Vacation rentals with a kayak in Leelanau County

JOLLI-LODGE~Beach Resort Leland

LITTLE BLUE 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.

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!

Lime Lake Therapy-HotTub/PingPong/LakeSide/Dock/AC

Quintessential up north cabin beautifully situated on a private hilltop setting with stunning lake views. Immaculate with soaring ceilings, open floor plan, & solid surface counters. Main floor master bedroom suite overlooking the sparkling blue waters of Lime Lake. Front porch and covered lakeside deck for enjoying nature and gorgeous water views. Private frontage across the street with a NEW dock, fire pit and picnic area. Pure, beautiful Leelanau at its best! 39 min. to ski Crystal Mt.!

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!

Lake cottage, kayaks, firepit, chefs kitchen

Welcome to Stillwater Cottage hosted by Wander North Rentals! Stillwater is a luxury cottage located on the rustically beautiful Mougey Lake in Omena. If you're looking for bigger water Omena Bay public access is just a short walk into Omena where you can visit the art gallery, Leelanau Cellars, and the country store. Omena is also a short drive from Northport, Suttons Bay, and Leland where there are many year round outdoor activities, shops, and restaurants to enjoy.

45 Degrees North Retreat - Bayside Loft

Enjoy year-round nature and activities that the Leelanau Peninsula offers! Boasting 25 wineries, oodles of walking and biking trails, and beautiful Michigan beaches, the Bayside Loft is 3 minutes from Suttons Bay and 20 minutes from Traverse City. This peaceful space has fast WiFi, view/sounds/access to the west arm of the Grand Traverse and Suttons Bays, seasonal access to our fire pit and two kayaks, boat mooring ball, games, and other TV entertainment options.

Renovated Riverfront Cottage with Sauna

Escape to this charming, private cottage on the Crystal River! Just minutes from downtown Glen Arbor, public beaches, Sleeping Bear Dunes National Lakeshore, and the Homestead Resort. Built in the 1990s and fully renovated in 2022, blending modern comforts with timeless charm. Surrounded by natural beauty, this cozy retreat offers the perfect setting for relaxation, outdoor adventure, and exploring the best of northern Michigan.

Tavi Haus: Lakefront~Kayaks~SUP~Sauna~Pool Table

🌊 Private Lakefront Modern Chalet 🧘 6-Person Barrel Sauna for Relaxation 🚤 Paddleboards & Kayaks Included 🔥 Cozy Lounge with Fireplace & Pool Table 📍 15 Mins to Sleeping Bear, 20 to TC Hosted by Catered Stays Rentals, we create the ideal guest experience. Enjoy seasonal kayaks and paddleboards (May–Sept) along with cozy spaces to relax inside and out. Perfect for families, friends, or pets to unwind and make memories.

Lakefront Lodging - A Nature Lover's Delight!

The 'Classic King' at Sunrise Landing has a king bed in a simple, yet cozy studio space. Featuring vintage tongue and groove cedar walls, a sitting area, microwave, fridge, flat screen TV, and, of course, sits just a step away from a great view of the sun rising over our private beach on lake Michigan. (Please note: This is not a full kitchenette, just a mini fridge and microwave in the studio unit).