Longwood holiday rentals

We found 1,279 holiday rentals — enter your dates for availability
Discover a selection of 33 homes and other holiday rentals in Longwood that are perfect for your trip. Holiday homes offer the best amenities for your stay with friends, family or just your pet, such as Wi-Fi and parking. No matter what you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Longwood

Showing deals for:6 Nov - 13 Nov

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why visit Longwood

  • Beautiful Parks: Enjoy the lush greenery and recreational areas perfect for picnics and outdoor activities.
  • Scenic Lakes: Explore serene lakes ideal for leisurely walks and tranquil views, enhancing your outdoor experience.
  • Art and Culture: Discover local art museums showcasing the vibrant creative community of Longwood.
  • Family-Friendly Activities: Engage in a variety of activities suitable for all ages, ensuring fun for the whole family.
  • Community Events: Participate in lively community events that highlight the city’s welcoming atmosphere and culture.

Popular types of accommodation in Longwood

Welcome to Longwood, Florida, a charming city nestled in the heart of Central Florida. Known for its beautiful parks and serene lakes, Longwood offers a plethora of outdoor activities and experiences. From scenic walking trails to vibrant community events, there’s something for everyone. When it comes to accommodation, you can choose from comfortable private holiday homes, villas, and condos, many featuring pools and air conditioning to ensure a relaxing stay. Enjoy your getaway in this delightful destination.

  • Private Holiday Homes: The top choice for visitors seeking a more personal touch, these homes provide a comfortable and spacious environment for families or groups.
  • Condos: A popular option for those who desire a blend of privacy and communal amenities, ideal for a relaxing getaway.
  • Villas: Luxurious and often spacious, villas offer a touch of elegance with private gardens and pools.
  • Apartments: Perfect for couples or solo travellers looking for convenience and accessibility in a homely setting.
  • Cottages: Quaint and charming, these cosy retreats are perfect for a peaceful escape in nature.**

Top attractions near Longwood

Longwood, Florida, is a charming city perfect for family and outdoor holidays, offering a delightful mix of urban parks, art museums, and serene lakes. Visitors can enjoy family-friendly activities and explore the beautiful natural surroundings, making it an ideal destination for those seeking a city-themed experience. With its inviting atmosphere and various attractions, Longwood caters to all types of travellers looking for memorable experiences in a picturesque setting.

  • Wekiwa Springs State Park: Enjoy outdoor adventures and scenic beauty in this national state park, located 13km from Longwood, offering a refreshing retreat into nature.
  • Casa Feliz Historic Home Museum: Explore cultural heritage at this historic home, situated 11km from Longwood, where history and tradition come alive.
  • Harry P. Leu Gardens: Discover family-friendly outdoor romance and botanical splendour in this garden, 14km from Longwood, perfect for leisurely strolls.

Things to do recommended for couples

Discover Longwood, Florida with your loved one. Enjoy a leisurely walk through charming local streets, savour a delightful meal at a cosy café, and immerse in the vibrant local culture. Experience an enchanting escape, perfect for couple travellers seeking authentic moments.

Things to do recommended for families

Families will enjoy exploring the attractions in Longwood, Florida, with plenty of parks and interactive museums to discover local heritage and culture. Ideal for children, these experiences offer engaging outdoor adventures and educational activities for a memorable family holiday.

Things to do recommended for groups

Experience the thrill of motor racing at Orlando Speedworld, located 29km from Longwood. Perfect for adrenaline seekers, this venue offers an exhilarating atmosphere and plenty of excitement for your group to enjoy together.

*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

Whether you’re travelling with a group, as a family, with your pets, or planning an extended stay, ensure you use the appropriate filters. Here are some Stayz booking tips for you.

  • Traveling to Longwood with a group: Consider how many bedrooms you'll require, together with facilities such as a fully-equipped kitchen or an outdoor area for a group gathering. Fortunately, you can apply filters for all these features, and more, on Stayz.
  • Traveling to Longwood with young kids: Travelling with young children can be quite demanding. It's important to prioritise their comfort and safety, as well as to look for age-appropriate facilities, like a private swimming pool. Additionally, considering your closeness to family-friendly attractions is a wise choice.
  • Taking your pets with you to Longwood: For many, a family holiday isn’t truly complete without their furry companion by their side. If this resonates with you, explore Stayz properties that welcome pets. The majority of pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Longwood: If you’re in search of holiday rentals offering discounts for stays of a month or more, you’ve come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include options such as a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Longwood

Longwood, Florida offers a delightful blend of family-friendly charm and urban vibrancy. Enjoy a pleasant stay in this convenient city, where diverse recreational options and scenic spots abound. The community’s welcoming atmosphere, coupled with measures for business and leisure travel, ensures an enriching experience during your visit.

  • Orlando: Located 18km from Longwood, Orlando is a dynamic city offering a rich palette of experiences for diverse travellers. Renowned for its family-friendly appeal, the city beckons those seeking a blend of entertainment and business opportunities. Visitors can immerse themselves in a vibrant mix of activities ranging from expansive shopping areas and arts centres to renowned theme parks and film studios. The urban landscape is dotted with venues hosting events and conferences, making Orlando a lively hub of culture and commerce.
  • Casselberry: Just 3km from Longwood, Casselberry presents a charming city experience with a focus on family and outdoor activities. This locale is ideal for visitors who appreciate a blend of urban and recreational pursuits. The area offers a range of engaging activities, including educational centres and golf courses, alongside urban parks and modern college campuses. The close proximity to theme parks further enhances its appeal, ensuring a balanced mix of leisure and learning.
  • Winter Springs: Also 3km from Longwood, Winter Springs is a delightful city that combines a family-friendly atmosphere with a love for the outdoors. The town invites travellers to explore its educational offerings, golf facilities, and various recreational venues. Highlights include nearby theme parks, modern college institutions, and scenic lakes, which add to the charm of this well-rounded destination. Winter Springs is an excellent choice for those seeking a blend of urban convenience and natural beauty.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 SunnyAverageSlightly Low
September80.2°F (26.8°C)Light RainMostly SunnySlightly HighSlightly Low
October75.0°F (23.9°C)Light RainMostly SunnySlightly LowAverage
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 Stayz is simple

Looking to save on your next journey? Being flexible with your travel dates can really pay off, as prices often fluctuate. You can also enjoy considerable savings by booking a longer stay. To locate a Stayz property that suits your budget, simply use our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Planning made easy

Stayz's groundbreaking Trip Board offers you a dedicated space to craft new journeys, pick up from where you last paused, or review and arrange your plans. You can easily access your previously saved and booked properties, which are organised under Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.

Vibrant Longwood will entice you

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

Activities and attractions in Longwood

Are you hoping to find things to do during your stay? Venture out of your holiday home and experience everything that makes Longwood a fun place to get away to. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Universal Studios Florida (17.5 mi / 28.2 km)
  • Universal Orlando Resort (17.7 mi / 28.5 km)
  • Universal’s Volcano Bay (18.6 mi / 29.9 km)
  • The Wizarding World of Harry Potter™ (17.4 mi / 28 km)
  • Universal CityWalk (17.7 mi / 28.4 km)
  • Universal’s Islands of Adventure (17.9 mi / 28.8 km)

Exploring the natural features in Longwood

Whether you're an adventurous traveller or just want to spend some time taking in the scenery, Longwood is a great place to get out in nature. These are some of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Boombah-Soldiers Creek Park (2.1 mi / 3.3 km)
  • Cranes Roost Park (3.8 mi / 6.2 km)
  • Sanlando Park (3.9 mi / 6.2 km)
  • Central Winds Park (4 mi / 6.5 km)
  • Red Bug Lake Park (4.6 mi / 7.4 km)
  • Lake Jesup (7.4 mi / 11.9 km)

How to get to and around Longwood

The nearest airport is in Orlando, FL (SFB-Orlando Sanford Intl.), located 7.6 mi (12.3 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to Orlando International 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 holiday home?
Wekiva Springs is one of the most popular neighbourhoods to get a Stayz holiday home in Longwood. Have a look at our comfy stays and then go out and discover this destination like a local.
What is the most popular type of holiday home accommodation in Longwood?
The most desirable types of holiday homes in Longwood are houses. Looking for something different? Stayz has numerous options to match the diverse needs of our guests, so you'll see holiday homes in lots of sizes and shapes. The ideal fit is ready and waiting for you — find yours today.
How much does it cost to rent a holiday home in Longwood?
The average price for a holiday home in Longwood is determined by several factors, like length of stay, property type and season. Whether you're in search of a sprawling villa with room to move around or a cosy cabin that's perfect for two, just enter your travel dates to see stays that offer great value.
How much does it cost to rent a beach house in Longwood?
The average price for a holiday home near the beach in Longwood will depend on when you'll be there and the type and size of property you're searching for. Find prices quickly and easily on Stayz by entering your travel dates. Then use our handy filter tool to choose the number of bedrooms and amenities that you prefer, like air conditioning, WiFi and a pool.
Are there pet-friendly holiday homes in Longwood?
Pack a suitcase for the pup in your life because Longwood has 15 holiday homes that roll out the welcome mat to pets. Let your four-legged buddy enjoy fun with the family at one of our pet-friendly holiday homes on Stayz. Simply enter your destination and dates, then check our "Pets allowed" filter box.
Can I rent a house with a pool in Longwood?
Check the "pool" box in our handy filter tool and take your pick of seven houses with private pools in Longwood on Stayz. Gentle soak, ball games or noodle joust? How you spend your free time is up to you when your holiday home has a swimming pool.
What are popular home amenities in Longwood?
Some of the most popular home amenities people prefer in Longwood are a fireplace, a nearby river and nearby museums. Whether you're hitting the road with your besties, family or even pets, Stayz holiday homes have the best amenities for beginning new traditions with the people you love.
Are there large group holiday homes in Longwood?
You can choose from two holiday properties in Longwood that can host 10 or more guests. Whether you're organising time away with the family or a celebration like an anniversary, there's enough space to get your favourite people together under one roof.
Are there holiday homes in Longwood that welcome kids?
Longwood has 15 family-friendly holiday homes to pick from. And booking a stay that welcomes little ones is easy with Stayz's "Properties good for families" filter. As well as having the entire place to yourselves, you'll get access to perks and conveniences like extra bedrooms, full kitchens and private pools.
What are the top attractions for families in Longwood?
Keeping the kids entertained during your stay in Longwood is easy with these awesome family-friendly attractions:

  • Central Florida Zoo & Botanical Gardens
  • Sanford Museum
  • Hannibal Square Heritage Centre

Can I find two-bedroom holiday homes in Longwood?
Take your pick of two two-bedroom homes in Longwood. Settle the kids into the second room or maybe fill it with a couple of your nearest and dearest friends. There's ample space for whoever's fortunate enough to be coming along.
Are there holiday homes with WiFi in Longwood?
Whether you want to keep up with the headlines, send a few emails or surf your social networks, there are eight holiday homes with WiFi in Longwood. Check the "WiFi" box when searching on Stayz and stay connected on your holiday.
How can I find holiday homes with air conditioning in Longwood?
Longwood has 14 holiday homes where you can chill out in air-conditioned comfort. To find a stay on Stayz offering this perk, choose your travel dates and use the filter tool to select the "air conditioning" box.
How old do you have to be to rent a holiday home in Longwood?
Age restrictions can differ across properties on Stayz, so check the rules of the holiday home in Longwood you're considering. But normally, it's 16, 18 or 21.
How long can I rent a holiday home in Longwood for?
The amount of time you can stay in a Longwood holiday home for depends on the property. Simply enter your dates of travel to see options that offer long-term stays. They come with everything you need to make your extended getaway more enjoyable and comfortable, like air conditioning and kitchens. Some properties might also offer weekly or monthly discounted prices, so you can stay even longer for less.