Owner Direct Vacation Rentals in Portland Head Light

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  4.  Maine
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  6.  Portland Head Light

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388 Portland Head Light Vacation Homes From $159

Looking for the ideal vacation rental in Portland Head Light? Discover an extensive gallery of private rentals offering space, comfort, and authentic local character. Owner Direct simplifies your search by matching you with verified property options.

Willard Square Family Home
Willard Square Family Home
House
South Portland, ME, USA
2.5k from Portland Head Light center

Internet, Security/Safety, View, Oceanfront, Fireplace/Heating, Pet Friendly, Sports/Activities

3 Bedrooms6 Guests
New to Booking
$655
Average price / night
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Unparalleled Luxury at This Oceanfront Home on a Private Peninsula
Unparalleled Luxury at This Oceanfront Home on a Private Peninsula
House
Cape Elizabeth, ME, 04107, United States
1.4k from Portland Head Light center

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

4 Bedrooms8 Guests
New to Booking
$1751
Average price / night
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Arlies Digs One Block To Willard Beach
Arlies Digs One Block To Willard Beach
House
South Portland, ME, USA
2.6k from Portland Head Light center

Fireplace/Heating, View, Pet Friendly, Security/Safety, Internet, Laundry, Guest Services

2 Bedrooms5 Guests
New to Booking
$545
Average price / night
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Unit 3- The Inn on Shore (duplicate)
Unit 3- The Inn on Shore (duplicate)
Apartment
Cape Elizabeth, ME, 04107, United States
1.8k from Portland Head Light center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

1 Bedroom4 Guests
9.6

Exceptional

9 reviews

$159
Average price / night
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South Portland Cottage
South Portland Cottage
House
South Portland, ME, USA
3.2k from Portland Head Light center

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

1 Bedroom2 Guests
7.6

Good

5 reviews

$216
Average price / night
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Coastal Farmhouse vibe, walk to restaurants,shops & beach, 7 Minutes to Portland
Coastal Farmhouse vibe, walk to restaurants,shops & beach, 7 Minutes to Portland
Apartment
Cape Elizabeth, ME, 04107, United States
1.8k from Portland Head Light center

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

2 Bedrooms4 Guests
New to Booking
$271
Average price / night
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House Island Luxury Residence - BellMoor
House Island Luxury Residence - BellMoor
House
Portland, ME, USA
3.3k from Portland Head Light center

Luxury, Accommodations, Villas, Vacation homes, Cottages, Lodgings, Beach, Places to stay

5 Bedrooms14 Guests
New to Booking
$4466
Average price / night
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Sweeping Ocean Views in Cape Elizabeth Maine
Sweeping Ocean Views in Cape Elizabeth Maine
Cottage
Cape Elizabeth, ME, 04107, United States
2.1k from Portland Head Light center

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

6 Bedrooms14 Guests
New to Booking
$1070
Average price / night
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House Island Private Residence - WatchHouse
House Island Private Residence - WatchHouse
House
Portland, ME, USA
3.4k from Portland Head Light center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Beach, Places to stay

4 Bedrooms9 Guests
New to Booking
$3600
Average price / night
Check Availability
Step right out the ocean is at your door! Amazing location and views!  Unit #3
Step right out the ocean is at your door! Amazing location and views! Unit #3
Apartment
South Portland, ME, 04106, United States
2.1k from Portland Head Light center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking

2 Bedrooms3 Guests
New to Booking
$243
Average price / night
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Entire Privately Owned Island Estate
Entire Privately Owned Island Estate
House
Portland, ME, USA
3.5k from Portland Head Light center

Internet, Parking, View, Balcony/Terrace, Fireplace/Heating, Air Conditioner, Security/Safety

9 Bedrooms23 Guests
New to Booking
$6800
Average price / night
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Distinguished classic coastal home overlooks Casco Bay and Maine’s rocky shore!
Distinguished classic coastal home overlooks Casco Bay and Maine’s rocky shore!
House
South Portland, ME, 04106, United States
2.2k from Portland Head Light center

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

3 Bedrooms7 Guests
10.0

Exceptional

4 reviews

$740
Average price / night
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The Weldon Hotel
The Weldon Hotel
Apartment
Portland, ME, USA
5.1k from Portland Head Light center

Apartments, Cheap, Accommodations, Parking, Serviced apartments, Pet-friendly, Lodgings, Places to stay, Self-catering

13 Bedrooms16 Guests
9.7

Exceptional

20 reviews

$535
Average price / night
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Walkable Beach Area Getaway
Walkable Beach Area Getaway
House
South Portland, ME, 04106, United States
2.3k from Portland Head Light center

AC, Dryer, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking, Outdoor Space

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$171
Average price / night
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Trendy Remodeled 2BR Loft in Portlands Old Port
Trendy Remodeled 2BR Loft in Portlands Old Port
Apartment
Portland, ME, USA
5.2k from Portland Head Light center

Apartments, Cheap, Accommodations, Lodgings, Vacation rentals, Places to stay, Self-catering

2 Bedrooms4 Guests
7.9

Good

10 reviews

$346
Average price / night
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OCEAN VIEWS!  WILLARD BEACH Cottage~2 min walk to beach, 9 mins to Old Port.
OCEAN VIEWS! WILLARD BEACH Cottage~2 min walk to beach, 9 mins to Old Port.
House
South Portland, ME, 04106, United States
2.3k from Portland Head Light center

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

3 Bedrooms8 Guests
10.0

Exceptional

43 reviews

$412
Average price / night
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Private Contemporary Artist's Tree House on two acres with perennial gardens.
Private Contemporary Artist's Tree House on two acres with perennial gardens.
Cottage
Unknown, 04107, United States
2.3k from Portland Head Light center

AC, Barbecue, Free Parking, Heater, Hot Tub, Internet, Kitchen, Living Area, Microwave

1 Bedroom2 Guests
10.0

Exceptional

59 reviews

$244
Average price / night
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OCEAN VIEWS, Rooftop Deck, HOT TUB, new back deck!  3-min walk to Willard Beach
OCEAN VIEWS, Rooftop Deck, HOT TUB, new back deck! 3-min walk to Willard Beach
House
South Portland, ME, 04106, United States
2.4k from Portland Head Light center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

4 Bedrooms12 Guests
10.0

Exceptional

22 reviews

$750
Average price / night
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Refurbished Brick, Waterfront Home on Cushing's Island.
Refurbished Brick, Waterfront Home on Cushing's Island.
House
Portland, ME, 04108, United States
2.4k from Portland Head Light center

Barbecue, Dryer, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking, Outdoor Space

5 Bedrooms10 Guests
10.0

Exceptional

15 reviews

$659
Average price / night
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Cozy Coastal Retreat: Steps to Beach, Expansive Yard
Cozy Coastal Retreat: Steps to Beach, Expansive Yard
House
South Portland, ME, 04106, United States
2.5k from Portland Head Light center

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

3 Bedrooms8 Guests
New to Booking
$537
Average price / night
Check Availability
Willard Beach: Cozy Apartment with a King Size Bed
Willard Beach: Cozy Apartment with a King Size Bed
Apartment
South Portland, ME, 04106, United States
2.5k from Portland Head Light center

AC, Crib, Fireplace, Free Parking, Heater, Internet, Kitchen, Microwave, TV

1 Bedroom2 Guests
10.0

Exceptional

1 reviews

$457
Average price / night
Check Availability

Pro Tip:
OwnerDirectVacationRental 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 in Portland Head Light.

Portland Head Light Vacation Rentals on the Map

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Endless Variety

From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.

Frequently Asked Questions

There are a lot of options in Portland Head Light. If you plan on staying in the Portland Head Light area, consider making a reservation for a few nights at one of these properties as these have been rated the top Vacation Rentals in Portland Head Light

You can explore 388 verified vacation rentals in Portland Head Light. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Portland Head Light vary depending on the season, property size, and location. Rates typically start from around $159 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Portland Head Light include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Portland Head Light welcome pets. Currently, 42 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it's recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Portland Head Light often include amenities such as Fireplace/Heating, Laundry, and View. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.