Best Vacation Homes in Leesburg
Cottage
2 Bedrooms
2 Baths
6 Guests
966 ft²
Fireplace/Heating
Balcony/Terrace
Kitchen
Parking
US $318/Night
7 Nights - US $2,225
House
10.0(1 Review)
2 Bedrooms
2 Baths
6 Guests
1205.56 ft²
Oceanfront- Fireplace/Heating
Ocean View- Balcony/Terrace
US $320/Night
7 Nights - US $2,240
Hotel
8.6(199 Reviews)
1 Bath
- Fireplace/Heating
Pool
Breakfast- Parking
US $139/Night
7 Nights - US $972
House
10.0(82 Reviews)
4 Bedrooms
2 Baths
12 Guests
1800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $583/Night
7 Nights - US $4,079
House
9.0(4 Reviews)
3 Bedrooms
2 Baths
10 Guests
1485.42 ft²
Private Beach- Oceanfront
- Fireplace/Heating
- Ocean View
US $451/Night
7 Nights - US $3,159
House
10.0(50 Reviews)
3 Bedrooms
1 Bath
8 Guests
960 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
View
US $301/Night
7 Nights - US $2,104
House
10.0(36 Reviews)
2 Bedrooms
1 Bath
7 Guests
947 ft²
Hot Tub- Fireplace/Heating
- Pool
- Ocean View
US $699/Night
7 Nights - US $4,892
House
10.0(27 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $627/Night
7 Nights - US $4,390
Leesburg Luxury Rentals
House
10.0(8 Reviews)
6 Bedrooms
4 Baths
30 Guests
4500 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $895/Night
7 Nights - US $6,268
House
2 Bedrooms
2 Baths
14 Guests
2500 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $743/Night
7 Nights - US $5,198
House
3 Bedrooms
2 Baths
12 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $693/Night
7 Nights - US $4,851
House
5 Bedrooms
4 Baths
14 Guests
3649 ft²
- Fireplace/Heating
- Balcony/Terrace
Pet Friendly- Kitchen
US $634/Night
7 Nights - US $4,439
Cottage
9.8(56 Reviews)
3 Bedrooms
2 Baths
8 Guests
1500 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $583/Night
7 Nights - US $4,082
House
10.0(1 Review)
1 Bedroom
1 Bath
8 Guests
- Fireplace/Heating
- Pet Friendly
Air Conditioner
Internet
US $512/Night
7 Nights - US $3,583
Cottage
10.0(14 Reviews)
3 Bedrooms
1 Bath
8 Guests
1482 ft²
- Fireplace/Heating
- Ocean View
- View
- Kitchen
US $512/Night
7 Nights - US $3,582
Cabin
2 Bedrooms
1 Bath
8 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
Child Friendly
US $506/Night
7 Nights - US $3,539
Leesburg Pet Friendly Vacation Rentals
Cottage
10.0(1 Review)
2 Bedrooms
1 Bath
6 Guests
850 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $284/Night
7 Nights - US $1,985
Apartment
9.0(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
925.7 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $182/Night
7 Nights - US $1,274
House
9.8(12 Reviews)
4 Bedrooms
2 Baths
8 Guests
1800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $363/Night
7 Nights - US $2,538
House
2 Bedrooms
1 Bath
6 Guests
861.11 ft²
- Pet Friendly
- Parking
- Air Conditioner
- Internet
US $310/Night
7 Nights - US $2,170
New
House
3 Bedrooms
1 Bath
8 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $342/Night
7 Nights - US $2,395
Cottage
10.0(9 Reviews)
2 Bedrooms
1 Bath
9 Guests
1087 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $309/Night
7 Nights - US $2,163
House
10.0(4 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $233/Night
7 Nights - US $1,634
Cabin
10.0(3 Reviews)
4 Bedrooms
3 Baths
10 Guests
3400 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $564/Night
7 Nights - US $3,950
Leesburg Large Vacation Homes
House
8.8(13 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $349/Night
7 Nights - US $2,440
House
10.0(10 Reviews)
4 Bedrooms
2 Baths
10 Guests
1384 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Kitchen
US $404/Night
7 Nights - US $2,826
Cottage
9.6(14 Reviews)
5 Bedrooms
4 Baths
14 Guests
3650 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $586/Night
7 Nights - US $4,099
Condo
5.0(1 Review)
2 Bedrooms
2 Baths
12 Guests
- Kitchen
- Air Conditioner
- Child Friendly
Laundry
US $400/Night
7 Nights - US $2,800
New
House
4 Bedrooms
3 Baths
14 Guests
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $757/Night
7 Nights - US $5,298
Why Choose Rent By Owner for your Leesburg 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 Leesburg
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here ensures you experience the region’s welcoming atmosphere and enjoy ideal weather conditions for your stay.
Peak Season Highlights
Summer (June to August)
During the warm summer months, this destination experiences its peak visitation period, making it ideal for enjoying outdoor activities and the region's natural beauty.
Average Temperature Daytime: around 85°F - Nighttime: around 65°F
Fall (September to November)
The vibrant fall foliage attracts visitors seeking picturesque scenery, perfect for exploring local landscapes and outdoor excursions.
Average Temperature Daytime: around 75°F - Nighttime: around 50°F
Off-Season Highlights
Winter (December to February)
With colder temperatures and fewer visitors, winter offers a quiet retreat for those looking to enjoy peaceful surroundings and indoor amenities.
Average Temperature Daytime: around 40°F - Nighttime: around 25°F
Spring (March to May)
Early spring sees fewer tourists as the area transitions from winter, providing a serene environment for sightseeing and relaxation.
Average Temperature Daytime: around 60°F - Nighttime: around 40°F
Weekly Weather Forecast for Leesburg
How to Book Your Leesburg 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 Leesburg
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 outdoor dining and grilling with a private barbecue area.
- Relax on spacious patios or decks overlooking scenic views of the region.
- Take advantage of lush private yards for outdoor activities or family gatherings.
- Make use of well-maintained walking trails or nearby nature paths.
- Benefit from access to outdoor sports facilities such as tennis courts or volleyball courts.
- Unwind at a personal fire pit ideal for evening campfires under the stars.
- Experience the convenience of ample parking options for boats, RVs, or additional vehicles.
Top Attractions Around Leesburg
What attractions are nearby?
Nearby, you can explore scenic outdoor activities, charming local shops, and family-friendly attractions that make this destination an ideal spot for a relaxing and enjoyable getaway.
Family Activities
- Leesburg Family Fun Center: Enjoy a day of arcade games and indoor entertainment designed to keep children and adults entertained in the area.
- Indiana Beach Amusement Resort: Spend quality time on thrilling rides and family-friendly attractions at this popular regional amusement park.
- Lake Tippecanoe: Experience outdoor activities like boating, fishing, and swimming, perfect for creating lasting memories with loved ones here.
- Local Nature Trails and Parks: Explore scenic hiking and biking paths that provide a relaxing way for families to connect with nature in this destination.
Adult Activities
- Exploring the Lake Tippecanoe: Enjoy a tranquil day by the water, engaging in activities like kayaking, fishing, or simply relaxing along the shores of this scenic lake in the region.
- Visiting local wineries and breweries: Discover the area's craft beverage scene with guided tours and tastings at nearby wineries and breweries that highlight the local flavor.
- Playing golf at area courses: Tee off at championship golf courses close to here, offering an enjoyable experience for both seasoned players and beginners alike.
- Participating in outdoor recreation at nature preserves: Take advantage of hiking trails, birdwatching, and picnicking opportunities within nearby nature preserves that showcase the region’s natural beauty.
Other Places to Stay in Leesburg, IN
Tippecanoe Lake
Leesburg Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Cuisine: Make sure to indulge in the area’s local dining options to enjoy authentic flavors unique to your destination.
- Plan Outdoor Activities: Take advantage of nearby outdoor spaces and activities to fully experience the natural beauty here.
- Visit Hidden Gems: Seek out lesser-known attractions and scenic spots to discover the region’s true charm away from typical tourist areas.
- Utilize Local Resources: Connect with local visitors' centers or guides for insider tips that can enhance your stay and help you navigate the area more effectively.
Transportation Options
- Leesburg Transit Bus Service: You can rely on this local bus service to navigate easily around the region and reach nearby attractions from your vacation rental.
- Public Transportation Options: Several regional transit options connect the area to larger cities, making it simple for you to explore beyond Leesburg itself.
- Private Car Rentals: Renting a car here provides flexibility and convenience, allowing you to visit scenic spots and amenities at your own pace.
- Taxi and Rideshare Services: On-demand services like taxis and rideshares offer quick and reliable transportation choices during your stay in this destination.
Local Customs Options
- Local Celebration of Heritage: Participating in community events and festivals here offers a glimpse into the area's rich history and cultural traditions.
- Respect for Nature and Waterways: You’ll find that environmental preservation and outdoor activities are highly valued by residents in this region.
- Traditional Southern Hospitality: Expect warm welcomes and friendly interactions when engaging with local hosts and vendors throughout the area.
- Emphasis on Community Gatherings: Neighborhood events and local markets are integral to social life and provide authentic experiences during your stay.
Leesburg Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Leesburg?
There are a lot of options in Leesburg. If you plan on staying in the Leesburg area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Leesburg:
- Tippy Cottage on the Lake
- Swim, fish, have fun at the sandbar & cruise the lake! Sleeps 8!
- Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!
- 1/2 acre Lake Front on Tippecanoe
- Memorable Vacation Awaits on Big Chapman Lake! Sleeps 8! Optional Pontoon!
- “Stay Anchored” Lake Tippecanoe channel front with pier and great lake views
- Modern Lakefront Home on Sechrist Lake (Barbee Chain of Lakes)
- The Old Stone Cottage at Tippy
- Irish Lakefront, Hot Tub! Pets, dock, fishing, kayaks, ice fishing, hunting!
- Lakefront Getaway in Leesburg w/Dock + Kayaks!
2. Which vacation homes in Leesburg are best for families?
If you are looking for a family-friendly vacation home in Leesburg, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Leesburg:
3. How many Rentbyowner vacation rentals are available in Leesburg?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 67 in the Leesburg 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 Leesburg.
4. What is the cancellation policy for vacation rentals in Leesburg, Indiana?
Cancellation policies vary by property. To understand the specific terms, please review the listing details or contact the property owner directly before booking.
5. Are there any additional fees I should be aware of when booking in this area?
Additional fees such as cleaning or service charges are often listed in the property description. Make sure to read the full listing details or ask the owner for clarification before completing your reservation.
6. How do I confirm my booking for a vacation rental in Leesburg?
Booking confirmation is typically sent once your reservation request has been accepted and payment processed. For any questions, reach out to the property owner through the platform for assistance.
7. What amenities are usually included in Leesburg vacation rentals?
Amenities vary by property but commonly include essentials like Wi-Fi, parking, and kitchen facilities. Check the specific listing for a complete list of available amenities to ensure it meets your needs.
8. Is there a minimum stay requirement for renting in this region?
Minimum stay requirements depend on the individual property. Review the listing details or contact the owner directly to confirm any stay restrictions before booking.
Leesburg Top Rated Vacation Rentals
Bed & Breakfast
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
225 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
US $100/Night
7 Nights - US $698
