Holiday Rentals in Osteen

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Our top choices for Osteen holiday rentals

9.2 out of 10, Wonderful, (240)
"We had a pleasant and comfortable stay. This cost less than a night at a Country Inn and Suites we were looking at but we all got our own bedroom. The beds were comfortable. I would definitely stay at this house again if in the area."
United States
Sherry
The price is €105
includes taxes & fees
5 Jan - 6 Jan 2026
Mid Century Charm! KSC,Port Canaveral,Cocoa and Bio-Lume Kayak,Pet Friendly!

Aparthotel in Daytona Beach

Silver Beach Club
3.5 star property
8.6 out of 10, Excellent, (72)
"Got the Two-Bedroom family suite was very roomy, The pool was nice. The hot tub wasn't working ,we had direct assets to the beaches, the staff was outstanding "
United States
Vickie
The price is €89
includes taxes & fees
4 Jan - 5 Jan 2026
Silver Beach Club

Condo resort in Coronado Beach

Ocean Beach Club
2.5 star property
10.0 out of 10, Exceptional, (1)
"Great spot, clean room, would love to stay again. "
United States
james
The price is €201
includes taxes & fees
4 Jan - 5 Jan 2026
Ocean Beach Club

Apartment in Sanford

Boho Nights
3.0 star property
9.0 out of 10, Wonderful, (7)
"Wonderful spot, and excellent hosts!"
United States
Thomas
Boho Nights

Holiday Home in Royal Oak Golf Country Club

Hello Sunshine 321.. Lift Off
9.0 out of 10, Wonderful, (22)
"The stay was great. The host was nice, a little hiccup with the check in process but the host fixed it for us. Host worked with us to accommodate for late check out. Would gladly stay again "
United States
Khalifa D.
Hello Sunshine 321.. Lift Off

Apartment in Sanford

The Blue Aztec
3.0 star property
9.6 out of 10, Exceptional, (13)
"Great location! Great Dining! "
United States
Lisa
The Blue Aztec

Apartment in Sanford

The Front Porch
3.0 star property
10.0 out of 10, Exceptional, (2)
"What a great space. 2 big bedrooms, and a great front porch apace with a hammock to watch the sunrise. Quite street just blocks from the center of downtown Sanford. I've used their properties 8-10 tines and ive never been disappointed. "
United States
Patrick
The Front Porch
9.6 out of 10, Exceptional, (16)
"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 €146
includes taxes & fees
24 Dec - 25 Dec
Luxury RV nested in a country setting, Only 9 minutes from Sanford airport!
9.8 out of 10, Exceptional, (43)
"Absolutely perfect location! It was truly one of the best places we have stayed at!"
United States
Jaelyn M.
The price is €220
includes taxes & fees
2 Jan - 3 Jan 2026
The Little Lake Mary Guest House • Warm, Cozy & Inviting
9.8 out of 10, Exceptional, (36)
"Love my stay what a wonderful place to get away I didn’t want to leave. It was very clean and had everything you needed for a long stay. Love the porch to have your morning coffee and to start your day Would love to stay again "
United States
Robert & Joy F.
The price is €132
includes taxes & fees
18 Jan - 19 Jan 2026
The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.
8.8 out of 10, Excellent, (14)
"Cozy little place to stay"
United States
Ruth P.
The price is €130
includes taxes & fees
22 Jan - 23 Jan 2026
The Sanford Foodie Guest House

Mobile Home in Union Park

“NATURE IN THE CITY”
2.0 star property
9.0 out of 10, Wonderful, (6)
" Did not expect to be in someone’s back yard but overall was a pleasant stay. "
United States
Jola L.
The price is €193
includes taxes & fees
24 Dec - 25 Dec
“NATURE IN THE CITY”

Cottage in Longwood

Tiny Hidden Cottage
9.2 out of 10, Wonderful, (58)
"Check in process and house were both great. "
United States
Marc H.
The price is €127
includes taxes & fees
24 Dec - 25 Dec
Tiny Hidden Cottage

Holiday Home in Titusville

To The Moon at Titusville/Space Coast/
9.2 out of 10, Wonderful, (31)
"Nice property close to restaurants and activities. Patio was really nice. Enclosed so no bugs. A few minutes walk to the park where we watched a SpaceX launch. Host was very attentive and friendly. Definitely would stay there again. "
United States
Kelly N.
The price is €206
includes taxes & fees
8 Jan - 9 Jan 2026
To The Moon at Titusville/Space Coast/

Apartment in Sanford

Totally 80's
3.0 star property
9.4 out of 10, Exceptional, (3)
"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 €134
includes taxes & fees
12 Jan - 13 Jan 2026
Totally 80's
9.6 out of 10, Exceptional, (10)
"The space was private, comfortable and very clean. Ashlee is an amazing hostess. "
United States
Belinda M.
The price is €125
includes taxes & fees
29 Dec - 30 Dec
A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood

Apartment in Orlando

Tiny house in Orlando
9.6 out of 10, Exceptional, (7)
"The women was very nice and the space was really cozy, and clean. It was close to stores and other places i really liked it"
United States
Jasper
Tiny house in Orlando

Aparthotel in Daytona Beach Shores

Tropical Suites at Sunglow Resort
4.5 star property
8.6 out of 10, Excellent, (61)
"The hotel was so clean and it had a nice pool. The staff were so friendly and helpful! Will definitely stay again in the future!"
United States
Michaela
Tropical Suites at Sunglow Resort
10.0 out of 10, Exceptional, (29)
"This was an excellent place to stay. Perfect for a couple. The entire place was extremely clean and very welcoming. We would absolutely stay here again. "
United States
Craig K.
The price is €160
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy Private Apartment - Stylish & Spotless — No sharing areas
10.0 out of 10, Exceptional, (6)
"Great host, and stayed connected with us."
United States
Christopher
The price is €223
includes taxes & fees
27 Dec - 28 Dec
Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
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 €89 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 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.