Vacation Home Rentals By Owner In Lakeside, MI

Showing 47 Of 47 Vacation Rentals

$543.54

Fantastic family home near the lake with WiFi and large deck

Lakeside, Michigan, United States

Friendly FarmsbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrAbsolutely fantastic both inside and out, Friendly Farms is more than ready to assist in making the best memories mere minutes from the clear waters of Lake Michigan! With a wooded surrounding, this home offers natural privacy, and the exterior is reminiscent of a classic farmhouse, allowing everyone to slip into the simpler lifestyle in no time. Step inside, and you will be greeted by the breathtaking interior featuring colorful decor, high-end furnishings, and an open layout that will be absolutely perfect for mingling and entertaining after a full day of adventure. When everyone wants a bit of fresh air, the front porch, back deck, hot tub, and firepit area with Adirondack chairs can all accommodate guests as the sun goes down. Plus, the well-equipped kitchen right inside will come in handy when appetites are high so bring along a few recipes to whip up using the high-end appliances provided! With so much fun just waiting to be had, what are you waiting for The lake lifestyle is calling!brbrThings to KnowbrFree high-speed WiFibr*A cat spends time at this home on occasion (not full time)brThis property is managed by Vacasa Michigan LLCbrbrParking notes: There is free parking available for 3 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 28 years of age to book. Guests under 28 must be accompanied by a parent or legal guardian for the duration of the reservation.

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Exceptional(6)

$557.99

/ Nightly

Private Vacation Home

Stylish & Well-Equipped Home with Private Outdoor Pool, WiFi, Deck, Gas Grill

Lakeside, Michigan, United States

Butterfly Pool HousebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrLight and airy, relaxed but stylish, Butterfly Cottage is a great place to get away from the city! There is a huge, fenced back yard with a sparkling private pool, a big lawn for games and sports, and a large deck from which to view it all. Best of all, Pier Street Beach in Lakeside is exactly one mile from the house so you can walk, bike, or drive to the beach as there is a tiny bit of roadside parking allowed.brbrThe house has an open, flowing layout and big windows that let the sunlight in. There‚Äôs a fireplace in the living area and a den where you can kick back and watch TV. The well-equipped kitchen has a pass-through to the dining room, which comfortably seats eight. There are three bedrooms on the upper level, beginning with the main bedroom suite that features a king bed. The main bathroom has a deep soaking tub and two additional bedrooms that share a full bathroom. There are another full bathroom and bedroom with a queen bed on the main level that is great for those who can't do a lot of stairs. There is also a large finished family room in the basement.brbrThere are plenty of other sources of adventure and entertainment close by, including the Four Winds Casino, great restaurants, art galleries, and interesting stores to explore. Butterfly House is in a peaceful country location on the east side of Red Arrow Highway but still close to the lake, with woods across the road and neighbors a discrete distance away. All the amenities and opportunities of Harbor country are right here so come and enjoy some pool time at this inviting house!brbrTHINGS TO KNOWbr*Please note that the pool is open from roughly May 15 - September 15 every year.brbrThe pool is open from Memorial Day through Labor Day. The pool will be heated to 80 degrees prior to your arrival. If you wish for the heat to increase, please contact Vacasa after you secure your booking. The cost for additional pool heat is $25/night.brbrThis property is managed by Vacasa Michigan LLC.brbrParking notes: There is free parking available for 3 vehicles.brbrPlease note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!brbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

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Exceptional(20)

$392.68

/ Nightly

Private Vacation Home

Dog-friendly cottage with private beach, screened porch, wood fireplace & AC

Lakeside, Michigan, United States

Lake Michigan AdventuresbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrWelcome to where relaxation meets convenience! This cute small cottage is the perfect choice for a friends' trip, couples retreat, or family vacation. Walk only 1,000 feet to reach Sunset Lane Association Beach, a private association beach for the immediate neighborhood only that also allows dogs.brbrLocated in the cute lakefront town of Lakeside, this ground-floor home is surrounded by beautiful trees and lush nature, offering a true 'get away from it all' feeling. Inside, an open floor plan seamlessly combines the living and dining areas and the well-appointed kitchenette. Snuggle up on any of the sofas by the wood-burning fireplace and stream a favorite movie or series on the smart TV. When mealtime comes around, the kitchenette will have your back with all the essential appliances needed to whip up everything, from full-course meals to quick snacks on the go. You can choose to dine indoors or delight yourself with nature in the outdoor dining area on the patio. There is a beautiful screened porch with comfortable seats that leads to the patio.brbrTHINGS TO KNOWbrThere are four backpack beach chairs and an umbrella.brStreaming is available using your own accounts.brThe fireplace is available in the non-summer months.brOne non-aggressive, non-shedding 40 lb. dog allowed.brKitchenette with a fridge, apartment-size stove and oven, microwave, and coffee maker. No dishwasher.brbrThis property is managed by Vacasa Michigan LLC.brbrIf you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. No more dogs are allowed.brParking notes: There is free parking available for 2 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

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Exceptional(9)

$282.64

/ Nightly

Private Vacation Home

Garden-style cottage with easy beach access, screened porch & small yard

Lakeside, Michigan, United States

Painted Porch CottagebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrWelcome to the Painted Porch Cottage, a garden-style cottage in residential Lakeside, Michigan. Fully equipped, this rustic cottage is just two blocks from a private sandy beach. When you aren't playing in the sand, a short car ride will lead you to numerous antique stores, farmers markets, wineries, u-pick farms, outdoor recreation rentals, and delicious dining options. brbrInside the Painted Porch Cottage, the cozy ambiance is abundant! The bright living room offers a lovely space to sit and watch TV. Steps away, the quaint kitchen provides a pleasant space to play chef and dine with your loved ones. When you aren't eating here, the charming dining room is perfect for family-style meals. brbrAdditional hangout spaces include the screened-in porch and the grassy yard with a barbecue grill. Before crawling under the bedroom's quilts, throw your swimsuits in the private washer/dryer for a refresh, and tune the central air-conditioning to your liking. WiFi access and an after-beach outdoor shower round out the cottage's perks. brbrThings to KnowbrCheck-in time: 4:00 PMbrCheck-out time: 10:00 AMbrThe fireplace is not operational.brAll guests shall abide by The Good Neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 PM to 8:00 AMbrNo smoking is permitted anywhere on the premises.brSubletting of the Painted Porch Cottage is not allowed.brThe cottage is a duplexed house and the owners with kids and a dog may stay in the second unit during your stay.brThis property is managed by Vacasa Michigan LLCbrbrParking notes: There is free parking available for 1 vehicle.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 28 years of age to book. Guests under 28 must be accompanied by a parent or legal guardian for the duration of the reservation.

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$583.43

/ Nightly

Private Vacation Home

Newly Remodeled Lakeview Home w/ screened porch, gas grill, & 300ft from beach

Lakeside, Michigan, United States

Lakeshore HavenbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrNestled in the serene beauty of Lakeside, Michigan, this fully renovated three-bedroom, two-bath home is the perfect retreat for up to eight guests. Located on Lakeshore Road, you‚Äôre only 300 feet from the pristine, wide sands of exclusive New Circle Beach (member access only), ideal for sun-drenched summer days by the water.brbrInside, the home is fresh, bright, and completely remodeled while maintaining its mid-century character through graceful archways, refinished plaster walls, original wood floors, and elegant 10-inch crown molding. Every room features all-new designer furniture and fixtures, creating a space that‚Äôs as comfortable as it is stylish. The living room boasts a sleek modern gas fireplace and a 75' Samsung Frame TV with a Sonos soundbar for cozy evenings. A small seasonal lake view can be enjoyed from both the living room and the screened-in porch.brbrThe gourmet kitchen is a showstopper, now featuring luxury appliances including a Wolf range and oven, Bosch dishwasher, Samsung refrigerator, microwave, country double sink, and Le Cuisinart cookware‚Äîperfect for creating memorable meals. Coffee lovers will appreciate the Keurig setup for a quick morning brew.brbrBook lovers will adore the custom-curated library stocked with art and photography books, mysteries, beach reads, and unique titles from around the globe, along with a delightful children‚Äôs section. For added convenience, a full-size Samsung washer and dryer are available in the home. Outdoors, enjoy dining on the back deck with seating for 10‚Äì12, cook up a feast on the gas grill, or relax on the screened-in porch with a view of the lake. brbrBeyond the doorstep, the charming harbor towns of Harbor Country await. Explore boutique shopping, art galleries, antique markets, and farm-to-table dining in Lakeside, Union Pier, and nearby New Buffalo. Wineries, breweries, and cider houses dot the countryside, offering tastings year-round. Outdoor enthusiasts can bike along scenic country roads, kayak the Galien River, or take long walks along the shoreline.brbrThis area shines in every season‚Äîsummer brings beach days, water sports, and vibrant farmers‚Äô markets; autumn offers crisp hikes through colorful foliage and wine tours amid harvest season; winter is perfect for quiet getaways, cozy fires, and holiday events; and spring blooms with fresh flowers, birdwatching, and peaceful strolls along the water.brbrWhether you‚Äôre planning a family beach vacation, a romantic seasonal escape, or a gathering with friends, this newly remodeled Lakeside gem offers the perfect blend of historic charm, modern luxury, and unbeatable proximity to everything that makes Harbor Country special.brbrParking notes: There is free parking available for 3 vehicles.brbrSecurity camera details: brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.

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Exceptional(5)

$605.4

/ Nightly

Private Vacation Home

Within walking distance to Lake Michigan, beach access, nice patio, W/D & WIFI

Lakeside, Michigan, United States

Four Bedrooms & a BeachbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrLocated just a few blocks from the picturesque shores of Lake Michigan, this charming house in Lakeside, MI, offers the perfect retreat for all seasons, being just walking distance away from Orchard Beach! Whether you're into summer water activities like boating, fishing, paddleboarding, and water skiing, or prefer the winter delights of ice fishing and ice skating, this home is ideally situated for all your outdoor adventures.brbrStep inside this cozy abode to find a well-appointed interior featuring a King Bed, Queen Bed, Double Bed, Twin Bed, and Bunk Bed, ensuring comfortable accommodations for the whole family. Enjoy modern amenities such as Netflix streaming, TV, and free WiFi, making it easy to unwind after a day of exploring the local area.brbrThe updated back patio provides a large fenced-in yard, which is a lovely space to relax and soak in the serene surroundings or fire up the gas grill for a nice meal, while the fully equipped kitchen with a fridge, stove, oven, dishwasher, microwave, and coffee maker allows you to prepare delicious meals during your stay. With a wood stove for cozy evenings, central AC for warm days, a washer/dryer for convenience, and all linens and towels provided, this home offers everything you need for a stress-free vacation.brbrExplore the charming town of Lakeside with its local eateries, arts, and entertainment options, or venture out to discover the array of attractions in the area. Whether you're seeking a summer getaway or a winter wonderland retreat, this family-friendly house is the perfect home base for your Lakeside adventure. Book your stay now and create unforgettable memories in this lovely Lakeside retreat!brbrParking notes: There is free parking available for 4 vehicles.brThis rental is located on floor 1.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.

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Exceptional(22)

$541.85

/ Nightly

Private Vacation Home

Fully-renovated lakefront home with beach cabana, association beach, & firepit

Lakeside, Michigan, United States

The Gatehouse on Orchard BeachbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrWith a gorgeous top-to-bottom renovation that was completed in 2020 and sporting new updates for 2023, this lakefront cottage in the heart of historic Lakeside is truly one of a kind. This modern home is situated on a mid-size bluff above Orchard Beach, a wide, 80-foot stretch of sand that's shared by association members only at the north end of a long, walkable beach on a natural cove of Lake Michigan. Enjoy access to a private beach cabana, with easy access to chairs, umbrellas, and beach toys to make your excursions on the shores truly memorable.brbrThis contemporary home is full of style and natural light, offering new appliances and fixtures throughout, an open and airy great room, and a fully equipped kitchen with an extra-large island and stainless steel appliances - all of which contribute to the authentic, beach-house ambience. Come home from the lakeshore each afternoon to rinse off the sand in the refreshing outdoor shower, get the gas grill going on the raised deck, or simply play with your kids in the spacious yard. Leave your swimsuits to spin in the private washer/dryer, and spend the evening hours telling stories in the warmth of the firepit outside.brbrTHINGS TO KNOWbrThere are 60 stairs leading down to the beach.brAn outdoor shower is available.brFour beach chairs are provided.brBoard games and a yard bag game are provided.brThis property is managed by Vacasa Michigan, LLC.brbrParking notes: There is free parking available for 2 vehicles.brbrPlease note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!brbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

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Rent a place that suits your needs

Private vacation home

View 39 Private vacation home

Most popular vacation rentals in Lakeside

Exceptional(22)

$536.00

/ Nightly

Cottage

Summer Weeks still available! Short walk to a private beach!

Lakeside, Michigan, United States

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Exceptional(22)

$938.98

/ Nightly

Cottage

LAKESIDE HOME WITH PRIVATE POOL and ASSOCIATION BEACH ACCESS!

Lakeside, Michigan, United States

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Exceptional(22)

$858.27

/ Nightly

Private vacation home

Relax on your own private beach on stunning Lake Michigan

Lakeside, Michigan, United States

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Exceptional(22)

$828.74

/ Nightly

Cottage

PRIVATE HOT TUB AND ASSOCIATION BEACH ACCESS!

Lakeside, Michigan, United States

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Sleeps

Exceptional(22)

$810.69

/ Nightly

Private vacation home

Gorgeous Lakeside Home With Pool, Hot Tub, And More!

Lakeside, Michigan, United States

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Bath

Sleeps

Exceptional(22)

$599.67

/ Nightly

Cottage

Stunning designer cottage just 2 blks to private beach.! Sleeps 8.

Lakeside, Michigan, United States

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Bath

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Exceptional(22)

$420.83

/ Nightly

Private vacation home

1000 FT to Assn Beach, Cute Cottage, Outdoor Dining

Lakeside, Michigan, United States

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Exceptional(22)

$316.19

/ Nightly

Cottage

Four Night Min! Lakeside Home With 800 Feet Of Association Beach!

Lakeside, Michigan, United States

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Exceptional(22)

$400.00

/ Nightly

Cottage

Short walk to the beach & backs up to the woods! Few dates left - May June Sept

Lakeside, Michigan, United States

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Exceptional(22)

$2155.41

/ Nightly

Private vacation home

Pool + Hot Tub | Fire Pit | Walk to Beach

Lakeside, Michigan, United States

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Bath

Sleeps

Vacation Home Rentals By Owner In Lakeside, MI

$543.54

$557.99

$392.68

$282.64

$583.43

$605.4

$541.85

Rent a place that suits your needs

Most popular vacation rentals in Lakeside

$536.00

$938.98

$858.27

$828.74

$810.69

$599.67

$420.83

$316.19

$400.00

$2155.41

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