Lakeside Rentals By Owner

There are a lot of options in Lakeside. If you plan on staying in the Lakeside area, consider making a reservation for a few nights at one of these properties as these have been rated the top Vacation Rentals in Lakeside:

• Brand New House, Sleeps 8, Private Beach Rights, Hot Tub!
• Beautiful Lakeside MI vacation home with association beach access Summer & Fall
• Peaceful Family Getaway!
• Stunning home w/Private Association Beach 2 Screened Porches
• Lakeside Escape Steps to Lake Michigan Beach!
• Relax on your own private beach on stunning Lake Michigan
• Near New Buffalo Lakeside Retreat w/Private Heated Pool Walk to Beach
• Stunning home with Pool/Hot Tub/Fire Pit/Screen Porch/Large Yard in Union Pier
• 2026 NOW OPEN! Lakefront Home With Private Beach!
• 4 bdrm, 3.5 bath retreat w/pool, spa, large yard & fire pit. 5 min walk to beach

There are many large, family-friendly vacation homes available in Lakeside; however, here are the most popular family rentals listed on our site:

• Bold Stump Cottage
• Painted Porch Cottage
• Brand New House, Sleeps 8, Private Beach Rights, Hot Tub!
• Sagewood
• Beautiful Lakeside MI vacation home with association beach access Summer & Fall
• Four Bedrooms & a Beach

Yes, there are 2 self-catering vacation homes in Lakeside that have hot tubs, swimming pools, & other amenities.

There are more than 2 luxury villas and vacation homes in or near Lakeside. Filter by price to compare find the most expensive places to stay on Montgomerycottages.

Yes, there are 2 pet friendly vacation homes and places to stays that are available in or near Lakeside that you may consider.