Vacation rentals with a pool in Leelanau County

Sugarloaf Condo B3

This is a beautifully furnished 4 bedroom condo in the heart of Leelanau County. It is certainly a one of a kind, tailored condo with personal touches labeling each room. Upstairs is the "Riesling" room with a king bed, tv and full bath. The "Merlot" room, also upstairs, has a king bed, full bath and extra sofa bed. Downstairs features 2 more bedrooms, the "Cabernet" room with another king bed and the "Chardonnay" room with twin bunk beds as well as a twin bed. Each room also has private baths.

Sugarloaf Condo E7

Sugarloaf Condo E7 has new owners and is new to the rental program. The owners have added many comforts that will not go unnoticed. This 2 bedroom condo features 3 full bathrooms. The main bedroom highlights a queen adjustable bed, full bath and lovely deck overlooking the outside heated pool. The second bedroom has 2 queen beds and another full bathroom. The kitchen is very well stocked and ready for your family meals. The open living area leads to the lower deck and pool. Lk MI beach 2 miles

Stylish The Shores Condo | Private Beach - 5716

THE TRUE NORTH presents... 🏖️ Stylish The Shores Condo | Private Beach w/ Views ➠ 5716 Escape to the peaceful side of Northern Michigan in this beautifully updated East Bay condo. Nestled among mature trees with a tranquil creek view, this cozy retreat offers the perfect blend of resort-style amenities and natural serenity. Enjoy private beach access, a spacious deck, and easy access to Traverse City, Elk Rapids, wineries, golf courses, and year-round outdoor adventures. Learn more below…👇

Up-North Suite Retreat

Our Maple City "Suite" Apartment offers guests all the amenities they desire, and easy access to anything they wish to do and see! Situated between Maple City and Cedar, you will be able to explore Lake Ann, Leland, Glen Arbor, Sleeping Bear Dunes National Lakeshore Park, Traverse City, and more, with relative ease as you take in the breath taking views of Leelanau county. The accommodations are clean, comfortable, spacious, secluded and will exceed your expectations - that is our goal!

Family retreat w/ pool near Sleeping Bear Dunes

Welcome to your Leelanau retreat - a four-floor townhouse at the base of the former Sugar Loaf ski area in Cedar, MI, surrounded by rolling hills and open green space. - Sleeps 8 | 4 bedrooms | 5 beds | 4 baths - Seasonal shared pool, resort access & private gas BBQ patio - Beach access nearby - Fully equipped kitchen w/ drip coffee maker & Keurig - Family-ready: crib, Pack 'n play, high chair & kids' toys available - Free washer/dryer in unit, Wifi, Fire TV & self check-in via lockbox

Sugarloaf Condo G4

Stylish condo that stands out with it's class. Open floor plan that draws your attention to detail. Decorated with comfort in mind, this two bedroom, 2 1/2 bath condo is sure to please. Upstairs has master king suite, as well as a second bedroom with 2 queen beds. Each bedroom has its own private full bath. The lower level has a patio that leads to outside heated pool and common grounds. Between Leland and Glen Arbor, G4 is perfectly located for easy access to Leelanau's beauty.

Charming Sugarloaf 2BR/2.5BA Townhome

Welcome to your perfect Up North getaway! This two-bedroom, 2.5-bath townhouse is centrally located in beautiful Leelanau County—just a short drive to Glen Arbor, Leland, and Suttons Bay. Whether you're here for the beaches, water sports, wine tasting, golf, local festivals, or scenic hiking trails, you'll be in the ideal spot to explore it all. Please note: A rental agreement is required before check-in. If you'd like to review a sample before booking, we're happy to provide one.

Sugarloaf Condo J5

Leelanau Peninsula 3 bedroom, 3 bath condo with an outside heated pool. 2 miles from Good Harbor beach with sleeping for 8. Great for families as well as couples wine getaways. Perfect spot in the center of the Leelanau Peninsula, this condo will accommodate your group very comfortably. Great family getaway or bring your friends for a wine weekend! Traverse City is only 20 minutes away while the charming towns of Glen Arbor and Leland are just 10.

Sugarloaf Cabin 4BD/4BR - pool/golf course

Enjoy an escape to the Leelanau Peninsula. Centrally-located between Sleeping Bear Dunes, Suttons Bay, Glen Arbor, Leland, and Traverse City, with both Lime Lake access and Good Harbor Bay beach just a few miles away. Our 4 bedroom townhouse is surrounded by nature. Whether you want to explore all that Northern Michigan has to offer or lounge by our pool, this is perfect for family vacations or weekend getaways with friends!

Elegant 2King Broom Apt Traverse City, MI -2 night

Nestled on 11 acres of mature trees in the Nottingham Forest on Leelanau Peninsula, this 2 king bedroom walkout apartment in the lower level of residence has a private entrance and features comfortable seclusion only 4 miles from beautiful downtown Traverse City. A beautiful second bathroom was just completed. A year-round enclosed heated in-ground pool. Hottub on outside upper deck open year round. No pets allowed.

Leelanau Townhouse Retreat at Sugarloaf

Excellent site for couples or families, enjoy access to hiking, swimming, golf, scenic views and access to shopping and other amenities in nearby Leland or Glen Arbor. Several wineries are also nearby. The pool is open from Memorial Day through Labor Day weekend. Two golf courses are immediately adjacent to the association property--Sugarloaf the Old Course and Manitou Passage.

Little Oasis - Up North Glamping

Reconnect with nature at this unforgettable escape. Our Little Oasis Retreat - is a new listing and we are still improving the landscaping and making other improvements, but we are confident that your stay will be exceptional. We look forward to welcoming guests in this new space and hearing what they love and what we can improve on! So stay with us, come Glamp IN-Style!