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Osteen Holiday 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, holiday rental in Osteen
Cottage on the River, holiday rental in Osteen
Cottage on the River, holiday rental in Osteen

Cottage on the River

Holiday Rental House
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., holiday rental in Osteen
Beautiful 2 story in Deltona, Florida- Close to beaches, Theme parks, Daytona., holiday rental in Osteen
Beautiful 2 story in Deltona, Florida- Close to beaches, Theme parks, Daytona., holiday rental in Osteen

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

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

Lake Monroe Floating Bungalow Downtown Historic Sanford

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

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

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

Home on Lake, Day Trip to Disney & Universal

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Blue Aztec, holiday rental in Osteen
The Blue Aztec, holiday rental in Osteen
The Blue Aztec, holiday 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, holiday rental in Osteen
9 mins away to Advent Health / Summer Sale-20% Off, holiday rental in Osteen
9 mins away to Advent Health / Summer Sale-20% Off, holiday rental in Osteen

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

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

NOT YOUR TYPICAL HOUSEBOAT: 60 FEET OF FUN!

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

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

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

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

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

Florida Vacation Rental on 5.5 Acres w/ Fire Pit!

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

RV on private property. fully self contained.

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Vacation in style near Everything Florida Offers, holiday rental in Osteen
Vacation in style near Everything Florida Offers, holiday rental in Osteen
Vacation in style near Everything Florida Offers, holiday 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, holiday rental in Osteen
The Cherry Blossom, The Cherry Blossom, holiday rental in Osteen
The Cherry Blossom, The Cherry Blossom, holiday 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, holiday rental in Osteen
Bella Breeze, holiday rental in Osteen
Bella Breeze, holiday 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, holiday rental in Osteen
Orlando Luxury cottage w/King bed Walking distance to shops restaurants and bars, holiday rental in Osteen
Orlando Luxury cottage w/King bed Walking distance to shops restaurants and bars, holiday 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
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30 Mins Travel Time to Disney , Daytona Beach, Orlando , NASA, holiday rental in Osteen
30 Mins Travel Time to Disney , Daytona Beach, Orlando , NASA, holiday rental in Osteen
30 Mins Travel Time to Disney , Daytona Beach, Orlando , NASA, holiday rental in Osteen

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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Lakefront Luxurious 38 ft Camper, holiday rental in Osteen
Lakefront Luxurious 38 ft Camper, holiday rental in Osteen
Lakefront Luxurious 38 ft Camper, holiday rental in Osteen

Lakefront Luxurious 38 ft Camper

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

NEW! Deltona Home Midway between Orlando and Daytona

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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4.7 miles from hospital/Summer Sale-20% Off, holiday rental in Osteen
4.7 miles from hospital/Summer Sale-20% Off, holiday rental in Osteen
4.7 miles from hospital/Summer Sale-20% Off, holiday rental in Osteen

4.7 miles from hospital/Summer Sale-20% Off

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Pleasant Point River Retreat, holiday rental in Osteen
Pleasant Point River Retreat, holiday rental in Osteen
Pleasant Point River Retreat, holiday rental in Osteen

Pleasant Point River Retreat

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Historic Maximalist Bungalow in Downtown Sanford with office, holiday rental in Osteen
Historic Maximalist Bungalow in Downtown Sanford with office, holiday rental in Osteen
Historic Maximalist Bungalow in Downtown Sanford with office, holiday rental in Osteen

Historic Maximalist Bungalow in Downtown Sanford with office

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Kick of your boots it’s Fun time!!, holiday rental in Osteen
Kick of your boots it’s Fun time!!, holiday rental in Osteen
Kick of your boots it’s Fun time!!, holiday rental in Osteen

Kick of your boots it’s Fun time!!

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

Home away from Home <3

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

Lovely Vacation Home w Garage

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Sunny Florida Retreat, holiday rental in Osteen
Sunny Florida Retreat, holiday rental in Osteen
Sunny Florida Retreat, holiday rental in Osteen

Sunny Florida Retreat

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Top Notch Villa, holiday rental in Osteen
The Top Notch Villa, holiday rental in Osteen
The Top Notch Villa, holiday rental in Osteen

The Top Notch Villa

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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3/2 Sunny Deltona Retreat, holiday rental in Osteen
3/2 Sunny Deltona Retreat, holiday rental in Osteen
3/2 Sunny Deltona Retreat, holiday rental in Osteen

3/2 Sunny Deltona Retreat

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozy Pool Home with Private Back Yard, holiday rental in Osteen
Cozy Pool Home with Private Back Yard, holiday rental in Osteen
Cozy Pool Home with Private Back Yard, holiday rental in Osteen

Cozy Pool Home with Private Back Yard

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

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

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Close to beach 30 min and Disney 45 min, holiday rental in Osteen
Close to beach 30 min and Disney 45 min, holiday rental in Osteen
Close to beach 30 min and Disney 45 min, holiday rental in Osteen

Close to beach 30 min and Disney 45 min

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Deltona Vacation Home w/ Gas Grill!, holiday rental in Osteen
Deltona Vacation Home w/ Gas Grill!, holiday rental in Osteen
Deltona Vacation Home w/ Gas Grill!, holiday rental in Osteen

Deltona Vacation Home w/ Gas Grill!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Quiet neighborhood close to Downtown Sanford, holiday rental in Osteen
Quiet neighborhood close to Downtown Sanford, holiday rental in Osteen
Quiet neighborhood close to Downtown Sanford, holiday rental in Osteen

Quiet neighborhood close to Downtown Sanford

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

Stunning home with screened patio & fenced yard

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

Bright, sunny, spacious house close to nearby attractions

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Live, Work & Play in Deltona Lakes, FL, holiday rental in Osteen
Live, Work & Play in Deltona Lakes, FL, holiday rental in Osteen
Live, Work & Play in Deltona Lakes, FL, holiday rental in Osteen

Live, Work & Play in Deltona Lakes, FL

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lk Mary Sanford Bombay sport complex~Beach ~Zoo~Downtown marina, holiday rental in Osteen
Lk Mary Sanford Bombay sport complex~Beach ~Zoo~Downtown marina, holiday rental in Osteen
Lk Mary Sanford Bombay sport complex~Beach ~Zoo~Downtown marina, holiday rental in Osteen

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Vacation and relaxation home, holiday rental in Osteen
Vacation and relaxation home, holiday rental in Osteen
Vacation and relaxation home, holiday rental in Osteen

Vacation and relaxation home

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Home, Sweet Home, holiday rental in Osteen
Home, Sweet Home, holiday rental in Osteen
Home, Sweet Home, holiday rental in Osteen

Home, Sweet Home

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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3 Bedroom  (647889) by Houzlet, holiday rental in Osteen
3 Bedroom  (647889) by Houzlet, holiday rental in Osteen
3 Bedroom  (647889) by Houzlet, holiday rental in Osteen

3 Bedroom (647889) by Houzlet

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

The Cozy Sanford Home

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

Home Away From Home-Spacious 8 Guests Pool Home

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

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

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

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

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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A river retreat caught between Florida's beaches and Orlando's Amusement Parks., holiday rental in Osteen
A river retreat caught between Florida's beaches and Orlando's Amusement Parks., holiday rental in Osteen
A river retreat caught between Florida's beaches and Orlando's Amusement Parks., holiday rental in Osteen

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

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Ninovan on the Shore, A river retreat with history, holiday rental in Osteen
Ninovan on the Shore, A river retreat with history, holiday rental in Osteen
Ninovan on the Shore, A river retreat with history, holiday rental in Osteen

Ninovan on the Shore, A river retreat with history

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Luxury Property | Groups Welcome | Private Pool, holiday rental in Osteen
Luxury Property | Groups Welcome | Private Pool, holiday rental in Osteen
Luxury Property | Groups Welcome | Private Pool, holiday rental in Osteen

Luxury Property | Groups Welcome | Private Pool

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Mediterranean/Spanish Estate Home on Lake Sidney, holiday rental in Osteen
Mediterranean/Spanish Estate Home on Lake Sidney, holiday rental in Osteen
Mediterranean/Spanish Estate Home on Lake Sidney, holiday rental in Osteen

Mediterranean/Spanish Estate Home on Lake Sidney

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Luxury 38 ft Camper, holiday rental in Osteen
Luxury 38 ft Camper, holiday rental in Osteen
Luxury 38 ft Camper, holiday rental in Osteen

Luxury 38 ft Camper

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Gorgeous waterfront property on the St. Johns River, holiday rental in Osteen
Gorgeous waterfront property on the St. Johns River, holiday rental in Osteen
Gorgeous waterfront property on the St. Johns River, holiday rental in Osteen

Gorgeous waterfront property on the St. Johns River

Holiday Rental House
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