Osteen vacation rentals

We found 518 vacation rentals — enter your dates for availability

Discover a selection of vacation rentals in Osteen that are perfect for your trip. Whether you're traveling with a group or just with your pet, vacation homes have the amenities you need and want for your stay, which might include a garden and WiFi. No matter what you're looking for, you'll find a rental that has what everyone needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Osteen

Showing deals for:Nov 14 - Nov 21
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Find out more about Osteen

Find out more about Osteen

Why visit Osteen

  1. Beautiful outdoor scenery: Osteen offers picturesque green spaces and nature preserves, perfect for relaxation and exploration.
  2. Family-friendly activities: The area is ideal for family vacations, providing a variety of outdoor adventures for all ages.
  3. Golfing opportunities: Golf enthusiasts can enjoy several nearby golf courses, complete with guides for an enhanced experience.
  4. Charming accommodations: A range of vacation rentals and budget-friendly hotels ensure a comfortable stay for every traveller.
  5. Nearby vibrant communities: Explore the friendly ambiance of surrounding cities, adding to your adventure in Osteen.

Popular types of accommodation in Osteen

Discover the charm of Osteen with a variety of vacation rentals to suit your needs. Whether you prefer a cozy condo, a spacious private vacation home, or a comfortable apartment, you'll find the perfect base for your adventures. Explore options for Osteen hotels, check nearby accommodations, and read reviews to make informed choices. With great hotel availability and competitive rates, your memorable getaway starts here!

  • Condos: The top choice for vacation rentals in Osteen, offering modern amenities and convenient locations for a comfortable stay.
  • Houses: A popular option for those seeking space and privacy, ideal for families or groups wanting a home-like experience.
  • Apartments: A great selection for solo travellers or couples, providing essential comforts in a compact setting.
  • Cottages: Charming and cozy, these rentals offer a rustic feel and a peaceful getaway in nature.
  • Villas: Luxurious and spacious, perfect for those looking to indulge during their stay in Osteen.**

Top attractions in Osteen

Osteen, Florida, is perfect for outdoor and family vacations, offering a delightful blend of natural scenery and cultural experiences. Visitors can explore urban parks, nature preserves, and nearby colleges. For golf enthusiasts, there are several golf courses in the area, along with comprehensive guides to enhance your golfing experience. Whether you seek adventure or a relaxing city vibe, Osteen has something for everyone.

  1. University of Central Florida: A vibrant and modern university, offering a bustling atmosphere with unique architecture and diverse student life, located 27.4km from Osteen.
  2. Lake Monroe: A picturesque lake perfect for romantic outings and outdoor activities, boasting beautiful scenery and beach vibes, just 11.3km from Osteen.
  3. Lake Monroe Conservation Area: A serene reserve offering opportunities for wildlife observation and nature walks, located a mere 4.8km from Osteen.

Things to do recommended for couples

For a romantic getaway in Osteen, consider visiting the Mayfair Country Club, just 16.1km away, for a touch of luxury. Alternatively, enjoy a unique experience at the Volusia County Skeet & Trap Club, located 22.5km from Osteen, where you can bond over some fun activities.

Things to do recommended for families

Experience family-friendly fun in Osteen with a visit to the Seminole County Sports Complex for wellness activities, explore the tranquil Green Springs Park, or enjoy a lively outing at AMF Deltona Lanes for arcade adventures. Each spot offers unique relaxation and excitement for all ages.

Things to do recommended for groups

Groups visiting Osteen can enjoy shopping at Seminole Towne Center, play a round of golf at Deltona Golf Club, or experience thrilling motor racing at New Smyrna Speedway. Each activity offers a unique blend of entertainment, sports, and adventure, perfect for creating memorable moments together.

What do I need to keep in mind when booking a vacation in Osteen

If you're planning a trip with a group, family, or pets, or if you're considering an extended stay, it's important to prioritize your preferences when filtering your options. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Osteen with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and many others on Vrbo.
  • Traveling to Osteen with young kids: Travelling with young children can present some challenges. It's important to prioritize their comfort and safety, along with ensuring that age-appropriate amenities, like private swimming pools, are available. Additionally, it's wise to think about your closeness to family-friendly attractions.
  • Taking your pets with you to Osteen: For many families, a trip isn't truly complete without their furry companions. If this resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Osteen: If you're in search of vacation rentals offering discounts for month-long stays, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to include features like a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay in Osteen

Osteen, Florida, is a hidden gem for outdoor enthusiasts and families alike. With its lovely green spaces and relaxing atmosphere, visitors can enjoy a picturesque getaway. Nearby cities offer a friendly vibe, perfect for budget travellers seeking adventure. Explore the scenic beauty of Osteen and its surrounding areas, where you can experience the charm of Florida's natural landscape and vibrant communities. It's a delightful spot for a memorable vacation!

  • Deltona Lakes: Located a mere 6.4km from Osteen, Deltona Lakes is a vibrant neighborhood known for its stunning outdoor scenery and family-friendly atmosphere. Visitors can enjoy various recreational activities, from leisurely walks in the nearby parks to motor racing events that thrill the adrenaline seekers. Key attractions include a local theme park and a stadium, as well as a picturesque lake that provides the perfect backdrop for relaxation and fishing. With its blend of nature and excitement, Deltona Lakes is an ideal spot for those looking to unwind while engaging in fun activities.
  • Lemon Bluff: Nestled within the vicinity of Osteen, Lemon Bluff is a charming village that offers a delightful escape for those seeking outdoor adventures and beach experiences. The area is known for its beautiful marina and access to serene river views, making it perfect for fishing and boating enthusiasts. Visitors can also indulge in local resorts and enjoy recreational areas that cater to families. The laid-back, scenic environment is ideal for leisurely days spent exploring the natural beauty surrounding Lemon Bluff, ensuring a memorable vacation experience.
  • Sanford: Just 11.3km away from Osteen, Sanford is a lively city that combines family fun with an array of outdoor and entertainment options. The city features various resorts and recreation parks, ideal for enjoying quality time with loved ones. Sanford is also home to several attractions, including a popular theme park and a marina, providing plenty of opportunities for adventure and relaxation. With its vibrant atmosphere and numerous activities, Sanford is a fantastic destination for tourists seeking a blend of excitement and family-oriented experiences.

Best time to go to Osteen

If you're planning a trip to Osteen, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs in March to April and September, while off-peak times, like August and October to November tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January59.9°F (15.5°C)Light RainMostly SunnyAverageSlightly Low
February63.7°F (17.6°C)Light RainMostly SunnyAverageAverage
March66.7°F (19.3°C)Light RainMostly SunnySlightly HighSlightly High
April71.8°F (22.1°C)Light RainMostly SunnySlightly HighAverage
May76.3°F (24.6°C)Light RainMostly SunnyAverageAverage
June80.2°F (26.8°C)Light RainMostly SunnyAverageSlightly High
July81.9°F (27.7°C)Light RainMostly SunnyAverageSlightly High
August82.0°F (27.8°C)Moderate RainMostly SunnySlightly LowAverage
September79.7°F (26.5°C)Light RainMostly SunnySlightly HighSlightly Low
October74.5°F (23.6°C)Light RainMostly SunnySlightly LowSlightly Low
November67.6°F (19.8°C)No Rain (Dry)Mostly SunnySlightly LowAverage
December63.7°F (17.6°C)No Rain (Dry)Mostly SunnyAverageAverage

Booking with Vrbo is simple

Are you hoping to save on your upcoming journey? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that aligns with your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect accommodation for your Canadian adventure!

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient platform for planning new adventures, refining your travel arrangements, or managing your current bookings. The properties you’ve saved or reserved are now conveniently categorized into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Beautiful Osteen will entice you

Experience the unique character of Osteen with a stay in a vacation home rental. Travelers appreciate the kayaking in this scenic city. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in Osteen

Are you hoping to discover things to do during your stay? Venture out of your vacation home and experience everything that makes Osteen a fun spot to vacation. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

  • Central Florida Zoo & Botanical Gardens (9.3 mi / 14.9 km)
  • Timacuan Golf Club (11.6 mi / 18.6 km)
  • Venetian Bay Golf Club (14.9 mi / 24 km)
  • Orlando Speedworld (21.4 mi / 34.4 km)
  • Sunglow Fishing Pier (23.9 mi / 38.5 km)
  • Mayfair Country Club (10.5 mi / 16.8 km)

Exploring the natural landscape of Osteen

Whether you're looking for adventure or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Osteen. These are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city center:

  • Lake Monroe (6.5 mi / 10.4 km)
  • Lake Jesup (8.8 mi / 14.2 km)
  • Lake Monroe Park (9.6 mi / 15.5 km)
  • Black Hammock Wilderness Area (10.1 mi / 16.3 km)
  • Black Bear Wilderness Area (11.5 mi / 18.5 km)
  • Boombah-Soldiers Creek Park (12.5 mi / 20.1 km)

How to get to and around Osteen

The nearest airport is in Orlando Sanford Intl. Airport (SFB), located 6.9 mi (11.1 km) from the city center. If you can't find a flight that's convenient for your trip, you could book a flight to Daytona Beach Intl. Airport (DAB), which is 24.2 mi (39 km) away.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Osteen?
The most in-demand types of vacation rentals in Osteen are houses. Prefer something different? Vrbo offers a variety of options to match the needs of our guests, so you'll see vacation properties in all sizes, and for all budgets. The perfect home away from home is waiting for you — grab yours today.
How much does it cost to rent a vacation rental in Osteen?
The average price for a vacation rental in Osteen depends on several factors, like length of stay, property type and season. Whether you're dreaming about a sprawling villa with a pool or a comfy cabin that's perfect for two, just add your travel dates to see stays with terrific value.
How much does it cost to rent a beach house in Osteen?
Prices for beach houses in Osteen may differ depending on the size and type of the property and time of year you're traveling. Simply enter your travel dates into Vrbo and how many guests to view your vacation rental options and prices. From there you can use our filter tool to tailor your search by ratings, amenities, nearby activities and more.
What are popular rental amenities in Osteen?
When it comes to rental amenities that people are looking for in Osteen, a barbecue grill, a garden and a nearby waterfront rank highest. With Vrbo vacation rentals, there are options to fit your style and taste, whether you're going on a vacation with family, friends or even pets.
What are the top attractions for families in Osteen?
You'll find loads of cool things to see and do with the family in Osteen, such as:

  • AMF Deltona Lanes
  • Gemini Springs Park
  • Green Springs Park

How old do you have to be to rent a vacation rental in Osteen?
We advise checking with the Osteen vacation rental you'd like on Vrbo as the age limit differs. However, it's generally 16, 18 or 21.
How long can I rent a vacation rental in Osteen for?
The length of time you can rent a vacation rental in Osteen differs according to the property. Simply enter your desired dates to see a list of options offering extended stays. With lots of features like air conditioning and kitchens, as well as some offering weekly or monthly discounts, you're sure to find the perfect place to call your home away from home in Osteen.

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