Osteen Vacation Rentals

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Vacation Rentals in Osteen

Hilton Garden Inn Orlando East/UCF Area
3.0 star property
8.8 out of 10, Excellent, 1,225 reviews
"I felt safe and I loved the quietness of the area "
The price is CA $155
CA $175 total
includes taxes & fees
Jun 16 - Jun 17
Hilton Garden Inn Orlando East/UCF Area
Fantasy Island Resort I
3.0 star property
8.4 out of 10, Very good, 55 reviews
"staff was very helpful and friendly "
The price is CA $158
CA $208 total
includes taxes & fees
Jun 5 - Jun 6
Fantasy Island Resort I
Silver Beach Club
2.0 star property
8.4 out of 10, Very good, 28 reviews
"Enjoyed the stay. Most definitely will return but for a longer stay!"
The price is CA $244
CA $274 total
includes taxes & fees
Jun 5 - Jun 6
Silver Beach Club
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Vacation Villas
3.0 star property
8.8 out of 10, Excellent, 262 reviews
"Condo was clean but dated from 1990's, Grounds overgrown around pool which was far from room. Grills are charcoal and old so we cooked in room. We did not know 2nd floor and I mentioned recent back surgery no interested in moving us. Charged my credit card money for cleaning fee and I had paid in full? Removed when I left but I had to check when I returned home. Then asked for customers to take out the garbage and then there was a tip envelope for maid? No daily maid service..."
Vacation Villas
Castaways Resort Studios
2.0 star property
5.8 out of 10, 60 reviews
"Was under construction no pool No access to beach do had to fill with workers working in the moo"
The price is CA $96
CA $202 total
includes taxes & fees
Jun 5 - Jun 6
Castaways Resort Studios
Pirates Cove Resort Studios
3.0 star property
6.4 out of 10, 108 reviews
"Our room was very nice, we have been here before and will be back again"
The price is CA $120
CA $229 total
includes taxes & fees
Jun 5 - Jun 6
Pirates Cove Resort Studios
Tropical Suites at Sunglow Resort
2.0 star property
7.4 out of 10, Good, 11 reviews
"THE PROPERTY IS CLEAN AND ACCESSIBLE. WE WOULD HAVE HAD A LOVELY VIEW BUT THE POOL IS UNDER CONSTRUCTION. STILL, WE ENJOYED OUR STAY. "
The price is CA $144
CA $462 total
includes taxes & fees
Jun 8 - Jun 9
Tropical Suites at Sunglow Resort
Shoreline Suites & Cabana Cottages
2.0 star property
8.8 out of 10, Excellent, 355 reviews
"The stay was perfect! Definitely home away from home, very pleased with the cleanliness, front service, and the location. "
The price is CA $190
CA $214 total
includes taxes & fees
Jun 5 - Jun 6
Shoreline Suites & Cabana Cottages
Budget Friendly OceanFront 7th Floor Condo-Clean & Comfortable-Close to Pier & Dining-SECURE WIFI!
8.8 out of 10, Excellent, 49 reviews
"Wasnt informed about pool and beach access being closed"
Budget Friendly OceanFront 7th Floor Condo-Clean & Comfortable-Close to Pier & Dining-SECURE WIFI!
Beach Front Suite w/ Amazing Ocean Views!
9.2 out of 10, Wonderful, 34 reviews
"Very clean and is stocked/organized with various items to make your stay comfortable. Very cute set up. Bed/pillows were super comfortable!!! Balcony on the beach with great views. Close to many restaurants/cafes within walking distance. Would definitely stay here again."
The price is CA $169
CA $446 total
includes taxes & fees
Jun 5 - Jun 6
Beach Front Suite w/ Amazing Ocean Views!
Ocean Front + Amazing Views | Sandbox Suite 902
9.2 out of 10, Wonderful, 45 reviews
"We had a blast!! The condo was perfect with the two bedrooms. One bedroom for me and my daughter with our own bathroom and the other one for my boyfriend and his son with their own bathroom. The sunrise was absolutely beautiful and easy access."
The price is CA $174
CA $555 total
includes taxes & fees
Jun 5 - Jun 6
Ocean Front + Amazing Views | Sandbox Suite 902
New Smyrna Beach Cozy Pool Home, Beach, Shopping & Restaurants
9.0 out of 10, Wonderful, 85 reviews
"No problems at all very easy to accesses and very close to the beach neighbors we also very nice"
New Smyrna Beach Cozy Pool Home, Beach, Shopping & Restaurants
Oceanfront Condo at Sunglow | Starfish Suite 901
9.4 out of 10, Exceptional, 33 reviews
"Despite a rocky beginning (faulty elevator that trapped my husband inside for 1-1/2 hours and remained inoperable until morning), this was an unfortunate and unforeseen event. The management team was outstanding, making sure that we were taken care of and our vacation ended well."
The price is CA $129
CA $396 total
includes taxes & fees
Jun 5 - Jun 6
Oceanfront Condo at Sunglow | Starfish Suite 901
New Smyrna Rv Bunkhouse Pool Private Family RV
9.4 out of 10, Exceptional, 49 reviews
"It was as advertised except listed 2 bedroom with 2 bath. There is only one bath. Another shower is available in another building."
New Smyrna Rv Bunkhouse Pool Private Family RV
Beach Front Studios in Daytona Beach
3.0 star property
7.4 out of 10, Good, 151 reviews
"Close to main street for biketoberfest "
The price is CA $134
CA $244 total
includes taxes & fees
Jun 5 - Jun 6
Beach Front Studios in Daytona Beach
Extraordinary view! Separate living room! We have full beach access and pool!
9.6 out of 10, Exceptional, 104 reviews
"Just as described. Accurate description. 2 large sofas. Ocean view was the best part of this place. Access to the pool will require a key, which I think it’s a great plan. Beach accessible was a plus, we didn’t have to walk far to get to it. We really love the location. We”ll definitely come back to this place."
The price is CA $136
CA $300 total
includes taxes & fees
Jun 23 - Jun 24
Extraordinary view! Separate living room! We have full beach access and pool!
Beautiful 2/1 Home - Walking Distance to the Beach
9.8 out of 10, Exceptional, 21 reviews
"the house was exactly what we expected. It was very cozy and had everything we needed for our stay. Would definitely recommend to anyone looking to stay in daytona. Will definitely be booking this again when i’m back in daytona!"
Beautiful 2/1 Home - Walking Distance to the Beach
Beautiful View of the Atlantic Ocean from your balcony
9.6 out of 10, Exceptional, 168 reviews
"The room was cozy and had everything we needed. We also really enjoyed sitting on the balcony."
Beautiful View of the Atlantic Ocean from your balcony
Oceanfront Tropical Hawaiian Studio
9.6 out of 10, Exceptional, 186 reviews
"Very nice"
The price is CA $157
CA $328 total
includes taxes & fees
Jun 9 - Jun 10
Oceanfront Tropical Hawaiian Studio
Lake Front Suite -Close to all Attractions
9.4 out of 10, Exceptional, 49 reviews
"The cottage is cute and quirky with a great view of the lake. It was very peaceful. We spent a day on the back porch working while looking at the lake. I think it is in need of a deep spring cleaning, however. I’m extremely sensitive to smells, and there was a strong pet odor, I opened the windows to help air out the unit. Overall, a good experience. Kyle was extremely helpful and kind."
Lake Front Suite -Close to all Attractions
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See all available properties in Osteen
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.

Osteen Vacation Rental Travel Info

Other types of properties in Osteen you may be interested in

The Alfond Inn
4.0 star property
9.4 out of 10, Exceptional, 1,006 reviews
"Beautiful. Close to Historic Downtown. "
The price is CA $367
CA $443 total
includes taxes & fees
Jun 10 - Jun 11
The Alfond Inn
The Shores Resort & Spa
4.0 star property
8.6 out of 10, Excellent, 1,300 reviews
"I loved the service from the staff, the amenities and the cleanliness. "
The price is CA $190
CA $257 total
includes taxes & fees
Jun 6 - Jun 7
The Shores Resort & Spa
Perry's Ocean Edge Resort
2.5 star property
8.2 out of 10, Very good, 1,395 reviews
"So far the room and services are good. But there's no lights around swimming pool outdoor. And no shower to clean the sand before re-entering to the resort. "
The price is CA $195
CA $240 total
includes taxes & fees
Jun 23 - Jun 24
Perry's Ocean Edge Resort
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.

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?

Pirates Cove Resort Studios: Visitors like this Osteen vacation home rental. It is on the beach and equipped with air-conditioning and free WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a stovetop, a microwave, and a coffee maker.

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.

Recent reviews of Osteen properties
Expedia verified reviews