Best Vacation Homes in Longwood
House
10.0(196 Reviews)
1 Bedroom
1 Bath
2 Guests
Private Pool
Hot Tub
Parking
Pool
US $132/Night
7 Nights - US $924
House
10.0(1 Review)
4 Bedrooms
2 Baths
8 Guests
1603.82 ft²
- Hot Tub
- Parking
- Pool
Balcony/Terrace
US $479/Night
7 Nights - US $3,355
Apartment
1 Bedroom
1 Bath
- Pool
Ocean View- Balcony/Terrace
View
US $364/Night
7 Nights - US $2,545
House
10.0(23 Reviews)
4 Bedrooms
3 Baths
14 Guests
- Parking
- Balcony/Terrace
Kitchen
Air Conditioner
US $403/Night
7 Nights - US $2,821
House
10.0(1 Review)
3 Bedrooms
2 Baths
10 Guests
1097.92 ft²
- Parking
Internet
Child Friendly
Security/Safety
US $189/Night
7 Nights - US $1,323
House
10.0(10 Reviews)
3 Bedrooms
2 Baths
6 Guests
1344 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $323/Night
7 Nights - US $2,264
House
10.0(6 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $395/Night
7 Nights - US $2,762
House
10.0(5 Reviews)
3 Bedrooms
2 Baths
6 Guests
2440 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $287/Night
7 Nights - US $2,009
Longwood Luxury Rentals
House
7.4(3 Reviews)
6 Bedrooms
5 Baths
16 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,672/Night
7 Nights - US $11,706
House
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $823/Night
7 Nights - US $5,758
House
9.6(10 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $710/Night
7 Nights - US $4,967
House
9.0(3 Reviews)
5 Bedrooms
4 Baths
10 Guests
75.35 ft²
- Parking
- View
- Air Conditioner
- Internet
US $452/Night
7 Nights - US $3,162
House
10.0(1 Review)
6 Bedrooms
3 Baths
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $447/Night
7 Nights - US $3,126
Ski Chalet
9.6(17 Reviews)
4 Bedrooms
3 Baths
8 Guests
- Hot Tub
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $435/Night
7 Nights - US $3,043
House
10.0(3 Reviews)
4 Bedrooms
3 Baths
8 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $369/Night
7 Nights - US $2,583
House
7.4(3 Reviews)
2 Bedrooms
1 Bath
5 Guests
700 ft²
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $365/Night
7 Nights - US $2,555
Longwood Pet Friendly Vacation Rentals
House
9.0(73 Reviews)
3 Bedrooms
2 Baths
8 Guests
Oceanfront- Hot Tub
- Parking
- Ocean View
US $208/Night
7 Nights - US $1,458
House
9.5(2 Reviews)
1 Bedroom
1 Bath
4 Guests
344.45 ft²
- Parking
- View
- Air Conditioner
- Internet
US $102/Night
7 Nights - US $717
House
9.0(16 Reviews)
3 Bedrooms
2 Baths
10 Guests
1938 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $233/Night
7 Nights - US $1,633
House
8.8(5 Reviews)
2 Bedrooms
1 Bath
5 Guests
699.65 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $286/Night
7 Nights - US $2,002
New
House
1 Bedroom
1 Bath
4 Guests
- Balcony/Terrace
- Air Conditioner
- Internet
Pet Friendly
US $172/Night
7 Nights - US $1,202
Cottage
3 Bedrooms
1 Bath
6 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $188/Night
7 Nights - US $1,318
House
10.0(17 Reviews)
4 Bedrooms
2 Baths
11 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $476/Night
7 Nights - US $3,330
House
10.0(3 Reviews)
3 Bedrooms
1 Bath
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $165/Night
7 Nights - US $1,152
Longwood Large Vacation Homes
House
10.0(34 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $287/Night
7 Nights - US $2,009
House
9.8(9 Reviews)
3 Bedrooms
2 Baths
10 Guests
1100 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $225/Night
7 Nights - US $1,577
House
5.0(12 Reviews)
3 Bedrooms
3 Baths
10 Guests
3000 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $407/Night
7 Nights - US $2,849
House
5.0(4 Reviews)
6 Bedrooms
4 Baths
16 Guests
4000 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
US $370/Night
7 Nights - US $2,590
House
2.0(1 Review)
3 Bedrooms
1 Bath
30 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $199/Night
7 Nights - US $1,393
House
5 Bedrooms
3 Baths
7 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $269/Night
7 Nights - US $1,882
Why Choose Rent By Owner for your Longwood Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Longwood
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit here ensures you experience the best of what this destination has to offer, whether you're seeking pleasant weather or lively local events in the area.
Peak Season Highlights
March to May
During spring, this destination experiences warm and pleasant weather, making it an ideal time for outdoor activities and exploring the local area.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
December to February
Winter months bring mild temperatures with less humidity, offering a comfortable climate for sightseeing and enjoying the region’s quieter atmosphere.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F
Off-Season Highlights
June to August
Summer in the area is marked by higher temperatures and increased humidity, which may lead to fewer visitors but provides opportunities for indoor leisure and water-based activities.
Average Temperature Daytime: 85°F to 92°F - Nighttime: 70°F to 75°F
September to November
Autumn features cooler weather and less crowded conditions, making it a peaceful time for those seeking a more relaxed experience while still enjoying the regional climate.
Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F
Weekly Weather Forecast for Longwood
How to Book Your Longwood Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Longwood
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor swimming pool to relax and unwind during your stay.
- Take advantage of spacious patios or decks perfect for outdoor dining and entertaining.
- Benefit from lush, landscaped gardens that provide a serene setting in the region.
- Make use of outdoor grilling areas to prepare meals with fresh ingredients from local markets.
- Experience the comfort of shaded lounging areas for relaxing afternoons in the sun.
- Utilize dedicated outdoor play spaces for children to enjoy active fun safely.
- Have access to scenic patios or balconies with views of the surrounding greenery, ideal for morning coffee or evening unwinding.
Top Attractions Around Longwood
What attractions are nearby?
In this charming area, you can enjoy a variety of outdoor activities, visit local parks, and explore community events that showcase the best of what the region has to offer during your stay.
Family Activities
- Longwood Historic Park: You can explore the area's history through engaging exhibits and scenic walking trails suited for family outings.
- Lakeside Park: Spend quality time near the water with picnicking, playground activities, and nature walks that are perfect for families looking to enjoy the outdoors.
- Crane's Roost Park: Attend family-friendly events or relax by the lake while enjoying a variety of recreational activities in this vibrant community space.
- St. Peter's Catholic Church Nature Trail: Discover local flora and fauna on this peaceful trail, ideal for educational family walks within the neighborhood.
Adult Activities
- Wekiwa Springs State Park: Explore the natural beauty of this nearby state park, where you can enjoy kayaking, hiking, and swimming amidst lush Florida landscapes.
- Crane’s Roost Park: Experience outdoor leisure at this popular urban park, perfect for relaxing walks, live community events, or enjoying scenic views of the Lake Brantley area.
- Historic Downtown Longwood: Discover charming shops, local eateries, and cultural attractions in the historic district that offers a taste of the area's rich history and vibrant community life.
- Altamonte Mall: Indulge in retail therapy and dine at diverse restaurants at this regional shopping center conveniently located in the region for a fun day out.
Other Places to Stay in Longwood, FL
North Orlando
Aiguille Rock Climbing Center
Rebounderz of Longwood
The Trophy Club Of Orlando
Big Tree Park
Boombah-Soldiers Creek Park
Diamond Player's Club - Wekiva
The Legacy at Alaqua Lakes
Alaqua Country Club
Wekiva Springs
Longwood Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead for Local Events: Check the area's event calendar during your stay to align your activities with local festivals or happenings that add a special touch to your visit.
- Explore Nearby Natural Spots: Take advantage of the region's parks and outdoor spaces to enjoy a relaxing day immersed in the natural beauty surrounding your vacation rental.
- Discover Local Dining Options: Savor authentic flavors at nearby restaurants offering regional cuisine, enhancing your experience of the destination.
- Utilize Convenient Transportation: Rent a vehicle or familiarize yourself with local transit to easily access key attractions and make the most of your time here.
Transportation Options
- Longwood SunRail Station: This commuter rail station offers convenient train services connecting you to major destinations across Central Florida, making travel in and around the area straightforward.
- Orlando International Airport: Located nearby, this airport provides extensive domestic and international flights, ensuring easy arrivals and departures for your stay.
- Local Bus Services: The region is well-served by bus routes that connect various neighborhoods and attractions, allowing you to explore comfortably without a car.
- Taxi and Ride-Sharing Services: Reliable options like taxis and ride-sharing apps are readily available here, offering quick and convenient transportation on demand.
Local Customs Options
- Southern Hospitality:** You will notice the warm and welcoming attitude of locals, reflecting the region’s tradition of Southern hospitality that makes visitors feel at home.
- Local Festivals:** Participating in community festivals offers a glimpse into the area's rich cultural heritage and the friendly spirit of its residents.
- Food Customs:** Enjoy the local cuisine, which features Southern-style dishes and fresh ingredients typical of this destination's culinary customs.
- Community Events:** Engaging in neighborhood events highlights the region’s close-knit community ties and appreciation for shared traditions.
Longwood Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Longwood?
There are a lot of options in Longwood. If you plan on staying in the Longwood area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Longwood:
- Relax by the pool at this retreat near parks, kayaking, and downtown.
- Tropical Oasis - Heated Luxury Pool - Game Room
- This Charming House with an outdoor pool, 3 bedrooms, 2 full baths.
- Downtown Historic Longwood steps to City park & SunRail
- The lakefront Brantley House
- WHOLE HOUSE Near Universal & Seaworld
- Private Outdoor Oasis w/Pool: Home in Longwood!
- Themed 6BR Home! Prime Location! Very Spacious! Close to Disney and Universal!
- A stunning retreat on a luxurious 2 acre estate
- Fire Pit + Private Yard: Family Home in Longwood!
2. How many vacation rentals have private pools in Longwood?
There are 1 vacation rentals with private pools near Longwood. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Longwood are best for families?
If you are looking for a family-friendly vacation home in Longwood, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Longwood:
4. How many Rentbyowner vacation rentals are available in Longwood?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 68 in the Longwood area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Longwood.
5. What is the cancellation policy for vacation rentals in this region?
Cancellation policies vary by property, so it's important to review the specific listing details. You can find this information on the booking page or by contacting the property owner directly to understand any fees or restrictions.
6. How do I check the availability of a vacation rental during my travel dates?
Availability is updated regularly on the listing. To confirm if your preferred dates are open, use the booking platform's calendar feature or reach out to the host for real-time updates.
7. Are there any additional fees I should be aware of when booking here?
Additional fees such as cleaning charges or service taxes may apply and are detailed in the listing. Always review the total price breakdown before confirming your reservation.
8. What amenities are typically included in vacation rentals in this area?
Most properties offer essential amenities like Wi-Fi, kitchen facilities, and parking. Specific features are listed in each property description, so reviewing those details will help determine if the rental meets your needs.
9. How do I contact the property owner if I have questions before booking?
You can message the owner directly through the booking platform's messaging system. This allows you to clarify any details about the property or the booking process before finalizing your stay.
Longwood Top Rated Vacation Rentals
House
10.0(1 Review)
4 Bedrooms
3 Baths
8 Guests
2300 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $550/Night
7 Nights - US $3,848
House
9.8(7 Reviews)
4 Bedrooms
2 Baths
8 Guests
1600 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $443/Night
7 Nights - US $3,103
House
8.8(6 Reviews)
2 Bedrooms
1 Bath
5 Guests
700 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $243/Night
7 Nights - US $1,700
House
7.2(5 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $259/Night
7 Nights - US $1,814
Apartment
5.0(1 Review)
2 Bedrooms
2 Baths
4 Guests
- Pool
- Kitchen
- Air Conditioner
- Child Friendly
US $171/Night
7 Nights - US $1,197
Apartment
5.0(1 Review)
2 Bedrooms
2 Baths
4 Guests
- Pool
- Kitchen
- Air Conditioner
- Internet
US $116/Night
7 Nights - US $812
House
4.9(16 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $215/Night
7 Nights - US $1,505
House
4.8(19 Reviews)
3 Bedrooms
2 Baths
9 Guests
2100 ft²
- Pool
- Kitchen
- Air Conditioner
- Internet
US $245/Night
7 Nights - US $1,715
