Vacation rentals in Osakis

Sunrise Lake Escape with hot tub and massage chair

Relax on Lake Osakis on 3 acres. Pet-friendly, private dock. Fire pit, outdoor shower, outdoor/indoor kitchen, fish cleaning area, grill, pellet smoker, hot tub. Main house sleeps 6. Guest house sleeps 4 (currently not permitted for use, anticipate permit in April)- two bedrooms, one bathroom. Guesthouse available for more than 6 guests at $100 per night $50 per stay additional cleaning fee. It is 3 season. RV electrical available. Pontoon for rent. No water in guest house October 17-April 15.

Treehouse (LOTR) Stargazer Skycabin

Our LOTR themed treehouse, along with our LOTR Wizard's Cottage, have been described as a "love letter to Tolkien himself." We have been featured on PBS and WJON radio. Joan and I live on the acreage, about 200 ft. from the Wizard's Cottage and very far from the treehouse, which is located on the back part of the acreage. It has a fenced-in portion that makes up the Shire Garden. Down the hill is our nod to Mordor. Feel free to visit and dare to open the "Mor Do(o)r." Diversity is welcome.

Lake Osakis Family Getaway: Game Room, Dock

Indulge in the warm comforts of our 8BR 4BA family getaway nestled on a gorgeous lakefront property in Osakis, MN. This spacious estate offers the perfect retreat from bustling crowds with its cozy design, convenient amenities, and scenic outdoors with a private dock. ✔ 8 Comfortable Bedrooms (Sleeps 24) ✔ Open Design Living ✔ Full Kitchen ✔ Game Room (Pool, Foosball, Bar) ✔ Deck & Backyard (Fire Pit, BBQ, Dining) ✔ Private Dock ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Free Parking See more below!

“Tiny Timber” Scandi cabin W/ Sauna, plunge tub!

Escape to the serenity of the Tiny Timber cabin, where stunning nature views and modern comfort await. This charming 450 sqft cabin offers a cozy respite from the hustle and bustle, with breathtaking scenic views that will leave you in awe. Nestled within reach -fantastic lakes, nearby restaurants, and a host of recreational activities, this is the perfect base for your getaway. Unwind, have a campfire, enjoy the sauna, play games or simply relax and soak in the beauty of the surroundings.

Suite Cherry No. 1

Enjoy a private, main floor, three room suite with private off street parking and private entrance. No stairs to climb, just a ramp onto the deck entrance. You will have a living room with a couch, recliner, TV and small dining table. The bedroom has a queen size bed and a well stocked kitchenette. The ensuite provides a closet, plenty of shelving, storage cabinet and a full bathroom with apartment size combination washer & dryer. We'd be happy to share our back deck with you as well.

The Maynard Cabin, a Civil War era log cabin

The Maynard Log Cabin was erected by a homesteader after the civil war. We have moved and restored it and made it available for rent. It is off the grid, but it has a complete functioning kitchen, wood stove and sitting room downstairs. There are two antique beds with new mattresses upstairs. There is no electricity but the cabin is furnished with kerosene lanterns. The bathroom facilities consist of wash basins and outhouse. The cabin is surrounded by 40 acres of woods and meadows.

Spacious Family Lake Retreat: Dock, Game Room, BBQ

Discover the tranquility and comfort in this 4BR 2BA lake getaway. Enjoy easy access to Lake Osakis from the private dock, sit around the fire pit, or spend the day exploring scenic Osakis! Outdoor bliss, warm design, and unparalleled serenity make this retreat perfect for a family vacation! ✔ 4 Comfortable Bedrooms ✔ Relaxing Living Room ✔ Game Room (Foosball, Arcade, Bar) ✔ 2 Full Kitchens ✔ Outdoors (BBQ, Dining, Fire Pit, Dock) ✔ Smart TVs ✔ Wi-Fi ✔ Parking Learn more below!

Cabin with private beach access to Lake Minnewaska

Take a break and unwind at this peaceful cabin. It is steps away from a privately owned beach for you to sit back, enjoy the sunrise/sunset with a firepit. 5 minute walk away from the well-known Barsness park. Also, 5 minute walk away from Lake Minnewaska public boat landing and public beach. Or enjoy a nice walk to go downtown Glenwood to enjoy all the city has to offer!! Not handicap accessible **Property is an approved short term rental and licensed with the City of Glenwood**

Spacious and beautiful Alexandria home

This home is set up like a duplex with owners occupying the top (we have 3 young children) & guests having full, private access to the bottom half. Guests are given a private garage ( not available November to April) & backyard w/ free firewood. Private entry gives access to 2,200 sq ft of space that includes a 3 seasons room w/ gas fireplace, laundry, & full kitchen. 1 open room, one private, & one partial room w/ no windows. Close to the bike trails, beaches, mini-golf, etc.

Farmer's Cabin - Serene Views, SAUNA, peaceful

Nestled at the end of a quiet dead-end road, our newly renovated, farm-themed cabin offers the ultimate cozy lake escape. Wake to peaceful water views, sip coffee on the large patio, and enjoy a flat sandy shore perfect for swimming and playing. We provide a raft, lily pad, paddle board, tons of water toys, and a relaxing sauna. Inside, everything is fresh, bright, and filled with charm — a perfect private retreat to unwind, recharge, and make lasting memories.

The Lake Place - A-Frame on Lake Miltona w/ Sauna

The Lake Place is a brand new A-frame cabin built to share our favorite place with you! Make memories in the cozy living room with friends around the electric fireplace, climb the ladder to the 3rd story loft for the view or perfect kid’s hideout, or open the oversized patio doors to visit the lake, just steps from our back door! We just added a brand new sauna for you and guests to use as well! Stay up to date with all the latest on IG @thelakeplacemiltona

Jake's on the Lake, Main Floor and Loft #2193

Wake up to gorgeous sunrises on beautiful Lake Louise! 2 bedrooms, 2 bathrooms, loft, living area and kitchen in lake home with separate entrance. Includes use of regulation pool table, paddle boards, kayaks, dock and deck. Family friendly with all the necessities. Minutes from The Chain of Lakes, Lake Brophy Park, Lake Carlos State Park, Carlos Creek Winery, Andes Tower Hills, the Central Lakes Trail, Big Ole Viking Statue, and the Runestone Museum,