Book Holiday Homes in Osteen
More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)
Book up 'til the last second - millions of rooms to crash tonight^
Featured Holiday Homes in Osteen

Pirates Cove Resort Studios

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

Family Friendly home with Fenced in Backyard to enjoy with kids & pets

Lake Front Suite -Close to all Attractions

Pool, 7 Bed 7 Bath, Direct Oceanfront, 4 Kitchens

BEACHFRONT NEWLY remodeled 4 bed/4 Bath 1/2 Block from the Main strip & shops!

Quaint Bungalow walking distance to downtown DeLand, 2 weeks maximum Stay

Deland Hideaway: Firepit + Pool Table on 2 acres!

Beachfront Property, Near Flagler Ave, Early Check in - Late Check Out
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 | 1392 Holiday Homes |
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Lowest Price | |
Highest Price | |
Popular accommodation | Pirates Cove Resort Studios, Mid Century Charm! KSC,Port Canaveral,Cocoa and Bio-Lume Kayak,Pet Friendly!, Family Friendly home with Fenced in Backyard to enjoy with kids & pets, Lake Front Suite -Close to all Attractions, Pool, 7 Bed 7 Bath, Direct Oceanfront, 4 Kitchens, BEACHFRONT NEWLY remodeled 4 bed/4 Bath 1/2 Block from the Main strip & shops! , Quaint Bungalow walking distance to downtown DeLand, 2 weeks maximum Stay, Deland Hideaway: Firepit + Pool Table on 2 acres!, Beachfront Property, Near Flagler Ave, Early Check in - Late Check Out |
Holiday Homes in Osteen
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The Shores Resort & Spa

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Nautilus Inn

Perry's Ocean Edge Resort
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Top picks
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.