Osteen Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • 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 rentals

Ocean Beach Club

Ocean Beach Club
2.5 star property
Coronado Beach
10.0 out of 10, Exceptional, (4 reviews)
"Great spot, clean room, would love to stay again. "
United States
james
The price is NZ$647
includes taxes & fees
14 Mar - 15 Mar
Ocean Beach Club

The Front Porch

The Front Porch
3.0 star property
Sanford
9.4 out of 10, Exceptional, (3 reviews)
"Enjoyed the place. Nice and relaxing. Close to downtown and lots of options for food. "
United States
Johnny
The Front Porch

Boho Nights

Boho Nights
3.0 star property
Sanford
9.4 out of 10, Exceptional, (11 reviews)
"Wonderful spot, and excellent hosts!"
United States
Thomas
Boho Nights

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, (250 reviews)
"Very clean and comfortable place to spend a night before our cruise. Beds were really comfortable "
United States
Fred
The price is NZ$257
includes taxes & fees
2 Mar - 3 Mar
Mid Century Charm! KSC,Port Canaveral,Cocoa and Bio-Lume Kayak,Pet Friendly!

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 Blue Aztec

At the Center of it All!

At the Center of it All!
Indian River City
9.8 out of 10, Exceptional, (149 reviews)
"Wonderful stay!"
United States
Mercedes d.
The price is NZ$412
includes taxes & fees
25 Mar - 26 Mar
At the Center of it All!

Brand NewPainted Vacation Hse NrUCF PetsOK Fenced

Brand NewPainted Vacation Hse NrUCF PetsOK Fenced
Orlando
9.6 out of 10, Exceptional, (16 reviews)
"My family stayed here with our pup and it was great. Plenty of room for everyone and a great yard space for all of us to enjoy. "
United States
Olivia S.
The price is NZ$483
includes taxes & fees
26 Feb - 27 Feb
Brand NewPainted Vacation Hse NrUCF PetsOK Fenced

Spacious & Private Guest Pool House Oasis

Spacious & Private Guest Pool House Oasis
Union Park
9.8 out of 10, Exceptional, (22 reviews)
"Great location , Very enjoy , private space, would book in the future for sure "
United States
Matt B.
The price is NZ$465
includes taxes & fees
8 Mar - 9 Mar
Spacious & Private Guest Pool House Oasis

Indian River Escape ~ Hot Tub ~ Steps to River

Indian River Escape ~ Hot Tub ~ Steps to River
Titusville
9.6 out of 10, Exceptional, (17 reviews)
"Pros = responsive property owner, clean place, location close to restaurants and movie theater. Cons = ant problem in the kitchen and living room area (beware if you bring a pet with you -- watch their food closely!), thermostat kept resetting to 78 degrees no matter what we turned it to, so it got hot in there. "
United States
Patricia
The price is NZ$435
includes taxes & fees
1 Mar - 2 Mar
Indian River Escape ~ Hot Tub ~ Steps to River

“NATURE IN THE CITY”

“NATURE IN THE CITY”
Union Park
9.0 out of 10, Wonderful, (6 reviews)
" Did not expect to be in someone’s back yard but overall was a pleasant stay. "
United States
Jola L.
The price is NZ$366
includes taxes & fees
6 Mar - 7 Mar
“NATURE IN THE CITY”

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, (38 reviews)
"Very nice clean cottage in a quiet secluded location. "
United States
Ervin M.
The price is NZ$250
includes taxes & fees
9 Mar - 10 Mar
The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.

Totally 80's

Totally 80's
3.0 star property
Sanford
7.6 out of 10, Good, (4 reviews)
"Cute, clean, and comfortable. Located in a safe neighborhood, the house had everything we needed for a great stay. Communication was timely and smooth—highly recommend."
United States
Serge
The price is NZ$233
includes taxes & fees
26 Mar - 27 Mar
Totally 80's

Serenity @ Court

Serenity @ Court
Sanford
9.8 out of 10, Exceptional, (9 reviews)
"Wonderful stay. The location was convenient, the property was clean and spacious, and the host was responsive and friendly. Great choice for anyone visiting the area."
United States
Karen H.
The price is NZ$263
includes taxes & fees
26 Feb - 27 Feb
Serenity @ Court

Sunshine Escape Guesthouse ☀

Sunshine Escape Guesthouse ☀
Orlando
9.6 out of 10, Exceptional, (14 reviews)
"The property was immaculately clean, stylish, roomy and private! It was so convenient to everything yet on the outskirts in a quiet peaceful neighborhood. "
United States
KELLY Z.
The price is NZ$285
includes taxes & fees
10 Mar - 11 Mar
Sunshine Escape Guesthouse ☀

Tiny Hidden Cottage

Tiny Hidden Cottage
Longwood
9.2 out of 10, Wonderful, (62 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 NZ$259
includes taxes & fees
24 Mar - 25 Mar
Tiny Hidden Cottage

The Little Lake Mary Guest House • Warm, Cozy & Inviting

The Little Lake Mary Guest House • Warm, Cozy & Inviting
Lake Mary
9.8 out of 10, Exceptional, (48 reviews)
"Absolutely perfect location! It was truly one of the best places we have stayed at!"
United States
Jaelyn M.
The price is NZ$474
includes taxes & fees
23 Mar - 24 Mar
The Little Lake Mary Guest House • Warm, Cozy & Inviting

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

Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
Orlando
10.0 out of 10, Exceptional, (9 reviews)
"Great host, and stayed connected with us."
United States
Christopher
The price is NZ$427
includes taxes & fees
26 Feb - 27 Feb
Charming 2-bedroom apartment with WiFi, AC in lovely Orlando

Sweetheart Cottage Near Downtown Lake Mary•Queen Bed, Fire Pit & Private Lanai

Sweetheart Cottage Near Downtown Lake Mary•Queen Bed, Fire Pit & Private Lanai
Lake Mary
10.0 out of 10, Exceptional, (18 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 NZ$428
includes taxes & fees
1 Mar - 2 Mar
Sweetheart Cottage Near Downtown Lake Mary•Queen Bed, Fire Pit & Private Lanai

Oceania Beach Club

Oceania Beach Club
3.0 star property
Central Beach
10.0 out of 10, Exceptional, (1 review)
"This place is a gem! We stayed 3 nights in a condo recently. It's the perfect walkable location to the beach and tons of bars and restaurants. The condo was extremely clean and comfortable! It was exactly what we needed. We can't wait to visit again!"
United States
Susan
The price is NZ$854
includes taxes & fees
2 Mar - 3 Mar
Oceania Beach Club

The Jazz Loft

The Jazz Loft
3.0 star property
Sanford
8.4 out of 10, Very good, (7 reviews)
"Amazing! They had everything I needed and were so flexible as I almost needed to extend my stay due to the storm. The vibe was great, very cool and seamless check in and access. Close to everything needed. I will definitely be returning! Can’t wait."
United States
Rae
The Jazz Loft
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.

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

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 favorite 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 depends 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 NZ$186 per night. Entering your travel dates in the search wizard you might find 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 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 a coffee maker.

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.