Resort holiday rentals in Kissimmee
Find and book unique resort rentals on Airbnb
Top-rated resort rentals in Kissimmee
Guests agree: these resort rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for resort rentals in Kissimmee
Family-friendly resort rentals
Resort in Celebration
Mystic Dunes Beautiful 2BR/2BA resort near Disney
10–17 Aug
Resort in Orlando
♥ Unforgettable vacations! Wonderful Resort! ✶ #1
18–25 Oct
Resort in Orlando
Amazing two-bedroom at Westgate Palace #12
11–18 May
Resort in Orlando
Book your next family vacation at Westgate Resorts
1–8 Jun
Resort in Kissimmee
Star Island Resort- 1 bedroom
24–31 May
Resort in Kissimmee
Orange Lake Country Club, Kissimmee, FLorida
26 May – 2 Jun
Resort in Kissimmee
KING - SUITE STYLE - ORLANDO AREA VACATION GETAWAY
25 Feb – 4 Mar
Resort in Kissimmee
5.0 out of 5 average rating, 5 reviewsOrlando FL Orange Lake Resort 2BR Close to Disney
3–10 Apr
Resort rentals with a pool
Resort in Orlando
4.67 out of 5 average rating, 3 reviews2 Bedroom Condo near Universal
31 Aug – 7 Sep
Resort in Kissimmee
4.75 out of 5 average rating, 4 reviewsStar Island Resort - 2 Bedroom Condo
28 Apr – 5 May
Resort in Orlando
5.0 out of 5 average rating, 5 reviewsSpacious 3 Bedroom condo Lake Buena Vista area
24 Jun – 1 Jul
Resort in Kissimmee
4.6 out of 5 average rating, 5 reviewsTimeshare at Westgate town center
8–15 Mar
Resort in Davenport
4.86 out of 5 average rating, 7 reviews6bd Resort wt PrivatePool/ FreeWaterAmenities90
30 Nov – 7 Dec
Resort in Orlando
5.0 out of 5 average rating, 5 reviewsBest Resort for Family Vacation in the Nation
12–19 May
Resort in Lake Buena Vista
4.8 out of 5 average rating, 5 reviewsDisney Dreams Come True 1 Bedroom Condo, #2
4–11 Jan
Resort in Orlando
4.75 out of 5 average rating, 4 reviewsResort Room at Westgate Lakes Resort and Spa
16–23 Aug
Resort rentals with a gym
Resort in Orlando
5.0 out of 5 average rating, 5 reviewsLas Palmeras Orlando - Studio
26 Jan – 2 Feb
Resort in Orlando
5.0 out of 5 average rating, 3 reviewsWyndham Bonnet Creek 2 BD/2 BA inside Disney World
23–30 Sep
Resort in Kissimmee
5.0 out of 5 average rating, 3 reviewsChristmas in Resort close to Disney theme parks
24 Sep – 1 Oct
Resort in Orlando
5.0 out of 5 average rating, 4 reviewsDisney Florida Resorts
16–23 Oct
Resort in Orlando
4.8 out of 5 average rating, 5 reviews4 Bedroom Westgate Lakes Resort & Spa
23–30 Mar
Resort in Orlando
4.67 out of 5 average rating, 3 reviewsWestgate lake resort & spa sleep up to 12 people
5–12 Jan
Resort in Celebration
5.0 out of 5 average rating, 3 reviewsSpecial Offers at Mystic Dunes Resort 2 Bedrooms
24 Jun – 1 Jul
Resort in Orlando
Marriott or Sheraton Orlando 1BR/Studio
13–20 Aug
Quick stats about resort rentals in Kissimmee
Total rentals
80 properties
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Rentals with a pool
80 properties have a pool
Family-friendly rentals
40 properties are a good fit for families
Total number of reviews
60 reviews
Nightly prices starting at
€ 37 before taxes and fees
Destinations to explore
- St Petersburg Holiday rentals
- Anna Maria Island Holiday rentals
- Sarasota Holiday rentals
- Tampa Holiday rentals
- Key West Holiday rentals
- Naples Holiday rentals
- Miami Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Boca Raton Holiday rentals
- West Palm Beach Holiday rentals
- Orlando Holiday rentals
- Resort rentals United States
- Resort rentals Orlando
- Waterfront rentals Kissimmee
- Rentals with a kayak Kissimmee
- Villa rentals Kissimmee
- Rentals with breakfast Kissimmee
- Beachfront rentals Kissimmee
- Monthly Rentals Kissimmee
- Rentals with a hot tub Kissimmee
- Cabin rentals Kissimmee
- Rentals with an EV charger Kissimmee
- Rentals with pools Kissimmee
- Family-friendly rentals Kissimmee
- Rentals with a firepit Kissimmee
- Townhouse rentals Kissimmee
- Apartment rentals Kissimmee
- Fitness-friendly rentals Kissimmee
- Rentals with an accessible-height bed Kissimmee
- Rentals with beach access Kissimmee
- Cottage rentals Kissimmee
- Wheelchair-accessible rentals Kissimmee
- Guest house rentals Kissimmee
- Rentals with a fireplace Kissimmee
- Family-friendly rentals Kissimmee
- Pet-friendly rentals Kissimmee
- Rentals with a cinema Kissimmee
- House rentals Kissimmee
- Rentals with a patio Kissimmee
- Smoking-friendly rentals Kissimmee
- Rentals with a washing machine and dryer Kissimmee
- Private suite rentals Kissimmee
- Rentals with an accessible-height toilet Kissimmee
- Flat rentals Kissimmee
- Rentals with a sauna Kissimmee
- Tiny house rentals Kissimmee
- Serviced apartment rentals Kissimmee
- Rentals with lake access Kissimmee
- Rentals with outdoor seating Kissimmee
- Hotel rentals Kissimmee
- Resort rentals Florida
- Resort rentals Florida
- Resort rentals Osceola County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom