Winter Park Vacation Rentals & Beach Rentals - 520 Rentals Available
520 Vacation rentals
Championsgate 58 - villa with pool, game room and theater room near Disney
Winter Park House
- 8 bedrooms 8
- 5 bathrooms
- sleeps 20 20
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$266.00
from $266.00 / night
Your search has been expanded 19.3 miles to include more rentals
Bargain Vacation Home near Disney
Kissimmee House - 19.2 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 1 night min
- Nearest beach 95 mi
- Child friendly
- Air conditioning
Responds fast! Avg. 1 hour 15 minutes
$98.00
from $98.00 / night
Lovely 4BR 3bth Regal Palms Townhouse
Orlando Townhouse - 11.8 miles away
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 1 hour 30 minutes
$130.00
from $130.00 / night
Magnificent 6 bedroom 5 bath Champions Gate home from $233nt
Orlando House - 11.8 miles away
- 6 bedrooms 6
- 5 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 1 hour 30 minutes
$267.00
from $267.00 / night
Disney/Orlando/Universal/Convention C/ Luxurious Executive 5*3Br Villa Vista Cay
Orlando Condo - 12.9 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$160.00
from $160.00 / night
Well Priced 4BR 3Bath pool home with semi-private view & game room from $133/nt
Orlando House - 11.8 miles away
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 1 hour 30 minutes
$153.00
from $153.00 / night
Lovely 4BR 3Bath pool home with conservation view & game room from $163/night
Orlando House - 11.8 miles away
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 1 hour 34 minutes
$187.00
from $187.00 / night
Gorgeous 3BR 2Bth Festival Resort Townhouse with Hot Tub and Arcade Machine
Orlando Townhouse - 11.8 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 1 hour 34 minutes
$181.00
from $181.00 / night
Lovely 5BR 4Bth Resort home with Private Pool, Spa and Gameroom
Orlando House - 11.8 miles away
- 5 bedrooms 5
- 4 bathrooms
- sleeps 10 10
- 5 nights min
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 1 hour 34 minutes
$170.00
from $170.00 / night
NEW 5 BR/Ensuite home w/ private pool in Luxury Resort w/ Lazy River from $213nt
Kissimmee House - 19.3 miles away
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 1 hour 34 minutes
$233.00
from $233.00 / night
Lovely 3BR 2Bth Windsor Hills Resort Condo, 2 Miles From Disney
Orlando Condo - 11.9 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 1 hour 34 minutes
$147.00
from $147.00 / night
Encore 8 bed 6.5 bath w. pool 5 miles to Disney
Orlando House - 18.6 miles away
- 8 bedrooms 8
- 7 bathrooms
- sleeps 16 16
- 4 nights min
- Swimming pool
- Child friendly
- Air conditioning
$287.00
from $287.00 / night
Beautiful 8BR 5bath Champions Gate home with Private Pool and Spa
Orlando House - 11.8 miles away
- 8 bedrooms 8
- 5 bathrooms
- sleeps 16 16
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 1 hour 34 minutes
$302.00
from $302.00 / night
Casa Vista Verde II Orlando Area 1/1 Pool Disney Daytona Universal Dream House &
Altamonte Springs Apartment - 6.6 miles away
- 1 bedroom 1
- 1 bathroom
- sleeps 8 8
- 3 nights min
- Swimming pool
- Child friendly
- Air conditioning
$104.00
from $104.00 / night
Comfy 3 bedroom 2 bath Windsor Hills Condo from $85nt
Orlando Condo - 11.8 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Child friendly
Responds fast! Avg. 1 hour 34 minutes
$104.00
from $104.00 / night
Stylish, Cheerful 6BR 5Bath STOREY LAKE home with private pool and spa
Orlando House - 11.8 miles away
- 6 bedrooms 6
- 5 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 3 hours 48 minutes
$267.00
from $267.00 / night
Gorgeous 6 bedroom 4.5 bath Resort home 2.5 miles to Disney from $243nt
Orlando House - 11.8 miles away
- 6 bedrooms 6
- 4 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 3 hours 48 minutes
$267.00
from $267.00 / night
Casa Vista Verde I Dream House & Vacation Paradise Orlando Area 5/2 Pool Disney
Altamonte Springs House - 6.3 miles away
- 5 bedrooms 5
- 2 bathrooms
- sleeps 20 20
- 3 nights min
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 1 hour 8 minutes
$213.00
from $213.00 / night
Orlando Area 5BR/2BA Home w/ Jacuzzi!
Wekiva Springs House - 6.7 miles away
- 5 bedrooms 5
- 2 bathrooms
- sleeps 12 12
- 3 nights min
- Child friendly
- Air conditioning
- Pet friendly
Responds fast! Avg. 1 hour 8 minutes
$213.00
from $213.00 / night
Lovely 6 bedroom 4 bath Resort home from $140nt
Orlando House - 11.8 miles away
- 6 bedrooms 6
- 4 bathrooms
- sleeps 12 12
- min stay varies
- Child friendly
Responds fast! Avg. 3 hours 55 minutes
$195.00
from $195.00 / night
Incredible 6 bedroom 4 bathroom Windsor Hills Resort home from $145nt
Orlando House - 11.8 miles away
- 6 bedrooms 6
- 4 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 3 hours 55 minutes
$195.00
from $195.00 / night
Fabulous 6 BR 4 bath Windsor Hills Resort home from $175nt
Orlando House - 11.8 miles away
- 6 bedrooms 6
- 4 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 3 hours 55 minutes
$195.00
from $195.00 / night
Luxury 5 BR 5.5 Bath Reunion Resort Home with Private Pool, 15 minutes to Disney
Orlando House - 11.8 miles away
- 5 bedrooms 5
- 6 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 3 hours 55 minutes
$290.00
from $290.00 / night
Amazing 9BR 6.5bth Solara Resort Home with Private Pool, Spa and Gameroom
Orlando House - 11.8 miles away
- 9 bedrooms 9
- 7 bathrooms
- sleeps 18 18
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$353.00
from $353.00 / night
Beautiful 6 bedroom 5 bath Paradise Palms home with South Facing Pool
Orlando House - 11.8 miles away
- 6 bedrooms 6
- 5 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$267.00
from $267.00 / night
Lovely, Well Priced 5BR 3Bth Home with Private Pool and Gameroom
Orlando House - 11.8 miles away
- 5 bedrooms 5
- 3 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 2 hours 53 minutes
$130.00
from $130.00 / night
Comfortable 3 bedroom 3 bath Resort condo from $110nt
Orlando Condo - 11.8 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 2 hours 55 minutes
$136.00
from $136.00 / night
Certificate of Excellence
Close to Disney Beautiful Pool Well Maintained
Orlando House - 5.2 miles away
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 1 hour 46 minutes
Travelers’ Choice award
$115.00
from $115.00 / night
LUXURY 5BR 5.5bath Reunion Resort home with private pool
Orlando House - 11.8 miles away
- 5 bedrooms 5
- 6 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 2 hours 52 minutes
$290.00
from $290.00 / night
Beautiful 5 Bedroom Home Near Disney From 188nt
Orlando House - 11.8 miles away
- 5 bedrooms 5
- 3 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 2 hours 52 minutes
$216.00
from $216.00 / night
Mod REUNION RESORT 3BR 2Bath condo 1King 2Queen golf course view from $123/nt
Orlando Condo - 11.8 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 2 hours 52 minutes
$153.00
from $153.00 / night
Inviting 4BR 3bth Home w/Private Pool, Spa & Gameroom 20 minutes from Legoland!
Orlando House - 11.8 miles away
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 2 hours 52 minutes
$153.00
from $153.00 / night
Stunning 5BR 5bth Champions Gate home with Private Pool, Spa and Gameroom
Orlando House - 11.8 miles away
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 2 hours 52 minutes
$227.00
from $227.00 / night
Spacious 5 Bedroom 3Bth Home w/Private Pool overlooking Golf Course & Gameroom
Orlando House - 11.8 miles away
- 5 bedrooms 5
- 3 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 2 hours 52 minutes
$204.00
from $204.00 / night
4BR 3 bath Champions Gate Townhouse with private splash pool
Orlando Townhouse - 11.8 miles away
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 2 hours 53 minutes
$147.00
from $147.00 / night
Luxe 8BR 5Bath Champions Gate Home with Private Pool, Spa and Gameroom
Orlando House - 11.8 miles away
- 8 bedrooms 8
- 5 bathrooms
- sleeps 16 16
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 2 hours 53 minutes
$302.00
from $302.00 / night
Gorgeous 6BR 6.5Bth Solterra Home with Private Pool, Spa and Gameroom
Orlando House - 11.8 miles away
- 6 bedrooms 6
- 7 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 2 hours 58 minutes
$189.00
from $189.00 / night
Elegant 5Bed 3.5Bath home pool/spa, 1King 4Queen beds & game room from $178nt
Orlando House - 11.8 miles away
- 5 bedrooms 5
- 4 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 1 hour 4 minutes
$204.00
from $204.00 / night
Lovely 5BR 4bth Champions Gate Townhouse w/Splash Pool
Orlando Townhouse - 11.8 miles away
- 5 bedrooms 5
- 4 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 2 hours 22 minutes
$159.00
from $159.00 / night
❤Cozy TownHome w/ Pool - Near Disney/Universal/SeaWorld/LegoLand❤
Kissimmee Townhouse - 19.1 miles away
- 5 bedrooms 5
- 4 bathrooms
- sleeps 11 11
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$330.00
from $330.00 / night
What is Travelers’ Choice award?
Tripadvisor gives a Travelers’ Choice award to accommodations, attractions and restaurants that consistently earn great reviews from travellers and are ranked within the top 10% of properties on Tripadvisor.