Osteen Vacation Rentals, Houses & More


1 - 38 of 90

View larger map

Areas near Osteen

1 / 139

SunShine Ranch

  • 8
  • 4
  • 1 night min

$36

Details

Great rentals within 20 miles that match your search

1 / 23

Large, lovely, renovated 1913 home on main block

  • 5
  • 8
  • 2 nights min

$201

Details

1 / 18

Rustic lakefront cabin for boating and relaxing

  • 1
  • 4
  • 2 nights min

$85

Details

1 / 43

Swiss-FL, with breakfast, has a kitchen y. near Stetson and Downtown

  • 1
  • 3
  • 1 night min

$49

Details

1 / 15

1152F - Fairvilla

  • 2
  • 4
  • 28 nights min

$72

Details

1 / 6

2BD/2BA Luxurious Condo available in Dolphin Cove

  • 2
  • 4
  • 30 nights min

$76

Details

1 / 30

Golfer's Dream 3/2 in Golf Course Community

  • 3
  • 10
  • 90 nights min

$88

Details

1 / 11

The Bedford House

  • 4
  • 8
  • 3 nights min

$201

Details

1 / 24

Golf, Tennis, Beach, and Quiet Relaxation

  • 3
  • 8
  • 30 nights min

$37

Details

1 / 18

Bird Nest Retreat

  • 4
  • 6
  • 7 nights min

$171

Details

1 / 24

BB202 Brae Burn

  • 2
  • 7
  • 28 nights min

$74

Details

1 / 28

The Cottage at Oviedo

  • 1
  • 4
  • 1 night min

$125

Details

1 / 26

Kate's Places/ Jasmine - Golfer's Dream Near Beach

  • 3
  • 7
  • 60 nights min

$73

Details

1 / 19

Ocean Front Boardwalk Property

  • Studio
  • 8
  • 7 nights min

$401

Details

1 / 24

Three-Bedroom Two Bath Lake View House at Gator's Nest

  • 3
  • 6
  • 3 nights min

$176

Details

1 / 6

Water Front Cabin - Mosquito Lagoon with Boat Slip!

  • 1
  • 4
  • 1 night min

$79

Details

1 / 66

Five-Bedroom House at Gator Palace

  • 5
  • 12
  • 3 nights min

$376

Details

1 / 17

PV131 Pine Valley

  • 2
  • 4
  • 28 nights min

$72

Details

1 / 23

EC165- 6 Bedroom Villa With Private Pool

  • 6
  • 14
  • Min stay varies

$305

Details

1 / 21

3150ft2 - Room 4 Rent House Share golf course pool

  • 3
  • 6
  • 7 nights min

$114

Details

1 / 7

Beautiful 3 Bedrom House In Orange City

  • 3
  • 8
  • 7 nights min

$450

Details

1 / 21

Family & Allergy Friendly Apt 1.5 Miles from Beach

  • 2
  • 4
  • 2 nights min

$100

Details

1 / 20

PRIVATE Waterfront Home * gorgeous POOL * 4 bedrooms * 3 1/2 baths* huge kitchen

  • 4
  • 8
  • 6 nights min

$499

Details

1 / 17

Old Florida Beach town Drive to Atlantic Ocean East of Orlando Attractions

  • 2
  • 4
  • Min stay varies

$76

Details

1 / 22

Sugarmill Country Club 7th Hole White - Remodeled 3/2.5

  • 3
  • 6
  • 30 nights min

$129

Details

1 / 10

Eden

  • 2
  • 4
  • 1 night min

$125

Details

1 / 46

Swiss-FL, with breakfast, has a kitchen, near Stetson and Downtown

  • 1
  • 3
  • 1 night min

$49

Details

1 / 20

Hammock House on the Wekiva River

  • 4
  • 10
  • 2 nights min

$250

Details

1 / 13

2br - 1000ft2 - Winter Park House

  • 2
  • 5
  • 7 nights min

$144

Details

1 / 25

***BOOK NOW FOR SUMMER - BEST LOCATION - CLOSEST BUILDING TO BEACH ACCESS***

  • 3
  • 6
  • Min stay varies

$200

Details

1 / 27

Ninovan on the Shore, A river retreat with history

  • 4
  • 13
  • 3 nights min

$285

Details

1 / 46

Swiss-FL, with breakfast (y) n. University and Downtown

  • 1
  • 3
  • 1 night min

$54

Details

1 / 30

EC192- Encore Club 6 Bedroom Pool Home

  • 6
  • 14
  • Min stay varies

$305

Details

1 / 19

Storey Lake Resort/AB2552

  • 5
  • 50
  • Min stay varies

$177

Details

1 / 21

Regal Palms/MS4785

  • 4
  • 50
  • Min stay varies

$118

Details

1 / 17

1124 Loch Lomond

  • 2
  • 6
  • 90 nights min

$121

Details

1 / 8

Mandy's Waterfront Oak Hill Paradise

  • 2
  • 6
  • 2 nights min

$123

Details

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more
See only the properties that can be booked online with Payment Protection.
Learn more