Book Holiday Homes in Osteen

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Featured Holiday Homes in Osteen

Pirates Cove Resort Studios

Pirates Cove Resort Studios

3 out of 5
3501 S Atlantic Ave Daytona Beach Shores FL
The price is AU$198 per night from 13 May to 14 May
AU$198
13 May - 14 May
includes taxes & fees
When you stay at Pirates Cove Resort Studios in Daytona Beach Shores, you'll be on the beach, a 1-minute drive from Beach at Daytona Beach and 8 minutes from ...
Opens in a new windowPirates Cove Resort Studios
Mid Century Charm! KSC,Port Canaveral,Cocoa and Bio-Lume Kayak,Pet Friendly!

Mid Century Charm! KSC,Port Canaveral,Cocoa and Bio-Lume Kayak,Pet Friendly!

Titusville FL
The price is AU$171 per night from 20 May to 21 May
AU$171
20 May - 21 May
includes taxes & fees
A stay at this vacation home places you in the heart of Titusville, within a 5-minute drive of Judge George Robbins House and Wager House.
Opens in a new windowMid Century Charm! KSC,Port Canaveral,Cocoa and Bio-Lume Kayak,Pet Friendly!
Daytona Beach XI

Daytona Beach XI

3.5 out of 5
701 S Atlantic Ave Daytona Beach FL
With a stay at Daytona Beach XI in Daytona Beach, you'll be next to a golf course, steps from Beach at Daytona Beach and a 2-minute drive from Daytona Beach ...
Opens in a new windowDaytona Beach XI
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 Newly Listed Port Orange  2BR/2BA with Loft Close to  Beach, Dining, & Speedway

Newly Listed Port Orange 2BR/2BA with Loft Close to Beach, Dining, & Speedway

Port Orange FL
Located in Port Orange, this vacation home is within a 15-minute drive of Daytona International Speedway and Beach at Daytona Beach.
Opens in a new window Newly Listed Port Orange 2BR/2BA with Loft Close to Beach, Dining, & Speedway
Hot Tub, Fire Pit, Near the Beach!

Hot Tub, Fire Pit, Near the Beach!

Edgewater FL
The price is AU$361 per night from 13 May to 14 May
AU$361
13 May - 14 May
includes taxes & fees
With a stay at this vacation home in Edgewater (Florida Shores), you'll be within a 10-minute drive of Edgewater United Methodist Church and Edgewater Alliance ...
Opens in a new windowHot Tub, Fire Pit, Near the Beach!
Spacious Orlando Retreat w/ Backyard Oasis • Near Downtown & Attractions

Spacious Orlando Retreat w/ Backyard Oasis • Near Downtown & Attractions

Orlando FL
Located in Orlando (Fairview Shores), this vacation home is within a 10-minute drive of Kia Center and Camping World Stadium.
Opens in a new windowSpacious Orlando Retreat w/ Backyard Oasis • Near Downtown & Attractions
2-bedroom house in beautiful Lake Helen with air conditioning

2-bedroom house in beautiful Lake Helen with air conditioning

Lake Helen FL
A stay at this vacation home places you in the heart of Lake Helen, within a 5-minute drive of Colby Alderman Park and Cassadaga Spiritualist Camp.
Opens in a new window2-bedroom house in beautiful Lake Helen with air conditioning
Brand New Luxury Modern 5BR/4.5BA+Game Room Home

Brand New Luxury Modern 5BR/4.5BA+Game Room Home

Altamonte Springs FL
Located in Altamonte Springs, this vacation home is within a 15-minute drive of Kia Center and Camping World Stadium.
Opens in a new windowBrand New Luxury Modern 5BR/4.5BA+Game Room Home
Bungalow on quiet street close to trendy cafes, pubs, and parks. Dogs welcome!

Bungalow on quiet street close to trendy cafes, pubs, and parks. Dogs welcome!

Orlando FL
Located in Orlando (Baldwin Park), this vacation home is within a 10-minute drive of Kia Center and Camping World Stadium.
Opens in a new windowBungalow on quiet street close to trendy cafes, pubs, and parks. Dogs welcome!
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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.

Osteen Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Osteen vacation homes are the perfect way for you to wing it.

Holiday houses in Osteen let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Osteen in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Osteen adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Osteen with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Osteen vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Osteen Holiday Homes essential information

Accommodation
1405 Holiday Homes
Lowest Price
AU$138
Highest Price
AU$361
Popular accommodation
Pirates Cove Resort Studios, Mid Century Charm! KSC,Port Canaveral,Cocoa and Bio-Lume Kayak,Pet Friendly!, Daytona Beach XI, Newly Listed Port Orange 2BR/2BA with Loft Close to Beach, Dining, & Speedway, Hot Tub, Fire Pit, Near the Beach!, Spacious Orlando Retreat w/ Backyard Oasis • Near Downtown & Attractions, 2-bedroom house in beautiful Lake Helen with air conditioning, Brand New Luxury Modern 5BR/4.5BA+Game Room Home, Bungalow on quiet street close to trendy cafes, pubs, and parks. Dogs welcome!

Top trending hotels in Osteen

Nautilus Inn

Nautilus Inn

2.5 out of 5
1515 S Atlantic Ave Daytona Beach FL
Fully refundableReserve now, pay when you stay
The price is AU$138 per night from 13 May to 14 May
AU$138
13 May - 14 May
includes taxes & fees
In the heart of Daytona Beach, Nautilus Inn is within a 5-minute drive of Daytona Beach Boardwalk and Ocean Walk Shoppes.
Opens in a new windowNautilus Inn
Hilton Orlando/Altamonte Springs

Hilton Orlando/Altamonte Springs

4 out of 5
350 S Northlake Blvd Altamonte Springs FL
Fully refundableReserve now, pay when you stay
The price is AU$196 per night from 31 May to 1 June
AU$196
31 May - 1 June
includes taxes & fees
With a stay at Hilton Orlando/Altamonte Springs in Altamonte Springs, you'll be in the business district, within a 15-minute drive of Kia Center and Cranes Roost ...
Opens in a new windowHilton Orlando/Altamonte Springs
Sheraton Orlando North Hotel

Sheraton Orlando North Hotel

3.5 out of 5
600 N Lake Destiny Dr Maitland FL
Fully refundableReserve now, pay when you stay
The price is AU$171 per night from 26 May to 27 May
AU$171
26 May - 27 May
includes taxes & fees
When you stay at Sheraton Orlando North Hotel in Maitland, you'll be in the business district, within a 15-minute drive of Kia Center and Camping World ...
Opens in a new windowSheraton Orlando North Hotel
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Perry's Ocean Edge Resort

Perry's Ocean Edge Resort

2.5 out of 5
2209 S Atlantic Ave Daytona Beach Shores FL
Fully refundableReserve now, pay when you stay
The price is AU$183 per night from 13 May to 14 May
AU$183
13 May - 14 May
includes taxes & fees
Located in Daytona Beach Shores (Melinda Cook), Perry's Ocean Edge Resort is steps from Beach at Daytona Beach and a 5-minute drive from Daytona Beach ...
Opens in a new windowPerry's Ocean Edge Resort
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See all available properties in Osteen
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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.

Top Picks

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^Subject to availability and chosen travel dates.