Osteen Holiday Rentals

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Holiday Rentals in Osteen

Hilton Garden Inn Orlando East/UCF Area
3.0 star property
8.8 out of 10, Excellent, (1226)
"Location "
The price is NZ$215
includes taxes & fees
16 Jun - 17 Jun
Hilton Garden Inn Orlando East/UCF Area
Fantasy Island Resort I
3.0 star property
8.4 out of 10, Very good, (55)
"Nice stay, could have been a little cleaner but customers service was great, location was great, and pool was excellent "
The price is NZ$194
includes taxes & fees
11 Jun - 12 Jun
Fantasy Island Resort I
Silver Beach Club
2.0 star property
8.4 out of 10, Very good, (28)
"Enjoyed the stay. Most definitely will return but for a longer stay!"
The price is NZ$297
includes taxes & fees
6 Jun - 7 Jun
Silver Beach Club
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Vacation Villas
3.0 star property
8.8 out of 10, Excellent, (262)
"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)
"Was under construction no pool No access to beach do had to fill with workers working in the moo"
The price is NZ$255
includes taxes & fees
12 Jun - 13 Jun
Castaways Resort Studios
Pirates Cove Resort Studios
3.0 star property
6.4 out of 10, (108)
"Our room was very nice, we have been here before and will be back again"
The price is NZ$272
includes taxes & fees
6 Jun - 7 Jun
Pirates Cove Resort Studios
Tropical Suites at Sunglow Resort
2.0 star property
7.4 out of 10, Good, (11)
"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 NZ$548
includes taxes & fees
8 Jun - 9 Jun
Tropical Suites at Sunglow Resort
Shoreline Suites & Cabana Cottages
2.0 star property
8.8 out of 10, Excellent, (355)
"The stay was perfect! Definitely home away from home, very pleased with the cleanliness, front service, and the location. "
The price is NZ$254
includes taxes & fees
6 Jun - 7 Jun
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)
"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)
"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 NZ$520
includes taxes & fees
12 Jun - 13 Jun
Beach Front Suite w/ Amazing Ocean Views!
Ocean Front + Amazing Views | Sandbox Suite 902
9.2 out of 10, Wonderful, (45)
"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 NZ$708
includes taxes & fees
9 Jun - 10 Jun
Ocean Front + Amazing Views | Sandbox Suite 902
New Smyrna Beach Cozy Pool Home, Beach, Shopping & Restaurants
9.0 out of 10, Wonderful, (85)
"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)
"The condo was the perfect size for two people. It was nicely kept and very clean. The balcony view of the ocean was amazing! Great location too!"
The price is NZ$550
includes taxes & fees
13 Jun - 14 Jun
Oceanfront Condo at Sunglow | Starfish Suite 901
New Smyrna Rv Bunkhouse Pool Private Family RV
9.4 out of 10, Exceptional, (49)
"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)
"Close to main street for biketoberfest "
The price is NZ$290
includes taxes & fees
17 Jun - 18 Jun
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)
"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 NZ$355
includes taxes & fees
23 Jun - 24 Jun
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)
"Great place to stay with friends. The house was clean and had an easy walk to a public beach access."
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)
"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)
"Very nice"
The price is NZ$388
includes taxes & fees
8 Jun - 9 Jun
Oceanfront Tropical Hawaiian Studio
Lake Front Suite -Close to all Attractions
9.4 out of 10, Exceptional, (49)
"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.

Other types of properties in Osteen you may be interested in

The Alfond Inn
4.0 star property
9.4 out of 10, Exceptional, (1009)
"Place is very nice new and clean. Problem is knowing how to get in there I drove around place 3 times as off the main road not great signage no parking other than limited street parking or Valet for me this is bad as I go in and out a lot hate waiting for Valet and having to move car every 4 hours on street to not get towed."
The price is NZ$525
includes taxes & fees
6 Jun - 7 Jun
The Alfond Inn
The Shores Resort & Spa
4.0 star property
8.6 out of 10, Excellent, (1304)
"Property was beautiful. Beach was breathtaking. Pool was clean. The amenities Were wonderful dining was actually perfect. Food was amazing."
The price is NZ$318
includes taxes & fees
17 Jun - 18 Jun
The Shores Resort & Spa
Perry's Ocean Edge Resort
2.5 star property
8.2 out of 10, Very good, (1385)
"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 NZ$284
includes taxes & fees
23 Jun - 24 Jun
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 holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Osteen holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Osteen. 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 Osteen. 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 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 holiday 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 Osteen short-term rentals, that won’t be hard to do.

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 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 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.

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