterpark!
15–22 Oct
₹10,457 per night
4.85 out of 5 average rating, 153 reviews
Guest favourite
Cabin in Davenport
$89! Cozy Cabin- Disney 20 Miles Away!
25 May – 1 Jun
₹7,616 per night
4.92 out of 5 average rating, 163 reviews
Guest favourite
Apartment in Kissimmee
Close To Disney! 3 Bedroom Condo in Windsor Palms
25 Aug – 1 Sep
₹7,640 per night
4.96 out of 5 average rating, 138 reviews
Guest favourite
Cottage in Davenport
$79! Cozy Cottage + Outdoor Fun -Close to Disney!
10–17 May
₹6,787 per night
4.92 out of 5 average rating, 122 reviews
Superhost
Home in Kissimmee
3 bedroom Orlando Florida pool home
5–12 Nov
₹8,664 per night
4.78 out of 5 average rating, 253 reviews
Guest favourite
Cottage in Kissimmee
Runaway Beach Club Private Patio:Disney, Universal
5–12 Nov
₹9,796 per night
4.98 out of 5 average rating, 132 reviews
Guest favourite
Home in Winter Garden
Cozy Winter Garden Home 20 MINUTES FROM DISNEY
25 Jan – 1 Feb
₹8,085 per night
4.92 out of 5 average rating, 164 reviews
Guest favourite
Tiny home in Kissimmee
Disney Tiny House Getaway!
10–17 Nov
₹6,704 per night
4.95 out of 5 average rating, 141 reviews
Guest favourite
Flat in Kissimmee
20min to Disney/Free Parking/Gym/Pool/Gated
27 May – 3 Jun
₹7,719 per night
4.95 out of 5 average rating, 20 reviews
Guest favourite
Guest house in Orlando
Guesthouse hosted by Yadier
19–26 May
₹8,821 per night
5.0 out of 5 average rating, 43 reviews
Guest favourite
Townhouse in Kissimmee
Summer Studio at Kissimmee
1–8 Aug
₹6,097 per night
5.0 out of 5 average rating, 9 reviews
Superhost
Flat in Kissimmee
2 Bedroom-2 Bathroom Spacious Condo Near Disney
2–9 Jan
₹7,758 per night
5.0 out of 5 average rating, 3 reviews

Quick stats about holiday rentals in Kissimmee

Total rentals

7.6T properties

Rentals with dedicated workspaces

3.9T properties have a dedicated workspace

Rentals with a pool

6.8T properties have a pool

Pet-friendly rentals

1.1T properties allow pets

Family-friendly rentals

6.6T properties are a good fit for families

Total number of reviews

2L reviews

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Osceola County
  5. Kissimmee