Osteen Vacation Rentals

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Our top choices for Osteen vacation rentals

Aparthotel in Daytona Beach

Silver Beach Club
3.0 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
$81 nightly
The price is $92
Jan 7 - Jan 8, 2026
Total with taxes and fees
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
$210 nightly
The price is $236
Jan 6 - Jan 7, 2026
Total with taxes and fees
Ocean Beach Club

Aparthotel in Daytona Beach Shores

Shoreline Suites & Cabana Cottages
2.0 star property
8.8 out of 10, Excellent, (380)
"Love the location and how cute the cabanas are. "
United States
Jennifer
$113 nightly
The price is $128
Jan 6 - Jan 7, 2026
Total with taxes and fees
Shoreline Suites & Cabana Cottages
9.2 out of 10, Wonderful, (242)
"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
$108 nightly
The price is $118
Jan 6 - Jan 7, 2026
Total with taxes and fees
Mid Century Charm! KSC,Port Canaveral,Cocoa and Bio-Lume Kayak,Pet Friendly!

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
$285 nightly
The price is $321
Jan 6 - Jan 7, 2026
Total with taxes and fees
Tropical Suites at Sunglow Resort
8.8 out of 10, Excellent, (38)
"We were initially surprised at the size of this "
United States
Helen P.
$135 nightly
The price is $149
Jan 4 - Jan 5, 2026
Total with taxes and fees
~ Ocean ~ Daze ~ Hideaway ~ Modern Studio near the Beach ~

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.
$198 nightly
The price is $220
Jan 2 - Jan 3, 2026
Total with taxes and fees
“NATURE IN THE CITY”

Aparthotel in Rio Mar Beaches

Fantasy Island Resort, Daytona Beach Shores
4.0 star property
8.8 out of 10, Excellent, (113)
"Clean room polite staff good amenities. "
United States
Werner
$117 nightly
The price is $132
Jan 14 - Jan 15, 2026
Total with taxes and fees
Fantasy Island Resort, Daytona Beach Shores
9.6 out of 10, Exceptional, (21)
"We enjoyed our two night stay. "
United States
Dave H.
$145 nightly
The price is $161
Jan 1 - Jan 2, 2026
Total with taxes and fees
Sea ~ Side ~ Hideaway ~ Studio Condo ~ near the Beach ~
10.0 out of 10, Exceptional, (112)
"this place was exactly as advertised it was great."
United States
carol r.
DIRECT OCEANFRONT CORNER UNIT - OCEAN VIEWS FROM LIVING ROOM AND BEDROOM

Condo in South Peninsula Historic District

#163 Ocean Jewel
8.8 out of 10, Excellent, (30)
"Great place"
United States
Jasmin
$150 nightly
The price is $166
Jan 3 - Jan 4, 2026
Total with taxes and fees
#163 Ocean Jewel

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
$215 nightly
The price is $241
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Front Porch
2.0 star property
10.0 out of 10, Exceptional, (1)
"It served its purpose for 2 nights. Wouldn’t recommend more than 2 people. Clean cozy and had come coffee in there. Very nice and responsive host. Perfect for a quick trip as it is on the smaller side but again it was perfect for my stay. "
United States
Mackenzie H.
$175 nightly
The price is $194
Jan 5 - Jan 6, 2026
Total with taxes and fees
Clean Luxury Boho in Orlando 25 min from Theme Parks
9.6 out of 10, Exceptional, (4)
"Loved the proximity to the wonderful bike and walking trail!"
United States
Sharon H.
$288 nightly
The price is $320
Jan 1 - Jan 2, 2026
Total with taxes and fees
COZY 2BR Condo with Pool bike-trail near lake beach fireplace SAFE community
8.8 out of 10, Excellent, (15)
"Cozy little place to stay"
United States
Ruth P.
$128 nightly
The price is $141
Jan 11 - Jan 12, 2026
Total with taxes and fees
The Sanford Foodie Guest House

Vacation Home in Daytona Beach Shores

Pirates Cove Resort Studios
3.0 star property
6.4 out of 10, (145)
"The room was clean and in a wonderful spot. Clean and easy access. I will be booking here again."
United States
Kiya
$139 nightly
The price is $148
Jan 4 - Jan 5, 2026
Total with taxes and fees
Pirates Cove Resort Studios

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
$140 nightly
The price is $157
Jan 4 - Jan 5, 2026
Total with taxes and fees
Totally 80's
9.4 out of 10, Exceptional, (10)
"Perfect place! My husband and I enjoyed our stay. The balcony facing the beach was amazing!! Overalll would stay there again :) "
United States
Savannah T.
$157 nightly
The price is $174
Jan 11 - Jan 12, 2026
Total with taxes and fees
Beachfront Suite in Daytona Beach, FL with Ocean Views!
9.8 out of 10, Exceptional, (36)
"much needed getaway! Lala's is comfortable, clean, fun, relaxing. Everything a beach getaway should be! "
United States
Stephanie S.
$244 nightly
The price is $270
Jan 5 - Jan 6, 2026
Total with taxes and fees
LaLa`s Beach House - Walking Distance to the Beach and Shopping

Apartment in Sanford

Boho Nights
3.0 star property
9.0 out of 10, Wonderful, (7)
"Wonderful spot, and excellent hosts!"
United States
Thomas
$145 nightly
The price is $162
Jan 18 - Jan 19, 2026
Total with taxes and fees
Boho Nights
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Osteen vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Osteen vacation 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 low season months. For more hustle and bustle, you may prefer to visit Osteen in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $92 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Osteen rentals

At Expedia, we put the best Osteen vacation 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 vacation.

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 vacation rentals in Osteen?

Yes, we have vacation rentals in Osteen close to Pell's Citrus & Nursery, or you can choose a more secluded option if you're looking for a relaxing stay.

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

Pirates Cove Resort Studios: You might want to consider this vacation home rental near Osteen, which 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 vacation rentals are there in Osteen?

Expedia has 3 vacation 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 vacation rental in Osteen like?

Vacation rentals are private properties you can stay in for several days or longer in Osteen. Vacation rentals provide amenities such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a sanitized environment, vacation rentals can provide a sense of privacy away from public hotel elevators and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a family trip.