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
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 ...
Pirates 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
A stay at this vacation home places you in the heart of Titusville, within a 5-minute drive of Clifton Lake and Judge George Robbins House.
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

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

Maitland
A stay at this vacation home places you in the heart of Maitland, a 3-minute drive from Winter Park Village and 6 minutes from Full Sail University.
Family Friendly home with Fenced in Backyard to enjoy with kids & pets
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Lake Front Suite -Close to all Attractions

Lake Front Suite -Close to all Attractions

Apopka
When you stay at this vacation home in Apopka, you'll be on the waterfront, within a 15-minute drive of Camping World Stadium and Kia Center.
Lake Front Suite -Close to all Attractions
Pool, 7 Bed 7 Bath, Direct Oceanfront, 4 Kitchens

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

Port Orange
When you stay at this vacation home in Port Orange, you'll be on the beach, within a 15-minute drive of Beach at Daytona Beach and Beach Street.
Pool, 7 Bed 7 Bath, Direct Oceanfront, 4 Kitchens
BEACHFRONT NEWLY remodeled 4 bed/4 Bath 1/2 Block from the Main strip & shops!

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

New Smyrna Beach
With a stay at this vacation home in New Smyrna Beach (Walker Grant), you'll be steps from New Smyrna Beach and 3 minutes by foot from Flagler Avenue.
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

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

DeLand
With a stay at this vacation home, you'll be centrally located in DeLand, within a 15-minute drive of Blue Spring State Park and Stetson University.
Quaint Bungalow walking distance to downtown DeLand, 2 weeks maximum Stay
Deland Hideaway: Firepit + Pool Table on 2 acres!

Deland Hideaway: Firepit + Pool Table on 2 acres!

DeLand
With a stay at this vacation home in DeLand, you'll be within a 15-minute drive of Blue Spring State Park and Lake Beresford Park.
Deland Hideaway: Firepit + Pool Table on 2 acres!
Beachfront Property, Near Flagler Ave, Early Check in - Late Check Out

Beachfront Property, Near Flagler Ave, Early Check in - Late Check Out

New Smyrna Beach
With a stay at this vacation home in New Smyrna Beach (Colin Park), you'll be steps from New Smyrna Beach and a 2-minute drive from Coronado Community United ...
Beachfront Property, Near Flagler Ave, Early Check in - Late Check Out
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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
1392 Holiday Homes
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

Top trending hotels in Osteen

The Shores Resort & Spa

The Shores Resort & Spa

4 out of 5
2637 S Atlantic Avenue, Daytona Beach Shores, FL
Fully refundableReserve now, pay when you stay
Located in Daytona Beach Shores, The Shores Resort & Spa is on the Strip, within a 10-minute drive of Jackie Robinson Ballpark and Ocean Walk Shoppes.
The Shores Resort & Spa
La Quinta Inn & Suites by Wyndham Orlando UCF

La Quinta Inn & Suites by Wyndham Orlando UCF

3 out of 5
11805 Research Pkwy, Orlando, FL
Fully refundableReserve now, pay when you stay
When you stay at La Quinta Inn & Suites by Wyndham Orlando UCF in Orlando, you'll be in the business district, just steps from Central Florida Research Park ...
La Quinta Inn & Suites by Wyndham Orlando UCF
Nautilus Inn

Nautilus Inn

2.5 out of 5
1515 S Atlantic Ave, Daytona Beach, FL
Fully refundableReserve now, pay when you stay
In the heart of Daytona Beach, Nautilus Inn is within a 5-minute drive of Daytona Beach Boardwalk and Ocean Walk Shoppes.
Nautilus Inn
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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
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 ...
Perry's Ocean Edge Resort
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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.

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^Subject to availability and chosen travel dates.