Osteen Holiday Homes from €197: Search Top House Rentals

Osteen Holiday Homes
Florida
United States of America
Holiday Homes
Expedia.ie

Osteen Travel Guide Hotels in Osteen Holiday Rentals in Osteen Osteen Car Hire Osteen Holiday Packages

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Osteen holiday homes

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

A living room with two patterned armchairs, a wooden coffee table, a potted plant, a large window with blinds, a wall-mounted TV, and a small shelf with decorative items.

A bedroom with a bed, a TV mounted on the wall, a dresser, and a potted plant.

A dining area with a wooden table set for four, a refrigerator, and a kitchen with a tiled backsplash and wooden cabinets.

1. Home Sweet Home

Home Sweet Home

Sanford

9.4 out of 10, Exceptional, (33 reviews)

9.4/10

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!"

Janice M.

The price is €281

€281

includes taxes & fees

19 Oct - 20 Oct

Home Sweet Home

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

A modern kitchen with a black countertop, a sink, a window, and a chandelier.

A modern living room with a dark grey sectional sofa, a wooden floor, and a potted plant in the foreground.

A dining area with a wooden table, black chairs, a ceiling fan, and a door with a wooden panel.

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)

9.6/10

Exceptional

(28 reviews)

"Beautiful place to stay near the airport "

Rodney

The price is €336

€336

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.

A modern kitchen with white cabinets, granite countertops, and a wooden floor.

A kitchen with white cabinets, a dishwasher, and a built-in pantry with shelves.

🍽️ Gather and graze, this vibrant dining nook set the stage for shared meals and conversation

3. Serene Sunshine State Escape

Serene Sunshine State Escape

Deltona Lakes

10.0 out of 10, Exceptional, (3 reviews)

10/10

Exceptional

(3 reviews)

"Very nice host and great place to stay!"

Wesley L.

The price is €426

€426

includes taxes & fees

21 Oct - 22 Oct

Serene Sunshine State Escape

A van interior with a sofa, pillows, a television, and an emergency door.

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)

10/10

Exceptional

(1 review)

"The home was spacious, pristine & one of the best stocked rentals we have stayed at."

RICHARD F.

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.

A living room with a sofa, a coffee table, a TV, and a ceiling fan.

A narrow hallway with beige tiled flooring, white walls, and a door at the end.

A two-story house with a small front yard and a satellite dish.

5. River City Retreat

River City Retreat

Sanford

9.6 out of 10, Exceptional, (21 reviews)

9.6/10

Exceptional

(21 reviews)

"Great place and quick, simple check in."

Dennis L.

The price is €197

€197

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.

A sunlit patio with a wooden floor, a bench, and outdoor furniture.

A bedroom with a wooden bed, a nightstand, a dresser, a mirror, and a ceiling fan.

A kitchen with white cabinets, a white refrigerator, a window with a view, and a coffee maker.

6. Bright & Cozy 3BR Retreat with Timeless Charm

Bright & Cozy 3BR Retreat with Timeless Charm

Sanford

10.0 out of 10, Exceptional, (1 review)

10/10

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!"

Lindsay P.

Bright & Cozy 3BR Retreat with Timeless Charm

A modern kitchen with white cabinetry, a large island with stools, and a refrigerator.

A living room with a beige sectional sofa, a coffee table, and a TV on a stand.

A sunlit porch with wicker furniture, a door with a keypad, and a window with blinds.

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)

10/10

Exceptional

(3 reviews)

"Loved staying at this place! Cute home and the renters gave us some great ideas."

Maria K.

The price is €259

€259

includes taxes & fees

9 Oct - 10 Oct

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

An outdoor seating area with a view of a sunset.

A hotel room with two single beds, a desk with a chair, a large mirror, and a ceiling fan.

A house with a front yard, surrounded by trees and plants.

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)

10/10

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."

Debra O.

Welcoming 2-bedroom house with AC in charming Sanford

A modern kitchen with stainless steel appliances, white cabinetry, and a central island.

A modern kitchen with white cabinets, a central island, and a dining area with wooden chairs.

A gaming setup with a TV, gaming consoles, and Star Wars figurines.

A living room with a foosball table, a television, and a Star Wars figure.

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)

10/10

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. "

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.

A modern kitchen with white cabinets, stainless steel appliances, and wooden flooring.

A dining area with a wooden table set for six, surrounded by chairs.

A cozy living room with a wooden ceiling, a large flat-screen TV, a beige sofa, a wicker chair, a coffee table, and a small side table with a lamp.

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)

10/10

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!"

Wendy K.

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.

A bedroom with a bed, a desk, and two rugs.

A modern house with a covered patio, large windows, and a dining area.

A dining area with a wooden table, chairs, and a chandelier.

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.

A flat-screen TV on a wooden stand with a cactus beside it, a window with curtains, and three framed pictures on the wall.

A two-story house with a covered porch and a small outdoor seating area.

A two-story house with a front porch, a black door, and a small seating area with chairs.

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)

10/10

Exceptional

(3 reviews)

"Five stars, nice large house, excellent location. I would rent again. "

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.

A bedroom with two beds, a window with blinds, a painting on the wall, and a ceiling light.

A modern living room with a flat-screen TV, a dining area with a white table and chairs, and a large window with blinds.

A room with a large flat-screen TV on a white stand, a blue door, and storage units with board games.

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)

9.6/10

Exceptional

(7 reviews)

"Great host, clean and comfortable house, quiet neighborhood. "

Russ B.

The price is €281

€281

includes taxes & fees

12 Oct - 13 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.

A modern kitchen with built-in appliances, a dining area with a table and chairs, a large window, and a ceiling fan.

A kitchen pantry with shelves holding glassware, bowls, and plates.

A modern kitchen with a central island, stainless steel appliances, and a ceiling fan.

14. The Getaway Experience

The Getaway Experience

Deltona Lakes

9.2 out of 10, Wonderful, (14 reviews)

9.2/10

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! "

Kris V.

The price is €371

€371

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.

A modern kitchen with blue cabinets, a large island, a dining area, and a view of the outdoors.

A living room with a sofa, coffee table, TV, and framed artwork on the walls.

A dining area with a table set for four, a sofa, and a coffee table in a room with white walls and a large window.

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)

9.4/10

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!"

Miriam R.

The price is €408

€408

includes taxes & fees

11 Oct - 12 Oct

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

A white building with a green door and a small porch area with plants.

A sunroom with a sofa, armchair, and a table with plants.

A dining area with a round table and chairs, a whiteboard, and a painting on the wall.

A neatly arranged bedroom with a bed, a television on a side table, a bookshelf, and a window with curtains.

16. Charming home with big patio!

Charming home with big patio!

Oviedo

9.8 out of 10, Exceptional, (26 reviews)

9.8/10

Exceptional

(26 reviews)

"Host was very helpful. It’s a nice place to stay. Very comfortable."

Sandranel B.

The price is €339

€339

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.

A modern living room with a blue sofa, a glass coffee table, and a dining area with four chairs.

A patio area with wicker furniture, a glass-top table, and a beige umbrella.

A modern living room with a flat-screen TV mounted above a fireplace, a glass coffee table, and a leather sofa.

17. Breezy Escape in Oviedo

Breezy Escape in Oviedo

Oviedo

10.0 out of 10, Exceptional, (12 reviews)

10/10

Exceptional

(12 reviews)

"Home was beautiful, neighborhood was very nice. Definitely staying again when in the area!"

Jeremy B.

The price is €317

€317

includes taxes & fees

12 Oct - 13 Oct

Breezy Escape in Oviedo

A bedroom with a bed, two bedside tables, a ceiling fan, and framed pictures on the wall.

A kitchen with a sink, stove, microwave, and cabinets.

A dining area with a wooden table and chairs, a chandelier, a cabinet, and a metal shelf with plants and decor.

A patio with a table and chairs, a hanging plant, and a patterned rug.

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 €1,137

€1,137

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.

A single-story house with a front porch, a mailbox, and a door with a number plate.

A living room with a dark blue wall, a flat-screen TV mounted above a black entertainment unit, a dark brown sectional sofa, a wooden coffee table with a small plant, and a dining table with chairs.

A black leather sofa with two patterned cushions, a window with blinds, and a view of a backyard with a wooden fence.

19. Charming 3-bedroom home away from home.

Charming 3-bedroom home away from home.

Chuluota

9.8 out of 10, Exceptional, (25 reviews)

9.8/10

Exceptional

(25 reviews)

"Perfect stay while visiting local family. "

Kerri W.

The price is €344

€344

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.

A modern kitchen with white cabinets, a microwave, and a refrigerator. There is a dining area with a table and chairs.

A residential house with a garage, a driveway with a geometric pattern, and a lawn.

A modern room with a flat-screen TV, a white dining table, potted plants, a small round table with decorative items, and a window with blinds.

20. The Longwood Escape • Modern Private Guesthouse Near Orlando

The Longwood Escape • Modern Private Guesthouse Near Orlando

Longwood

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.

View all properties