Holiday rentals with a kayak in Leelanau County

Cottage with Fireplace at Anchor Inn

1940s beach side Inn looking to fulfill your vintage lake cottage dreams! We're on the west bay of Traverse City on M22. Your gateway to the villages of Leelanau and only 8 minutes from downtown. This listing is for a duplex style cottage. Want to watch the sunrise on a private beach? A midnight swim in Lake Michigan? Come stay at the vintage Anchor Inn and feel free to use our sauna, kayaks, firepits, beach chairs, firewood, charcoal grills, playground, cornhole, e-bike rentals, and much more!

Bear Feet Retreat

Nestled along the shores of Little Traverse Lake, our beautiful home is bathed in natural light and just minutes from the Lake Michigan Wine Trail and Sleeping Bear Dunes. From the moment you arrive, this elegant waterfront retreat will make you feel instantly at home. This spacious 5-bedroom, 4.5-bath vacation rental offers a variety of luxurious amenities, including an 80-foot dock (available from Memorial Day to Labor Day), a private deck, and a fully equipped kitchen—everything you need for

Cheerful cottage with amazing beachfront hangout

This special place is close to everything, making it easy to plan your visit. It is 5 minutes to downtown TC and within 15-20 to the Old Mission and Leelanau Peninsula wineries! The home is located directly on West Grand Traverse Bay. It has 3 bedrooms, and will sleep 6 comfortably. The expansive deck has breathtaking views of power island. It has ample outdoor patio furniture and a fireable to create ambiance. Below is an amazing beachfront entertainment area with 2 TV's, an outdoor bathroom.

JOLLI-LODGE~Beach Resort Leland

AUGUST is one of over 20 rental units at the Jolli-Lodge, a family-run resort since 1956. Nestled in the forest near Leland, on the largest private Lake Michigan access in the area, guests enjoy the beach, tranquil property, free kayaks, paddle boards, and bicycles. Jolli-Lodge is the original Leelanau resort with laid-back, up-north style. No extra charge for weekly s’more roasts, beach bonfires or magnificent sunsets! PETS WELCOME in all units except: Gameroom, Master Studio, lodge rooms.

Private BeachM22! wine country Amazing Fall Colors

Your family will love to relax here! Best beach in the area, great for small swimmers and big swimmers alike. Warm and shallow, and the cottage is recently updated with all the comforts of home. Close to some of the world best wineries, skiing and ice fishing. Spend days kayaking with provided kayaks. New beds, organic bamboo bedding, fully stocked kitchen, and a beach side fire pit will help you create lasting memories for years to come. Pets allowed with pet fee, please read rules

Leelanau charmer, 3 mins 2 beach

Please note: July and August 2025, we provide weekly rental only, FRIDAY to FRIDAY. Welcome to The Watercolor Cottage, an updated home in an incredible location. Walk 3 mins east for sunrises at Vic Steimel Beach Park, or 3 mins west to the public sandy shore of Suttons Bay. The cottage provides a serene home base for all things Leelanau, with everything considered for an easy vacation. We're happy to provide recs for the best hikes, restaurants, and day trips around!

Modern West Bay Cabin

Newly built modern inspired cabin situated along M22 between Traverse City and Suttons Bay. This custom-built home offers sunrise views over West Harbor Bay and private beach access across the street. Minutes from the best wineries and restaurants the north has to offer. The bright interior and vaulted ceilings create a warm space to gather. The cabin sleeps 6-8 and offers unique built in beds and outdoor shower for a rinse after a long day at the beach.

BeaverTales - a Beaver Island lake front cottage

Welcome to BeaverTales, your private lakefront getaway. 153' of Lake Michigan shore, with a cozy interior. Very private, with a single cottage barely visible to the south, and endless unspoiled beach to the north. Walk or bike to Lake Geneserath or Beaver Head Light. Gas grill, charcoal grill, well-equipped kitchen with staples. Well behaved dogs are welcome. You will enjoy beautiful sunrises, preparing you for each day of fun on Beaver Island.

Glen Arbor Waterfront Condo - Great Lakes 43

Come visit our peaceful retreat in Glen Arbor with stunning Lake Michigan views. Located in The Homestead Resort, enjoy our scenic riverfront location with beach access right outside your door. Our 3 bed / 2.5 bath unit accommodates 6 people with additional sofa bed if needed. This private rental does not allow access to resort pools, but you have complete beach access as well as use of 2 kayaks to enjoy. Laundry access in the building.