A sunset over a calm lake with islands and a bridge.

Holiday Homes in Osteen

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Osteen holiday homes

A modern kitchen with light-colored cabinets, stainless steel appliances, and a herringbone-patterned backsplash.

1. Home Sweet Home

Home Sweet Home
Sanford
9.4 out of 10, Exceptional, (33 reviews)
"The house was perfect for our three night stay. The location was a short distance to all our activities. It was super clean and had very nice updates. The area was quiet and the house very comfortable. If we are in the area again, we’ll definitely stay there again!"
United States
Janice M.
The price is NZ$550
includes taxes & fees
20 Oct - 21 Oct
Home Sweet Home
A neatly made bed with white linens and towels, a dark door, and two framed artworks on the wall.

2. Tranquil 3-bedroom house in Sanford with AC, WiFi

Tranquil 3-bedroom house in Sanford with AC, WiFi
Sanford
9.6 out of 10, Exceptional, (28 reviews)
"Beautiful place to stay near the airport "
United States
Rodney
The price is NZ$654
includes taxes & fees
12 Oct - 13 Oct
Tranquil 3-bedroom house in Sanford with AC, WiFi
A living room with a white sofa, a black leather sofa, a ceiling fan, and a large mirror on the wall.

3. Serene Sunshine State Escape

Serene Sunshine State Escape
Deltona Lakes
10.0 out of 10, Exceptional, (3 reviews)
"Very nice host and great place to stay!"
United States
Wesley L.
The price is NZ$818
includes taxes & fees
11 Oct - 12 Oct
Serene Sunshine State Escape
Private kitchen

4. Cozy 3BR Retreat - Near Bars, Zoo & Lake Trails

Cozy 3BR Retreat - Near Bars, Zoo & Lake Trails
Downtown Sanford
10.0 out of 10, Exceptional, (1 review)
"The home was spacious, pristine & one of the best stocked rentals we have stayed at."
United States
RICHARD F.
The price is NZ$936
includes taxes & fees
12 Oct - 13 Oct
Cozy 3BR Retreat - Near Bars, Zoo & Lake Trails
A modern kitchen with dark cabinets, a stainless steel refrigerator, and a dining area with a glass table and white chairs.

5. River City Retreat

River City Retreat
Sanford
9.6 out of 10, Exceptional, (21 reviews)
"Great place and quick, simple check in."
United States
Dennis L.
The price is NZ$382
includes taxes & fees
15 Oct - 16 Oct
River City Retreat
A living room with a brown leather sofa, a white ottoman, a coffee table, a dining area with a table and chairs, and a wall with framed pictures.

6. Bright & Cozy 3BR Retreat with Timeless Charm

Bright & Cozy 3BR Retreat with Timeless Charm
Sanford
10.0 out of 10, Exceptional, (1 review)
"Our stay at Arcadia was perfect! The house was fully stocked with EVERYTHING you might need. Our host was great to work with. And having the golf cart to go downtown for dinner and shopping was icing on the cake. Would definitely stay here again!"
United States
Lindsay P.
The price is NZ$752
includes taxes & fees
8 Nov - 9 Nov
Bright & Cozy 3BR Retreat with Timeless Charm
A modern kitchen with white cabinetry, a large island with stools, and a refrigerator.

7. Charming 2-bedroom house in DeBary with AC- Close to highway andhiking Trail

Charming 2-bedroom house in DeBary with AC- Close to highway andhiking Trail
Plantation Estates
10.0 out of 10, Exceptional, (3 reviews)
"Loved staying at this place! Cute home and the renters gave us some great ideas."
United States
Maria K.
The price is NZ$502
includes taxes & fees
12 Oct - 13 Oct
Charming 2-bedroom house in DeBary with AC- Close to highway andhiking Trail
A modern kitchen with white cabinetry, a central island with bar stools, a built-in microwave, and a window with a view.

8. Welcoming 2-bedroom house with AC in charming Sanford

Welcoming 2-bedroom house with AC in charming Sanford
Sanford
10.0 out of 10, Exceptional, (5 reviews)
"This was excellent in every way. Beautifully decorated that created a warm atmosphere. Beds were very comfortable. If I’m in the area again, I will definitely stay there."
United States
Debra O.
The price is NZ$576
includes taxes & fees
9 Oct - 10 Oct
Welcoming 2-bedroom house with AC in charming Sanford
A modern kitchen with stainless steel appliances, white cabinetry, and a central island.

9. The Billiard: super fun home close to downtown with fully-fenced yard

The Billiard: super fun home close to downtown with fully-fenced yard
Downtown Sanford
10.0 out of 10, Exceptional, (5 reviews)
"Just a great house with a great vibe in a good location for tons of fun. Very clean house and a great host. This was our second time staying here and it was still an amazing house. "
United States
Matt R.
The Billiard: super fun home close to downtown with fully-fenced yard
A two-story yellow house with a porch, surrounded by lush greenery and trees.

10. Historic Downtown Sanford Sunshine Cottage with Tree Top Suite!

Historic Downtown Sanford Sunshine Cottage with Tree Top Suite!
Sanford
10.0 out of 10, Exceptional, (29 reviews)
"Really cute cottage with charming eclectic style. Stayed with two adults and four teens and everyone had plenty of space with comfortable sleeping. Would absolutely stay again!"
United States
Wendy K.
The price is NZ$761
includes taxes & fees
11 Oct - 12 Oct
Historic Downtown Sanford Sunshine Cottage with Tree Top Suite!
A modern living room with a sofa, coffee table, and ottoman. A dining area with a wooden table and chairs is visible. A TV is mounted on the wall.

11. The Sanford Ave House with fully-fenced yard

The Sanford Ave House with fully-fenced yard
Downtown Sanford
The Sanford Ave House with fully-fenced yard
A modern kitchen with white cabinets, stainless steel appliances, granite countertops, and pendant lighting.

12. The Hub on Cypress Ave - walk to downtown Sanford

The Hub on Cypress Ave - walk to downtown Sanford
Downtown Sanford
10.0 out of 10, Exceptional, (3 reviews)
"Five stars, nice large house, excellent location. I would rent again. "
United States
Beth D.
The Hub on Cypress Ave - walk to downtown Sanford
A modern kitchen with white cabinets, a granite countertop, and a blue door with a view of greenery.

13. Backyard BBQ home - Blue Spring to Daytona

Backyard BBQ home - Blue Spring to Daytona
Orange City
9.6 out of 10, Exceptional, (7 reviews)
"Great host, clean and comfortable house, quiet neighborhood. "
United States
Russ B.
The price is NZ$538
includes taxes & fees
11 Oct - 12 Oct
Backyard BBQ home - Blue Spring to Daytona
A modern kitchen with grey cabinets, a central island with bar stools, a stainless steel trash can, and a dining area with a glass table and chairs.

14. The Getaway Experience

The Getaway Experience
Deltona Lakes
9.2 out of 10, Wonderful, (14 reviews)
"Loved having 3 king beds and 2.5 bathrooms. We didn’t stay in much as we were visiting family but we slept great! "
United States
Kris V.
The price is NZ$732
includes taxes & fees
21 Oct - 22 Oct
The Getaway Experience
A bedroom with a bed, bedside table, lamp, TV, fireplace, and a window with curtains.

15. Sanford's Sunset - Pet-friendly home, 4BR/sleeps 10

Sanford's Sunset - Pet-friendly home, 4BR/sleeps 10
Sanford
9.4 out of 10, Exceptional, (20 reviews)
"Thank you so much we had a wonderful visit and so great to be able to bring our dog he really loved the back yard!"
United States
Miriam R.
The price is NZ$818
includes taxes & fees
13 Oct - 14 Oct
Sanford's Sunset - Pet-friendly home, 4BR/sleeps 10
A white building with a green door and a small porch area with plants.

16. Charming home with big patio!

Charming home with big patio!
Oviedo
9.8 out of 10, Exceptional, (26 reviews)
"Host was very helpful. It’s a nice place to stay. Very comfortable."
United States
Sandranel B.
The price is NZ$654
includes taxes & fees
12 Oct - 13 Oct
Charming home with big patio!
A swimming pool with a covered patio area, surrounded by plants and a white fence.

17. Breezy Escape in Oviedo

Breezy Escape in Oviedo
Oviedo
10.0 out of 10, Exceptional, (12 reviews)
"Home was beautiful, neighborhood was very nice. Definitely staying again when in the area!"
United States
Jeremy B.
The price is NZ$596
includes taxes & fees
18 Oct - 19 Oct
Breezy Escape in Oviedo
A bedroom with a bed, two bedside tables, a ceiling fan, and framed pictures on the wall.

18. Disney & Daytona Retreat - Cozy Home with Private Yard Near Top Attractions

Disney & Daytona Retreat - Cozy Home with Private Yard Near Top Attractions
DeBary
The price is NZ$2,180
includes taxes & fees
9 Oct - 10 Oct
Disney & Daytona Retreat - Cozy Home with Private Yard Near Top Attractions
A kitchen with white cabinets, a stainless steel trash can, a microwave, an oven, and a refrigerator.

19. Charming 3-bedroom home away from home.

Charming 3-bedroom home away from home.
Chuluota
9.8 out of 10, Exceptional, (25 reviews)
"Perfect stay while visiting local family. "
United States
Kerri W.
The price is NZ$664
includes taxes & fees
9 Oct - 10 Oct
Charming 3-bedroom home away from home.
A modern kitchen with a microwave, coffee maker, and potted plants. There is a seating area with a sofa and a coffee table.

20. The Longwood Escape • Modern Private Guesthouse Near Orlando

The Longwood Escape • Modern Private Guesthouse Near Orlando
Longwood
The price is NZ$287
includes taxes & fees
20 Oct - 21 Oct
The Longwood Escape • Modern Private Guesthouse Near Orlando
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Osteen Hotel Reviews

HomeTowne Studios by Red Roof Orlando - UCF Area

HomeTowne Studios by Red Roof Orlando - UCF Area

10/10 Excellent
"Good"
Jose 1-night trip
Posted 2 days ago
HomeTowne Studios by Red Roof Orlando - UCF Area

Find out more about Osteen

Osteen Holiday Homes information

Number of reviews
194
Accommodation
1444 Holiday Homes
Lowest Price
NZ$287
Highest Price
NZ$2,180