Holiday Rentals in Osteen

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Our top choices for Osteen holiday rentals

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 €195
includes taxes & fees
29 Mar - 30 Mar
The Blue Aztec

Boho Nights

Boho Nights
3.0 star property
Sanford
9.4 out of 10, Exceptional, (12 reviews)
"Wonderful spot, and excellent hosts!"
United States
Thomas
The price is €128
includes taxes & fees
30 Mar - 31 Mar
Boho Nights

“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 €194
includes taxes & fees
27 Mar - 28 Mar
“NATURE IN THE CITY”

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 €200
includes taxes & fees
30 Mar - 31 Mar
At the Center of it All!

The Front Porch

The Front Porch
3.0 star property
Sanford
9.0 out of 10, Wonderful, (4 reviews)
"Enjoyed the place. Nice and relaxing. Close to downtown and lots of options for food. "
United States
Johnny
The price is €186
includes taxes & fees
31 Mar - 1 Apr
The Front Porch

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, (40 reviews)
"Very nice clean cottage in a quiet secluded location. "
United States
Ervin M.
The price is €133
includes taxes & fees
30 Mar - 31 Mar
The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.

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, (256 reviews)
"Very clean and comfortable place to spend a night before our cruise. Beds were really comfortable "
United States
Fred
The price is €112
includes taxes & fees
6 Apr - 7 Apr
Mid Century Charm! KSC,Port Canaveral,Cocoa and Bio-Lume Kayak,Pet Friendly!

Totally 80's

Totally 80's
3.0 star property
Sanford
7.8 out of 10, Good, (7 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 €121
includes taxes & fees
29 Mar - 30 Mar
Totally 80's

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 €128
includes taxes & fees
30 Mar - 31 Mar
The Jazz Loft

Luxury RV nested in a country setting, Only 9 minutes from Sanford airport!

Luxury RV nested in a country setting, Only 9 minutes from Sanford airport!
Geneva
9.6 out of 10, Exceptional, (18 reviews)
"This place was perfect for me and my dad and my son to stay at while my son played ball close by."
United States
Kevin D.
The price is €148
includes taxes & fees
1 Apr - 2 Apr
Luxury RV nested in a country setting, Only 9 minutes from Sanford airport!

Spring Break Special Private Lanai & Outdoor Oasis

Spring Break Special Private Lanai & Outdoor Oasis
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.
Spring Break Special Private Lanai & Outdoor Oasis

Sunshine Escape Guesthouse ☀

Sunshine Escape Guesthouse ☀
Orlando
9.4 out of 10, Exceptional, (15 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 €151
includes taxes & fees
6 Apr - 7 Apr
Sunshine Escape Guesthouse ☀

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 €139
includes taxes & fees
27 Mar - 28 Mar
Serenity @ Court

Tiny Hidden Cottage

Tiny Hidden Cottage
Longwood
9.4 out of 10, Exceptional, (63 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 €129
includes taxes & fees
31 Mar - 1 Apr
Tiny Hidden Cottage

Yania's Cozy Getaway

Yania's Cozy Getaway
Azalea Park
9.6 out of 10, Exceptional, (13 reviews)
"We had an excellent stay while we attended EDCO. We were able to check-in early and the place was cozy and had everything we needed for our long weekend, even a secluded patio where we enjoyed our coffee time The location was perfect...only 15 minutes away from the venue and all the places we planned to eat. We would definitely stay here again!"
United States
Sabrina D.
The price is €154
includes taxes & fees
30 Mar - 31 Mar
Yania's Cozy Getaway

Disney Spring Break Stylish Retreat with Private Pool & Magical Night Lights

Disney Spring Break Stylish Retreat with Private Pool & Magical Night Lights
Lake Mary
9.6 out of 10, Exceptional, (49 reviews)
"Absolutely perfect location! It was truly one of the best places we have stayed at!"
United States
Jaelyn M.
The price is €231
includes taxes & fees
7 Apr - 8 Apr
Disney Spring Break Stylish Retreat with Private Pool & Magical Night Lights

The Blue Aztec

The Blue Aztec
Sanford
10.0 out of 10, Exceptional, (13 reviews)
"Came to the area for some live music at a local venue one evening. Blue Aztec was very clean and comfortable, oh and AC was ice cold! "
United States
Rob
The price is €153
includes taxes & fees
29 Mar - 30 Mar
The Blue Aztec

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 €241
includes taxes & fees
28 Mar - 29 Mar
Spacious & Private Guest Pool House Oasis

Bella Breeze

Bella Breeze
2.5 star property
Sanford
9.6 out of 10, Exceptional, (10 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 €128
includes taxes & fees
13 Apr - 14 Apr
Bella Breeze

Home Sweet Home

Home Sweet Home
Sanford
9.6 out of 10, Exceptional, (24 reviews)
"It was a great location for our trip and everything was true to the listing. The host was very responsive and helpful."
United States
K B.
The price is €283
includes taxes & fees
31 Mar - 1 Apr
Home Sweet Home
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, apart-hotels, 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 €104 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 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 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 Monroe Conservation Area and Lake Jesup 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.