Osteen vacation rentals

We found 501 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.
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Find out more about Osteen

Find out more about Osteen

Why visit Osteen

  1. Outdoor Adventures: Enjoy the beautiful scenery with ample opportunities for hiking, biking, and exploring local parks.
  2. Family-Friendly Attractions: Discover a variety of activities suitable for all ages, ensuring fun for the whole family.
  3. Charming Atmosphere: Experience the relaxed vibe and friendly locals that make Osteen a welcoming destination.
  4. Rich Cultural Experience: Visit historic churches and modern colleges to immerse yourself in the area's unique culture.
  5. Variety of Accommodations: Choose from cozy condos to spacious homes, offering comfortable options for your stay.

Popular types of accommodation in Osteen

If you're considering a getaway in Osteen, you're in for a treat! Our most popular vacation rentals include cozy condos, spacious private homes, and comfortable apartments. Whether you're looking for a charming house with a patio area or a unique stay near feelgood farms, we have plenty of options to suit your needs. Discover the perfect Osteen house for rent and enjoy a relaxing escape!

  • Condos: The top choice for vacation rentals in Osteen, offering modern amenities and convenient access to local attractions.
  • Houses: A popular option for families and groups, providing ample space and a home-like atmosphere.
  • Apartments: Ideal for solo travelers or couples seeking a cozy space with essential facilities.
  • Villas: Spacious and luxurious, perfect for those looking to indulge during their stay.
  • Cottages: Quaint and charming, these rentals offer a unique, rustic experience close to nature.**

Top attractions in Osteen

Osteen, Florida, is a fantastic destination for outdoor and family vacations, offering beautiful scenery and a variety of attractions. Visitors can explore local urban parks, historic churches, and modern colleges, all while enjoying a rich cultural experience. Whether you're traveling solo, with family, or friends, Osteen provides ample opportunities for adventure and relaxation in a charming setting.

  1. University of Central Florida: A vibrant educational hub located 17 miles from Osteen, this modern university offers a lively atmosphere, with beautiful campus grounds and various cultural events that reflect the diversity of student life.
  2. Lake Monroe: Just 7 miles away, Lake Monroe is a picturesque destination perfect for romantic outings, beach activities, and enjoying stunning outdoor scenery, making it ideal for relaxation and recreation.
  3. Blue Spring State Park: Located 13 miles from Osteen, this national park is a paradise for adventure seekers, featuring scenic trails and opportunities for outdoor activities like swimming and kayaking in a breathtaking natural setting.

Things to do recommended for couples

For a romantic getaway in Osteen, indulge in luxury at Mayfair Country Club, embrace adventure with a thrilling skydive at Skydive DeLand, or enjoy some fun together at Congo River Golf in Altamonte Springs. Each experience offers a unique way to bond and create lasting memories.

Things to do recommended for families

Families visiting Osteen can enjoy a day at the Seminole County Sports Complex for some outdoor fun, relax at Green Springs Park, or have a blast at AMF Deltona Lanes with arcade games and bowling. Each spot offers great family vibes and memorable experiences.

Things to do recommended for groups

In Osteen, your group can shop at the Seminole Towne Center, enjoy outdoor activities at Deltona Golf Club, and experience culture and entertainment at the Wayne Dench Performing Arts Center, all within a short drive from your base.

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

When planning your trip—whether you're traveling with a group, family, pets, or seeking extended stays—be sure to adjust your filters according to your key preferences. Here are some helpful tips for booking on Vrbo.

  • Traveling to Osteen with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor areas for group gatherings. Fortunately, Vrbo allows you to filter for all of these options and much more.
  • Traveling to Osteen with young kids: Traveling with young kids can be quite demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Osteen: For many families, a vacation wouldn’t feel complete without their furry companion. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Osteen: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Osteen

Osteen, Florida, offers a delightful blend of outdoor adventures and family-friendly attractions. Nestled in Central Florida, visitors can explore verdant valleys and experience the charm of former farmland. With its relaxed atmosphere and friendly locals, Osteen serves as a perfect base to discover nearby cities that reflect Florida's vibrant culture. Enjoy scenic views and budget-friendly options while creating unforgettable memories in this picturesque region.

  • Orlando: Located 25 miles away from Osteen, Orlando is a vibrant city known for its family-friendly entertainment and business opportunities. It is a central hub for tourists seeking exhilarating experiences, with world-renowned theme parks and film studios at your doorstep. Visitors can enjoy shopping at bustling retail areas, exploring arts centers, and indulging in luxurious resorts. The city's attractions, including iconic landmarks and event conference venues, make it a must-visit destination for all types of travelers.
  • Deltona Lakes: Just 4 miles from Osteen, Deltona Lakes is a charming neighborhood perfect for outdoor enthusiasts and families alike. Known for its scenic beauty, it offers a wealth of recreational opportunities, including parks, lakes, and motor racing venues. Visitors can revel in the area's natural landscapes or spend time at local resorts that cater to a relaxing getaway. With its proximity to theme parks and lush green spaces, Deltona Lakes is an ideal spot for those looking for adventure and connection with nature.
  • Lemon Bluff: Nestled within the Osteen area, Lemon Bluff is a delightful city attracting travelers who appreciate outdoor activities and family-friendly experiences. The region features various recreational areas, resorts, and motor racing venues that keep visitors engaged. Highlights include access to marinas, theme parks, and museums, making it a well-rounded destination for leisure and education. Whether you're exploring the natural surroundings or enjoying local attractions, Lemon Bluff offers a unique blend of outdoor fun and cultural exploration.

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 SunnyAverageAverage
February63.7°F (17.6°C)Light RainMostly SunnyAverageSlightly High
March66.7°F (19.3°C)Light RainMostly SunnySlightly HighSlightly High
April71.8°F (22.1°C)Light RainMostly SunnySlightly HighSlightly High
May76.3°F (24.6°C)Light RainMostly SunnyAverageAverage
June80.2°F (26.8°C)Light RainMostly SunnyAverageAverage
July81.9°F (27.7°C)Light RainMostly SunnyAverageAverage
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 LowSlightly Low
December63.7°F (17.6°C)No Rain (Dry)Mostly SunnyAverageAverage

Booking with Vrbo is simple

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, extending your stay can lead to significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental. We’re here to help you find the perfect option!

Save more with One Key

Plan your group getaway by booking an eligible Vrbo property and enjoy the benefits of earning OneKeyCash™ on your reservation. Being the organizer truly pays off! When you join our travel rewards program, One Key, you'll gain immediate access to exclusive member savings and the opportunity to earn and redeem OneKeyCash™ on qualifying bookings. Sign up today and begin saving on your travels!

Vrbo Trips: Effortless planning

Vrbo's Trip Board offers a user-friendly platform where you can easily plan new trips, resume your previous arrangements, or manage your existing travel plans. You'll discover your saved or booked properties neatly organized under categories such as Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply go to: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

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)
  • New Smyrna Beach Golf Course (18.4 mi / 29.7 km)
  • Crane Lakes Golf and Country Club (18.8 mi / 30.3 km)
  • Orlando Speedworld (21.4 mi / 34.4 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:

  • New Smyrna Beach (20.8 mi / 33.5 km)
  • Lake Monroe Conservation Area (3.1 mi / 4.9 km)
  • 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)

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

How much does it cost to rent a vacation rental in Osteen?
Several factors can determine what you’ll pay for your vacation rental in Osteen, including the length of stay, season and type of property. Still, all our vacation homes have something in common — incredible value. Just enter your travel dates to find your ideal fit.
How much does it cost to rent a beach house in Osteen?
Prices for beach houses in Osteen vary depending on the type and size of the property and when you plan to travel. All you have to do is enter your travel dates into Vrbo and the number of guests to see available options and prices. From there you can use our filters to tailor your search results by ratings, nearby activities, amenities and more.
What are popular rental amenities in Osteen?
When it comes to rental amenities that people prefer in Osteen, a nearby waterfront, a firepit and a garden rank highest. With Vrbo vacation homes, there are choices to suit your style and taste, whether you’re on a trip with friends, family or even pets.
What are the top attractions for families in Osteen?
Give the kids a good time at these top family-friendly attractions in Osteen:

  • Wiregrass Prairie Preserve
  • Pell’s Citrus & Nursery

How old do you have to be to rent a vacation rental in Osteen?
It’s a good idea to check with the Osteen vacation home you’re considering on Vrbo as the minimum age differs. However, normally it’s 16, 18 or 21.
How long can I rent a vacation rental in Osteen for?
The amount of time you can book an Osteen vacation rental for is down to the property. Just enter your preferred travel dates to browse available options offering extended stays. They include all the things you need to make your extended break more enjoyable and comfortable, like laundries and air conditioning. Some properties may also offer discounted weekly or monthly prices, so you can have a longer stay for less.
Does Vrbo offer discounts for vacation homes in Osteen?
In Osteen, you’ll find some great discounts and deals for weekly and monthly discounts on vacation rentals, as well as newly listed homes on Vrbo. Whether you’re off on a weekend escape or an extended stay, we have a variety of options to suit every kind of traveler.

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