Winter Springs Vacation Rentals, Vacation Home Rentals & more


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Areas near Winter Springs

1 / 18

Bird Nest Retreat

  • 4
  • 6
  • 7 nights min

$171

Details

Great rentals within 20 miles that match your search

1 / 11

The Bedford House

  • 4
  • 8
  • 3 nights min

$201

Details

1 / 44

Brand new 3-story townhome at Vista Cay Resort, close to supermarket

  • 3
  • 8
  • 2 nights min

$169

Details

1 / 4

Grand Hotel Orlando

  • 1
  • 4
  • 2 nights min

$150

Details

1 / 26

Two-Bedroom Gator Cottage

  • 2
  • 4
  • 3 nights min

$100

Details

1 / 19

Vista Cay-Orlando-3 Bedroom Ventura-VC115

  • 3
  • 8
  • Min stay varies

$129

Details

1 / 30

Villa 8135 Sun Palm Drive, Windsor Palms

  • 5
  • 12
  • Min stay varies

Inquire for Rates

Details

1 / 27

Surfs Up Theme - Winter Park/Orlando

  • 1
  • 2
  • Min stay varies

$76

Details

1 / 15

Urban Oasis Downtown Bungalow

  • 3
  • 6
  • 3 nights min

$120

Details

1 / 26

Studio with a kitchen in Enclave Suites Orlando

  • 1
  • 2
  • 2 nights min

$89

Details

1 / 26

VISTA CAY PENTHOUSE CABANA 3 BEDROOMS SLEEPS 8

  • 3
  • 8
  • Min stay varies

$170

Details

1 / 27

Villa 1458 Moon Valley Dr, Champions Gate

  • 6
  • 16
  • Min stay varies

Inquire for Rates

Details

1 / 19

VISTA CAY CLASSIC CLOSE TO THE CONVENTION CENTER AND I-DRIVE

  • 3
  • 6
  • 2 nights min

$140

Details

1 / 20

3 bed/4 bath Luxury Townhouse Near I-Drive

  • 3
  • 8
  • 1 night min

$150

Details

1 / 24

Villa 8208 Fan Palm Way, Windsor Palms Orlando

  • 4
  • 10
  • Min stay varies

Inquire for Rates

Details

1 / 49

Spend your next Orlando vacation in this beautiful condo located in Vista Cay

  • 3
  • 6
  • 2 nights min

$143

Details

1 / 66

1454 Myrtlewood Street, Champions Gate, Orlando

  • 7
  • 15
  • Min stay varies

$347

Details

1 / 30

Vacation in luxury in this beautifully decorated 3BD/2BA condo!

  • 3
  • 8
  • 2 nights min

$169

Details

1 / 12

** 2/2 Golf Community vacation condo near Airport.

  • 2
  • 8
  • 2 nights min

$75

Details

1 / 7

Westgate Palace - Fri-Fri, Sat-Sat, Sun-Sun only!

  • 2
  • 6
  • 7 nights min

$312

Details

1 / 15

Serene Home Away from Home

  • 2
  • 4
  • 3 nights min

$60

Details

1 / 24

Vista Cay 3BR, 2BTH condo right next to The Convention Center VC146

  • 3
  • 8
  • Min stay varies

$148

Details

1 / 26

4 BED 3 BATH LUX VISTA CAY # 08

  • 3
  • 8
  • 4 nights min

$139

Details

1 / 8

Executive Apartment

  • 2
  • 4
  • 7 nights min

$86

Details

1 / 28

Villa 176 Watersong Resort, Orlando

  • 5
  • 10
  • 7 nights min

$298

Details

1 / 40

Aviana 7Br/4.5Bt Villa with Pool, Games

  • 7
  • 22
  • Min stay varies

$249

Details

1 / 35

3 Bedroom at Westgate Resort and Spa Wonderful Vac

  • 3
  • 12
  • 7 nights min

$284

Details

1 / 22

COMFORT INN INTERNATIONAL DR ~ SLEEPS 4 ~ FREE WIFI/FREE SHUTTLES/FREE BREAKFAST

  • Studio
  • 4
  • 1 night min

$80

Details

1 / 66

Beautiful three-story townhome with 3 bedrooms and 3.5 baths

  • 3
  • 8
  • 2 nights min

$167

Details

1 / 26

Villa 2605, Windsor Hills Resort, Orlando, Flroida

  • 6
  • 14
  • 5 nights min

$348

Details

1 / 48

Disney new 6 Bed/6br Luxury Jacuzzi Pool Home at ChampionsGate

  • 6
  • 14
  • Min stay varies

$100

Details

1 / 71

Stunning 3-bedroom first floor condo with modern furnishings & relaxing patio

  • 3
  • 8
  • 2 nights min

$167

Details

1 / 10

3 BD Furnished Quaint Altamonte / North Orlando

  • 3
  • 6
  • 5 nights min

$100

Details

1 / 56

Penthouse with spectacular lakeview!!!

  • 3
  • 10
  • 2 nights min

$188

Details

1 / 58

3-bedroom, 3.5 bath townhome perfect for a family getaway!

  • 3
  • 8
  • 2 nights min

$167

Details

1 / 56

1st floor end unit with amazing lake view next to clubhouse, gym and pool.

  • 3
  • 8
  • 2 nights min

$188

Details

1 / 6

Disneyworld Orlando Florida

  • 2
  • 8
  • 7 nights min

$199

Details

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Turquoise Paradise

  • 1
  • 3
  • 1 night min

$46

Details

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