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Osteen Vacation Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
50 rentals in Osteen.
Cottage on the River, vacation rental in Osteen
Cottage on the River, vacation rental in Osteen
Cottage on the River, vacation rental in Osteen

Cottage on the River

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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The following properties within 20 miles of Osteen match all your filters:
Beautiful 2 story in Deltona, Florida- Close to beaches, Theme parks, Daytona., vacation rental in Osteen
Beautiful 2 story in Deltona, Florida- Close to beaches, Theme parks, Daytona., vacation rental in Osteen
Beautiful 2 story in Deltona, Florida- Close to beaches, Theme parks, Daytona., vacation rental in Osteen

Beautiful 2 story in Deltona, Florida- Close to beaches, Theme parks, Daytona.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Lake Monroe Floating Bungalow Downtown Historic Sanford, vacation rental in Osteen
Lake Monroe Floating Bungalow Downtown Historic Sanford, vacation rental in Osteen
Lake Monroe Floating Bungalow Downtown Historic Sanford, vacation rental in Osteen

Lake Monroe Floating Bungalow Downtown Historic Sanford

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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EARLY CHECK IN! PRIVATE OASIS! CLEAN 4 BEDROOM, LAKE VIEW HOME!, vacation rental in Osteen
EARLY CHECK IN! PRIVATE OASIS! CLEAN 4 BEDROOM, LAKE VIEW HOME!, vacation rental in Osteen
EARLY CHECK IN! PRIVATE OASIS! CLEAN 4 BEDROOM, LAKE VIEW HOME!, vacation rental in Osteen

EARLY CHECK IN! PRIVATE OASIS! CLEAN 4 BEDROOM, LAKE VIEW HOME!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Home on Lake, Day Trip to Disney & Universal, vacation rental in Osteen
Home on Lake, Day Trip to Disney & Universal, vacation rental in Osteen
Home on Lake, Day Trip to Disney & Universal, vacation rental in Osteen

Home on Lake, Day Trip to Disney & Universal

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Blue Aztec, vacation rental in Osteen
The Blue Aztec, vacation rental in Osteen
The Blue Aztec, vacation rental in Osteen

The Blue Aztec

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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9 mins away to Advent Health / Summer Sale-20% Off, vacation rental in Osteen
9 mins away to Advent Health / Summer Sale-20% Off, vacation rental in Osteen
9 mins away to Advent Health / Summer Sale-20% Off, vacation rental in Osteen

9 mins away to Advent Health / Summer Sale-20% Off

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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NOT YOUR TYPICAL HOUSEBOAT: 60 FEET OF FUN!, vacation rental in Osteen
NOT YOUR TYPICAL HOUSEBOAT: 60 FEET OF FUN!, vacation rental in Osteen
NOT YOUR TYPICAL HOUSEBOAT: 60 FEET OF FUN!, vacation rental in Osteen

NOT YOUR TYPICAL HOUSEBOAT: 60 FEET OF FUN!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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30 minutes to Orlando, Daytona Speedway & 15 minutes to Boombah Sports Complex., vacation rental in Osteen
30 minutes to Orlando, Daytona Speedway & 15 minutes to Boombah Sports Complex., vacation rental in Osteen
30 minutes to Orlando, Daytona Speedway & 15 minutes to Boombah Sports Complex., vacation rental in Osteen

30 minutes to Orlando, Daytona Speedway & 15 minutes to Boombah Sports Complex.

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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⭐️ Pool ⭐️ Game Room ⭐️ BBQ ⭐️ Fire Pit ⭐️ Coffee Bar, vacation rental in Osteen
⭐️ Pool ⭐️ Game Room ⭐️ BBQ ⭐️ Fire Pit ⭐️ Coffee Bar, vacation rental in Osteen
⭐️ Pool ⭐️ Game Room ⭐️ BBQ ⭐️ Fire Pit ⭐️ Coffee Bar, vacation rental in Osteen

⭐️ Pool ⭐️ Game Room ⭐️ BBQ ⭐️ Fire Pit ⭐️ Coffee Bar

Rental Home
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Florida Vacation Rental on 5.5 Acres w/ Fire Pit!, vacation rental in Osteen
Florida Vacation Rental on 5.5 Acres w/ Fire Pit!, vacation rental in Osteen
Florida Vacation Rental on 5.5 Acres w/ Fire Pit!, vacation rental in Osteen

Florida Vacation Rental on 5.5 Acres w/ Fire Pit!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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RV on private property. fully self contained., vacation rental in Osteen
RV on private property. fully self contained., vacation rental in Osteen
RV on private property. fully self contained., vacation rental in Osteen

RV on private property. fully self contained.

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Vacation in style near Everything Florida Offers, vacation rental in Osteen
Vacation in style near Everything Florida Offers, vacation rental in Osteen
Vacation in style near Everything Florida Offers, vacation rental in Osteen

Vacation in style near Everything Florida Offers

Condo/Apartment
0 bedrooms
0 bathrooms
Sleeps 7
Match: Sleeps
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The Cherry Blossom, The Cherry Blossom, vacation rental in Osteen
The Cherry Blossom, The Cherry Blossom, vacation rental in Osteen
The Cherry Blossom, The Cherry Blossom, vacation rental in Osteen

The Cherry Blossom, The Cherry Blossom

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Bella Breeze, vacation rental in Osteen
Bella Breeze, vacation rental in Osteen
Bella Breeze, vacation rental in Osteen

Bella Breeze

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Orlando Luxury cottage w/King bed Walking distance to shops restaurants and bars, vacation rental in Osteen
Orlando Luxury cottage w/King bed Walking distance to shops restaurants and bars, vacation rental in Osteen
Orlando Luxury cottage w/King bed Walking distance to shops restaurants and bars, vacation rental in Osteen

Orlando Luxury cottage w/King bed Walking distance to shops restaurants and bars

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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30 Mins Travel Time to Disney , Daytona Beach, Orlando , NASA, vacation rental in Osteen
30 Mins Travel Time to Disney , Daytona Beach, Orlando , NASA, vacation rental in Osteen
30 Mins Travel Time to Disney , Daytona Beach, Orlando , NASA, vacation rental in Osteen

30 Mins Travel Time to Disney , Daytona Beach, Orlando , NASA

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Lakefront Luxurious 38 ft Camper, vacation rental in Osteen
Lakefront Luxurious 38 ft Camper, vacation rental in Osteen
Lakefront Luxurious 38 ft Camper, vacation rental in Osteen

Lakefront Luxurious 38 ft Camper

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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NEW! Deltona Home Midway between Orlando and Daytona, vacation rental in Osteen
NEW! Deltona Home Midway between Orlando and Daytona, vacation rental in Osteen
NEW! Deltona Home Midway between Orlando and Daytona, vacation rental in Osteen

NEW! Deltona Home Midway between Orlando and Daytona

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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4.7 miles from hospital/Summer Sale-20% Off, vacation rental in Osteen
4.7 miles from hospital/Summer Sale-20% Off, vacation rental in Osteen
4.7 miles from hospital/Summer Sale-20% Off, vacation rental in Osteen

4.7 miles from hospital/Summer Sale-20% Off

Rental Home
2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
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Pleasant Point River Retreat, vacation rental in Osteen
Pleasant Point River Retreat, vacation rental in Osteen
Pleasant Point River Retreat, vacation rental in Osteen

Pleasant Point River Retreat

Rental Home
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Historic Maximalist Bungalow in Downtown Sanford with office, vacation rental in Osteen
Historic Maximalist Bungalow in Downtown Sanford with office, vacation rental in Osteen
Historic Maximalist Bungalow in Downtown Sanford with office, vacation rental in Osteen

Historic Maximalist Bungalow in Downtown Sanford with office

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Kick of your boots it’s Fun time!!, vacation rental in Osteen
Kick of your boots it’s Fun time!!, vacation rental in Osteen
Kick of your boots it’s Fun time!!, vacation rental in Osteen

Kick of your boots it’s Fun time!!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Home away from Home <3, vacation rental in Osteen
Home away from Home <3, vacation rental in Osteen
Home away from Home <3, vacation rental in Osteen

Home away from Home <3

Rental Home
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Lovely Vacation Home w Garage, vacation rental in Osteen
Lovely Vacation Home w Garage, vacation rental in Osteen
Lovely Vacation Home w Garage, vacation rental in Osteen

Lovely Vacation Home w Garage

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Sunny Florida Retreat, vacation rental in Osteen
Sunny Florida Retreat, vacation rental in Osteen
Sunny Florida Retreat, vacation rental in Osteen

Sunny Florida Retreat

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Top Notch Villa, vacation rental in Osteen
The Top Notch Villa, vacation rental in Osteen
The Top Notch Villa, vacation rental in Osteen

The Top Notch Villa

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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3/2 Sunny Deltona Retreat, vacation rental in Osteen
3/2 Sunny Deltona Retreat, vacation rental in Osteen
3/2 Sunny Deltona Retreat, vacation rental in Osteen

3/2 Sunny Deltona Retreat

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Cozy Pool Home with Private Back Yard, vacation rental in Osteen
Cozy Pool Home with Private Back Yard, vacation rental in Osteen
Cozy Pool Home with Private Back Yard, vacation rental in Osteen

Cozy Pool Home with Private Back Yard

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Top Notch Villa, few minutes to Disney, Universal, Daytona speed way. Bike w/spe, vacation rental in Osteen
Top Notch Villa, few minutes to Disney, Universal, Daytona speed way. Bike w/spe, vacation rental in Osteen
Top Notch Villa, few minutes to Disney, Universal, Daytona speed way. Bike w/spe, vacation rental in Osteen

Top Notch Villa, few minutes to Disney, Universal, Daytona speed way. Bike w/spe

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Close to beach 30 min and Disney 45 min, vacation rental in Osteen
Close to beach 30 min and Disney 45 min, vacation rental in Osteen
Close to beach 30 min and Disney 45 min, vacation rental in Osteen

Close to beach 30 min and Disney 45 min

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Deltona Vacation Home w/ Gas Grill!, vacation rental in Osteen
Deltona Vacation Home w/ Gas Grill!, vacation rental in Osteen
Deltona Vacation Home w/ Gas Grill!, vacation rental in Osteen

Deltona Vacation Home w/ Gas Grill!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Quiet neighborhood close to Downtown Sanford, vacation rental in Osteen
Quiet neighborhood close to Downtown Sanford, vacation rental in Osteen
Quiet neighborhood close to Downtown Sanford, vacation rental in Osteen

Quiet neighborhood close to Downtown Sanford

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stunning home with screened patio & fenced yard, vacation rental in Osteen
Stunning home with screened patio & fenced yard, vacation rental in Osteen
Stunning home with screened patio & fenced yard, vacation rental in Osteen

Stunning home with screened patio & fenced yard

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Bright, sunny, spacious house close to nearby attractions, vacation rental in Osteen
Bright, sunny, spacious house close to nearby attractions, vacation rental in Osteen
Bright, sunny, spacious house close to nearby attractions, vacation rental in Osteen

Bright, sunny, spacious house close to nearby attractions

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Live, Work & Play in Deltona Lakes, FL, vacation rental in Osteen
Live, Work & Play in Deltona Lakes, FL, vacation rental in Osteen
Live, Work & Play in Deltona Lakes, FL, vacation rental in Osteen

Live, Work & Play in Deltona Lakes, FL

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Lk Mary Sanford Bombay sport complex~Beach ~Zoo~Downtown marina, vacation rental in Osteen
Lk Mary Sanford Bombay sport complex~Beach ~Zoo~Downtown marina, vacation rental in Osteen
Lk Mary Sanford Bombay sport complex~Beach ~Zoo~Downtown marina, vacation rental in Osteen

Lk Mary Sanford Bombay sport complex~Beach ~Zoo~Downtown marina

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Vacation and relaxation home, vacation rental in Osteen
Vacation and relaxation home, vacation rental in Osteen
Vacation and relaxation home, vacation rental in Osteen

Vacation and relaxation home

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Home, Sweet Home, vacation rental in Osteen
Home, Sweet Home, vacation rental in Osteen
Home, Sweet Home, vacation rental in Osteen

Home, Sweet Home

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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3 Bedroom  (647889) by Houzlet, vacation rental in Osteen
3 Bedroom  (647889) by Houzlet, vacation rental in Osteen
3 Bedroom  (647889) by Houzlet, vacation rental in Osteen

3 Bedroom (647889) by Houzlet

Condo/Apartment
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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The Cozy Sanford Home, vacation rental in Osteen
The Cozy Sanford Home, vacation rental in Osteen
The Cozy Sanford Home, vacation rental in Osteen

The Cozy Sanford Home

Rental Home
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Home Away From Home-Spacious 8 Guests Pool Home, vacation rental in Osteen
Home Away From Home-Spacious 8 Guests Pool Home, vacation rental in Osteen
Home Away From Home-Spacious 8 Guests Pool Home, vacation rental in Osteen

Home Away From Home-Spacious 8 Guests Pool Home

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Deltona Private Oasis Awaits! ONLY 30MIN T0 DAYTONA, 45MIN TO DISNEY & UNIVERSAL, vacation rental in Osteen
Deltona Private Oasis Awaits! ONLY 30MIN T0 DAYTONA, 45MIN TO DISNEY & UNIVERSAL, vacation rental in Osteen
Deltona Private Oasis Awaits! ONLY 30MIN T0 DAYTONA, 45MIN TO DISNEY & UNIVERSAL, vacation rental in Osteen

Deltona Private Oasis Awaits! ONLY 30MIN T0 DAYTONA, 45MIN TO DISNEY & UNIVERSAL

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Cozy Family Home with Private Yard 30 Mi to Beaches! by RedAwning, vacation rental in Osteen
Cozy Family Home with Private Yard 30 Mi to Beaches! by RedAwning, vacation rental in Osteen
Cozy Family Home with Private Yard 30 Mi to Beaches! by RedAwning, vacation rental in Osteen

Cozy Family Home with Private Yard 30 Mi to Beaches! by RedAwning

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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A river retreat caught between Florida's beaches and Orlando's Amusement Parks., vacation rental in Osteen
A river retreat caught between Florida's beaches and Orlando's Amusement Parks., vacation rental in Osteen
A river retreat caught between Florida's beaches and Orlando's Amusement Parks., vacation rental in Osteen

A river retreat caught between Florida's beaches and Orlando's Amusement Parks.

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Ninovan on the Shore, A river retreat with history, vacation rental in Osteen
Ninovan on the Shore, A river retreat with history, vacation rental in Osteen
Ninovan on the Shore, A river retreat with history, vacation rental in Osteen

Ninovan on the Shore, A river retreat with history

Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
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Luxury Property | Groups Welcome | Private Pool, vacation rental in Osteen
Luxury Property | Groups Welcome | Private Pool, vacation rental in Osteen
Luxury Property | Groups Welcome | Private Pool, vacation rental in Osteen

Luxury Property | Groups Welcome | Private Pool

Rental Home
4 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
More info
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Mediterranean/Spanish Estate Home on Lake Sidney, vacation rental in Osteen
Mediterranean/Spanish Estate Home on Lake Sidney, vacation rental in Osteen
Mediterranean/Spanish Estate Home on Lake Sidney, vacation rental in Osteen

Mediterranean/Spanish Estate Home on Lake Sidney

Rental Home
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
More info
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Luxury 38 ft Camper, vacation rental in Osteen
Luxury 38 ft Camper, vacation rental in Osteen
Luxury 38 ft Camper, vacation rental in Osteen

Luxury 38 ft Camper

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Gorgeous waterfront property on the St. Johns River, vacation rental in Osteen
Gorgeous waterfront property on the St. Johns River, vacation rental in Osteen
Gorgeous waterfront property on the St. Johns River, vacation rental in Osteen

Gorgeous waterfront property on the St. Johns River

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Showing results 1-50 of 50
Frequently Asked Questions about Osteen