Vacation Rentals & Villas in Winter Park

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4,542 villas

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Surprise Yourself With Unforgettable Deluxe Villa w/ Private Pool+Spa+Baby Gears

Four Corners villa

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 18

Match: Hair dryer Golf course on site or within 15 min walk

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Price per night from

$402

Match: Hair dryer Golf course on site or within 15 min walk

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Price per night from

$137

Match: Hair dryer Golf course on site or within 15 min walk

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Price per night from

$402

Make It Easy on Yourself |Great Location+Fabulous High-End Living Space

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$125

Treat Yourself and Family to a Deluxe Villa w/ Superb Rooms+Private Hot Tub

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

“A good choice for our family” This place was as expected, except that the floors needed mopping. This home is advertised as children friendly, but bare feet and small children soon became dirty by crawling on these floors! We began our stay by double mopping both ground and upper floors, as well as the stairs. Other than that, we were happy with our stay, and would choose this place again!

Match: Hair dryer Golf course on site or within 15 min walk

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Price per night from

$137

Match: Hair dryer Golf course on site or within 15 min walk

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Price per night from

$402

Seek Thrills in a Urban Condo w/ Great Value Location+Patio+Premium Resort

Kissimmee apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$125

⭐Deluxe Villa+Private Pool+Hot Tub+Theatre Room+Pool with Waterslides⭐

ChampionsGate villa

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 18

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Price per night from

$401

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Price per night from

$114

Look No Further, Be at Ease ✦ Remarkable Value at Modern Private Oasis

Kissimmee house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Hair dryer Golf course on site or within 15 min walk

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Price per night from

$114

Family & Friends Unite For Fun✩Amazing Villa w/ Unique Upscale Amenities

Davenport villa

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 20

“Amazing” We had a family of 10 and it was enough space for us. The kids loved the pool and movie room. I liked house to house was so updated and beautiful. We definitely would stay here again.

Match: Hair dryer Golf course on site or within 15 min walk

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Price per night from

$330

Match: Hair dryer Golf course on site or within 15 min walk

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Price per night from

$402

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House of Views-3 Bedroom 3 bath nestled on a beautiful golf course

Mesa house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Hair dryer, Golf course on site or within 15 min walk

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Price per night from

$601

Miami! Ocean View at HYDE Beach 2912

Hollywood apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 49 minutes

1 of 2 match: Hair dryer, Golf course on site or within 15 min walk

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Price per night from

$138

Miami! Ocean View at Hyde Beach 2712

Hollywood apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 49 minutes

1 of 2 match: Hair dryer, Golf course on site or within 15 min walk

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Price per night from

$336

HYDE Beach Resort 1512 - Hollywood Beach by AmmosVR

Hollywood apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 49 minutes

1 of 2 match: Hair dryer, Golf course on site or within 15 min walk

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Price per night from

$336

HYDE Beach Resort 2012 - Hollywood Beach by AmmosVR

Hollywood apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 49 minutes

1 of 2 match: Hair dryer, Golf course on site or within 15 min walk

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Price per night from

$336

HYDE Beach Resort 3312 - Hollywood Beach by AmmosVR

Hollywood apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 49 minutes

1 of 2 match: Hair dryer, Golf course on site or within 15 min walk

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Price per night from

$403

HYDE Beach Resort PH12 - Hollywood Beach by AmmosVR

Hollywood apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 49 minutes

1 of 2 match: Hair dryer, Golf course on site or within 15 min walk

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Price per night from

$403

Miami Beach! Beautifull bay view 15th for 4 guests

North Bay Village apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 2 hours 49 minutes

1 of 2 match: Hair dryer, Golf course on site or within 15 min walk

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Price per night from

$171

Miami - Hollywood Beach at Tides 1A. 4 guests

Hollywood apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 49 minutes

1 of 2 match: Hair dryer, Golf course on site or within 15 min walk

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Price per night from

$114

Miami! Hyde Beach Resort 1704 up to 6 guests

Hollywood apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 49 minutes

1 of 2 match: Hair dryer, Golf course on site or within 15 min walk

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Price per night from

$297

Miami - Sunny Isles at Marenas Resort 1908 with ocean views for 6 guests

Sunny Isles Beach apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 49 minutes

1 of 2 match: Hair dryer, Golf course on site or within 15 min walk

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Price per night from

$177

4 BDRM,GAME ROOM,2 MASTER BDRMS,2 LIV RMS.10MIN TO DISNEY. PRV POOL SUN ALL DAY

ChampionsGate house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Hair dryer, Golf course on site or within 15 min walk

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Price per night from

$166

Tonto Verde Destination

Rio Verde house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Hair dryer, Golf course on site or within 15 min walk

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Price per night from

$223

Fox Run -- Sleeps 10 - 12, Only 1 mile from Okemo Jackson Gore Base

Ludlow townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

1 of 2 match: Hair dryer, Golf course on site or within 15 min walk

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Price per night from

$458

Luxury 2BR Suite at Vacation Village at Weston

Weston hotel apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 3 hours 15 minutes

1 of 2 match: Hair dryer, Golf course on site or within 15 min walk

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Price per night from

$1,144

Private Relaxing Golf Retreat- Private Pool/Spa 2516 sq ft

Palm Desert house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 4

Responds fast! avg. 22 minutes

1 of 2 match: Hair dryer, Golf course on site or within 15 min walk

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Price per night from

$401

Studio with Panoramic Views at Beach Walk 27th Floor

Hallandale Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 49 minutes

1 of 2 match: Hair dryer, Golf course on site or within 15 min walk

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Price per night from

$79

1BR Getaway next to South Point Casino

Las Vegas hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 15 minutes

1 of 2 match: Hair dryer, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$1,144

Amazing Villa with south facing pool and conservation view

Orlando villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Hair dryer, Golf course on site or within 15 min walk

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Price per night from

$228

Marenas 1 bedroom Bay view 25th floor

Sunny Isles Beach apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 2 hours 49 minutes

1 of 2 match: Hair dryer, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$201

Windsor Palms Resort Condo Taina

Kissimmee apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Hair dryer, Golf course on site or within 15 min walk

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Price per night from

$132

Spacious villa, South Facing Pool with Lake View close to Disney

Clermont villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Hair dryer, Golf course on site or within 15 min walk

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Price per night from

$166

NEW! Relaxing Getaway - Heated Pool, Game Room, BBQ Grill and More

La Quinta house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Hair dryer, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$217

Lovely SPACIOUS Home Near Beach/Food/Golf/Fun/Shopping/Gym and More

Port Saint Lucie house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

1 of 2 match: Hair dryer, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$458

DISNEY DREAM LUXURY HOME PRIVATE WATERPARK POOL SPA

Kissimmee house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

“Perfect- it was better than what we had imagined.” The communication with the owner was what really surprised me. He was very responsive to all of my questions prior to our arrival. The house was very clean and in a great location. We were 15 minutes from Magic Kingdom and had many stores around the location of the house. I would not doubt to referred this home to anyone looking to spend a weekend in Orlando. We will definitely visit again!

1 of 2 match: Hair dryer, Golf course on site or within 15 min walk

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Price per night from

$457

Lovely 1Bd/2bath + Bunk Room & 2 Queen Sofa Beds

Panama City Beach condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Hair dryer, Golf course on site or within 15 min walk

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Price per night from

$515

Viewing 38 of 4,542
rentals in Winter Park

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