Osteen Vacation Rentals

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Our top choices for Osteen vacation rentals

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
The price is CA $154
CA $289 total
includes taxes & fees
May 31 - Jun 1
The Front Porch

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, (271 reviews)
"Quiet area easy to access."
United States
Amanda
The price is CA $116
CA $188 total
includes taxes & fees
Jun 6 - Jun 7
Mid Century Charm! KSC,Port Canaveral,Cocoa and Bio-Lume Kayak,Pet Friendly!

At the Center of it All!

At the Center of it All!
Indian River City
9.8 out of 10, Exceptional, (153 reviews)
"Great stay! Very responsive hosts! Would recommend and would stay again!"
United States
Jennifer C.
The price is CA $185
CA $321 total
includes taxes & fees
May 25 - May 26
At the Center of it All!

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
The price is CA $270
CA $673 total
includes taxes & fees
Jun 3 - Jun 4
Oceania Beach Club

Incredible Private Lakefront Cottage Retreat

Incredible Private Lakefront Cottage Retreat
Altamonte Springs
10.0 out of 10, Exceptional, (36 reviews)
"The host was easy to contact and the cottage was very cozy with all necessary amenities. The lakeside location was both beautiful and peaceful, especially considering it is so close to 436 and I4. We definitely plan to return. "
United States
Carol G.
The price is CA $185
CA $496 total
includes taxes & fees
May 25 - May 26
Incredible Private Lakefront Cottage Retreat

The Jazz Loft

The Jazz Loft
3.0 star property
Sanford
8.6 out of 10, Excellent, (8 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 CA $74
CA $175 total
includes taxes & fees
May 24 - May 25
The Jazz Loft

Ocean Beach Club

Ocean Beach Club
3.0 star property
Coronado Beach
9.8 out of 10, Exceptional, (20 reviews)
"The place was great, clean, right in the beach. Perfect spot!"
United States
Andrew
Ocean Beach Club

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.
The price is CA $185
CA $496 total
includes taxes & fees
Jun 20 - Jun 21
Hello Sunshine 321.. Lift Off

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 CA $101
CA $309 total
includes taxes & fees
May 26 - May 27
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, (24 reviews)
"Quiet neighborhood, good location."
United States
River
The price is CA $217
CA $389 total
includes taxes & fees
May 25 - May 26
Quiet retreat 15 minutes from downtown Orlando, Orlando Airport International!

Boho Nights

Boho Nights
3.0 star property
Sanford
9.6 out of 10, Exceptional, (14 reviews)
"Great location very clean awesome decor "
United States
Heather
The price is CA $75
CA $176 total
includes taxes & fees
May 24 - May 25
Boho Nights

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.
The price is CA $223
CA $546 total
includes taxes & fees
May 25 - May 26
3Bdrm Home Near Downtown Orlando and Winter park

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, (27 reviews)
The price is CA $198
CA $556 total
includes taxes & fees
May 31 - Jun 1
Tranquil 3-bedroom house in Sanford with AC, WiFi

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
The price is CA $94
CA $198 total
includes taxes & fees
May 24 - May 25
Bella Breeze

Beautiful Beachfront Resort Condo

Beautiful Beachfront Resort Condo
3.0 star property
Daytona Beach
9.0 out of 10, Wonderful, (16 reviews)
"Beyond expectations!!!"
Canada
Sara
The price is CA $182
CA $360 total
includes taxes & fees
Jun 6 - Jun 7
Beautiful Beachfront Resort Condo

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
The price is CA $461
CA $1,023 total
includes taxes & fees
May 27 - May 28
Oceanfront Penthouse Pool Hot Tub Beach Access

Charming 3-bedroom home away from home.

Charming 3-bedroom home away from home.
Chuluota
9.8 out of 10, Exceptional, (25 reviews)
"Great stay. Will definitely use again! "
United States
Sharon S.
The price is CA $206
CA $519 total
includes taxes & fees
May 24 - May 25
Charming 3-bedroom home away from home.

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
9.4 out of 10, Exceptional, (19 reviews)
"Wonderful host. Very comfortable accommodations. We enjoyed it very much."
United States
Bobbijo A.
The price is CA $134
CA $232 total
includes taxes & fees
May 24 - May 25
Luxury RV nested in a country setting, Only 9 minutes from Sanford airport!

Mira Bella North - 1BR Tiny House in Lake Helen

Mira Bella North - 1BR Tiny House in Lake Helen
Lake Helen
10.0 out of 10, Exceptional, (3 reviews)
"Absolutely beautiful! We loved it. The animals are wonderful. "
United States
Christin L.
The price is CA $136
CA $227 total
includes taxes & fees
May 28 - May 29
Mira Bella North - 1BR Tiny House in Lake Helen

Hot Tub, Fire Pit, Near the Beach!

Hot Tub, Fire Pit, Near the Beach!
Florida Shores
9.8 out of 10, Exceptional, (37 reviews)
"Overall great location and the house was perfect."
United States
Becca W.
The price is CA $289
CA $366 total
includes taxes & fees
May 25 - May 26
Hot Tub, Fire Pit, Near the Beach!
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Osteen. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Daytona Beach XI: Visitors like this Osteen vacation home rental. It is located by the ocean and offers an arcade game room, air-conditioning, and free WiFi to help you feel perfectly comfortable in your new surroundings.

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 Ashby Park and Lake Jesup Conservation Area 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.