Vacation Home Rentals By Owner In La Pointe, WI

Library Street Cottage | Cozy 2BR Downtown Retreat | Walk to Ferry & DiningbrbrWelcome to Library Street Cottage, a charming and cozy two-bedroom home in the heart of downtown. Perfect for couples, small families, or friends traveling together, this inviting space offers comfort, convenience, and walkability.brbr Sleeping ArrangementsbrTwo comfortable queen bedroomsbrFull bathroom with all the essentialsbr The SpacebrRelax in the welcoming living room, gather for meals in the dining area, and enjoy the convenience of a fully equipped kitchen for home-cooked meals. Whether you're staying for a weekend or longer, you'll feel right at home.brbr Prime LocationbrLocated at the corner of Colonel Woods and Rice Street, just two blocks from the Ferry, you’ll have easy access to local restaurants, shops, and downtown attractions — all within walking distance.brbr☀️ Outdoor LivingbrStart your morning or unwind in the evening on the front deck, the perfect spot to soak up the sunshine, read a good book, or simply relax.brbrLibrary Street Cottage offers the ideal blend of charm, comfort, and location. We look forward to hosting you!brbrItems that you will need to bring:brbrFoodbrBeveragesbrCondiments (including salt & pepper, ketchup, mustard, oils etc. - WI Department of Health & Human Services requires all condiments must be removed after each rental)brAdditional towels for going to the beach (bath towels provided are for use inside the property not to be taken outside or to the beach)brbrTown of La Pointe Permit # - C-2025-62brbrKitchen Basics - Dishes, Glassware, Utensils, Cutlery, Pots & PansbrMicrowave, Toaster, Coffee PotbrElectric Stove & OvenbrLinens ProvidedbrOne towel set provided for each guest (please use towels at the property only)brGas GrillbrDeck on Front of CottagebrComplimentary start-up supplies of: Toilet Tissue, Paper Towels, Garbage Bags, Dish Soap, Dishwasher soap along with Hand Soap and Shampoo for each bathroombrbrCheck in Time: 4:00 PMbrCheck Out Time: 10:00 AMbr50% due at time of ReservationbrbrMadeline Island Vacations Terms & Conditions

Library Street Cottage - Charming Cottage located in Town, walk to Shops and Restaurants

La Pointe, Wisconsin, United States

Bed

Bath

Sleeps

$710.83

Island Time Townhome – Sunsets… Joni’s Beach… So Close to Everything!br4 Bedrooms | 4 Bathrooms | Sleeps 10 | 2,300 sq ftbrbrWelcome to Island Time — a beautifully updated three-level townhome located in the heart of town on stunning Madeline Island. Situated directly across from Joni’s Beach and overlooking Lake Superior, this spacious retreat offers unforgettable sunsets and walkable access to everything the island has to offer.brbr The Location – Truly UnbeatablebrWalk just 60 paces from the front door to the sandy shores of Joni’s Beach. The park features:brbrBoat dockbrPicnic pavilion & tablesbrGrillsbrChildren’s playgroundbrCrystal-clear Lake Superior watersbrHead north along Main Street for a short stroll into downtown La Pointe, where you’ll find the Madeline Island Museum, charming locally owned shops, and restaurants.brbrWalk south and you’ll reach:brbrThe Pub at Madeline IslandbrMadeline Island Yacht ClubbrMadeline Island Golf Club (Robert Trent Jones, Sr. design)brBike the serene streets, stroll the shoreline, or simply relax and watch the sun dip into Lake Superior — Island Time truly lives up to its name.brbr The TownhomebrFirst Level (ADA Accessible)brTwo off-street parking spaces with ramp accessbrQueen bedroom with fully handicap-accessible en-suite bathbrOpen-concept great room with full kitchen, dining, and living areabrScreened-in porch with additional dining and lounge seatingbrDirect beach access from the front doorbrSecond LevelbrLake-facing bedroom with two full beds, en-suite bath & private deckbrBedroom with two twin beds and en-suite bathbrFull laundry roombrThird LevelbrNewly renovated primary suitebrKing bedbrLake viewsbrLuxurious en-suite half bathbrbr A Kitchen That Has It AllbrFully stocked with high-quality cookware and thoughtful extras:brbrAir fryerbrNinja blenderbrCrockpotbrPopcorn makerbrCoffee maker & grinderbrFour-slice toasterbrGas grill (right outside back door) + grilling toolsbrWater bottles, beverage coolers & freezer ice packsbrbr Beach & Recreation Gear IncludedbrNo need to overpack — Island Time is fully stocked for fun:brbrOutdoor FunbrbrBeach chairs, umbrellas & blanketsbrSand toysbrVolleyball & beach volleyball setbrBadminton setbrBasketball, kickball, frisbeesbrYoga matsbrIndoor EntertainmentbrbrSmart TVs throughoutbrAlexa-enabled smart home systembrSpeakersbrBoard gamesbrBooksbrMultiple gathering spacesbrbr♿ ADA AccessiblebrRamp access from parking into the first floor, with a fully accessible bedroom, bathroom, and living area.brbr Modern & SmartbrIsland Time is designed as a smart home with:brbrAlexa controlsbrSmart TVsbrCharging stationsbrIntegrated speaker systembrControl lights, play music, and stream your favorites with ease.brbr✨ Why Guests Love Island TimebrStunning Lake Superior sunsets from all three levelsbrDirect access to Joni’s BeachbrWalk to town, dining, marina & golfbrSpacious layout ideal for families & groupsbrFully stocked for beach days and cozy nightsbrWhether you’re cliff jumping, kayaking, biking quiet streets, or pausing each evening to watch the sunset from the dock, Island Time offers the perfect balance of adventure and tranquility.brbrWhen you arrive, you’ll feel it — life slows down, the air feels lighter, and you’re fully immersed in island time.brbrAmenities:brKitchen Basics - Dishes, Glassware, Utensils, Cutlery, Pots & PansbrRefrigerator, Stove, Oven, Microwave, Toaster & Coffee MakerbrLinens for each BedbrBath Towels for the number of guests listed on the reservationbrGas GrillbrComplimentary start-up supplies of: Toilet Tissue, Paper Towels, Garbage Bags, DishbrSoap, Dishwasher soap along with Hand Soap and Shampoo for each bathroombrItems that you will need to bring:brFoodbrbrBeveragesbrCondiments (including salt & pepper, ketchup, mustard, oils etc. - WI Department ofbrHealth & Human Services requires that all condiments must be removed after eachbrrental)brAdditional towels for going to the beach (bath towels provided are for use inside thebrproperty not to be taken outside or to the beach)brTown of La Pointe Permit # - C-2025-31brbrMadeline Island Vacations Terms & Conditions

Parkside Condo 1 - Condo Conveniently Located Across from Joni`s Beach

La Pointe, Wisconsin, United States

4

Bed

Bath

10

Sleeps

$578.88

Heersema House – A Peaceful Lakeside Retreat at Sunset BaybrWelcome to Heersema House, a serene escape tucked along Sunset Bay on beautiful Madeline Island. Located on Big Bay Road with views of Lake Superior just across the way, this thoughtfully designed home offers the perfect balance of relaxation, comfort, and island adventure.brbrFrom the moment you step inside, you’ll feel it — a sense of calm that invites you to slow down, breathe deeply, and truly unwind.brbr The SpacebrDesigned with character and comfort in mind, Heersema House is a warm and welcoming retreat.brbrCozy living room with fireplacebrBeautiful wrap-around screened porch — ideal for morning coffee or evening relaxationbrCurated selection of books for unplugged downtimebrOutdoor shower on the side deck (perfect after the beach!)brSpend your mornings reading on the porch, your afternoons exploring, and your evenings listening to the quiet sounds of nature.brbr Sleeping ArrangementsbrSecond Floor:brbrKing bedroom plus day bedbrBedroom with two twin bedsbrBedroom with trundle bed (Guests must bring their own bedding if using the trundle.)brFirst Floor:brbrQueen bedbrbr BathroomsbrFirst-floor bathroom featuring a charming clawfoot tubbrSecond-floor bathroom with showerbrbr Location HighlightsbrLake Superior views across the roadbrEasy bike ride to Big Bay Town ParkbrQuick drive or ride into the town of La PointebrPeaceful Sunset Bay settingbrWhether you're heading to Town Park for hiking and beach time, cruising into town for shops and dining, or simply enjoying a quiet evening by the fire, Heersema House makes it easy to enjoy island life at your own pace.brbr✨ Why Guests Love Heersema HousebrQuiet lakeside settingbrScreened porch for relaxing any time of daybrCozy fireplace ambiancebrOutdoor shower for easy beach livingbrClose to both Town Park and downtownbrIf you're looking for a peaceful retreat with charm, character, and an unbeatable location near Lake Superior, Heersema House is ready to welcome you home.brbrItems that you will need to bring:brbrFoodbrBeveragesbrCondiments (including salt & pepper, ketchup, mustard, oils etc. - WI Department of Health & Human Services requires all condiments must be removed after each rental)brAdditional towels for going to the beach (bath towels provided are for use inside the property not to be taken outside or to the beach)brbrTown of La Pointe Permit # - D 2025-60brbrAmenities:brbr- Kitchen Basics - Dishes, Glassware, Utensils, Cutlery, Pots & Pansbr- Refrigerator, Stove, Oven, Dishwasher, Microwave, Toaster & Coffee Makerbr- No Dishwasherbr- Telephone (local calls only)br- Satellite TVbr- DVD Playerbr- CD Playerbr- Wrap Around Screen Porchbr- Charcoal Grill (please bring your own charcoal and lighter fluid)br- Outdoor Showerbr- Lake Access (across Big Bay Road)br- Complimentary start-up supplies of: Toilet Tissue, Paper Towels, Garbage Bags, Dish Soap, Dishwasher soap along with Hand Soap and Shampoo for each bathroombrbrExtra notes:brbrCheck in Time: 4:00 PMbrCheck Out Time: 10:00 AMbr50% due at time of ReservationbrbrMadeline Island Vacations Terms & Conditions

Heersema House - Nestled in the woods with Lake Superior Access across the Street

La Pointe, Wisconsin, United States

Bed

Bath

Sleeps

$584.62

Jackson’s on Lake Superior | 200’ Private Sandy Beach | Cape Cod CharmbrWelcome to Jackson’s — a timeless Cape Cod-style retreat on beautiful Madeline Island. With breathtaking views of Lake Superior and 200 feet of private sandy beach, this two-level getaway offers the perfect blend of old-world charm and modern comfort.brbrWhether you're seeking peaceful relaxation or outdoor adventure, Jackson’s is your ideal island sanctuary.brbr The Settingbr200 feet of private sandy beachbrPanoramic Lake Superior viewsbrSouthern-facing home filled with natural sunlightbrSpectacular sunrises and unforgettable sunset skiesbrStart your morning with coffee overlooking the water and end your evening gathered around the fire pit beneath a canopy of stars.brbr The HomebrDesigned to comfortably host up to six guests, Jackson’s features:brbr3 Bedroomsbr2 Full BathroomsbrTwo spacious levels of livingbrThe inviting living room centers around a classic Franklin stove, creating a warm and cozy atmosphere on cooler evenings. Enjoy family game nights, relax with a good book, or gather around the piano for music-filled memories that add a touch of nostalgia to your stay.brbrLarge windows and a thoughtful layout make the home feel bright, airy, and welcoming throughout the day.brbr Outdoor LivingbrPrivate fire pit for evening gatheringsbrExpansive sandy shoreline for swimming, sunbathing, and beach walksbrPeaceful waterfront setting ideal for unwindingbrStep directly from the yard to the sand and enjoy the simple pleasures of island life.brbr Explore the IslandbrAdventure awaits just beyond your doorstep. Explore the hiking trails and dramatic shoreline at Big Bay Town Park or browse the local shops, galleries, and restaurants in the charming town of La Pointe.brbrFrom kayaking and beachcombing to dining and island exploration, Madeline Island offers something for everyone.brbr✨ Why Guests Love Jackson’sbrRare 200’ stretch of private sandy beachbrStunning Lake Superior viewsbrCozy Franklin stove & pianobrBright, sun-filled Cape Cod designbrPerfect for families and small groupsbrIf you’re dreaming of a classic Lake Superior escape filled with beach days, bonfires, and unforgettable moments, Jackson’s is ready to welcome you.brbrTown of La Pointe Permit # - D-2025-45brbrItems that you will need to bring:brbrFoodbrBeveragesbrCondiments (including salt & pepper, ketchup, mustard, oils etc. - WI Department of Health & Human Services requires all condiments must be removed after each rental)brAdditional towels for going to the beach (bath towels provided are for use inside the property not to be taken outside or to the beach)brbrItems provided:brbrKitchen Basics - Dishes, Glassware, Utensils, Cutlery, Pots & PansbrRefrigerator, Stove, Oven, Microwave, Toaster & Coffee MakerbrT.V. with Amazon Fire StickbrDVDbrWIFIbrWood Burning Franklin StovebrDeck overlooking Lake SuperiorbrCharcoal Grill (please bring your own charcoal and liter fluid)brLinens for each BedbrBath Towels for the number of guests listed on the reservationbrComplimentary start-up supplies of: Toilet Tissue, Paper Towels, Garbage Bags, Dish Soap, Dishwasher soap along with Hand Soap and Shampoo for each bathroombrbrCheck in Time: 4:00 PMbrCheck Out Time: 10:00 AMbr50% due at time of ReservationbrbrMadeline Island Vacations Terms & Conditions

Jackson`s - 200 Feet of Sand Beach

La Pointe, Wisconsin, United States

Bed

Bath

Sleeps

$757.66

Miriam’s Retreat | Lakefront Escape on Madeline IslandbrWelcome to Miriam’s Retreat, a spacious and inviting 4-bedroom, 3-bathroom home perfect for families, friends, or groups of up to 10 guests. Nestled on North Shore Road, just six miles from downtown La Pointe, this two-story retreat offers a serene lakeside setting with private access to Lake Superior.brbr The Spacebr4 Bedrooms:brbrMain level: 2 Queen bedroomsbrLoft: King primary bedroombrLower level: Full bed + 2 Twin bedsbr3 Bathrooms, including an outdoor shower for a refreshing rinse after lake timebrOpen-concept kitchen and living area with wood-burning fireplacebrSpacious deck and screened-in gazebo with lake viewsbrLarge outdoor fire pit for evening gatheringsbrEnjoy quality time together, whether cooking meals in the fully equipped kitchen, relaxing in the living room, or watching the sun set from the deck.brbr Outdoor LivingbrPrivate dock with direct Lake Superior accessbrScreened-in gazebo and deck for dining or loungingbrFire pit area perfect for marshmallows, storytelling, and stargazingbrBeautiful lake views from nearly every anglebrSpend your days swimming, kayaking, or simply unwinding in the tranquil surroundings of North Shore Road.brbr✨ Why Guests Love Miriam’s RetreatbrSpacious layout ideal for families or groupsbrStunning lake views and private dock accessbrOpen-concept living with cozy wood-burning fireplacebrScreened-in gazebo and fire pit for outdoor enjoymentbrMiriam’s Retreat is your ultimate Madeline Island getaway — offering comfort, adventure, and unforgettable moments by Lake Superior.brbrItems that you will need to bring:brbrFoodbrBeveragesbrCondiments (including salt & pepper, ketchup, mustard, oils etc. - WI Department of Health & Human Services requires all condiments must be removed after each rental)brAdditional towels for going to the beach (bath towels provided are for use inside the property not to be taken outside or to the beach)brbrTown of La Pointe Permit # - D 2025-65brbrAmenities:brbrKitchen Basics - Dishes, Glassware, Utensils, Cutlery, Pots & PansbrRefrigerator, Stove, Oven, Dishwasher, Microwave, Toaster & Coffee MakerbrDishwasherbrFlat Screen TV - CablebrWIFIbrWood Burning FireplacebrFirepit in backyardbrScreened-in GazeboPorchbrDeck overlooking Lake SuperiorbrGas GrillbrLinens for each bedbrBath Towels for each registered guestbrComplimentary start-up supplies of: Toilet Tissue, Paper Towels, Garbage Bags, Dish Soap, Dishwasher soap along with Hand Soap and Shampoo for each bathroombrbrExtra notes:brbrCheck in Time: 4:00 PMbrCheck Out Time: 10:00 AMbr50% due at time of ReservationbrbrMadeline Island Vacations Terms & Conditions

Miriam`s Retreat - Overlooking Lake Superior with Staircase Lake Superior Access!

La Pointe, Wisconsin, United States

Bed

Bath

Sleeps

$612.94

Mad Pad | Golf Course Retreat on Madeline IslandbrWelcome to Mad Pad, a one-of-a-kind custom-built home situated right on the 15th hole of the Robert Trent Jones, Sr.–designed Madeline Island Golf Club. Combining unique history with modern comfort, part of the original home was moved from the mainland and rebuilt on the island, giving this property a story as special as its setting.brbrAccommodating up to 8 guests, Mad Pad is ideal for families, friends, or golf enthusiasts looking for a scenic and memorable getaway.brbr The Homebr3 Bedrooms & 2 BathroomsbrScreened porch overlooking the golf coursebrSpacious living areas with plenty of room to relax and gatherbrAccommodations for up to 8 guests (base rate for 4; $25/night per guest above 4)brEnjoy serene mornings watching golfers pass by or relax on the porch with a book as the sun sets over the greens.brbr Bedroom ConfigurationbrBedroom 1: King BedbrBedroom 2: Queen BedbrBedroom 3: Queen BedbrLoft Area: 3 Twin BedsbrPerfect for families or groups, with flexible sleeping arrangements for everyone.brbr✨ Why Guests Love Mad PadbrStunning golf course locationbrScreened porch with peaceful viewsbrUnique history — part of the original home was relocated from the mainlandbrSpacious, comfortable interior for groups or familiesbrWhether you’re here to play a few rounds, enjoy island life, or simply relax in a scenic setting, Mad Pad offers a truly special Madeline Island experience.brbrItems that you will need to bring: FoodbrBeveragesbrCondiments (including salt & pepper, ketchup, mustard, oils etc. - WI Department of Health & Human Services requires all condiments must be removed after each rental)brAdditional towels for going to the beach (bath towels provided are for use inside the property not to be taken outside or to the beach)brbrTown of La Pointe Permit # - D 2024-41brbrAmenities:brbrFlat Screen | Wireless Router | Limit 1 Dog | Wood Burning StovebrbrKitchen Basics - Dishes, Glassware, Utensils, Cutlery, Pots & PansbrRefrigerator, Stove, Oven, Microwave, Dishwasher, Toaster & Coffee MakerbrLinens for each BedbrBath Towels for the number of guests listed on the reservationbrGas GrillbrWasher & DryerbrComplimentary start-up supplies of: Toilet Tissue, Paper Towels, Garbage Bags, Dish Soap, Dishwasher soap along with Hand Soap and Shampoo for each bathroombrbrExtra notes:brbrCheck in Time: 4:00 PMbrCheck Out Time: 10:00 AMbr50% due at time of ReservationbrbrMadeline Island Vacations Terms & Conditions

MadPad - Unique Family Home located right on the Golf Course!

La Pointe, Wisconsin, United States

Bed

Bath

Sleeps

$859.32

Seven Hearts | Spacious Lakefront Estate on Madeline IslandbrWelcome to Seven Hearts, a warm and inviting home just minutes from downtown La Pointe, yet perfectly private for a true island getaway. With 4 bedrooms and 2 baths in the main house plus a guest house with 2 bedrooms and 1 bath, this property is ideal for family gatherings, multi-generational vacations, or groups of friends seeking comfort, space, and lakefront relaxation.brbr The SpacebrMain House:brbrBedrooms & Baths: 4 bedrooms, 2 full bathrooms (main floor & upstairs)brLiving & Dining: Open layout with abundant windows overlooking the deck and yardbrFamily Room: Cozy space for reading, relaxing, or gathering with gamesbrKids’ Game Area: Upstairs table and play space for family funbrKitchen: Center island with seating for conversation while cookingbrGuest House:brbr2 bedrooms, 1 full bath with showerbrFull kitchen, living & dining areabrPrivate deck to relax outdoorsbrbr Outdoor & Lakefront HighlightsbrLarge deck overlooking the yard toward Lake SuperiorbrPrivate dock with water access for swimming, sunbathing, or sunset viewsbrPerfect setting to unwind, enjoy water activities, and soak in the natural beauty of the islandbrbrSeven Hearts offers a rare combination of spacious accommodations, lakefront access, and family-friendly amenities, making it the perfect home base to explore Madeline Island while enjoying the ultimate in relaxation and comfort.brbrItems that you will need to bring:brbrFoodbrBeveragesbrCondiments (including salt & pepper, ketchup, mustard, oils etc. - WI Department of Health & Human Services requires all condiments must be removed after each rental)brAdditional towels for going to the beach (bath towels provided are for use inside the property not to be taken outside or to the beach)brbrTown of La Pointe Permit # - D 2025-69brbrAmenities:brbrKitchen Basics - Dishes, Glassware, Utensils, Cutlery, Pots & PansbrRefrigerator, Stove, Oven, Dishwasher, Microwave, Toaster & Coffee MakerbrDVD PlayerbrWood Burning FireplacebrLinens for each BedbrBath Towels for the number of guests listed on the reservationbrCharcoal Grill (please bring your own charcoal & lighter fluid)brComplimentary start-up supplies of: Toilet Tissue, Paper Towels, Garbage Bags, Dish Soap, Dishwasher soap along with Hand Soap and Shampoo for each bathroombrbrExtra notes:brbrCheck in Time: 4:00 PMbrCheck Out Time: 10:00 AMbr50% due at time of ReservationbrbrMadeline Island Vacations Terms & Conditions

Seven Hearts - Family Home with Guest House and Lake Superior Access!

La Pointe, Wisconsin, United States

Bed

Bath

Sleeps

$358.97

Stolen Oaks | Charming Cottage Near Madeline Island TownbrEscape to Stolen Oaks, a cozy 2-bedroom, 2-bath cottage located just three miles from downtown La Pointe and just beyond the Madeline Island Airport. Perfect for couples, small families, or friends seeking a peaceful island retreat, this home offers comfort, convenience, and easy access to the island’s natural beauty.brbr The SpacebrBedrooms:brbrBedroom 1: Queen bedbrBedroom 2: Full (double) bedbrBathrooms: 2 full bathsbrSun Porch: Relax with morning coffee or unwind with a good bookbrFull Kitchen: Fully equipped for preparing meals at homebrbr Location & HighlightsbrJust 3 miles from Madeline Island Town Park, featuring 2 miles of sandy beach and scenic hiking trailsbrQuiet, private setting near the airport, yet still close to townbrIdeal for exploring the island or enjoying a relaxing getawaybrbrStolen Oaks is your peaceful home base for discovering the charm of Madeline Island, combining cozy comforts with easy access to beaches, hiking, and island adventures.brbrItems that you will need to bring:brbrFoodbrBeveragesbrCondiments (including salt & pepper, ketchup, mustard, oils etc. - WI Department of Health & Human Services requires all condiments must be removed after each rental)brAdditional towels for going to the beach (bath towels provided are for use inside the property not to be taken outside or to the beach)brbrTown of La Pointe Permit # - D 2025-74brbrAmenities:brbrKitchen Basics - Dishes, Glassware, Utensils, Cutlery, Pots & PansbrRefrigerator, Stove, Oven, Microwave, Toaster & Coffee MakerbrLinens provided for each bed, guests to provide linens for pull out sofa sleeperbrThree Season Sun PorchbrBath Towels for the number of guests listed on the reservationbrCharcoal Grill (please bring your own charcoal and starter fluid)brComplimentary start-up supplies of: Toilet Tissue, Paper Towels, Garbage Bags, Dish Soap, Dishwasher soap along with Hand Soap and Shampoo for each bathroombrbrExtra notes:brbrCheck in Time: 4:00 PMbrCheck Out Time: 10:00 AMbr50% due at time of ReservationbrbrMadeline Island Vacations Terms & Conditions

Stolen Oaks - Cottage with All-seasons Porch, located near the Airport!

La Pointe, Wisconsin, United States

Bed

Bath

Sleeps

$438.14

Lakefront Cottage | Chebomnicon Bay & Porcupine Mountain ViewsbrEscape to a classic Madeline Island getaway at this lakefront cottage overlooking Chebomnicon Bay, with breathtaking views stretching all the way to Michigan’s Porcupine Mountains. Perfect for summer escapes, this three-bedroom home combines comfort, convenience, and unforgettable scenery.brbr The SettingbrLakefront location with stunning water and mountain views (Lake access across the street)brFurnished deck for morning coffee or evening sunsetsbrEasy Lake Superior access across Middle RoadbrSurrounded by woods and the peaceful sounds of naturebrStart your day on the deck with panoramic views, stroll to the water, or relax as the waves lap the shoreline.brbr The Cottagebr3 Bedrooms: King, Queen, and Double bedsbr2 Full Bathrooms, including one en-suite in the primary bedroombrAir conditioning for warm summer daysbrComfortable living and dining spaces, ideal for relaxing or entertainingbrWhether you’re preparing meals in the fully equipped kitchen or enjoying quiet time in the living room, the cottage offers a warm and inviting home base.brbr Location HighlightsbrShort drive to downtown La PointebrClose to Big Bay State Park and Town Park for hiking, swimming, and beach daysbrIdeal for families or small groups seeking adventure and relaxationbrbr✨ Why Guests Love This CottagebrPanoramic lake and mountain viewsbrLakefront access just steps awaybrSpacious deck and comfortable living spacesbrPerfect location between town and island parksbrThis Madeline Island cottage is your ideal summer retreat for soaking in the beauty of Lake Superior while enjoying all the comforts of home.brbrItems that you will need to bring:brbrFoodbrBeveragesbrCondiments (including salt & pepper, ketchup, mustard, oils etc. - WI Department of Health & Human Services requires all condiments must be removed after each rental)brAdditional towels for going to the beach (bath towels provided are for use inside the property not to be taken outside or to the beach)brbrTown of La Pointe # - D 2025-64brbrAmenities:brbrFlat Screen TV | Wireless Router | Off-Street Parking | Outdoor Firepit KitchenbrbrKitchen Basics - Dishes, Glassware, Utensils, Cutlery, Pots & PansbrRefrigerator, Stove, Oven, Microwave, Toaster & Coffee Maker, DishwasherbrCentral heat & air conditioningbrLinens for each BedbrBath Towels for the number of guests listed on the reservationbrOutdoor Fire PitbrCharcoal Grill (please bring your own charcoal & liter fluid)brWasher & DryerbrLake Access (across Middle Road)brVHS PlayerbrTelephone (local calls only)brComplimentary start-up supplies of: Toilet Tissue, Paper Towels, Garbage Bags, Dish Soap, Dishwasher soap along with Hand Soap and Shampoo for each bathroombrbrExtra notes:brbrCheck in Time: 4:00 PMbrCheck Out Time: 10:00 AMbr50% due at time of ReservationbrbrMadeline Island Vacations Terms & Conditions

Mary Ann`s - Located on Beautiful Russell Bay with Lake Access across the Street!

La Pointe, Wisconsin, United States

Bed

2

Bath

6

Sleeps

$753.61

Lucy’s Farm House | North End Lakefront Retreat on Madeline IslandbrWelcome to Lucy’s Farm House, a beautifully renovated lakefront home on the North End of Madeline Island. With 250 feet of private sandy beach and stunning views of Michigan Island and Stockton Island, this peaceful retreat is perfect for relaxing, unwinding, and reconnecting with nature.brbr The SettingbrPrivate sandy beach with expansive lake viewsbrWrap-around three-season porch for morning coffee or evening relaxationbrOutdoor shower for a refreshing rinse after the beachbrFire pit for cozy nights under the starsbrEnjoy sunsets over the lake, peaceful mornings listening to the waves, and leisurely evenings by the fire.brbr The HomebrThis newly renovated farmhouse blends comfort with classic charm:brbr3 Bedroomsbr1.5 BathroomsbrFull kitchen with modern appliancesbrSpacious dining room for family mealsbrWrap-around three-season porch connecting indoor and outdoor livingbrbr Bedroom ConfigurationbrSecond Floor: 2 King bedrooms with a shared half bathbrFirst Floor: Queen bedroom with full bath (shower only)brIdeal for families, friends, or couples looking for a relaxing getaway.brbr✨ Why Guests Love Lucy’s Farm Housebr250 feet of private sandy beachbrStunning views of Michigan and Stockton IslandsbrWrap-around porch and cozy fire pitbrOutdoor shower for easy beach livingbrPeaceful North End location away from the hustle and bustlebrLucy’s Farm House is your perfect lakeside escape on Madeline Island, offering privacy, comfort, and unforgettable waterfront moments.brbrItems that you will need to bring:brbrFoodbrBeveragesbrCondiments (including salt & pepper, ketchup, mustard, oils etc. - WI Department of Health & Human Services requires all condiments must be removed after each rental)brAdditional towels for going to the beach (bath towels provided are for use inside the property not to be taken outside or to the beach)brbrTown of La Pointe Permit # - D 2025-63brbrAmenities:brbrKitchen Basics - Dishes, Glassware, Utensils, Cutlery, Pots & PansbrRefrigerator, Stove, Oven, Microwave, Toaster & Coffee MakerbrSmart TVbrWIFIbrFire pit built in on the patiobrGas GrillbrLinens for each bed (if you plan on using the twin bed on the porch, you must provide your own bedding)brBath Towels for each registered guestbrComplimentary start-up supplies of: Toilet Tissue, Paper Towels, Garbage Bags, Dish Soap, Dishwasher soap along with Hand Soap and Shampoo for each bathroombrbrExtra notes:brbrCheck in Time: 4:00 PMbrCheck Out Time: 10:00 AMbr50% due at time of ReservationbrbrMadeline Island Vacations Terms & Conditions

Lucy`s Farm House - Beautiful Property with over 250 Feet of Sand Beach!

La Pointe, Wisconsin, United States

Bed

Bath

Sleeps

$702.59

Waterfront Living at Its BestbrStep outside and enjoy direct access to the harbor. Take in panoramic water views from the deck, sip your morning coffee as the sun rises, or unwind in the evening with a breathtaking sunset. Feeling adventurous Use the swimming ladder and jump right into the lake for a refreshing swim.brbrBringing a boat The property features a spacious “L”-shaped dock, making it easy to tie up and enjoy life on the water.brbr Cozy & Comfortable InteriorbrInside, you’ll find a warm and inviting living space centered around a beautiful stone fireplace with gas insert — enjoy the glow and warmth of a fire at the flip of a switch.brbrEvery bedroom is outfitted with premium Optimum Sealy Posturepedic mattresses, ensuring restful nights after days spent exploring the island.brbrSleeping Arrangements:brBedroom 1: Queen bed + Flat Screen TVbrBedroom 2: Queen bed + Flat Screen TVbrBedroom 3: Queen bed + Sitting area with Flat Screen TV just outside in a comfortable porcelain tile lounge spacebrbr☀️ The Perfect Island EscapebrWhether you’re relaxing indoors by the fire or enjoying the breeze on the deck overlooking the harbor, Harbor Beach House is designed for comfort and connection to the water. It’s the ideal home base for couples, families, or friends looking to unwind and experience the charm of Madeline Island.brbrCome stay, relax, and make unforgettable waterfront memories at Harbor Beach House.brbrItems that you will need to bring:brbrFoodbrBeveragesbrCondiments (including salt & pepper, ketchup, mustard, oils etc. - WI Department of Health & Human Services requires all condiments must be removed after each rental)brAdditional towels for going to the beach (bath towels provided are for use inside the property not to be taken outside or to the beach)brbrTown of La Pointe Permit # - D 2025-59brbrAmenities:brbrKitchen Basics - Dishes, Glassware, Utensils, Cutlery, Pots & PansbrRefrigerator, Stove, Oven, Microwave, Toaster & Coffee MakerbrLinens for each BedbrbrGas GrillbrMini-Splits (Heat & A/C)brComplimentary start-up supplies of: Toilet Tissue, Paper Towels, Garbage Bags, Dish Soap, Dishwasher soap along with Hand Soap and Shampoo for each bathroombrbrExtra notes:brbrCheck in Time: 4:00 PMbrCheck Out Time: 10:00 AMbr50% due at time of ReservationbrbrMadeline Island Vacations Terms & Conditions

Harbor Beach House - Right on the Water, located Downtown La Pointe!

La Pointe, Wisconsin, United States

Bed

Bath

Sleeps

$507.69

Welcome to Evelyn’s Place — your peaceful waterfront retreat on the shores of Lake Superior, located on beautiful Madeline Island.brbrFrom the moment you arrive and take in the sweeping lake views, you’ll feel the stress melt away. Whether you're here to unplug, explore the island, or simply soak in the scenery, Evelyn’s Place offers the perfect setting.brbr The SettingbrEnjoy stunning Lake Superior views right from the property. Start your mornings with coffee by the water and wind down in the evening as the lake reflects the changing sky.brbrThis cozy waterfront cabin invites you to slow down and savor island life.brbr The CabinbrThoughtfully designed for comfort and relaxation, this quaint two-bedroom, one-bath cabin is ideal for up to four guests.brbrBedroom 1: Queen BedbrBedroom 2: Queen BedbrFull bathroombrPrivate reading room — perfect for quiet moments with a good bookbrInviting living spaces filled with natural lightbrbr Indoor & Outdoor DiningbrScreened porch with plenty of room for outdoor diningbrDining room just off the kitchen for cozy meals insidebrFully equipped kitchen for preparing your favorite dishesbrWhether you're cooking a family dinner or enjoying takeout after a day of exploring, the layout makes gathering easy and comfortable.brbr✨ Why Guests Love Evelyn’s PlacebrDirect Lake Superior viewsbrPeaceful, private settingbrScreened porch for relaxing summer eveningsbrComfortable layout for couples or small familiesbrA true Northwoods waterfront experiencebrIf you’re ready for the perfect Lake Superior getaway on Madeline Island, Evelyn’s Place is waiting to welcome you.brbrItems that you will need to bring:brbrFoodbrBeveragesbrCondiments (including salt & pepper, ketchup, mustard, oils etc. - WI Department of Health & Human Services requires all condiments must be removed after each rental)brAdditional towels for going to the beach (bath towels provided are for use inside the property not to be taken outside or to the beach)brbrTown of La Pointe Permit # - D 2025-57brbrAmenities:brbrKitchen Basics - Dishes, Glassware, Utensils, Cutlery, Pots & PansbrRefrigerator, Stove, Oven, Microwave, Toaster & Coffee MakerbrFlat Screen TV - CablebrWIFIbrWood Burning StovebrFire Pit in backyardbrScreen PorchbrGas GrillbrBath Towels for each registered guestbrLinens for each bedbrComplimentary start-up supplies of: Toilet Tissue, Paper Towels, Garbage Bags, Dish Soap, Dishwasher soap along with Hand Soap and Shampoo for each bathroombrbrExtra notes:brbrCheck in Time: 4:00 PMbrCheck Out Time: 10:00 AMbr50% due at time of ReservationbrbrMadeline Island Vacations Terms & Conditions

Evelyn`s Place - Charming Cottage with Spectacular Lake Superior Views!

La Pointe, Wisconsin, United States

Bed

Bath

Sleeps

$379.06

Cedarberry Bluff | Secluded Lake Superior Cottage on Madeline IslandbrEscape to Cedarberry Bluff, a private and serene cottage perched on a bluff overlooking the South Shore of Lake Superior. This idyllic retreat is perfect for those looking to unplug, unwind, and soak in breathtaking views—whether for a romantic getaway, honeymoon, anniversary, or a quiet retreat for up to four guests.brbr The SpacebrInside, the cottage is cozy, thoughtfully designed, and well-equipped:brbrDownstairs Bedroom: Full (double) bedbrUpstairs Loft: Queen bedbrLiving Area: Comfortable seating with attached dining spacebrKitchen: Full galley kitchen for easy meal prepbrBathroom: ShowerbrSleeps: Up to 4 guestsbrbr Outdoor LivingbrPrivate lakeside fire pit for evening gatherings or stargazingbrSpectacular sunsets over Lake SuperiorbrQuiet bluff setting offering peace, privacy, and unforgettable viewsbrbr✨ HighlightsbrSecluded and private—perfect for relaxation and solitudebrClose enough to Madeline Island attractions for adventure, yet tucked away for true tranquilitybrIdeal for couples, small families, or anyone seeking a nature-filled escapebrWhether it’s sipping morning coffee while watching the waves, relaxing by the fire, or simply enjoying the quiet beauty of the South Shore, Cedarberry Bluff offers the ultimate Lake Superior retreat.brbrTown of La Pointe Permit # - D 2025-54brbrAmenities:brbrKitchen Basics - Dishes, Glassware, Utensils, Cutlery, Pots & PansbrRefrigerator, Stove, Oven, Toaster & Coffee MakerbrFlat Screen TV - CablebrWIFIbrGas FireplacebrPropane GrillbrFire Pit overlooking Lake SuperiorbrLinens for each BedbrBath Towels for the number of guests listed on the reservationbrComplimentary start-up supplies of: Toilet Tissue, Paper Towels, Garbage Bags, Dish Soap, Dishwasher soap along with Hand Soap and Shampoo for each bathroombrbrExtra notes:brbrCheck in Time: 4:00 PMbrCheck Out Time: 10:00 AMbr50% due at time of ReservationbrbrMadeline Island Vacations Terms & Conditions

Cedarberry Bluff - Charming Cottage with Lake Superior Views!

La Pointe, Wisconsin, United States

2

Bed

1

Bath

4

Sleeps

$554.07

Sláinte | Modern Cottage Steps from Madeline Island MarinabrExperience the perfect blend of comfort, convenience, and island charm at Sláinte, a beautifully appointed cottage on Madeline Island. Ideally located just steps from the Marina, within walking distance of the Madeline Island Golf Club, and minutes from downtown La Pointe with its locally-owned shops, restaurants, and historical museum.brbr The SpacebrAccommodates: Up to 6 guests, perfect for two couples, families, or small groupsbrBedrooms: 3 spacious bedrooms for privacy and comfortbrBathrooms: 3 full bathrooms, ensuring space for everyonebrLiving Area: Open floor plan with vaulted ceilings, a cozy fireplace, and direct access from the kitchenbrKitchen: Fully equipped for home-cooked mealsbrOutdoor Spaces: Private screened porch and deck, perfect for relaxing and enjoying the outdoorsbrClimate Comfort: Central air for summer and a fireplace for spring or fallbrbr✨ HighlightsbrPrime location near Marina, Golf Club, and downtown La PointebrSpacious and open living areas with vaulted ceilings and fireplacebrPrivate outdoor spaces for quiet mornings or sunset eveningsbrModern amenities blended with classic island charmbrEasy access to all of Madeline Island’s shops, restaurants, recreation, and naturebrbrWhether you’re seeking a relaxing island getaway, golf adventures, or a family-friendly retreat, Sláinte offers a stylish and comfortable home base to explore everything Madeline Island has to offer.brbrItems that you will need to bring:brbrFoodbrBeveragesbrCondiments (including salt & pepper, ketchup, mustard, oils etc. - WI Department of Health & Human Services requires all condiments must be removed after each rental)brAdditional towels for going to the beach (bath towels provided are for use inside the property not to be taken outside or to the beach)brbrTown of La Pointe Permit # - D 2025-72brbrAmenities:brbrKitchen Basics - Dishes, Glassware, Utensils, Cutlery, Pots & PansbrRefrigerator, Stove, Oven, Dishwasher, Microwave, Toaster & Coffee MakerbrWasher/DryerbrFlat Screen Smart TV - Netflix, YouTube TV, Disney PlusbrCentral A/CbrWIFIbrWood Burning FireplacebrPortable Fire Pit in backyardbrScreen PorchbrCharcoal Grill Bring charcoal and lighter fluidbrBath towels for the number of guests listed on the reservationbrComplimentary start-up supplies of: Toilet Tissue, Paper Towels, Garbage Bags, Dish Soap, Dishwasher soap along with Hand Soap and Shampoo for each bathroombrbrExtra notes:brbrCheck in Time: 4:00 PMbrCheck Out Time: 10:00 AMbr50% due at time of ReservationbrbrMadeline Island Vacations Terms & Conditions

Slainte - Cottage located near Downtown La Pointe with Screened-in Porch!

La Pointe, Wisconsin, United States

Bed

Bath

Sleeps

$310.39

This is our guest house. It is very nicely appointed with hardwood cabinets, tile and hardwood floors, and professional grade appliances. The lower level has an open living/dining area with a fully equipped galley kitchen. Large dining table. Patio doors with view of the lake. There is a full bath down. One bedroom with one queen and one full bed. Upstairs is queen bed with sitting area, and small bedroom with queen bed. Bath up is shower/toilet only. brbrThis house sits on owner's homestead with a spectacular view of the Apostle Islands from a high bank. Access the large permanent pier by stairs (about 125) or by electric tram to shore end of dock. There is a swim ladder if you care to venture into the cold, clear waters of Lake Superior. Many guests do, and describe the experience as spiritual. brbrThe dock sits at the south end of Hidden Beach, which is accessible only to residents of the local development. Most of the time you will have the beach to yourself. Enjoy watching the fishing and sailboats heading towards anchorages at Stockton Island. Eagles nest and perch in the tall pines along the shore.

Guest House on Owners Lakefront Property

La Pointe, Wisconsin, United States

Bed

2

Bath

7

Sleeps

$785.05

Bean Ravine | Waterfront Post & Beam Cabin + Guest House on Madeline IslandbrbrWelcome to Bean Ravine, a peaceful island retreat where rustic cabin charm meets modern comfort. Nestled on the quiet north end of Madeline Island, this custom-built post & beam cabin is surrounded by towering trees, birdsong, and stunning waterfront views. It’s the perfect escape for families, friends, or anyone looking to unplug and experience the beauty of Lake Superior.brbrThe SpacebrStep inside and experience the warmth of a true Northwoods cabin. The handcrafted post & beam construction, cozy furnishings, and thoughtful décor create a welcoming atmosphere that blends seamlessly with the surrounding wilderness.brbrThe property includes a main cabin and a separate guest house, giving your group both space and privacy.brbrMain Cabinbrbr3 comfortable bedroomsbr2 full bathroomsbrSpacious living area with classic cabin characterbrFully equipped kitchenbrLarge windows that bring in natural light and forest viewsbrGuest HousebrLocated just steps from the main cabin, the guest house includes:brbr1 full-size bedbrPrivate bathroombrKitchenettebrPerfect for additional guests or a quiet private spacebrWaterfront & Outdoor ExperiencebrOne of the highlights of Bean Ravine is the private dock. Start your morning with coffee by the water, take a refreshing swim in Lake Superior, or relax in the sun while enjoying peaceful lake views.brbrThe surrounding woods provide a soundtrack of rustling leaves and birdsong, making every moment feel connected to nature.brbrLocationbrWhile Bean Ravine feels wonderfully secluded, you’re still close to everything Madeline Island has to offer:brbrScenic hiking and nature trailsbrLocal shops, galleries, and restaurantsbrBeaches and water activitiesbrEasy drives to explore the island’s unique charmbrPerfect ForbrFamily vacationsbrFriend getawaysbrNature loversbrRelaxing island escapesbrWhether you're swimming from the dock, exploring island trails, or simply relaxing with Lake Superior views, Bean Ravine offers a memorable Northwoods getaway where nature and comfort meet.brbrItems you will need to bring:brFoodbrBeveragesbrCondiments (including salt & pepper, ketchup, mustard, oil etc. - WI Department of Health requires all condiments removed between each rental)brAdditional towels for going to the beach (bath towels provided are for use inside the property not to be taken outside or to the beach)brbrTown of La Pointe Permit # - D 2025-51brbrAmenities:brbrKitchen Basics - Dishes, Glassware, Utensils, Cutlery, Pots & PansbrRefrigerator, Stove, Oven, Microwave, Toaster & Coffee MakerbrDishwasherbrFlat Screen TVbrWIFIbrWood Burning FireplacebrbrExtra notes:brbrCheck in Time: 4:00 PMbrCheck Out Time: 10:00 AMbr50% due at time of ReservationbrbrMadeline Island Vacations Terms & Conditions

Bean Ravine - Unique Cabin overlooking Lake Superior!

La Pointe, Wisconsin, United States

Bed