Osteen Holiday Rentals

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Our top choices for Osteen holiday rentals

The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.

The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.
Lake Helen
9.8 out of 10, Exceptional, (41 reviews)
"Very nice clean cottage in a quiet secluded location. "
United States
Ervin M.
The price is AU$212
includes taxes & fees
18 Apr - 19 Apr
The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.

Tiny Hidden Cottage

Tiny Hidden Cottage
Longwood
9.4 out of 10, Exceptional, (66 reviews)
"Great little cottage, it was easy to locate and access the property. Nice quiet area and we really enjoyed our stay."
United States
Anna M.
The price is AU$205
includes taxes & fees
19 Apr - 20 Apr
Tiny Hidden Cottage

At the Center of it All!

At the Center of it All!
Indian River City
9.8 out of 10, Exceptional, (151 reviews)
"Wonderful stay!"
United States
Mercedes d.
The price is AU$328
includes taxes & fees
21 Apr - 22 Apr
At the Center of it All!

“Best Stay Ever” – Recent Guest

“Best Stay Ever” – Recent Guest
Lake Mary
9.8 out of 10, Exceptional, (51 reviews)
"Everything was wonderful! We loved the location and the house was cozy and comfortable. "
United States
Mike B.
The price is AU$374
includes taxes & fees
29 Apr - 30 Apr
“Best Stay Ever” – Recent Guest

Boho Nights

Boho Nights
3.0 star property
Sanford
9.6 out of 10, Exceptional, (14 reviews)
"Wonderful spot, and excellent hosts!"
United States
Thomas
The price is AU$200
includes taxes & fees
19 Apr - 20 Apr
Boho Nights

Cozy Private Apartment - Stylish & Spotless — No sharing areas

Cozy Private Apartment - Stylish & Spotless — No sharing areas
Orlando
10.0 out of 10, Exceptional, (31 reviews)
"Awesome place to stay! Clean as a whistle, and nice and private! "
United States
N T.
The price is AU$260
includes taxes & fees
19 Apr - 20 Apr
Cozy Private Apartment - Stylish & Spotless — No sharing areas

Yania's Cozy Getaway

Yania's Cozy Getaway
Azalea Park
9.6 out of 10, Exceptional, (14 reviews)
"Very quiet and clean. Great place to relax."
United States
Anonymous traveller
The price is AU$248
includes taxes & fees
21 Apr - 22 Apr
Yania's Cozy Getaway

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 AU$224
includes taxes & fees
13 May - 14 May
Studio in the heart of Orlando

The Jazz Loft

The Jazz Loft
3.0 star property
Sanford
8.4 out of 10, Very good, (7 reviews)
"Location, location, location!!! What a cute and fun space. I thoroughly enjoyed my entire Jazz Loft experience. Look fwd to next trip! "
United States
Deborah
The price is AU$194
includes taxes & fees
16 Apr - 17 Apr
The Jazz Loft

Bella Breeze

Bella Breeze
2.5 star property
Sanford
9.8 out of 10, Exceptional, (12 reviews)
"The place was very clean, the bed was comfortable, the communication with owners was excellent. It was a nice place to stay while we were in town. "
United States
Michael
The price is AU$200
includes taxes & fees
19 Apr - 20 Apr
Bella Breeze

Mira Bella South - 1BR Tiny Home in Lake Helen

Mira Bella South - 1BR Tiny Home in Lake Helen
Lake Helen
10.0 out of 10, Exceptional, (6 reviews)
"I’m so glad I found this place. It’s a perfect location— close enough to get to Daytona easily, but it’s a peaceful and quiet country paradise to relax at the end of the day. The host is thoughtful and responds immediately and the place was spotless with everything you could possibly need. An easy 5 stars, and I’d give it a 6th for being able to view the rocket launches if they’d let me. The donkey and ducks deserve a few stars too."
United States
Trent
The price is AU$229
includes taxes & fees
16 Apr - 17 Apr
Mira Bella South - 1BR Tiny Home in Lake Helen

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!
Whispering Oaks
9.2 out of 10, Wonderful, (261 reviews)
"Very clean and comfortable place to spend a night before our cruise. Beds were really comfortable "
United States
Fred
The price is AU$174
includes taxes & fees
27 Apr - 28 Apr
Mid Century Charm! KSC,Port Canaveral,Cocoa and Bio-Lume Kayak,Pet Friendly!

Spacious & Private Guest Pool House Oasis

Spacious & Private Guest Pool House Oasis
Union Park
9.8 out of 10, Exceptional, (22 reviews)
"Great stay in Orlando"
United States
Eddie T.
The price is AU$389
includes taxes & fees
30 Apr - 1 May
Spacious & Private Guest Pool House Oasis

Unwind in DeLand: Fire Pit Nights & Downtown Delights!

Unwind in DeLand: Fire Pit Nights & Downtown Delights!
Downtown DeLand Historic District
8.8 out of 10, Excellent, (6 reviews)
"Wonderful quick getaway for the Microbrew fest."
United States
Paul E.
The price is AU$322
includes taxes & fees
26 Apr - 27 Apr
Unwind in DeLand: Fire Pit Nights & Downtown Delights!

The Blue Aztec

The Blue Aztec
3.0 star property
Sanford
9.6 out of 10, Exceptional, (13 reviews)
"Great location! Great Dining! "
United States
Lisa
The price is AU$291
includes taxes & fees
19 Apr - 20 Apr
The Blue Aztec

The Cozy Crash Pad: Tiny House Experience

The Cozy Crash Pad: Tiny House Experience
Orlando
9.0 out of 10, Wonderful, (24 reviews)
"The host communicated when needed. A great stay for a quick trip. "
United States
Jamee O.
The price is AU$211
includes taxes & fees
20 Apr - 21 Apr
The Cozy Crash Pad: Tiny House Experience

The Front Porch

The Front Porch
3.0 star property
Sanford
9.2 out of 10, Wonderful, (5 reviews)
"Enjoyed the place. Nice and relaxing. Close to downtown and lots of options for food. "
United States
Johnny
The price is AU$302
includes taxes & fees
19 Apr - 20 Apr
The Front Porch

Charming 2-bedroom apartment with WiFi, AC in lovely Orlando

Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
Orlando
9.8 out of 10, Exceptional, (12 reviews)
"Great host, and stayed connected with us."
United States
Christopher
The price is AU$361
includes taxes & fees
16 Apr - 17 Apr
Charming 2-bedroom apartment with WiFi, AC in lovely Orlando

Salty ~ Tides Studio Condo near the Beach

Salty ~ Tides Studio Condo near the Beach
Bostwick Park
9.2 out of 10, Wonderful, (25 reviews)
"Both the beach view and the pool were great"
United States
rick b.
The price is AU$252
includes taxes & fees
21 Apr - 22 Apr
Salty ~ Tides Studio Condo near the Beach

Relax Tonight. Cozy, Quiet and Super Clean.

Relax Tonight. Cozy, Quiet and Super Clean.
Lake Mary
10.0 out of 10, Exceptional, (19 reviews)
"An excellent location for stays in Lake Mary. It has everything a single or a couple needs to feel at home."
United States
Kanzeda C.
The price is AU$353
includes taxes & fees
6 May - 7 May
Relax Tonight. Cozy, Quiet and Super Clean.
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

Find out more about Osteen

Everything you need to know about Osteen holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Osteen holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Osteen holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Osteen holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Osteen. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Osteen holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Osteen holiday rentals we have selected for you start as low as AU$152 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Osteen rentals

At Expedia, we put the best Osteen holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Osteen rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Osteen holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Osteen. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Osteen?

Yes, there are holiday rentals in Osteen close to Pell's Citrus & Nursery, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Osteen has to offer?

Pirates Cove Resort Studios: This holiday home rental outside of Osteen is on the beach, and equipped with air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a stovetop, a microwave and kitchenware.

How many holiday rentals are there in Osteen?

Expedia has 3 holiday rentals for your stay in Osteen.

What’s there to see and do in Osteen?

Lake Jesup and Lake Monroe Conservation Area are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Pell's Citrus & Nursery. Lake Jesup Conservation Area and Lake Ashby Park are other places to visit while you're in town.

What’s a holiday rental in Osteen like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Osteen. Holiday rentals feature extras such as WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from public hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for families.