Longwood Accommodations

Relax by the pool at this retreat near parks, kayaking, and downtown.

Highly Rated

House

Relax by the pool at this retreat near parks, kayaking, and downtown.

10.0

Exceptional

(196 Reviews)

1 Bedroom 1 Bath 2 Guests

AU $189/Night 7 Nights - AU $1,322

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Private Outdoor Oasis w/Pool: Home in Longwood!

House

Private Outdoor Oasis w/Pool: Home in Longwood!

10.0

Exceptional

(1 Review)

4 Bedrooms 2 Baths 8 Guests 1603.82 ft²

AU $686/Night 7 Nights - AU $4,799

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Pool Access! Dog-friendly Retreat 16 Mi to Orlando

Apartment

Pool Access! Dog-friendly Retreat 16 Mi to Orlando

1 Bedroom 1 Bath

AU $520/Night 7 Nights - AU $3,640

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House

Tropical Oasis - Heated Luxury Pool - Game Room

10.0

Exceptional

(23 Reviews)

4 Bedrooms 3 Baths 14 Guests

AU $576/Night 7 Nights - AU $4,035

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Fire Pit + Private Yard: Family Home in Longwood!

House

Fire Pit + Private Yard: Family Home in Longwood!

10.0

Exceptional

(1 Review)

3 Bedrooms 2 Baths 10 Guests 1097.92 ft²

AU $270/Night 7 Nights - AU $1,892

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House

This Charming House with an outdoor pool, 3 bedrooms, 2 full baths.

10.0

Exceptional

(10 Reviews)

3 Bedrooms 2 Baths 6 Guests 1344 ft²

AU $463/Night 7 Nights - AU $3,238

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Longwood Private Suite - Near Orlando - Modern, Private Entrance, Fast WiFi

House

Longwood Private Suite - Near Orlando - Modern, Private Entrance, Fast WiFi

9.5

Exceptional

(2 Reviews)

1 Bedroom 1 Bath 4 Guests 344.45 ft²

AU $147/Night 7 Nights - AU $1,026

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House

Downtown Historic Longwood steps to City park & SunRail

10.0

Exceptional

(6 Reviews)

3 Bedrooms 2 Baths 6 Guests

AU $564/Night 7 Nights - AU $3,951

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House

Spacious and relaxing Home - Longwood, Florida

9.0

Exceptional

(3 Reviews)

5 Bedrooms 4 Baths 10 Guests 75.35 ft²

AU $646/Night 7 Nights - AU $4,523

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House

The lakefront Brantley House

10.0

Exceptional

(5 Reviews)

3 Bedrooms 2 Baths 6 Guests 2440 ft²

AU $408/Night 7 Nights - AU $2,853

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House

Pool Access! Dog-Friendly Retreat 16 Mi to Orlando

8.8

Fabulous

(5 Reviews)

2 Bedrooms 1 Bath 5 Guests 699.65 ft²

AU $409/Night 7 Nights - AU $2,864

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House

WHOLE HOUSE Near Universal & Seaworld

10.0

Exceptional

(3 Reviews)

4 Bedrooms 3 Baths 8 Guests

AU $528/Night 7 Nights - AU $3,695

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More Top-Rated Accommodations in Longwood Area

Why Choose Rent By Owner for your Longwood Accommodations?

What makes our Accommodations 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 Accommodations stay?

To make the most of your stay, consider visiting during the region’s shoulder seasons when the weather is pleasant and crowds are fewer, allowing you to enjoy everything this destination has to offer without the busy peak times in Longwood, Florida.

Peak Season Highlights

March to May (Spring)

During the spring months, this destination experiences a surge in visitors attracted by pleasant weather and outdoor activities, making it an ideal time to explore the area.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F

December to February (Winter)

The winter season attracts travelers seeking mild climates and festive events, providing a comfortable climate for exploring local attractions and enjoying seasonal festivities.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F

Off-Season Highlights

June to August (Summer)

In the summer months, the region experiences fewer visitors due to high temperatures, offering a quieter experience for those looking for more peaceful accommodations.

Average Temperature Daytime: 85°F to 95°F - Nighttime: 70°F to 75°F

September to November (Fall)

Autumn brings a slowdown in travel as temperatures moderate and the region becomes less crowded, making it a good time for relaxed visits and affordable stays.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F

Weekly Weather Forecast for Longwood

How to Book Your Longwood Accommodations

What's our booking process?

Our platform allows you to browse a curated selection of accommodations. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

Search Properties

Use our filters to find the right property that fits your needs.

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Longwood

More Top-Rated Accommodations in Longwood Area

Common Accommodations Amenities

What amenities can you expect?

Our Accommodations 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 outdoor grilling and dining areas for entertaining family and friends.
Relax by private swimming pools, perfect for warm Florida days.
Take advantage of spacious patios or decks for outdoor lounging and sunbathing.
Explore beautifully landscaped gardens or yard spaces to unwind or play outdoor games.
Make use of dedicated outdoor seating areas to enjoy the pleasant weather.
Benefit from access to nearby parks or natural preserves for outdoor activities.
Utilize shaded pergolas or cabanas for comfortable outdoor relaxation in this sunny region.

Top Attractions Around Longwood

What attractions are nearby?

In this charming destination, you can explore a variety of nearby outdoor pursuits and cultural attractions that showcase the best of the region, making your stay truly memorable.

Family Activities

Lake Lotus Nature Preserve Explore this natural sanctuary featuring walking trails and educational programs that are perfect for a family day out in the area.
Continuous Education Center Engage your family with interactive exhibits and wildlife encounters at this local center dedicated to environmental awareness.
Westmonte Park Enjoy outdoor activities such as playgrounds, sports fields, and picnic areas ideal for family fun in the region.
Longwood Historic Trail Discover the area's rich history on this scenic trail, offering an educational experience suitable for all ages.

Adult Activities

Lake Brantley Park Enjoy a relaxing day outdoors with scenic walking trails and lakeside picnicking in this popular park.
White Birch Sports Complex Engage in competitive sports or casual recreation at this well-maintained facility designed for adults seeking active leisure.
The Renaissance Theatre Experience live performances, concerts, and cultural events that showcase the vibrant arts scene of the region.
Golfing at Timacuan Golf Club Play a round of golf on championship courses set amidst lush landscapes, perfect for enthusiasts visiting here.

Other Places to Stay in Longwood, FL

Longwood Travel Tips

How Can You Make the Most of Your Stay?

Plan Your Activities in Advance: Research local parks, shopping centers, and dining options to maximize your time during your stay in the area.
Choose a Central Location: Select an accommodation close to major attractions and essential amenities for convenience and easier exploration.
Utilize Local Transportation: Take advantage of nearby transit services or rent a vehicle to effortlessly navigate around this vibrant destination.
Explore Hidden Gems: Talk to locals or check online resources for lesser-known spots that provide authentic experiences unique to the region.

Transportation Options

Personal Vehicles: Renting a car offers you the flexibility to explore the area and visit nearby attractions at your own pace.
Shuttle Services: Convenient shuttle options are available for direct transport to major airports and key locations within the region.
Public Transit: Local bus systems provide an economical way to get around without the need for driving, connecting you to popular spots.
Taxis and Rideshares: Rideshare services and taxis offer quick, reliable transportation for short trips around here’s charming neighborhoods.

Local Customs Options

Southern Hospitality: Visitors often notice the warm and welcoming attitude that reflects the region's tradition of Southern hospitality, making your stay in the area more comfortable and friendly.
Local Festivals and Events: Participating in community festivals and events is a common way for residents to celebrate their heritage, offering you an authentic cultural experience during your visit.
Respect for Nature: The region’s emphasis on environmental preservation encourages visitors to adhere to local wildlife protection guidelines and enjoy outdoor activities responsibly.
Traditional Cuisine: Enjoying regional dishes at local eateries highlights the area's culinary customs, which are rooted in a rich history of Southern flavors and hospitality.

Frequently Asked Questions about Longwood Accommodations

1. What are the top Accommodations 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 Accommodations in Longwood:

2. How many Accommodations are available in Longwood?

Currently, the total number of properties listed by RBO in 2026 is over 63 in the Longwood area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Accommodations in Longwood. 

3. What is the cancellation policy for accommodations in Longwood, Florida?

Cancellation policies vary depending on the specific property listing. You should review the cancellation terms listed on the booking page or contact the property owner directly for detailed information.

4. Are there any additional fees I should be aware of when booking here?

Additional fees such as cleaning fees, service charges, or local taxes are typically outlined in the property listing. Be sure to read all details carefully before confirming your reservation.

5. What amenities can I expect during my stay?

Amenities differ between properties, so it's best to check the individual listing for details like Wi-Fi, parking, kitchen facilities, or other features available during your visit.

6. How do I secure a booking at a preferred property?

Booking is confirmed once you complete the reservation process and receive confirmation from the host or owner. For special requests or inquiries, contacting the property owner directly can help ensure your needs are met.

7. Is there a minimum stay requirement in this destination?

Minimum stay requirements depend on the property or listing policies. These details are specified in the listing, so reviewing them beforehand will help plan your visit accordingly.