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Wireless Internet
Air conditioning
Swimming pool
Private pool

Heated pool
Private indoor pool
Balcony or terrace
Washing machine
Garden
Internet access
DVD player
Grill
Cot available
Sea view
Safe
Dishwasher
Satellite TV
Children's pool
Pool or snooker table
Table tennis
Games room
Fax machine
Shared outdoor pool (heated)
Clothes dryer
Private outdoor pool (unheated)
Private outdoor pool (heated)
Shared indoor pool
Shared outdoor pool (unheated)
Cribs
Ceiling Fans
Video player
Climbing frame
Boat available
Fridge
Stereo system
Kettle
Toaster
Iron
Hair dryer
Stove
Freezer
Staffed property
Microwave
Linen provided
Towels provided
Bicycles available
Swing set or jungle gym
Trampoline
Private fishing lake or river
Housekeeping Included

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Pets
Pets allowed
Parking
Car not required

Children under 5
Smoking allowed
Non-Smoking property
Smoking - Ask
Wheelchair adapted
Wheelchair accessible

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Beach or lakeside relaxation
City breaks
Walking trips
Tennis in town

Nightlife
Water sports
Horse riding
Fishing
Cycling trips
Golf course on site or within 15 min walk
Golf within 30mins drive
Lakefront
Waterfront

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2,695 villas

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Winter Park-College Park-Orlando-1

Winter Park house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 25 minutes

Price per night from

$92

The Cottage on Lake Fairview, Orlando.

Winter Park house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 49 minutes

Price per night from

$590

2br - 1000ft2 - Winter Park House

Winter Park house

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$120

Winter Park-College Park-Orlando -2

Winter Park house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 25 minutes

Price per night from

$92

"Lakeside" in old Winter Park (exclusive 32789zip)

Winter Park villa

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$801

Championsgate 58 - villa with pool, game room and theater room near Disney

Winter Park house

8 bedrooms / 5 bathrooms / sleeps 20

Price per night from

$266

Winter Park, Florida Luxury Vacation Rental

Winter Park house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$220

Great rentals within 20 miles that match your search

Sheraton Vistana Fountains II - Timeshare

Kissimmee hotel apartment

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$176

Marriott Cypress Harbor 2 bedroom sleeps 6

Orlando house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$373

Westgate Lakes Resort & Spa Near Universal Studios Area

Orlando studio

Studio / 1 bathroom / sleeps 4

Price per night from

$195

Peaceful Cozy East Orlando Home (Bedroom 1)

Orlando guest house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$59

BEAUTIFUL 2BR/2BA CONDO AT VISTA CAY RESORT

Orlando house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$170

Christmas get away in Orlando, FL

Orlando condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$328

2 Bedroom Condo WestGate Palace

Kissimmee condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$367

Beautiful 1 Bedroom Condo To Rent

Orlando condo

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$262

LUXURY Town Center Villa Disney Studio APT

Orlando villa

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$227

A great little apartment in College Park, Orlando.

Orlando apartment

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 3 hours 49 minutes

Price per night from

$147

A week of dream in a resort

Orlando house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$228

Marriott's Grande Vista # 1

Orlando villa

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$366

Golf Resort and Magic of world Disney

Orlando house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$130

Paul's Place at Ventura

Ventura apartment

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$117

Wyndham Bonnet Creek 9560 Via Encinas, Lake Buena Vista, Orlando, FL

Orlando apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$426

2br - 1100ft2 - FLORIDA VACATION

Orlando villa

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$159

XMAS AT DISNEY WORLD- 54 ACRE RESORT W/WATERPARK

Orlando hotel apartment

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$328

Beautiful Garage Apartment Just North Of Downtown

Orlando apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$151

5* Sheraton Vistana Resort, 2BR/2BA, close to Disney/Universal, many amenities

Orlando hotel apartment

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$209

Bedroom for Renting . 1 - 3 can sleep

Orlando house

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$105

Ocean Front Boardwalk Property

Wildwood studio

Studio / 2 bathrooms / sleeps 8

Price per night from

$524

Beautiful Large Studio Condo on the Lake

Orlando apartment

/ 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 53 minutes

Price per night from

$261

Lovely 4BR 3bth Regal Palms Townhouse

Orlando townhouse

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 30 minutes

Price per night from

$149

Oviedo Charmer

Goldenrod house

3 bedrooms / 2 bathrooms / sleeps 11

Price per night from

$184

2br - 2200ft2 - Beautiful one story 2 bed/3bath

Orlando house

2 bedrooms / 3 bathrooms / sleeps 4

Price per night from

$412

A great loft apartment in College Park, Orlando.

Orlando apartment

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 49 minutes

Price per night from

$147

Marriott's Cypress Harbor Resort

Orlando house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$394

3 bed/2 both Lake Front home

Lake Mary house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$132

Westgate Lakes Resort and SPA

Orlando condo

3 bedrooms / 2 bathrooms / sleeps 12

Price per night from

$563

2 BD 2 BA Bonnet Creek In Gates of Disney World FL

Celebration villa

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$348

VH2 | STOREY LAKE - TOWNHOME, WITH PRIVATE POOL 4B/3B

Kissimmee townhouse

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$217

Viewing 38 of 2,695
rentals in Winter Park

Also consider

Four Corners 3,772 properties
Kissimmee 3,070 properties
Davenport 1,991 properties
Orlando 1,494 properties
ChampionsGate 1,249 properties
Reunion 976 properties
Loughman 611 properties
Haines City 274 properties
Pine Castle 223 properties
Intercession City 86 properties
Bay Lake 47 properties
The Villages 24 properties
Dunnellon 22 properties
Windermere 16 properties
Ocala 15 properties
Lake Placid 15 properties
Buena Ventura Lakes 13 properties
Sanford 12 properties
Lake Wales 11 properties
Poinciana 11 properties
Winter Garden 10 properties
Oviedo 10 properties
Okeechobee 10 properties
Lakeland 8 properties
Sebring 8 properties
Winter Haven 8 properties
Ocklawaha 6 properties
Silver Springs 5 properties
Altamonte Springs 5 properties
Frostproof 5 properties
Riverview 7 properties

COVID-19 Update

Vacation Rentals & Villas in Winter Park

Per night

2,695 villas

Viewing 38 of 2,695rentals in Winter Park

Also consider

Viewing 38 of 2,695
rentals in Winter Park