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Leelanau County Holiday Rentals

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466 rentals in Leelanau County.
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Prime Private Lake Michigan Waterfront!!!, holiday rental in Leelanau County
Prime Private Lake Michigan Waterfront!!!, holiday rental in Leelanau County
Prime Private Lake Michigan Waterfront!!!, holiday rental in Leelanau County

Prime Private Lake Michigan Waterfront!!!

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
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Quiet Retreat in the woods, near Empire Beach, holiday rental in Leelanau County
Quiet Retreat in the woods, near Empire Beach, holiday rental in Leelanau County
Quiet Retreat in the woods, near Empire Beach, holiday rental in Leelanau County

Quiet Retreat in the woods, near Empire Beach

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Homestead condo, Beautiful view of Lake Mi, A/C,cable WiFi, Aug,29-Sep 5  avail, holiday rental in Leelanau County
Homestead condo, Beautiful view of Lake Mi, A/C,cable WiFi, Aug,29-Sep 5  avail, holiday rental in Leelanau County
Homestead condo, Beautiful view of Lake Mi, A/C,cable WiFi, Aug,29-Sep 5  avail, holiday rental in Leelanau County

Homestead condo, Beautiful view of Lake Mi, A/C,cable WiFi, Aug,29-Sep 5 avail

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lake Michigan Beachfront Condo with A/C! Sunsets over Sleeping Bear Bay, holiday rental in Leelanau County
Lake Michigan Beachfront Condo with A/C! Sunsets over Sleeping Bear Bay, holiday rental in Leelanau County
Lake Michigan Beachfront Condo with A/C! Sunsets over Sleeping Bear Bay, holiday rental in Leelanau County

Lake Michigan Beachfront Condo with A/C! Sunsets over Sleeping Bear Bay

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Weaver House on the pristine Crystal River in Glen Arbor, holiday rental in Leelanau County
The Weaver House on the pristine Crystal River in Glen Arbor, holiday rental in Leelanau County
The Weaver House on the pristine Crystal River in Glen Arbor, holiday rental in Leelanau County

The Weaver House on the pristine Crystal River in Glen Arbor

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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All Seasons Log Cabin Rental, holiday rental in Leelanau County
All Seasons Log Cabin Rental, holiday rental in Leelanau County
All Seasons Log Cabin Rental, holiday rental in Leelanau County

All Seasons Log Cabin Rental

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Charming Horse Farm Country Cottage on  Rolling Hills, holiday rental in Leelanau County
Charming Horse Farm Country Cottage on  Rolling Hills, holiday rental in Leelanau County
Charming Horse Farm Country Cottage on  Rolling Hills, holiday rental in Leelanau County

Charming Horse Farm Country Cottage on Rolling Hills

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
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Serenity, White Beaches, & Crystal Blue Waters!

Holiday Rental House
4 bedrooms
6 bathrooms
Sleeps 9
Match: Sleeps
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~Now Booking 2021 Hard Cider/Wine Tour and Winter Getaway dates, holiday rental in Leelanau County
~Now Booking 2021 Hard Cider/Wine Tour and Winter Getaway dates, holiday rental in Leelanau County
~Now Booking 2021 Hard Cider/Wine Tour and Winter Getaway dates, holiday rental in Leelanau County

~Now Booking 2021 Hard Cider/Wine Tour and Winter Getaway dates

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 7
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New! Glen Arbor, walk to town, theater, pool table, 60 game arcade

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
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Quiet, Private, Waterfront - Luxury on 125 Ft. of Suttons Bay, holiday rental in Leelanau County
Quiet, Private, Waterfront - Luxury on 125 Ft. of Suttons Bay, holiday rental in Leelanau County
Quiet, Private, Waterfront - Luxury on 125 Ft. of Suttons Bay, holiday rental in Leelanau County

Quiet, Private, Waterfront - Luxury on 125 Ft. of Suttons Bay

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
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Great Location Next to Fishtown in Leland Harbor House, holiday rental in Leelanau County
Great Location Next to Fishtown in Leland Harbor House, holiday rental in Leelanau County
Great Location Next to Fishtown in Leland Harbor House, holiday rental in Leelanau County

Great Location Next to Fishtown in Leland Harbor House

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Breathtaking Waterfront Home on West Bay  - M22, holiday rental in Leelanau County
Breathtaking Waterfront Home on West Bay  - M22, holiday rental in Leelanau County
Breathtaking Waterfront Home on West Bay  - M22, holiday rental in Leelanau County

Breathtaking Waterfront Home on West Bay - M22

Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
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Like New Luxury Home, Lake Leelanau, Outdoor Kitchen, HotTub, Pontoon, holiday rental in Leelanau County
Like New Luxury Home, Lake Leelanau, Outdoor Kitchen, HotTub, Pontoon, holiday rental in Leelanau County
Like New Luxury Home, Lake Leelanau, Outdoor Kitchen, HotTub, Pontoon, holiday rental in Leelanau County

Like New Luxury Home, Lake Leelanau, Outdoor Kitchen, HotTub, Pontoon

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Northerness Cottage; a Short Ride to America's #1 Rated Beach!, holiday rental in Leelanau County
Northerness Cottage; a Short Ride to America's #1 Rated Beach!, holiday rental in Leelanau County
Northerness Cottage; a Short Ride to America's #1 Rated Beach!, holiday rental in Leelanau County

Northerness Cottage; a Short Ride to America's #1 Rated Beach!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
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1 Bdrm Condo on Lake Michigan (sleeps 4)-Homestead Resort M22 Glen Arbor, holiday rental in Leelanau County
1 Bdrm Condo on Lake Michigan (sleeps 4)-Homestead Resort M22 Glen Arbor, holiday rental in Leelanau County
1 Bdrm Condo on Lake Michigan (sleeps 4)-Homestead Resort M22 Glen Arbor, holiday rental in Leelanau County

1 Bdrm Condo on Lake Michigan (sleeps 4)-Homestead Resort M22 Glen Arbor

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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New Luxury Waterfront Home minutes from Suttons Bay and Traverse City, holiday rental in Leelanau County
New Luxury Waterfront Home minutes from Suttons Bay and Traverse City, holiday rental in Leelanau County
New Luxury Waterfront Home minutes from Suttons Bay and Traverse City, holiday rental in Leelanau County

New Luxury Waterfront Home minutes from Suttons Bay and Traverse City

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Suttons Bay Beach Road Cottage, holiday rental in Leelanau County
Suttons Bay Beach Road Cottage, holiday rental in Leelanau County
Suttons Bay Beach Road Cottage, holiday rental in Leelanau County

Suttons Bay Beach Road Cottage

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Family-Friendly Waterfront Retreat for Larger Groups, holiday rental in Leelanau County
Family-Friendly Waterfront Retreat for Larger Groups, holiday rental in Leelanau County
Family-Friendly Waterfront Retreat for Larger Groups, holiday rental in Leelanau County

Family-Friendly Waterfront Retreat for Larger Groups

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 18
Match: Sleeps
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Couples Retreat. Perfect getaway with all the amenities., holiday rental in Leelanau County
Couples Retreat. Perfect getaway with all the amenities., holiday rental in Leelanau County
Couples Retreat. Perfect getaway with all the amenities., holiday rental in Leelanau County

Couples Retreat. Perfect getaway with all the amenities.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Waterfront Home on Suttons Bay, 232 ft. Secluded Beach, holiday rental in Leelanau County
Waterfront Home on Suttons Bay, 232 ft. Secluded Beach, holiday rental in Leelanau County
Waterfront Home on Suttons Bay, 232 ft. Secluded Beach, holiday rental in Leelanau County

Waterfront Home on Suttons Bay, 232 ft. Secluded Beach

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Smittys GA 'Right In The Middle Of It All', holiday rental in Leelanau County
Smittys GA 'Right In The Middle Of It All', holiday rental in Leelanau County
Smittys GA 'Right In The Middle Of It All', holiday rental in Leelanau County

Smittys GA 'Right In The Middle Of It All'

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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NEW REMODEL Homestead Beachfront Condo - Epic Sunsets Over Sleeping Bear Bay, holiday rental in Leelanau County
NEW REMODEL Homestead Beachfront Condo - Epic Sunsets Over Sleeping Bear Bay, holiday rental in Leelanau County
NEW REMODEL Homestead Beachfront Condo - Epic Sunsets Over Sleeping Bear Bay, holiday rental in Leelanau County

NEW REMODEL Homestead Beachfront Condo - Epic Sunsets Over Sleeping Bear Bay

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Fantastic Cottage - Great Price - So Peaceful and Beautiful, holiday rental in Leelanau County
Fantastic Cottage - Great Price - So Peaceful and Beautiful, holiday rental in Leelanau County
Fantastic Cottage - Great Price - So Peaceful and Beautiful, holiday rental in Leelanau County

Fantastic Cottage - Great Price - So Peaceful and Beautiful

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cozy Winter 5BR House, Gas Fireplace, Walk to Wineries! OPEN in Dec-Feb, holiday rental in Leelanau County
Cozy Winter 5BR House, Gas Fireplace, Walk to Wineries! OPEN in Dec-Feb, holiday rental in Leelanau County
Cozy Winter 5BR House, Gas Fireplace, Walk to Wineries! OPEN in Dec-Feb, holiday rental in Leelanau County

Cozy Winter 5BR House, Gas Fireplace, Walk to Wineries! OPEN in Dec-Feb

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Private Suttons Bay Waterfront Home with Wi-Fi, Central Air, Near Traverse City, holiday rental in Leelanau County
Private Suttons Bay Waterfront Home with Wi-Fi, Central Air, Near Traverse City, holiday rental in Leelanau County
Private Suttons Bay Waterfront Home with Wi-Fi, Central Air, Near Traverse City, holiday rental in Leelanau County

Private Suttons Bay Waterfront Home with Wi-Fi, Central Air, Near Traverse City

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Quaint cottage on Crystal River-Fireplace,central air, pet welcome, holiday rental in Leelanau County
Quaint cottage on Crystal River-Fireplace,central air, pet welcome, holiday rental in Leelanau County
Quaint cottage on Crystal River-Fireplace,central air, pet welcome, holiday rental in Leelanau County

Quaint cottage on Crystal River-Fireplace,central air, pet welcome

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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The Wheeler Family Cottage on Beautiful North Lake Leelanau, holiday rental in Leelanau County
The Wheeler Family Cottage on Beautiful North Lake Leelanau, holiday rental in Leelanau County
The Wheeler Family Cottage on Beautiful North Lake Leelanau, holiday rental in Leelanau County

The Wheeler Family Cottage on Beautiful North Lake Leelanau

Holiday Rental House
7 bedrooms
4 bathrooms
Sleeps 17
Match: Sleeps
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2 Bed/1BTH - close to village/wineries..unparalleled sunsets, holiday rental in Leelanau County
2 Bed/1BTH - close to village/wineries..unparalleled sunsets, holiday rental in Leelanau County
2 Bed/1BTH - close to village/wineries..unparalleled sunsets, holiday rental in Leelanau County

2 Bed/1BTH - close to village/wineries..unparalleled sunsets

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Suttons Bay Vacation Rentals  'The Otter Limit', holiday rental in Leelanau County
Suttons Bay Vacation Rentals  'The Otter Limit', holiday rental in Leelanau County
Suttons Bay Vacation Rentals  'The Otter Limit', holiday rental in Leelanau County

Suttons Bay Vacation Rentals 'The Otter Limit'

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Guest House on Secluded Shetland Creek ~ Quiet 20 Acres Of Beautiful Woods, holiday rental in Leelanau County
Guest House on Secluded Shetland Creek ~ Quiet 20 Acres Of Beautiful Woods, holiday rental in Leelanau County
Guest House on Secluded Shetland Creek ~ Quiet 20 Acres Of Beautiful Woods, holiday rental in Leelanau County

Guest House on Secluded Shetland Creek ~ Quiet 20 Acres Of Beautiful Woods

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Modern Cottage In A Great Leland Location, holiday rental in Leelanau County
Modern Cottage In A Great Leland Location, holiday rental in Leelanau County
Modern Cottage In A Great Leland Location, holiday rental in Leelanau County

Modern Cottage In A Great Leland Location

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Charming Farm on acclaimed M-22*Fireplace*Central Air*minutes to Town/Beach, holiday rental in Leelanau County
Charming Farm on acclaimed M-22*Fireplace*Central Air*minutes to Town/Beach, holiday rental in Leelanau County
Charming Farm on acclaimed M-22*Fireplace*Central Air*minutes to Town/Beach, holiday rental in Leelanau County

Charming Farm on acclaimed M-22*Fireplace*Central Air*minutes to Town/Beach

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The Tree House in the Heart of Sleeping Bear National Lakeshore, holiday rental in Leelanau County
The Tree House in the Heart of Sleeping Bear National Lakeshore, holiday rental in Leelanau County
The Tree House in the Heart of Sleeping Bear National Lakeshore, holiday rental in Leelanau County

The Tree House in the Heart of Sleeping Bear National Lakeshore

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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In the heart of Glen Arbor - Walking distance to shops, dining and beaches, holiday rental in Leelanau County
In the heart of Glen Arbor - Walking distance to shops, dining and beaches, holiday rental in Leelanau County
In the heart of Glen Arbor - Walking distance to shops, dining and beaches, holiday rental in Leelanau County

In the heart of Glen Arbor - Walking distance to shops, dining and beaches

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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2 bedroom condo on Lake Michigan - Inside Homestead Resort on M-22 in Glen Arbor

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Thistledown on Lake Michigan, holiday rental in Leelanau County
Thistledown on Lake Michigan, holiday rental in Leelanau County
Thistledown on Lake Michigan, holiday rental in Leelanau County

Thistledown on Lake Michigan

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Chic condo tucked in the wooded dunes of Lake MI, holiday rental in Leelanau County
Chic condo tucked in the wooded dunes of Lake MI, holiday rental in Leelanau County
Chic condo tucked in the wooded dunes of Lake MI, holiday rental in Leelanau County

Chic condo tucked in the wooded dunes of Lake MI

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Walk Everywhere - Now booking Winter 2020 Summer/Fall 2021 - SUTTONS BAY IN TOWN, holiday rental in Leelanau County
Walk Everywhere - Now booking Winter 2020 Summer/Fall 2021 - SUTTONS BAY IN TOWN, holiday rental in Leelanau County
Walk Everywhere - Now booking Winter 2020 Summer/Fall 2021 - SUTTONS BAY IN TOWN, holiday rental in Leelanau County

Walk Everywhere - Now booking Winter 2020 Summer/Fall 2021 - SUTTONS BAY IN TOWN

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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In the Heart of Suttons Bay - 2bdr/2bth Condo with Free WiFi - Walk Everywhere, holiday rental in Leelanau County
In the Heart of Suttons Bay - 2bdr/2bth Condo with Free WiFi - Walk Everywhere, holiday rental in Leelanau County
In the Heart of Suttons Bay - 2bdr/2bth Condo with Free WiFi - Walk Everywhere, holiday rental in Leelanau County

In the Heart of Suttons Bay - 2bdr/2bth Condo with Free WiFi - Walk Everywhere

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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A Private, Handbuilt Cottage Overlooking Lake Michigan 3 Miles From Northport, holiday rental in Leelanau County
A Private, Handbuilt Cottage Overlooking Lake Michigan 3 Miles From Northport, holiday rental in Leelanau County
A Private, Handbuilt Cottage Overlooking Lake Michigan 3 Miles From Northport, holiday rental in Leelanau County

A Private, Handbuilt Cottage Overlooking Lake Michigan 3 Miles From Northport

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Leland Village River Front Beauty ~ Peaceful Neighborhood ~ Swim Off The Dock!, holiday rental in Leelanau County
Leland Village River Front Beauty ~ Peaceful Neighborhood ~ Swim Off The Dock!, holiday rental in Leelanau County
Leland Village River Front Beauty ~ Peaceful Neighborhood ~ Swim Off The Dock!, holiday rental in Leelanau County

Leland Village River Front Beauty ~ Peaceful Neighborhood ~ Swim Off The Dock!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Unique Cabin with Private Beach on Lake Michigan, holiday rental in Leelanau County
Unique Cabin with Private Beach on Lake Michigan, holiday rental in Leelanau County
Unique Cabin with Private Beach on Lake Michigan, holiday rental in Leelanau County

Unique Cabin with Private Beach on Lake Michigan

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Secluded Lake Michigan Beachfront Cabin on Cathead Bay Surrounded by State Park, holiday rental in Leelanau County
Secluded Lake Michigan Beachfront Cabin on Cathead Bay Surrounded by State Park, holiday rental in Leelanau County
Secluded Lake Michigan Beachfront Cabin on Cathead Bay Surrounded by State Park, holiday rental in Leelanau County

Secluded Lake Michigan Beachfront Cabin on Cathead Bay Surrounded by State Park

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Northport Village Home ,3 blocks to Barb's Bakery and The Willowbrook!, holiday rental in Leelanau County
Northport Village Home ,3 blocks to Barb's Bakery and The Willowbrook!, holiday rental in Leelanau County
Northport Village Home ,3 blocks to Barb's Bakery and The Willowbrook!, holiday rental in Leelanau County

Northport Village Home ,3 blocks to Barb's Bakery and The Willowbrook!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautifully Furnished Log Home on Secluded Shetland Creek, holiday rental in Leelanau County
Beautifully Furnished Log Home on Secluded Shetland Creek, holiday rental in Leelanau County
Beautifully Furnished Log Home on Secluded Shetland Creek, holiday rental in Leelanau County

Beautifully Furnished Log Home on Secluded Shetland Creek

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Elegant Log Cabin home - Perfect for your up north get away!, holiday rental in Leelanau County
Elegant Log Cabin home - Perfect for your up north get away!, holiday rental in Leelanau County
Elegant Log Cabin home - Perfect for your up north get away!, holiday rental in Leelanau County

Elegant Log Cabin home - Perfect for your up north get away!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Immaculate 9 Bedroom Beachfront Home on Grand Traverse Bay Sleeps 24, holiday rental in Leelanau County
Immaculate 9 Bedroom Beachfront Home on Grand Traverse Bay Sleeps 24, holiday rental in Leelanau County
Immaculate 9 Bedroom Beachfront Home on Grand Traverse Bay Sleeps 24, holiday rental in Leelanau County

Immaculate 9 Bedroom Beachfront Home on Grand Traverse Bay Sleeps 24

Holiday Rental House
11 bedrooms
4 bathrooms
Sleeps 20
Match: Sleeps
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Chalet Style Home Near Empire Beach, holiday rental in Leelanau County
Chalet Style Home Near Empire Beach, holiday rental in Leelanau County
Chalet Style Home Near Empire Beach, holiday rental in Leelanau County

Chalet Style Home Near Empire Beach

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Sleeping Bear Dunes Hidden Gem ~ Perfect Family Getaway!, holiday rental in Leelanau County
Sleeping Bear Dunes Hidden Gem ~ Perfect Family Getaway!, holiday rental in Leelanau County
Sleeping Bear Dunes Hidden Gem ~ Perfect Family Getaway!, holiday rental in Leelanau County

Sleeping Bear Dunes Hidden Gem ~ Perfect Family Getaway!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Frequently Asked Questions about Leelanau County