Photo by Jw

Longwood vacation rentals

We found 1,182 vacation rentals — enter your dates for availability

Discover a selection of 30 homes and other vacation rentals in Longwood that are perfect for your trip. Vacation homes provide the best amenities for you and your friends, family, or even pets, like WiFi and parking. At the end of the day, you'll find a rental for everyone's needs, including a place that is accessible or non-smoking.

Vacation rentals with weekly discounts - Longwood

Showing deals for:Apr 24 - May 1

Image gallery for Private guest studio in the heart of orlando.

Room
9.8 out of 10, Exceptional, (54 reviews)
Exceptional
(54 reviews)

Private guest studio in the heart of orlando.

Orlando

8% off
Price is $80
$562 for 7 nights
All fees included
Private guest studio in the heart of orlando.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Longwood

Why visit Longwood

  • Outdoor Adventures: Enjoy the picturesque urban parks and beautiful lakes, perfect for hiking, picnicking, and family outings.
  • Family-Friendly Activities: Explore various attractions that cater to visitors of all ages, ensuring fun for everyone.
  • Charming Neighborhoods: Discover the lovely Springwood Village, where you can experience local culture and scenic views.
  • Vibrant Arts Scene: Visit local art museums that showcase the rich creative talent of the area.
  • Comfortable Accommodations: Choose from a variety of vacation rentals, including spacious homes and cozy condos.

Popular types of accommodation in Longwood

If you're considering a getaway to Longwood, you're in for a treat. Our most popular vacation rentals include private homes, condos, and villas, each offering ample windows for natural light and spacious layouts with multiple rooms. Whether you prefer the charm of a lovely apartment or the comfort of a house rental, you'll find plenty of options to suit your needs. Enjoy a relaxing stay in this beautiful destination.

  • Houses: The top choice for travelers in Longwood, these homes offer spacious living and a home-like atmosphere, perfect for families or groups.
  • Condos: Ideal for those seeking a blend of comfort and convenience, condos provide modern amenities and often come with resort-style features.
  • Villas: Offering a touch of luxury, villas are popular for their spacious layouts and private outdoor areas.
  • Apartments: A great option for solo travelers and couples, apartments provide a cozy stay with essential amenities.
  • Cottages: Charming and quaint, cottages are perfect for a peaceful retreat, often located in serene settings.**

Top attractions near Longwood

Longwood, Florida, is perfect for outdoor, family, and city-themed vacations. Visitors can enjoy a variety of attractions, including urban parks, beautiful lakes, and art museums. Whether you're traveling solo, with family, or friends, Longwood offers diverse experiences that cater to all interests. Explore the local points of interest and embrace the vibrant atmosphere that Longwood has to offer for an unforgettable getaway.

  • Wekiwa Springs State Park: This beautiful state park offers a unique blend of adventure and natural beauty. Enjoy hiking trails, swimming in crystal-clear springs, and kayaking through scenic waterways, all while immersing yourself in the serene outdoors.
  • Boombah-Soldiers Creek Park: A family-friendly urban park with a vibrant atmosphere. It features playgrounds, sports fields, and picnic areas, making it an ideal spot for outdoor fun and relaxation in a lively city setting.
  • Rollins College: A picturesque modern college campus known for its beautiful architecture and vibrant cultural scene. Stroll through the scenic grounds, explore museums, and enjoy the rich history and arts of this esteemed institution.

Things to do recommended for couples

For a romantic getaway in Longwood, indulge in the luxury of Alaqua Country Club. Enjoy live music at The Social, just 11 miles away, or embark on a fun adventure at Congo River Golf, located 5 miles from Longwood. Create unforgettable memories together.

Things to do recommended for families

During your family vacation in Longwood, explore the natural beauty at Kelly Park, just 11 miles away, or enjoy sports at the Seminole County Sports Complex, located 8 miles away. For an adrenaline rush, head to Lil 500 Go-Karts, only 4 miles from Longwood.

Things to do recommended for groups

Explore the vibrant Altamonte Mall for shopping and entertainment, enjoy a round of golf at The Trophy Club of Orlando, or challenge your group at Casselberry Golf Club, both offering excellent outdoor sports vibes just a short drive away from Longwood.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

If you're traveling with a group, family, pets, or planning an extended stay, be sure to use the appropriate filters to meet your needs. Here are some helpful booking tips for Vrbo to assist you.

  • Traveling to Longwood with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor area for group gatherings. Luckily, Vrbo allows you to filter for all these options and more.
  • Traveling to Longwood with young kids: Traveling with young kids can present some challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, keeping in mind your closeness to family-friendly attractions can enhance your experience.
  • Taking your pets with you to Longwood: For many families, a trip isn't truly finished without their furry companion joining the fun. If that resonates with you, take a look at Vrbo listings that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and cozy beds, ensuring that your whole family feels at home.
  • Planning for a long term stay visiting Longwood: If you're searching for vacation rentals that offer 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 rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Longwood

Longwood, Florida, offers a delightful blend of outdoor adventures and family-friendly activities, making it an ideal destination for vacationers. Explore the charming neighborhoods like Springwood Village, where you can soak in the local lifestyle and enjoy scenic views. With a variety of housing options and a welcoming atmosphere, Longwood provides the perfect base for discovering nearby cities and enjoying the vibrant culture of Central Florida.

  • Orlando: Located 11 miles from Longwood, Orlando is a vibrant city renowned for its family-friendly attractions and entertainment-themed experiences. Visitors flock to this bustling metropolis for its world-famous theme parks, including Walt Disney World and Universal Studios, which promise endless fun for all ages. In addition to thrilling rides and character encounters, Orlando boasts a rich arts scene with numerous galleries and theaters. The city offers an array of shopping options, from luxury malls to quirky boutiques, making it a prime destination for those looking to indulge in retail therapy. Don’t miss the opportunity to attend exciting events at the Orange County Convention Center, a hub for conferences and exhibitions.
  • Casselberry: A mere 2 miles from Longwood, Casselberry is a charming city that appeals to those seeking a family-oriented, outdoor experience. The city features beautiful parks and recreational areas, perfect for picnicking and outdoor activities. Visitors can explore the local shopping mall, which offers a variety of retail options and dining experiences. Casselberry is also home to educational institutions and cultural hubs, making it a great spot for learning and exploration. Proximity to theme parks and a modern college university adds to the city's appeal for both families and young adults.
  • Winter Springs: Also located 2 miles from Longwood, Winter Springs is a delightful city that combines outdoor adventures with family-friendly activities. Known for its scenic parks and golf courses, it’s an excellent destination for nature lovers and sports enthusiasts alike. The area is rich in community events and features a number of educational centers. With nearby access to theme parks and stunning beaches, Winter Springs provides a well-rounded experience for visitors looking to enjoy both relaxation and recreation. This welcoming city encapsulates the charm of Central Florida living.

Best time to go to Longwood

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

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January60.1°F (15.6°C)Light RainMostly SunnyAverageAverage
February64.0°F (17.8°C)Light RainMostly SunnyAverageSlightly Low
March67.5°F (19.7°C)Light RainMostly SunnySlightly HighAverage
April72.5°F (22.5°C)Light RainMostly SunnyAverageAverage
May77.0°F (25.0°C)Light RainMostly SunnyAverageAverage
June81.0°F (27.2°C)Light RainMostly SunnyAverageSlightly High
July82.4°F (28.0°C)Light RainMostly SunnySlightly HighSlightly High
August82.6°F (28.1°C)Moderate RainMostly SunnyAverageAverage
September80.2°F (26.8°C)Light RainMostly SunnySlightly HighSlightly Low
October75.0°F (23.9°C)Light RainMostly SunnySlightly LowSlightly Low
November68.0°F (20.0°C)No Rain (Dry)Mostly SunnySlightly LowAverage
December64.0°F (17.8°C)No Rain (Dry)Mostly SunnySlightly LowSlightly High

Booking with Vrbo is a breeze

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Also, extending your stay can result in significant savings. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to refine your search by price, location, and type of vacation rental.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your entire reservation. Being the planner truly has its benefits. When you join our travel rewards program, One Key, you’ll gain access to exclusive member discounts and earn OneKeyCash on eligible bookings. Sign up today and begin enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo's Trip Board is designed to help you plan your travels with ease. Here, you can start new trip ideas, refine your existing plans, or manage your bookings all in one place. Your saved or booked properties are conveniently categorized into Potential, Upcoming, or Current Trips for better organization. To check out the Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Exciting Longwood will entice you

The lake and surrounding scenery provide a peaceful ambiance to your vacation home in Longwood. Well known for its shopping, restaurants and golfing, this cosmopolitan city won't disappoint. Universal Studios Florida and Universal Orlando Resort are just a couple of the must-sees in the area. Are you looking for specific amenities for your getaway? Many of our vacation rentals feature full kitchens and laundry facilities.

Activities and attractions in Longwood

Are you looking for attractions to see while you're in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Longwood a fun place to get away. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Universal Studios Florida (17.5 mi / 28.2 km)
  • Universal Orlando Resort (17.7 mi / 28.5 km)
  • The Wizarding World of Harry Potter™ (17.4 mi / 28 km)
  • Universal’s Islands of Adventure (17.9 mi / 28.8 km)
  • Universal’s Volcano Bay (18.6 mi / 29.9 km)
  • The Legacy at Alaqua Lakes (4.6 mi / 7.4 km)

Exploring the natural features in Longwood

Whether you're looking for fun outdoor activities or just want to take in the scenery, Longwood is a great place to get outside. Here are some of the area’s noteworthy sights, all within 30 miles (48.2 km) of the city center:

  • Boombah-Soldiers Creek Park (2.1 mi / 3.3 km)
  • Cranes Roost Park (3.8 mi / 6.2 km)
  • Red Bug Lake Park (4.6 mi / 7.4 km)
  • Lake Jesup (7.4 mi / 11.9 km)
  • Sylvan Lake Park (7.4 mi / 11.9 km)
  • Lake Virginia (8 mi / 12.9 km)

How to get to and around Longwood

The nearest airport is in Orlando Sanford Intl. Airport (SFB), located 7.6 mi (12.3 km) from the city center. If you can't find a flight that works for your travel itinerary, you could also fly into Orlando Intl. Airport (MCO), which is 18.9 mi (30.4 km) away.

Catch a ride on the metro at Longwood Station for ease of access to the rest of the city.

Frequently asked questions

What is the best area to stay in Longwood when booking a vacation rental?
When considering a vacation rental in Longwood, Florida, a popular area to stay is the charming neighborhood surrounding Historic Longwood. This area boasts a delightful blend of picturesque scenery and community charm, making it a superb base for exploring the region. The historic downtown district features beautiful architecture and local shops, providing a quaint backdrop for leisurely strolls. Additionally, you'll find the Longwood Historic District, where you can enjoy the unique character of the area.

Another great option is the vicinity near Lake Mary, which is just a short drive from Longwood. This area offers a range of vacation rentals and is renowned for its vibrant dining scene and shopping options. The nearby Central Florida Zoo & Botanical Gardens is a fantastic attraction for families, featuring a variety of animal exhibits and lush gardens to explore.

In terms of availability, both areas generally have a good number of vacation rental properties, suiting different group sizes and preferences.
How much does it cost to rent a vacation home in Longwood?
Prices for vacation rentals in Longwood vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Longwood to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Longwood vacation house rentals?
You can find great discounts on house rentals in Longwood on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of vacation rental accomodation in Longwood?
In Longwood, vacation houses are the most common type of rental, with about 25 available throughout the area. These houses typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and often outdoor patios or gardens, ideal for families or groups looking for a comfortable stay. Additionally, there are several cottages, condos, and chalets, each offering unique amenities and cozy settings that cater to different preferences.
Are there any family house rentals in Longwood?
In Longwood, Florida, families will find a variety of rental homes available—around 22 options throughout the area. This charming locale, known for its picturesque parks and welcoming community, offers spacious properties superb for group gatherings. Many homes include amenities such as fully equipped kitchens, dining areas, and comfortable living rooms, ensuring plenty of space for everyone to relax and enjoy their time together.

Visitors can take advantage of outdoor areas, which often feature private yards or patios, ideal for family activities and barbecues. The nearby Lake Mary and Wekiva Springs State Park provide opportunities for outdoor adventures, including hiking and picnicking, making it easy to explore the natural beauty of Central Florida.
Can I rent a vacation home with a pool or hot tub in Longwood?
In Longwood, Florida, there are several vacation homes available for rent that feature pools and hot tubs. This charming suburban area, located just north of Orlando, offers a range of properties suitable for families or groups. Many vacation rentals come with private pools, outdoor seating areas, and barbecue grills, making it a superb setting for relaxation and entertainment. Additionally, travelers can expect amenities like fully equipped kitchens, spacious living areas, and sometimes even game rooms or home theaters for added enjoyment. Find your rental in Longwood with a pool or a hot tub.
Can I find long-stay vacation rentals in Longwood?
A long-stay vacation rental in Longwood is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Longwood?
In Longwood, Florida, there are several pet-friendly house rentals available for travelers seeking a comfortable stay. These vacation homes typically feature spacious layouts, fully equipped kitchens, and outdoor areas such as fenced yards or patios, making them ideal for families and their furry companions. Many properties also offer amenities like private pools, laundry facilities, and Wi-Fi, ensuring a convenient and enjoyable experience.

The area is known for its proximity to beautiful parks, such as the nearby Wekiva Springs State Park, which offers scenic trails and opportunities for outdoor activities with pets. Additionally, the Longwood Historic District provides charming surroundings where visitors can explore local shops and eateries, further enhancing their stay. See all pet-friendly rentals in Longwood.
Are there any remote work vacation rentals in Longwood?
In Longwood, Florida, there are numerous remote work vacation rentals available, with around 31 options to choose from. This charming city, located just north of Orlando, offers a variety of accommodations that cater specifically to remote workers. Many of these properties feature dedicated workspaces, including desks and ergonomic chairs, ensuring a comfortable and productive environment. Additionally, high-speed Wi-Fi is commonly provided, allowing for seamless connectivity during work hours.

Travelers can expect well-equipped kitchens for meal preparation and spacious living areas for relaxation after a day of work. The area is also known for its pleasant parks and nearby lakes, providing opportunities for outdoor activities during breaks. Longwood's proximity to Orlando means that tenants can easily access attractions, dining, and shopping options, making it an ideal spot for mixing work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Longwood vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Longwood with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Longwood?
In Longwood, popular vacation rental amenities include WiFi, kitchens equipped for meal preparation, blenders for smoothies or snacks, coffee and tea makers for morning beverages, and patios for enjoying the pleasant Florida weather.
When is the best time to visit Longwood for a vacation rental?
March is the most popular time to visit Longwood, Florida, making it an ideal choice for vacation rentals. During this month, the mild weather and blooming landscapes create a picturesque setting for outdoor activities and sightseeing. With temperatures typically ranging from the mid-50s to the low 80s Fahrenheit, you'll find comfortable conditions superb for exploring the area's scenic parks and gardens.

The peak season in Longwood, spanning from February to April, attracts travelers eager to enjoy the beautiful Florida spring. This is a fantastic time for travelers, as the region offers a variety of activities, including walking tours, nature hikes, and visits to the local attractions. The warm weather allows for plenty of outdoor exploration, such as visiting the nearby Central Florida Zoo or enjoying a leisurely stroll through the lush parks.

If you're looking for a more budget-friendly option, November presents a wonderful opportunity to experience Longwood without the crowds. This month features delightful weather and the chance to enjoy the area's natural beauty at a more relaxed pace, making it superb for those who appreciate a quieter atmosphere.

Ultimately, the best time to book a vacation rental in Longwood depends on your preferences.
How early should I book a Longwood vacation rental?
Book your Longwood vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Longwood?
In Longwood, Florida, visitors can explore several attractions that showcase the area's natural beauty and history. The city is home to the historic Longwood Historic District, where charming old homes and buildings reflect the region's past. Nearby, the beautiful Wekiwa Springs State Park offers opportunities for outdoor activities such as hiking, swimming, and canoeing amidst stunning natural scenery.

For those interested in gardens, the nearby Harry P. Leu Gardens in Orlando provides a picturesque setting with lush landscapes and a variety of plant species, just a short drive from Longwood.
Can I change or cancel my Longwood home rental booking on Vrbo?
To find Longwood vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Longwood vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

More Vacation Ideas