Osteen Vacation Rentals

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Our top choices for Osteen vacation rentals

Hello Sunshine 321.. Lift Off

Hello Sunshine 321.. Lift Off
Royal Oak Golf Country Club
8.8 out of 10, Excellent, (23 reviews)
"Great location for the wedding we attended. Perfect size for our quick trip. We enjoyed staying here."
United States
Ed S.
$307 nightly
The price is $339
May 9 - May 10
Total with taxes and fees
Hello Sunshine 321.. Lift Off

At the Center of it All!

At the Center of it All!
Indian River City
9.8 out of 10, Exceptional, (152 reviews)
"Wonderful stay!"
United States
Mercedes d.
$210 nightly
The price is $232
May 11 - May 12
Total with taxes and fees
At the Center of it All!

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
$200 nightly
The price is $225
May 11 - May 12
Total with taxes and fees
The Front Porch

Cozy 4bed 2bth villa - daytona beach

Cozy 4bed 2bth villa - daytona beach
4.0 star property
Deltona Lakes
10.0 out of 10, Exceptional, (1 review)
"Very clean amd conveniently located "
United States
joe
$412 nightly
The price is $463
May 12 - May 13
Total with taxes and fees
Cozy 4bed 2bth villa - daytona beach

Ocean Beach Club

Ocean Beach Club
3.0 star property
Coronado Beach
9.8 out of 10, Exceptional, (16 reviews)
"The place was great, clean, right in the beach. Perfect spot!"
United States
Andrew
$341 nightly
The price is $384
May 17 - May 18
Total with taxes and fees
Ocean Beach Club

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, (267 reviews)
"Our family stayed here for one night before a cruise, and it was ideal for the 7 of us. The proximity to the cruise terminal was beneficial, the check-in process was simple, and property was in good condition."
United States
Thesley
$112 nightly
The price is $123
May 20 - May 21
Total with taxes and fees
Mid Century Charm! KSC,Port Canaveral,Cocoa and Bio-Lume Kayak,Pet Friendly!

Oceania Beach Club

Oceania Beach Club
3.0 star property
Central Beach
10.0 out of 10, Exceptional, (4 reviews)
"The condo was absolutely beautiful. The staff was amazing. Definitely going to book again!"
United States
CATHERINE
$428 nightly
The price is $472
May 12 - May 13
Total with taxes and fees
Oceania Beach Club

Cozy studio in fabulous Orlando close to everything

Cozy studio in fabulous Orlando close to everything
Orlando
9.8 out of 10, Exceptional, (19 reviews)
"The host is wonderful and the place was exactly what I needed. The bed was extremely comfortable and the neighborhood really quiet. I will definitely be back and stay here again."
United States
Robin L.
$150 nightly
The price is $166
May 9 - May 10
Total with taxes and fees
Cozy studio in fabulous Orlando close to everything

Tiny Hidden Cottage

Tiny Hidden Cottage
Longwood
9.4 out of 10, Exceptional, (67 reviews)
"Great place, found the heater, thank you!Would stay again, just pull the bed away from the wall for us old folk "
United States
Susan J.
$135 nightly
The price is $148
May 11 - May 12
Total with taxes and fees
Tiny Hidden Cottage

Silver Beach Club

Silver Beach Club
3.0 star property
Daytona Beach
8.8 out of 10, Excellent, (113 reviews)
"Rooms were clean and staff was super helpful "
United States
Tina
$96 nightly
The price is $108
May 12 - May 13
Total with taxes and fees
Silver Beach Club

Hot Tub, Fire Pit, Near the Beach!

Hot Tub, Fire Pit, Near the Beach!
Florida Shores
10.0 out of 10, Exceptional, (35 reviews)
"Overall great location and the house was perfect."
United States
Becca W.
$236 nightly
The price is $262
May 11 - May 12
Total with taxes and fees
Hot Tub, Fire Pit, Near the Beach!

Oceanfront Penthouse Pool Hot Tub Beach Access

Oceanfront Penthouse Pool Hot Tub Beach Access
2.0 star property
Daytona Beach Shores
10.0 out of 10, Exceptional, (2 reviews)
"The stay was so great I wish we could have stayed longer. I will be back. "
United States
Danielle
$612 nightly
The price is $689
May 12 - May 13
Total with taxes and fees
Oceanfront Penthouse Pool Hot Tub Beach Access

Bella Breeze

Bella Breeze
2.5 star property
Sanford
9.8 out of 10, Exceptional, (12 reviews)
"Great location for restaurants and river trail. Very well stocked so it is an easy and comfortable stay."
United States
Nancy
$141 nightly
The price is $158
May 11 - May 12
Total with taxes and fees
Bella Breeze

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
$220 nightly
The price is $237
May 17 - May 18
Total with taxes and fees
The Blue Aztec

Quiet retreat 15 minutes from downtown Orlando, Orlando Airport International!

Quiet retreat 15 minutes from downtown Orlando, Orlando Airport International!
Azalea Park
9.6 out of 10, Exceptional, (23 reviews)
"We came to Orlando for my uncle’s funeral and the love and hospitality Ms.Yolette showed our family was appreciated and will never be forgotten. "
United States
Beulah B.
$254 nightly
The price is $281
May 10 - May 11
Total with taxes and fees
Quiet retreat 15 minutes from downtown Orlando, Orlando Airport International!

Totally 80's

Totally 80's
3.0 star property
Sanford
8.4 out of 10, Very Good, (10 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
$135 nightly
The price is $151
May 10 - May 11
Total with taxes and fees
Totally 80's

Tranquil 3-bedroom house in Sanford with AC, WiFi

Tranquil 3-bedroom house in Sanford with AC, WiFi
Sanford
9.8 out of 10, Exceptional, (26 reviews)
"This home was great for our family. What we particularly liked were all the extras - laundry detergent, coffee pods, water in the fridge etc. etc. We enjoyed the neighborhood too. It was a great stay."
United States
Melanie S.
$360 nightly
The price is $398
May 10 - May 11
Total with taxes and fees
Tranquil 3-bedroom house in Sanford with AC, WiFi

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)
"Very clean and hospitable. Recommend staying here for sure!"
United States
Kyle Y.
$233 nightly
The price is $259
May 10 - May 11
Total with taxes and fees
Charming 2-bedroom apartment with WiFi, AC in lovely Orlando

3Bdrm Home Near Downtown Orlando and Winter park

3Bdrm Home Near Downtown Orlando and Winter park
Orlando
10.0 out of 10, Exceptional, (4 reviews)
"Nice place , will book again "
United States
Kadijah J.
$357 nightly
The price is $396
May 11 - May 12
Total with taxes and fees
3Bdrm Home Near Downtown Orlando and Winter park

Daytona 2BR Getaway Parking Family & Pet-friendly

Daytona 2BR Getaway Parking Family & Pet-friendly
3.0 star property
Daytona Beach
$362 nightly
The price is $381
May 12 - May 13
Total with taxes and fees
Daytona 2BR Getaway Parking Family & Pet-friendly
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 $108 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: Visitors like this Osteen vacation home rental. It 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 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.