Osteen Vacation Rentals

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May 2 - May 3
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May 3 - May 4
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May 3 - May 5
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May 10 - May 12

Vacation Rentals in Osteen

Hilton Garden Inn Orlando East/UCF Area
Terrace/patio
Hilton Garden Inn Orlando East/UCF Area
3.0 star property
8.8 out of 10, Excellent, (1209)
"What a friendly greeting I received upon arrival. I was given options regarding floor levels and I thought that was just another nudge in “going the extra mile”. "
The price is $114
$128 total
includes taxes & fees
May 9 - May 10
Hilton Garden Inn Orlando East/UCF Area
Fantasy Island Resort I
Condo, 2 Bedrooms, 2 Bathrooms | Free WiFi, bed sheets
Fantasy Island Resort I
3.0 star property
8.2 out of 10, Very Good, (43)
"The staff was so nice and helpful. I enjoyed my stay. Everything was so nice and clean. I will stay again! Pool area was clean and pool was heated which was very nice. Thank you for having us!"
The price is $116
$153 total
includes taxes & fees
May 5 - May 6
Fantasy Island Resort I
Castaways Resort Studios
Pool
Castaways Resort Studios
2.0 star property
5.8 out of 10, (55)
"Everything was great. We enjoyed our stay! "
The price is $88
$168 total
includes taxes & fees
May 5 - May 6
Castaways Resort Studios
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Pirates Cove Resort Studios
Premium Studio, 2 Queen Beds, Kitchen, Ocean View | Desk, soundproofing, iron/ironing board, free WiFi
Pirates Cove Resort Studios
3.0 star property
6.4 out of 10, (103)
"The family and myself love it. Next time trip to Florida definitely I will choose this place again"
The price is $98
$179 total
includes taxes & fees
May 13 - May 14
Pirates Cove Resort Studios
Shoreline Suites & Cabana Cottages
Outdoor pool, open 8:00 AM to 10:00 PM, pool umbrellas, sun loungers
Shoreline Suites & Cabana Cottages
2.0 star property
8.8 out of 10, Excellent, (351)
"We had a great time staying here. The place was great. We will be back next year. Thank you! "
The price is $99
$112 total
includes taxes & fees
May 19 - May 20
Shoreline Suites & Cabana Cottages
Vacation Villas
Full-size fridge, microwave, oven, stovetop
Vacation Villas
3.0 star property
8.8 out of 10, Excellent, (261)
"Nice place would definitely stay there again."
Vacation Villas
Silver Beach Club
Basic Studio | Terrace/patio
Silver Beach Club
2.0 star property
8.2 out of 10, Very Good, (20)
"We were surprised on how well maintain is the property. "
The price is $179
$201 total
includes taxes & fees
May 5 - May 6
Silver Beach Club
Tropical Suites at Sunglow Resort
Exterior
Tropical Suites at Sunglow Resort
2.0 star property
7.0 out of 10, Good, (8)
"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 $124
$359 total
includes taxes & fees
May 4 - May 5
Tropical Suites at Sunglow Resort
Budget Friendly OceanFront 7th Floor Condo-Clean & Comfortable-Close to Pier & Dining-FREE HBO/WIFI!
Outdoor dining
Budget Friendly OceanFront 7th Floor Condo-Clean & Comfortable-Close to Pier & Dining-FREE HBO/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-FREE HBO/WIFI!
Extraordinary view! Separate living room! We have full beach access and pool!
Smart TV, table tennis
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 $100
$218 total
includes taxes & fees
May 16 - May 17
Extraordinary view! Separate living room! We have full beach access and pool!
Beautiful View of the Atlantic Ocean from your balcony
Aerial view
Beautiful View of the Atlantic Ocean from your balcony
9.6 out of 10, Exceptional, (166)
"What an amazing stay!! The hotel is a little rough around the egdes, but the ROOM, its like a totally different environment. Ask for more towels and tp and the owner without question brought it right over. Loved having access to the back door, takes you right to the beach. We saw dolphins from the balcony and it was amazing!! Within walking distance from pretty much everything you could need or want. When we come back next year, this will be the first place i look at to rent. Loved it!!"
Beautiful View of the Atlantic Ocean from your balcony
New Smyrna Beach Cozy Pool Home, Beach, Shopping & Restaurants
Beach nearby
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
Beach Front Studios in Daytona Beach
Exclusive Apartment, Kitchen, Ocean View | 1 bedroom, desk, soundproofing, free WiFi
Beach Front Studios in Daytona Beach
3.0 star property
7.4 out of 10, Good, (150)
"Close to main street for biketoberfest "
The price is $89
$169 total
includes taxes & fees
May 6 - May 7
Beach Front Studios in Daytona Beach
Oceanfront Tropical Hawaiian Studio
Outdoor dining
Oceanfront Tropical Hawaiian Studio
9.6 out of 10, Exceptional, (184)
"I loved the balcony. I enjoyed sitting out there and sipping a beverage. Access to the pool or beach was easy. I had a question about the parking pass and the response was nearly immediate."
The price is $115
$241 total
includes taxes & fees
May 20 - May 21
Oceanfront Tropical Hawaiian Studio
New Smyrna Rv Bunkhouse Pool Private Family RV
Beach nearby
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
Oceanfront, Amazing Views | Sandbox Suite 902
On the beach
Oceanfront, 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 $149
$450 total
includes taxes & fees
May 5 - May 6
Oceanfront, Amazing Views | Sandbox Suite 902
Getaway New Smyrna Beach, Sun, Pool, Shopping.
Getaway New Smyrna Beach, Sun, Pool, Shopping.
9.2 out of 10, Wonderful, (94)
"Overall great stay. I would power wash the pool area. The spider webs hanging from the celling was really uncomfortable. I wasn't sure if something was going to drop on me or in the water."
Getaway New Smyrna Beach, Sun, Pool, Shopping.
Oceanfront Penthouse w/ Breathtaking Views!
On the beach
Oceanfront Penthouse w/ Breathtaking Views!
9.2 out of 10, Wonderful, (32)
"This place was exactly as described. Beatiful views, easy access to beach, even though the past storms had ruined the previous one. Clean and friendly staff. Great experience."
The price is $125
$326 total
includes taxes & fees
May 6 - May 7
Oceanfront Penthouse w/ Breathtaking Views!
9 beds! Walk 2 Beach | Game Room | Cowboy Pool | Mini Golf! PETS OK!
Fridge, microwave, oven, stovetop
9 beds! Walk 2 Beach | Game Room | Cowboy Pool | Mini Golf! PETS OK!
10.0 out of 10, Exceptional, (7)
"Guys weekend for Daytona 500. Very convenient, and a perfect place to stay. Comfortable clean and well maintained. The host was very accommodating and responsive. Thx!"
The price is $232
$594 total
includes taxes & fees
May 14 - May 15
9 beds! Walk 2 Beach | Game Room | Cowboy Pool | Mini Golf! PETS OK!
Breezy Pool Home!
Fridge, microwave, oven, stovetop
Breezy Pool Home!
9.0 out of 10, Wonderful, (49)
"Nice house! Owner is very accommodating! "
The price is $119
$223 total
includes taxes & fees
May 5 - May 6
Breezy Pool Home!
Don't see what you're looking for?
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

Number of vacation rentals
3
Popular accommodation
Osteen private vacation homes
Known landmarks
AMF Deltona Lanes, Gemini Springs Park and Deltona Golf Club
International airports
Orlando, FL (MCO-Orlando Intl.) and Orlando, FL (ORL-Orlando Executive)

Other types of properties in Osteen you may be interested in

Perry's Ocean Edge Resort
Poolside bar
Perry's Ocean Edge Resort
2.5 star property
8.2 out of 10, Very Good, (1360)
"Friendly staff. Great pools and right on the beach. Cute little pool side bar, and close enough to all the action but not in the thick of it. Lots of dining options close by. Great donuts!!!"
The price is $135
$167 total
includes taxes & fees
Jun 2 - Jun 3
Perry's Ocean Edge Resort
La Quinta Inn & Suites by Wyndham Orlando Lake Mary
Lobby
La Quinta Inn & Suites by Wyndham Orlando Lake Mary
2.5 star property
8.4 out of 10, Very Good, (1645)
"I love the breakfast option. I only have one complaint or better yet a suggestion... update your TV's to WIFI 50"-65" tv's that you can be casted to from any mobile device such as any smart phone, tablet and/or laptop computer. "
The price is $80
$90 total
includes taxes & fees
May 14 - May 15
La Quinta Inn & Suites by Wyndham Orlando Lake Mary
The Shores Resort & Spa
View from room
The Shores Resort & Spa
4.0 star property
8.4 out of 10, Very Good, (1308)
"Stuff"
The price is $121
$168 total
includes taxes & fees
Jun 2 - Jun 3
The Shores Resort & Spa
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.

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 $88 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 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

Days Inn by Wyndham Daytona Oceanfront

Days Inn by Wyndham Daytona Oceanfront

5/5 Excellent
"The view out back "
A verified traveler stayed at Days Inn by Wyndham Daytona Oceanfront
Posted 1 day ago
Days Inn by Wyndham Daytona Oceanfront