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
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Osteen holiday homes

A neatly made bed with white linens and towels, a dark door, and two framed artworks on the wall.

1. 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 €328
includes taxes & fees
17 Sept - 18 Sept
Tranquil 3-bedroom house in Sanford with AC, WiFi
A modern kitchen with light-colored cabinets, stainless steel appliances, and a herringbone-patterned backsplash.

2. 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 €266
includes taxes & fees
2 Sept - 3 Sept
Home Sweet Home
A covered porch with two blue chairs and a small table, wooden flooring, and a door with a 'Home Sweet Home' sign.

3. Historic Hotspot • Walk to Downtown Fun • Luxury Beds

Historic Hotspot • Walk to Downtown Fun • Luxury Beds
Downtown Sanford
10.0 out of 10, Exceptional, (18 reviews)
"Ideal location, easy walk to food and fun."
United States
Steven H.
The price is €186
includes taxes & fees
25 Aug - 26 Aug
Historic Hotspot • Walk to Downtown Fun • Luxury Beds
A modern kitchen with white cabinetry, a large island with stools, and a refrigerator.

4. 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 €245
includes taxes & fees
24 Aug - 25 Aug
Charming 2-bedroom house in DeBary with AC- Close to highway andhiking Trail
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, (20 reviews)
"Great place and quick, simple check in."
United States
Dennis L.
The price is €186
includes taxes & fees
31 Aug - 1 Sept
River City Retreat
A living room with a white sofa, a black leather sofa, a ceiling fan, and a large mirror on the wall.

6. 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 €404
includes taxes & fees
21 Sept - 22 Sept
Serene Sunshine State Escape
A modern kitchen with white cabinets, a granite countertop, and a blue door with a view of greenery.

7. 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 €229
includes taxes & fees
24 Aug - 25 Aug
Backyard BBQ home - Blue Spring to Daytona
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 €285
includes taxes & fees
24 Aug - 25 Aug
Welcoming 2-bedroom house with AC in charming Sanford
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.

9. 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 €356
includes taxes & fees
24 Aug - 25 Aug
The Getaway Experience
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, (28 reviews)
"We absolutely loved this house! So cute and ample space. The outdoor space was so nice to grill and hangout!"
United States
Danielle C.
The price is €360
includes taxes & fees
24 Aug - 25 Aug
Historic Downtown Sanford Sunshine Cottage with Tree Top Suite!
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.

11. 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 €367
includes taxes & fees
24 Aug - 25 Aug
Bright & Cozy 3BR Retreat with Timeless Charm
A modern kitchen with white cabinetry, a stainless steel refrigerator, a microwave, and a large island with stools.

12. Lux 4 bed Mins! To HCA & Advent & Gemini Springs

Lux 4 bed Mins! To HCA & Advent & Gemini Springs
DeBary
10.0 out of 10, Exceptional, (1 review)
"Property was fabulous, clean and nice. Easy check in and host communicated in a timely manner. I highly recommend this property."
United States
Elisabeth G.
The price is €336
includes taxes & fees
1 Sept - 2 Sept
Lux 4 bed Mins! To HCA & Advent & Gemini Springs
A kitchen with white cabinets, a stainless steel trash can, a microwave, an oven, and a refrigerator.

13. Charming 3-bedroom home away from home.

Charming 3-bedroom home away from home.
Chuluota
9.8 out of 10, Exceptional, (25 reviews)
"Great layout, clean, plenty of amenities, quiet neighborhood. Host was very friendly and responsive. "
United States
Mary B.
The price is €324
includes taxes & fees
24 Aug - 25 Aug
Charming 3-bedroom home away from home.
A modern kitchen with white cabinets, stainless steel appliances, granite countertops, and pendant lighting.

14. 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)
"This house has everything. Beautiful space, close to downtown- you can walk to dinner if needed. Plenty of space for big groups."
United States
Southern S.
The Hub on Cypress Ave - walk to downtown Sanford

15. Stylish 2BR Downtown DeLand • Outdoor Fire Pit & Relaxed Vibes

Stylish 2BR Downtown DeLand • Outdoor Fire Pit & Relaxed Vibes
Downtown DeLand Historic District
9.4 out of 10, Exceptional, (11 reviews)
"Great location for our needs and comfortable. "
United States
Michelle M.
The price is €205
includes taxes & fees
24 Aug - 25 Aug
Stylish 2BR Downtown DeLand • Outdoor Fire Pit & Relaxed Vibes
A swimming pool with a covered patio area, chairs, and a view of the sunset.

16. Spacious & Private Guest Pool House Oasis

Spacious & Private Guest Pool House Oasis
Union Park
9.8 out of 10, Exceptional, (28 reviews)
"The pool house looked exactly like the pictures and it was a very comfortable place to stay. My husband and I really enjoyed it and would definitely stay there again in the future."
United States
Dionne T.
The price is €237
includes taxes & fees
24 Aug - 25 Aug
Spacious & Private Guest Pool House Oasis
A spacious living area with a wooden floor, a ceiling fan, a large sofa, and a rustic barn door.

17. Sunny 5-bedroom Family Central Florida Getaway - AC, WiFi & Private Garden

Sunny 5-bedroom Family Central Florida Getaway - AC, WiFi & Private Garden
Downtown Sanford
10.0 out of 10, Exceptional, (8 reviews)
"Property was well maintained and very clean. Location is amazing and response from host was extremely quick!!!! Highly recommend property!!!"
United States
Anonymous traveller
Sunny 5-bedroom Family Central Florida Getaway - AC, WiFi & Private Garden
A bedroom with a bed, a mirror, a wardrobe, and a floral artwork on the wall.

18. Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!

Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
Casselberry
9.8 out of 10, Exceptional, (54 reviews)
"The residence met all of our needs for an entertaining/relaxing stay."
United States
Kevin K.
The price is €219
includes taxes & fees
24 Aug - 25 Aug
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
A bed with white bedding and two blue pillows with a coral reef design, a tall green plant beside the bed, and a window with grey curtains in the background.

19. Studio in the heart of Orlando

Studio in the heart of Orlando
Azalea Park
9.4 out of 10, Exceptional, (6 reviews)
"Can’t complain. Would re book for sure."
United States
Matthew
The price is €139
includes taxes & fees
25 Aug - 26 Aug
Studio in the heart of Orlando
A compact room with a bed, a small table with plates, a microwave, and a green wall with a neon sign.

20. CUTE and COZY studio w/ jacuzzi!

CUTE and COZY studio w/ jacuzzi!
Azalea Park
8.8 out of 10, Excellent, (8 reviews)
"Very cozy for the two of us! No more space than we needed. It was perfect for our stay. The hot tub was a very nice addition! Highly recommend for couples or single travelers. "
United States
Callie B.
CUTE and COZY studio w/ jacuzzi!
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

Holiday Inn Resort Daytona Beach Oceanfront by IHG

Holiday Inn Resort Daytona Beach Oceanfront by IHG

10/10 Excellent
"Everyone were so nice I literally loved everything I will definitely will be staying there again"
Liset 3-night trip
Posted 2 hours ago
Holiday Inn Resort Daytona Beach Oceanfront by IHG

Find out more about Osteen

Osteen Holiday Homes information

Number of reviews
190
Accommodation
1471 Holiday Homes
Lowest Price
€139
Highest Price
€404