Vacation Rentals By Owner In La Pointe, WI

$584.62

Jackson`s - 200 Feet of Sand Beach

La Pointe, Wisconsin, United States

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

3

Bed

2

Bath

6

Sleeps

$354.09

/ Nightly

Condo

Marina Point 502A - Condo In Town

La Pointe, Wisconsin, United States

Marina Point Condo 502A | Cozy 2-Bedroom Escape on Madeline IslandbrWelcome to Marina Point Condo 502A, a comfortable 2-bedroom, 2-bathroom retreat just a short distance from the heart of Madeline Island’s downtown. Whether you’re here to relax or explore the island’s natural beauty, this condo offers the perfect base for your getaway.brbr The SpacebrStep inside to an open-concept living area designed for comfort and connection:brbr2 Bedrooms, each with a queen bed for a restful night’s sleepbr2 Full Bathrooms, providing privacy and conveniencebrFully equipped kitchen for cooking your favorite mealsbrDining area and cozy living space for relaxing and gatheringbrEnjoy a welcoming, bright interior that makes it easy to unwind after a day of island adventures.brbr Outdoor LivingbrShared gas grill for outdoor cookingbrFire pit area for evening gatherings under the starsbrPerfect for roasting marshmallows, sharing stories, or simply enjoying the peaceful surroundingsbrThe outdoor space enhances your stay with opportunities for both fun and relaxation.brbr LocationbrJust minutes from downtown La PointebrEasy access to local shops, restaurants, and island attractionsbrPeaceful setting with all the conveniences of town nearbybrbr✨ Why Guests Love Marina Point Condo 502AbrCozy, inviting 2-bedroom layoutbrOpen-concept living and dining spacesbrScreened porch and shared outdoor amenitiesbrIdeal for couples, small families, or friendsbrThis charming condo is the perfect home base for your next Madeline Island escape, offering comfort, convenience, and a taste of island life.brbrTown of La Pointe Permit # - D-2025-47

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$459.23

/ Nightly

Cabin

50 Acres Private Cabin Nestled in the Woods

La Pointe, Wisconsin, United States

Secluded Woodland Retreat | 50-Acre Madeline Island EscapebrEscape to tranquility at this stunning 50-acre woodland property on Madeline Island, a perfect hideaway for families, couples, or small groups seeking peace, privacy, and nature. Designed with craftsman-style finishes, this home blends rustic charm with modern comfort for an unforgettable island retreat.brbr The SpacebrBedrooms:brbrFirst level: Two cozy bedrooms, thoughtfully appointed for restful sleepbrLoft: Two twin beds, perfect for children or extra guestsbrLiving Area: Open-concept kitchen, dining, and living space ideal for family meals and gatheringsbrKitchen: Fully equipped for all your cooking needsbrExtras: Wood-burning stove for warmth and ambiance, screened-in porch to enjoy serene forest viewsbrBathrooms: [Add details if known]brSleeps: 6 comfortablybrbr Outdoor LivingbrExpansive 50-acre property offering plenty of space to explore, hike, and unwindbrFire pit for evening gatherings under the starsbrSurrounded by quiet forest, perfect for reading, meditation, or simply reconnecting with naturebrbr✨ HighlightsbrSecluded and private—feel worlds away from the hustle and bustlebrRustic craftsmanship meets modern comforts throughout the homebrIdeal for families, couples, or small groups seeking a nature-filled retreatbrStep outside to hear the whispering trees, gather around the fire, and breathe in the fresh air—this woodland escape is the ultimate place to relax, recharge, and reconnect with nature.brbrItems you will need to bring:brbrFoodbrBeveragesbrCondiments (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 Rental Permit Number: D 2025-02

Bed

Bath

Sleeps

$345.77

/ Nightly

Condo

Marina Point - Condo In Town

La Pointe, Wisconsin, United States

Marina Point Condo 501A | Cozy 2-Bedroom Getaway on Madeline IslandbrWelcome to Marina Point Condo 501A, a comfortable 2-bedroom, 2-bathroom retreat located just a short distance from the heart of Madeline Island’s downtown. Whether you’re seeking a peaceful getaway or an adventure exploring the island’s natural beauty, this condo offers the perfect home base.brbr The SpacebrStep inside to a warm, open-concept living area designed for comfort and connection:brbr2 Bedrooms, each with a queen bed for restful sleepbr2 Bathrooms, providing space and privacy for all guestsbrFully equipped kitchen for cooking your favorite mealsbrDining area and cozy living space for relaxing and gatheringbrScreened porch for enjoying your morning coffee or an afternoon readbrThe thoughtful layout makes it easy to unwind, share meals, or simply enjoy each other’s company.brbr Outdoor LivingbrShared gas grill for outdoor cookingbrFire pit area for evening gatheringsbrSpace to roast marshmallows, share stories, or stargaze in peacebrThe outdoor area creates the perfect setting for relaxing after a day of island adventures.brbr LocationbrJust a short distance to downtown La PointebrEasy access to local dining, shops, and island attractionsbrPeaceful yet convenient — enjoy the best of both worldsbrbr✨ Why Guests Love Marina Point Condo 501AbrCozy and inviting 2-bedroom layoutbrScreened porch and shared outdoor spacesbrModern kitchen and comfortable living areasbrClose to town yet private enough for a relaxing escapebrIdeal for couples, small families, or friends, this charming condo is the perfect place to enjoy the beauty and tranquility of Madeline Island.brbrTown of La Pointe Permit # - D-2025-46

Bed

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Sleeps

$757.66

/ Nightly

Private Vacation Home

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

La Pointe, Wisconsin, United States

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

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Sleeps

$1469.83

/ Nightly

Lodge

Sunset Bay Lodge.

La Pointe, Wisconsin, United States

Welcome to one of Madeline Island’s newer and unique properties great for medium to large groups (sleeps up to 24 in beds). brbrThis property sits on over 5 acres with 300 feet of waterfront. It faces western sunsets and is surrounded by beautiful forest. There are two buildings: a lodge and a guest cabin. Bud’s Oasis (a fun local bar) is located at the entrance of the driveway. The property is within walking, biking or running distance to La Pointe where there are restaurants, bars, shops, a library, a public sand beach, the ferry docks and a golf course. People can purchase a daily or weekly pool and hot tub pass from the Inn on Madeline Island (which is located next to the marina). brbrPlease note: we charge $15 per person per night over a total of 6 people. We also charge a $325 non refundable cleaning fee and a $500 garbage/recycling removal fee if garbage is not disposed of by tenants (the raccoons are a big problem). There is a garbage and recycling collection facility on the island (http://townoflapointewi.gov/cms/files/recycling_guide.pdf).brbrMain Building:brThe main lodge was finished in 2014. It is a light filled, lofty open space with a pine ceiling and cedar trim. It boasts a gourmet kitchen with a Décor stove, commercial sized fridge/freezer and two dining areas. Twelve-foot tall windows allowing for incredible views of the trees and lake surround the sunken living room area. In the same room: games and books line the shelves and a play area for children is great for keeping an eye on the little ones. A large loft is complete with a ping pong/air hockey table and comfortable seating for TV viewing. The TV also has Blue Ray, a DVD player. The loft has a queen sized futon.brbrThere are three bedrooms plus a sleeping area in the loft. Two are master bedrooms each with a king sized bed. One has a pull out love seat (full sized) and the other has a queen/double bunk bed. The third bedroom has a queen – this bedroom is another upstairs area - with a twin bed. The TV loft has a queen futon. There are two full bathrooms and one half bath. One of the bathrooms has a tub; both have showers. brbrTwo west-facing decks face the lake; both of them are off the master bedrooms. One is large and covered while the other is smaller and more intimate. There is a combination charcoal and gas grill outside the front door. brbrGuest Cabin:brThe guest cabin was finished in 2002. The guest cabin is a cozy, two-level and timber-framed house with a sauna. It has a kitchenette with a Wolf stove, a small refrigerator and convection oven. There is a TV with Blue Ray, a DVD player. A deck off the upstairs living/kitchen area faces the lake. There are two bedrooms. One with a queen size bed and twin bunks and the other with a double bed bunk bed with a single trundle bed pull out. A queen sofa bed is in the living area/kitchenette. There is a full bath with a walk-in shower next to the sauna while the other half bath is upstairs. brbrThere are stairways leading to a 78 foot long crib dock with a 50 foot L added to it which adds over 1000 square feet outdoor area. There is a small beach on either side with mixed sand and rock bottom. We have parked one 28 foot boat on the inside of the L of the dock with no problem.brbrThis is an incredible retreat for large or small groups. Plan a family reunion or a get-away with friends. This could be a perfect place for a weekend seminar or workshop as well. We do not allow weddings to take place at our cabin.brbrWatch the sunsets while sitting under the canopy of pine trees. Listen to the birds all day and the frogs and owls during the night. There is a local bald eagle with a nearby nest. In the winter, there is a mating coyote pair who like to hunt on the ice between the island and the mainland. We also have a local ermine family who are incredibly adorable but very shy and fast. Swim, canoe or kayak in crystal clear water in summer or snowshoe, cross-country ski or snow mobile in the winter.brbrSome Rules:brbrDogs are allowed with a one-time $75 charge for each dog. They are not allowed on any furniture and please trim their nails before coming. When you leave the cabin for an outing: bring the dog along, kennel or tie them up outside. Also clean up after the dog!brbrYou will need to bring all your own food, beverages, condiments and spices. Beach towels are not available so please bring your own. Bathroom towels cannot be used as beach towels or for wiping dirty animals clean.brbr

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Sleeps

$695.8

/ Nightly

Country House

Beautiful home on Madeline Island summer specials

La Pointe, Wisconsin, United States

For a special call 715 2 09 150 4. This beautiful 5 bedroom, 2 bath + outside shower , two story home sits on 6 beautiful acres. This home has been renovated with all new mattresses and bedding, appliances , bar/ ice machine, and an all around make over.br Conveniently located just a mile and a half from all of the fine dining,gift shops, and beaches in downtown LaPointe, you can bike there in less than 10 minutes, or take your car and be there in 5. The Big Bay Town and State Parks are about 5 miles from the house.br This house includes, a front and back deck for stargazing and grilling, a private balcony off the master bedroom, an outdoor shower, a bright spacious living room, screened sun room with games, and open kitchen/dining room to make and serve your family a wonderful homemade island meal!br Enjoy seeing lots of varied wildlife out your backdoor as the property butts up to the ever expanding Madeline Island Wilderness Preserve. brbrAn additional payment request for 6.5% will be sent upon booking for a room accommodations tax that is mandatory per our town ordinance.br br We hope you come and stay with us and have a vacation to remember for a lifetime!!

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Sleeps

$612.94

/ Nightly

Private Vacation Home

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

La Pointe, Wisconsin, United States

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

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Bath

Sleeps

$859.32

/ Nightly

Private Vacation Home

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

La Pointe, Wisconsin, United States

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

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Sleeps

$358.97

/ Nightly

Private Vacation Home

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

La Pointe, Wisconsin, United States

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

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Bath

Sleeps

$438.14

/ Nightly

Private Vacation Home

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

La Pointe, Wisconsin, United States

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

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Sleeps

$418.06

/ Nightly

Cabin

Wilderness Retreat - Secluded cottage tucked away in the Woods!

La Pointe, Wisconsin, United States

Wilderness Retreat | Secluded Woodland Cabin on Madeline IslandbrEscape to Wilderness Retreat, a charming cabin tucked into the woods of Madeline Island, perfect for those looking to unplug, relax, and immerse themselves in nature. Located just eight miles from downtown La Pointe, this secluded getaway balances privacy with easy access to town, beaches, and local attractions.brbr The SpacebrAccommodates: Ideal for families or small groupsbrBedrooms: 3 totalbrbr2 main-floor bedrooms with queen bedsbrLoft with a full-size bed and cozy sitting area overlooking the kitchen and living spacebrBathrooms: 1.5brLiving Area: Open-concept great room with living, dining, and kitchen spacesbrOutdoor Spaces: Screened porch overlooking the peaceful woods and an outdoor shower for post-beach or post-hike refreshmentbrEntertainment & Connectivity: Smart TV and Wi-Fibrbr✨ HighlightsbrSecluded woodland setting with island wildlife and towering treesbrScreened porch perfect for morning coffee or evening relaxationbrOutdoor shower for refreshing island livingbrLoft retreat with views over the main living areabrEasy drive to downtown La Pointe, beaches, and local attractionsbrA peaceful getaway to unwind, recharge, and stargaze under Madeline Island skiesbrbrWhether you're sipping coffee while listening to the birds, gathering in the open great room, or enjoying a quiet evening under the stars, Wilderness Retreat is the ultimate blend of comfort, privacy, and island serenity.brbrItems that you will need to bring:brbrFoodbrBeveragesbrCondiments (including salt and pepper, ketchup, mustard, etc. - WI Department of Health requires all condiments removed between each rental)brBeach Towels (bath towels that we provide are for interior use only)brbrTown of La Pointe Permit # - D 2025-79brbrItems Provided:brbrKitchen Basics - Dishes, Glassware, Utensils, Cutlery, Pots & PansbrRefrigerator, Stove, Oven, Microwave, Toaster & Coffee MakerbrLinens for each Bed - if you plan on using the futon in the loft, you are responsible for bringing your own bedding for it.brBath Towels for the number of guests listed on the reservationbrComplimentary start-up supplies of: Toilet Tissue, Paper Towel, Garbage Bags along with Hand Soap and Shampoo/Conditioner for each bathroombrGas GrillbrbrExtra notes:brbrCheck in Time: 4:00 PMbrCheck Out Time: 10:00 AMbr50% due at time of ReservationbrbrMadeline Island Vacations Terms & Conditions, please click here

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Sleeps

$507.69

/ Nightly

Private Vacation Home

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

La Pointe, Wisconsin, United States

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

2

Bed

1

Bath

4

Sleeps

$753.61

/ Nightly

Private Vacation Home

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

La Pointe, Wisconsin, United States

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

Bed

Bath

Sleeps

$702.59

/ Nightly

Private Vacation Home

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

La Pointe, Wisconsin, United States

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

Bed

Bath

Sleeps

$379.06

/ Nightly

Private Vacation Home

Cedarberry Bluff - Charming Cottage with Lake Superior Views!

La Pointe, Wisconsin, United States

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

Bed

Bath

Sleeps

$512.25

/ Nightly

Cabin

Cozy Pines Cabin - Wonderful Sunsets with Lake Superior Access!

La Pointe, Wisconsin, United States

Welcome to Cozy Pines Cabin, your peaceful waterfront retreat on beautiful Madeline Island.brbrNestled in the woods near Grants Point, this charming cabin offers stunning west-facing views over the south channel and across Chequamegon Bay—the perfect setting for unforgettable sunsets.brbr The SettingbrWake up to sparkling lake views and end your day with breathtaking sunsets from your private cedar deck.brbrNew stairway leading down to your private dockbrExpansive cedar deck with outdoor seatingbrWestward-facing shoreline for incredible sunset viewsbrFire pit area for cozy evening gatherings under the starsbrWhether you're sipping your morning coffee or roasting marshmallows at night, this peaceful lakeside setting is pure island magic.brbr The CabinbrCozy Pines Cabin blends rustic charm with everything you need for a comfortable stay:brbrTwo comfortable bedroomsbrInviting living roombrDedicated dining areabrGlass-enclosed porch with oversized windows showcasing panoramic lake viewsbrThe bathroom includes a shower and offers both indoor access and a convenient outdoor entrance from the back deck—perfect after a day on the water.brbr AmenitiesbrFully equipped kitchen for easy meal prepbrPrivate dock for shoreline accessbrOutdoor fire pitbrSpacious deck with seatingbrbr✨ Why You’ll Love ItbrSpectacular sunset views over Chequamegon BaybrPrivate dock accessbrQuiet wooded setting near Grants PointbrBright lake-view porchbrIdeal for couples or small families seeking a peaceful island escapebrIf you're dreaming of serene lake views, crackling campfires, and the natural beauty of Madeline Island, Cozy Pines Cabin is ready 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 2025-53brbrAmenities:brbrKitchen Basics - Dishes, Glassware, Utensils, Cutlery, Pots & PansbrRefrigerator, Stove, Oven, Microwave, Toaster & Coffee MakerbrFlat Screen TVbrWIFIbrFire pit in yardbrCharcoal Grill (guests provides charcoal and lighter 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 bathroombrbrExtra notes:brbrCheck in Time: 4:00 PMbrCheck Out Time: 10:00 AMbr50% due at time of ReservationbrbrMadeline Island Vacations Terms & Conditions

2

Bed

4

Sleeps

$554.07

/ Nightly

Private Vacation Home

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

La Pointe, Wisconsin, United States

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

Bed

Bath

Sleeps

$481.89

/ Nightly

Cabin

Charming Vintage 1950's Cottage

La Pointe, Wisconsin, United States

The Cedar Lodge is a cozy, updated vintage cottage with remarkable views of Lake Superior. Across the road is a private beach along with an extra-wide, permanent dock on lake Superior that provides a perfect place to relax and play on a sandy beach. brbrThis two-bedroom, two-bathroom cabin is ideal for up to 4 guests. The kitchen comes with microwave and dishwasher and is well-stocked, including cookware, utensils, and spices outside a gas grill and charcoal grill (please bring your charcoal and lighter fluid). There is a screen porch with rocking chairs along with a large expansive deck. A wood-burning fireplace anchors the main room with a stack of dry firewood provided stacked next to the shed. A TV with premium cable channels is on-site along with highspeed WIFI and a landline phone.brbrThe cabin is 3 miles from the town of LaPointe, where you'll find a coffee shop, restaurants, bars, ice cream, groceries, and souvenir shopping. There are tennis courts available as well as a Robert Trent Jones-designed golf course. brbrRules and things to note:br-Dogs are allowed with a one-time $50 charge for each dog. br

Bed

Bath

Sleeps

$310.39

/ Nightly

Private Vacation Home

Guest House on Owners Lakefront Property

La Pointe, Wisconsin, United States

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.

3

Bed

2

Bath

7

Sleeps

Vacation Rentals By Owner In La Pointe, WI

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$379.06

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$554.07

$481.89

$310.39

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