Winter Park Vacation Rentals & Beach Rentals - 183 Rentals Available

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183 Vacation rentals

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1 / 18

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

$278.00

from $278.00 / night

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Your search has been expanded 19.7 miles to include more rentals

1 / 31

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

“Excellent place to spend your vacation in. I am glad we stayed!There was one little issue with the heater not on but I called and they came right out and fixed it. We had a great time and enjoyed the home a lot! I hope to use again in the future...”

- Review left on 11/26/2017

$130.00

Very Good (31 reviews)

from $130.00 / night

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1 / 50

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

Excellent (5 reviews)

from $233.00 / night

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1 / 54

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

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1 / 33

Relaxing 4Bed 3Bath PARADISE PALMS townhouse w/private splash pool from $123/nt

Orlando Townhouse - 11.8 miles away

4 bedrooms 4
3 bathrooms
sleeps 8 8
min stay varies

Swimming pool
Child friendly
Air conditioning

$147.00

from $147.00 / night

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1 / 23

Lovely 5 Bedroom 3.5 Bath Home w/Private Pool and Gameroom 15 Minutes to Disney

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. 3 hours 2 minutes

$204.00

Excellent (1 reviews)

from $204.00 / night

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1 / 21

Economical, Cozy 3BR 2Bath Condo w/resort pool 2 miles from Disney from $85/nt

Orlando Condo - 11.8 miles away

3 bedrooms 3
2 bathrooms
sleeps 6 6
min stay varies

Swimming pool
Child friendly
Air conditioning

$104.00

from $104.00 / night

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1 / 30

Beautiful 5 bedroom 4.5 bath home from 145 nt

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 30 minutes

“Me and my family enjoyed ourself at this facility. Nice, clean and quiet area. We Will be booking again in the future...”

- Review left on 09/19/2017

$132.00

Excellent (1 reviews)

from $132.00 / night

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1 / 17

4 Bedroom 3 Bath Home with Private Pool 7 miles to Disney

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. 3 hours 28 minutes

$153.00

from $153.00 / night

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1 / 12

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. 3 hours 33 minutes

“I stayed for 5months at this house and it was great. Had everything needed to cook, fenced in backyard for my dog, neighbors were great and I was only 10 minutes from give kids the world where I volunteered. Lots of places to eat and close to all...”

- Review left on 04/11/2016

$104.00

Excellent (9 reviews)

from $104.00 / night

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1 / 25

Cozy 3 bedroom 2.5 bath Townhouse from $90nt

Orlando Townhouse - 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 44 minutes

$104.00

from $104.00 / night

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1 / 28

Luxury 6 bedroom 4 bath home from $135nt

Orlando House - 11.8 miles away

6 bedrooms 6
4 bathrooms
sleeps 12 12
min stay varies

Child friendly

Responds fast! Avg. 2 hours 52 minutes

“Great atmosphere awesome home very clean plenty of space. Really enjoyed ourselves, very impressed hope home is available next time we need one...”

- Review left on 11/13/2017

$155.00

Very Good (2 reviews)

from $155.00 / night

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1 / 15

Lovely 4BR 3Bth Home with Private Pool and Gameroom 8 Mile to Disney

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 55 minutes

$199.00

from $199.00 / night

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1 / 24

Luxury 6 bedroom 5.5 bath Watersong Resort home from $155nt

Orlando House - 11.8 miles away

6 bedrooms 6
7 bathrooms
sleeps 12 12
min stay varies

Child friendly

Responds fast! Avg. 1 hour 33 minutes

$178.00

Excellent (1 reviews)

from $178.00 / night

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1 / 22

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. 1 hour 33 minutes

$195.00

Average (1 reviews)

from $195.00 / night

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1 / 30

The Force is with this striking 6 BR 5.5 bath Watersong Resort home from $170nt!

Orlando House - 11.8 miles away

6 bedrooms 6
6 bathrooms
sleeps 12 12
min stay varies

Child friendly

Responds fast! Avg. 1 hour 43 minutes

$178.00

from $178.00 / night

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1 / 43

Elegant, Stylish 5BR 4.5Bath Solara Resort Home w/ Private Pool, Spa & Foosball

Orlando House - 11.9 miles away

5 bedrooms 5
5 bathrooms
sleeps 10 10
min stay varies

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 1 hour 43 minutes

$159.00

Excellent (4 reviews)

from $159.00 / night

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1 / 45

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. 1 hour 43 minutes

$189.00

from $189.00 / night

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1 / 22

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. 1 hour 43 minutes

$195.00

Excellent (1 reviews)

from $195.00 / night

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1 / 28

Spectacular 6 bedroom 5 bath Watersong Resort home from $219nt

Orlando House - 11.8 miles away

6 bedrooms 6
5 bathrooms
sleeps 12 12
min stay varies

Child friendly

Responds fast! Avg. 1 hour 43 minutes

$265.00

from $265.00 / night

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1 / 56

Luxury 8BR 5 bath Storey Lake home with private pool and game room

Kissimmee House - 19.4 miles away

8 bedrooms 8
5 bathrooms
sleeps 16 16
min stay varies

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 1 hour 43 minutes

$336.00

from $336.00 / night

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1 / 34

Elegant 6 BR 4.5 Bath SOLTERRA home with private pool & gameroom from $160nt

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 43 minutes

$184.00

from $184.00 / night

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1 / 24

Enchanting 3 BR 2.5 BATH resort townhouse with private pool from $150/nt

Orlando Townhouse - 11.8 miles away

3 bedrooms 3
3 bathrooms
sleeps 7 7
min stay varies

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 1 hour 43 minutes

“The location was perfect. Only took us about 15-20 minutes to get to Disney. The kids loved the pirate room with all the dress up accessories and pirate themed toys. The house had everything we needed and the beds were all very cozy. Would highly...”

- Review left on 05/08/2018

$172.00

Excellent (11 reviews)

from $172.00 / night

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1 / 36

Inviting 5BR 4Bath Solterra Resort home with Private Pool and Spa

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 43 minutes

$181.00

from $181.00 / night

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1 / 31

Luxe, Modern 4BR 3.5Bath WINDSOR at WESTSIDE townhouse w/pool from $120/night

Orlando Townhouse - 11.8 miles away

4 bedrooms 4
4 bathrooms
sleeps 8 8
min stay varies

Child friendly

Responds fast! Avg. 1 hour 43 minutes

$138.00

from $138.00 / night

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1 / 19

Lovely 4 bedroom 2 bath home from $110nt

Orlando House - 11.8 miles away

4 bedrooms 4
2 bathrooms
sleeps 8 8
min stay varies

Child friendly
Air conditioning
Private garden

Responds fast! Avg. 1 hour 43 minutes

$132.00

from $132.00 / night

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1 / 21

Elegant 5 bedroom 5 bath Windsor Hills Resort home from $140nt

Orlando House - 11.8 miles away

5 bedrooms 5
5 bathrooms
sleeps 10 10
min stay varies

Child friendly

Responds fast! Avg. 1 hour 43 minutes

$161.00

from $161.00 / night

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1 / 21

Beautiful 5 bedroom 4.5 bath Watersong Resort home from $135nt

Orlando House - 11.8 miles away

5 bedrooms 5
5 bathrooms
sleeps 10 10
min stay varies

Child friendly

Responds fast! Avg. 1 hour 43 minutes

$155.00

from $155.00 / night

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1 / 39

Close Disney,Seaworld and Convention Ctr,4BR/3BA townhome with lake view

Kissimmee Townhouse - 19.7 miles away

4 bedrooms 4
3 bathrooms
sleeps 10 10
min stay varies

Nearest beach 99 mi
Swimming pool
Child friendly

Responds fast! Avg. 41 minutes

$114.00

from $114.00 / night

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1 / 28

From $90/nt,4BR 1900sqft townhome,lake view,Near Disney,Seaworld,Convention Ctr

Kissimmee Apartment - 19.7 miles away

4 bedrooms 4
3 bathrooms
sleeps 10 10
min stay varies

Beach/lakeside relaxation
Nearest beach 97 mi
Swimming pool

Responds fast! Avg. 41 minutes

“We really enjoyed our stay at this beautiful rental. The property was well kept, clean and we didn't had any issues the time we spent there. I really liked that the property didn't have carpet. 2 master bedrooms for the adults and 2 smaller rooms...”

- Review left on 01/05/2017

$114.00

Very Good (22 reviews)

from $114.00 / night

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1 / 63

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
3 nights min

Swimming pool
Child friendly
Air conditioning

“Excellent apartment close to all parks and shopping centres also a short drive from airport a major plus after a full days travel.have stayed in vista cay a few times and always found it to be in immaculate condition and as I said previously the...”

- Review left on 07/18/2016

$263.00

Very Good (5 reviews)

from $263.00 / night

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1 / 29

Modern 3BR 3Bath resort town house with private splash pool from $128/night

Orlando Townhouse - 11.8 miles away

3 bedrooms 3
3 bathrooms
sleeps 6 6
min stay varies

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 1 hour 43 minutes

$113.00

from $113.00 / night

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1 / 24

Cozy 2 bedroom 2 bath Resort condo from $74nt

Orlando Condo - 11.8 miles away

2 bedrooms 2
2 bathrooms
sleeps 4 4
min stay varies

Child friendly

Responds fast! Avg. 1 hour 43 minutes

$85.00

from $85.00 / night

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1 / 36

Beautiful 6 Bedroom Home Near Disney From 160nt

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 43 minutes

“This was an amazing experience for my family! The house was beautiful! Everything was perfect. Management was on point and if I could give 10 stars I would...”

- Review left on 01/29/2018

$184.00

Excellent (4 reviews)

from $184.00 / night

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1 / 33

Contemporary 6BR 6BA pool home w/game room & Frozen themed bedroom from $160/nt

Orlando House - 11.8 miles away

6 bedrooms 6
6 bathrooms
sleeps 12 12
min stay varies

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 1 hour 45 minutes

$167.00

from $167.00 / night

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1 / 32

Luxurious 5 bedroom 4.5 bath Watersong Resort home from $135nt

Orlando House - 11.8 miles away

5 bedrooms 5
5 bathrooms
sleeps 10 10
min stay varies

Child friendly

Responds fast! Avg. 1 hour 45 minutes

$238.00

from $238.00 / night

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1 / 31

Lovely 5 Bedroom 4 Bath Home with Private Pool, Spa and Game Room

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 45 minutes

$176.00

from $176.00 / night

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1 / 29

Amazing 8 bedroom 5 bath Champions Gate home from $280nt

Orlando House - 11.8 miles away

8 bedrooms 8
5 bathrooms
sleeps 19 19
min stay varies

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 1 hour 45 minutes

$292.00

from $292.00 / night

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1 / 40

NEW 7BR 4.5Bath WATERSONG pool, spa, awesome game room, themed rooms!!!

Orlando House - 11.8 miles away

7 bedrooms 7
5 bathrooms
sleeps 14 14
min stay varies

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 1 hour 45 minutes

“We had a wonderful trip! Home looked just as the pictures described. Game room was amazing pool was refreshing after a long day at the park. Will definitely like to stay again...”

- Review left on 06/18/2018

$201.00

Very Good (4 reviews)

from $201.00 / night

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1 / 45

Beautiful 7BR 6 bath Champions Gate home w/pool and gameroom from $180 a night!

Orlando House - 11.8 miles away

6 bedrooms 6
6 bathrooms
sleeps 14 14
min stay varies

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 1 hour 45 minutes

$207.00

Excellent (1 reviews)

from $207.00 / night

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