Vacation Rentals with Pool in Pleasantview Winery, MI: Compare 10+ Sites & Save

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  2. Vacation Rentals with Pool
  3.  USA

  4.  Michigan

  5.  Petoskey
  6.  Pleasantview Winery

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78 Best Vacation Rentals with Pool in Pleasantview Winery (Starting from $166)

Hideaway Valley Condo 36
Hideaway Valley Condo 36
Apartment
Pleasantview Winery, Harbor Springs, Michigan, USA
2.1k from Pleasantview Winery center

Apartments, Cheap, Accommodations, Pools, Lodgings, Places to stay, Family, Ski resorts, Condos

3 Bedrooms6 Guests
9.5

Superb

2 reviews

$187
Average price / night
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Beautiful Hideaway #2: Come play in Harbor Springs!
Beautiful Hideaway #2: Come play in Harbor Springs!
Condo
Harbor Springs, MI, 49740, United States
2.0k from Pleasantview Winery center

AC, Balcony, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms10 Guests
9.4

Superb

32 reviews

$302
Average price / night
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Heart & Soul Hideaway
Heart & Soul Hideaway
Apartment
Harbor Springs, MI, USA
2.1k from Pleasantview Winery center

Apartments, Accommodations, Pools, Lodgings, Vacation rentals, Places to stay, Ski resorts

4 Bedrooms7 Guests
New to Booking
$201
Average price / night
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This condominium is a 3 bedroom(s), 2.5 bathrooms, located in Harbor Springs, MI.
This condominium is a 3 bedroom(s), 2.5 bathrooms, located in Harbor Springs, MI.
Condo
Harbor Springs, MI, 49740, United States
2.1k from Pleasantview Winery center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

3 Bedrooms6 Guests
10.0

Exceptional

10 reviews

$531
Average price / night
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The Highlands at Harbor Springs
The Highlands at Harbor Springs
Resort
Harbor Springs, MI, USA
2.3k from Pleasantview Winery center

Accommodations, Pools, Resorts, Parking, Romantic, 3-star, Lodgings, Hot tubs, Places to stay

193 Bedrooms74 Guests
8.5

Very Good

48 reviews

$359
Average price / night
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Gorgeous 4 bedroom condo - 10 minutes from Harbor Springs & Ski Resorts
Gorgeous 4 bedroom condo - 10 minutes from Harbor Springs & Ski Resorts
Condo
Harbor Springs, MI, 49740, United States
2.1k from Pleasantview Winery center

AC, Balcony, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms7 Guests
9.6

Exceptional

9 reviews

$412
Average price / night
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7 Mi to Dwtn - Family Condo in Harbor Springs!
7 Mi to Dwtn - Family Condo in Harbor Springs!
Apartment
Harbor Springs, MI, USA
2.9k from Pleasantview Winery center

Apartments, Cheap, Accommodations, Pools, Parking, Spa, Lodgings, Hot tubs, Places to stay

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$360
Average price / night
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Updated Phase 2 Hideaway Valley Condo Nestled in the Woods
Updated Phase 2 Hideaway Valley Condo Nestled in the Woods
Condo
Harbor Springs, MI, 49740, United States
2.1k from Pleasantview Winery center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms10 Guests
10.0

Exceptional

65 reviews

$325
Average price / night
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1 Mi to Nubs Nob Ski Resort Harbor Springs Condo
1 Mi to Nubs Nob Ski Resort Harbor Springs Condo
Apartment
Harbor Springs, MI, USA
2.9k from Pleasantview Winery center

Apartments, Accommodations, Pools, Parking, Spa, Lodgings, Hot tubs, Places to stay, Condos

2 Bedrooms6 Guests
New to Booking
$409
Average price / night
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Professionally Updated, Spacious, & Stylish- 4-bedroom, 3.5-bath condo
Professionally Updated, Spacious, & Stylish- 4-bedroom, 3.5-bath condo
Condo
Harbor Springs, MI, 49740, United States
2.2k from Pleasantview Winery center

AC, Balcony, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$529
Average price / night
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Pet-Friendly Harbor Springs Home Hot Tub and Pool!
Pet-Friendly Harbor Springs Home Hot Tub and Pool!
House
Harbor Springs, MI, USA
3.0k from Pleasantview Winery center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

3 Bedrooms8 Guests
4.0

Review score

1 reviews

$852
Average price / night
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Scenic condo
Scenic condo
Condo
Harbor Springs, MI, 49740, United States
2.2k from Pleasantview Winery center

AC, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen

4 Bedrooms10 Guests
9.8

Exceptional

80 reviews

$310
Average price / night
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Harbor Cove #9
Harbor Cove #9
Apartment
Harbor Springs, MI, USA
3.2k from Pleasantview Winery center

Apartments, Accommodations, Pools, Lodgings, Places to stay, Family, Ski resorts

3 Bedrooms2 Guests
8.7

Fabulous

3 reviews

$220
Average price / night
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Hideaway condo, excellent layout, sleeps 10.  Btwn Harbor Springs and Petoskey
Hideaway condo, excellent layout, sleeps 10. Btwn Harbor Springs and Petoskey
Condo
Harbor Springs, MI, 49740, United States
2.2k from Pleasantview Winery center

AC, Balcony, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen

4 Bedrooms10 Guests
9.4

Superb

61 reviews

$304
Average price / night
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Harbor Springs Retreat
Harbor Springs Retreat
House
Harbor Springs, MI, USA
3.2k from Pleasantview Winery center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Ski resorts

1 Bedroom8 Guests
New to Booking
$361
Average price / night
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Hideaway Valley #3 - Close to Ski Hills & Harbor Springs! Seasonal Pool!
Hideaway Valley #3 - Close to Ski Hills & Harbor Springs! Seasonal Pool!
Condo
Harbor Springs, MI, 49740, United States
2.3k from Pleasantview Winery center

AC, Balcony, Barbecue, Internet, Kitchen, Living Area, Microwave, No Smoking, Pool

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$351
Average price / night
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Secluded Harbor Springs Condo
Secluded Harbor Springs Condo
House
Pleasantview Winery, Harbor Springs, Michigan, USA
3.3k from Pleasantview Winery center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Family

3 Bedrooms11 Guests
10.0

Exceptional

1 reviews

$511
Average price / night
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Newly Renovated Hideaway Condo - Hike, Swim, Ski, Golf All Close By!
Newly Renovated Hideaway Condo - Hike, Swim, Ski, Golf All Close By!
Condo
Harbor Springs, MI, 49740, United States
2.3k from Pleasantview Winery center

AC, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet

4 Bedrooms9 Guests
10.0

Exceptional

34 reviews

$417
Average price / night
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Harbor Springs Condo with Fireplace Near Skiing!
Harbor Springs Condo with Fireplace Near Skiing!
Apartment
Harbor Springs, MI, USA
3.3k from Pleasantview Winery center

Apartments, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Beach, Places to stay, Ski resorts

3 Bedrooms8 Guests
New to Booking
$253
Average price / night
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Updated wooded 3 BR end unit condo, sunrise view, pool, trails, close to Lake MI
Updated wooded 3 BR end unit condo, sunrise view, pool, trails, close to Lake MI
Condo
Harbor Springs, MI, 49740, United States
2.3k from Pleasantview Winery center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms8 Guests
9.8

Exceptional

71 reviews

$244
Average price / night
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Resort-Style Harbor Springs Home Near Ski Resort!
Resort-Style Harbor Springs Home Near Ski Resort!
House
Harbor Springs, MI, USA
3.4k from Pleasantview Winery center

Accommodations, Pools, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Vacation rentals

3 Bedrooms8 Guests
6.5

Good

2 reviews

$649
Average price / night
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Cozy Getaway Near All the FUN! Harbor Springs/Petoskey
Cozy Getaway Near All the FUN! Harbor Springs/Petoskey
Condo
Harbor Springs, MI, 49740, United States
2.8k from Pleasantview Winery center

AC, Crib, Dryer, Extra Bed, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub

1 Bedroom4 Guests
10.0

Exceptional

57 reviews

$166
Average price / night
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Harbor Springs Condo, 2400 Sq. Ft., 5 Bedroom, 3 Bath, 3 Levels, Very Clean
Harbor Springs Condo, 2400 Sq. Ft., 5 Bedroom, 3 Bath, 3 Levels, Very Clean
Condo
Harbor Springs, MI, 49740, United States
3.0k from Pleasantview Winery center

AC, Arcade, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub

5 Bedrooms14 Guests
10.0

Exceptional

62 reviews

$750
Average price / night
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Harbor Cove #68 - SKI! Sandy Beach!
Harbor Cove #68 - SKI! Sandy Beach!
Condo
Harbor Springs, MI, 49740, United States
3.0k from Pleasantview Winery center

Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms7 Guests
9.4

Superb

16 reviews

$315
Average price / night
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Valleys Chalet - Harbor Springs/Petoskey Condo
Valleys Chalet - Harbor Springs/Petoskey Condo
Condo
Harbor Springs, MI, 49740, United States
3.0k from Pleasantview Winery center

AC, Balcony, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater

3 Bedrooms10 Guests
10.0

Exceptional

17 reviews

$324
Average price / night
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Cozy Condo Near Boyne Highlands & Nub’s Nob – Pools, Trails & Fireplace!
Cozy Condo Near Boyne Highlands & Nub’s Nob – Pools, Trails & Fireplace!
Condo
Harbor Springs, MI, 49740, United States
3.1k from Pleasantview Winery center

AC, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

1 Bedroom4 Guests
10.0

Exceptional

1 reviews

$210
Average price / night
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Harbor Springs Adventure Base—Beach, Trails & Skiing
Harbor Springs Adventure Base—Beach, Trails & Skiing
House
Harbor Springs, MI, 49740, United States
3.1k from Pleasantview Winery center

AC, Barbecue, Dryer, Fireplace, Fitness Equipment, Internet, Kitchen, Living Area, Microwave

4 Bedrooms8 Guests
8.0

Good

1 reviews

$625
Average price / night
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Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals with Pool in Pleasantview Winery.

Pleasantview Winery Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 78 verified vacation rentals with a pool in Pleasantview Winery. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Pleasantview Winery vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $166 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Pleasantview Winery offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Pleasantview Winery welcome pets. Currently, 6 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Pleasantview Winery often include additional outdoor features such as Pool, Fireplace/Heating, and Sports/Activities. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Pleasantview Winery offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.