Holiday rentals in Leesburg

Lake Wawasee, Outdoor TV, Surround Sound, Bikes

☀️55” Outdoor TV w/ Covered Patio ☀️3 Bedrooms, 1 King, 1 Queen, Bunk Room ☀️Sleeps 12 People ☀️Flatscreen TVs w/ YouTube TV ☀️Surround Sound System in Living Room ☀️Record Player/Bluetooth Speaker ☀️ Fire Table ☀️Fully Stocked Kitchen ☀️ Fireplace ☀️Beach Cruiser Bicycles ☀️High Speed WiFi ☀️Washer & Dryer 🌊 Located down the street from Indiana’s largest natural lake, Lake Wawasee, you will find everything you could possibly enjoy while you stay in Syracuse, IN at the Wawasee FROG house.

Location · Value · Cleanliness

Sunrise on Sawmill | Kayaks, Firepit, & Games!

Have fun with the whole family at this newly updated lake home on Sawmill Lake (part of the Barbee Chain offering access to fishing, swimming, boating and water sports). Features four bedrooms (sleeps 14 comfortably), 3 full bathrooms, an arcade + game flex zone in the basement with a futon, plenty of indoor and outdoor dining + lounging area, a lakefront firepit area-seating up to 10; complete with hanging egg chairs and custom cedar benches, kayaks and paddle boat are ready to go at the dock!

Family · Location · Outdoor spaces

Dewart Lakefront Cottage

Escape to our charming Lake Cottage, nestled on the peaceful Dewart Lake in Syracuse, IN. Whether you're seeking a relaxing weekend or an adventurous getaway, this cozy retreat offers stunning lake views, beautiful sunrises and sunsets, private access on an all sport lake and all the comforts you need for a memorable stay anytime of the year. Enjoy the lake with kayaks, fishing from the pier and space for a boat, BBQ grill, smart TVs and campfire pit are just a few amenities we have to offer.

Location · Family · Amenities

Lakehouse, kayaks, dock, fishing, fence for pets!

Beautiful lakefront home on the Barbee chain of lakes. Small, but all you need!! This guesthouse features a kitchen, family room, firepit, dock for your boat, and a fenced in side yard for your dogs!! We supply 2 kayaks with lifejackets and a grill. King size bed in the bedroom! We have a loft for the kids that they will love!!! This house has the best views and best fishing on the chain! Must be 21 to book and show ID after booking confirmation. Plenty of parking. Come make some memories!!

Family · Location · Check-in

Tippecanoe Lake-Family Friendly-4Bedroom

Have fun with the whole family at this stylish place. A newly renovated home that has a warm and comforting feel throughout. Country living that includes 4-bedrooms featuring 2 master bedrooms. The large kitchen is accommodating for all with brand new appliances, luxury vinyl flooring, quartz countertops and specialty bars. Cozy seating areas with a game corner, social media friendly area with beautiful natural lighting to capture the moment. Marina and public lake access minutes away.

Family · Location · Layout

Relax 15 guests can enjoy Holidays & Everyday

Beautiful home in a quiet neighborhood on Barbee Chain of 7 Lakes ,Irish Lake Channel.Can be used for reunion corporate event birthday, bachelor bachelorette parties,fire pit Corn hole boards along with a fully stocked kitchen. Oklahoma Joe’s Gas &charcoal grill with a smoker box, 4 bedrooms 2 bath fenced in back yard for pets &kids.Pet fees apply. Parking for trailers trucks 2 Beautiful decks with gorgeous sunsets.Nice beach close by.Pontoons available to rent separately at the home.

Location · Family · Outdoor spaces

Lake Front + Private Pier + Fire Pit + Kayaks

We invite you to come enjoy your time away at our delightful summer lake front cottage on Little Barbee Lake. Close proximity to Big Barbee Lake (all sports lake) Little Barbee is part of the Barbee Chain of Lakes with plenty of room to boat and fish. Bring your own boat or jet ski as the dock is steps away from the cottage. ••• Sunday AND Holiday check-ins may be available depending on our cleaning schedule! Please contact me and we'll do our very best to accommodate your schedule!

Family · Location · Condition

Tippy Lake Retreat | Kayaks, Bonfires & Lake Views

UNIQUE, SPACIOUS, and HAS IT ALL! Views and Sunsets of Lake Tippecanoe - All Sports Lake; second to none! Space to sleep a minimum of 12, 2 full baths with private w/c, walk-in showers, a gas fireplace, amazing 1940's Century boat island, lake access and pier use just steps away, pier space for personal watercraft boat rentals available, please ask for promo code! Kayaks, paddle boards, reverse osmosis water, charcoal grill, outdoor seating, fire pit, artificial grass area, and more!

Location · Family · Walkability

Cozy cottage on Irish Lake!

Come stay and play! This home offers everything you need to have a getaway at the lake. Wake up and enjoy a sunrise kayak ride around the lily pads watching the wildlife. Or sit on the deck with a cup of coffee. This adorable cottage with 1 bedroom, a sleeping loft and 1.5 baths lets you enjoy all the Barbee Chain has to offer. There are only a few steps off the deck to the private pier so bring your boat! There are convenient places to rent one if you don’t want to bring your own.

Family · Location · Bathroom

Charming Lake House

New Cleaners- On Crystal Lake in Warsaw, Indiana is a 6-bedroom house fully stocked with everything you need for a comfortable stay- Wi-Fi,, a fully equipped kitchen, washer/dryer, and all the necessary linens/towels. The lake house is located on a no-wake lake, making it ideal for swimming, fishing, and paddleboarding. The house also has a kayak and canoe available for guests to use. After a day on the lake, guests can relax on the deck or around the fire pit. No pets. EV charger.

Location · Value · Air conditioning

The Retreat at Cabin Creek Farms

Escape to our peaceful country cabin nestled down a quiet lane surrounded by rolling farmland and grazing cows. Enjoy spacious accommodations with a wrap-around patio perfect for morning coffee, cozy evenings by the indoor fireplace, and scenic hiking trails right at your doorstep. Your perfect rural getaway awaits! Small events for up to 30 people are allowed upon request before with an extra fee, if interested in hosting an event please request before making the reservation!

Location · Family · Indoor spaces

Lakefront House w/ Dock, Firepit & Kayaks

Wake up to sunrise over Pike Lake in this thoughtfully curated lakefront retreat designed for calm, connection, and comfort. With a private dock, firepit, three-season sunroom, and peaceful shoreline, this home is ideal for families, couples, or remote professionals seeking a restorative escape. Professionally managed and intentionally furnished, it blends effortless lakeside living with the reliability of a well-run stay—just minutes from Warsaw’s dining, parks, and trails.

Family · Location · Kitchen