Vacation rentals near Portland Head Light
We found 2,141 vacation rentals — enter your dates for availability
Discover a selection of private vacation rentals near Portland Head Light that provide the perfect home base for your trip. Whether you’re traveling with friends, family, or even pets, vacation rentals have the amenities you need and want for your stay, which might include hot tub and a washer and dryer. No matter what you're looking for, you'll be sure to find a rental for everyone's needs, including a place that's non-smoking or offers accessibility.
Vacation rentals with weekly discounts - Portland Head Light
Showing deals for:Nov 14 - Nov 21
Image gallery for Down the road from Bayview Beach on Ferry Rd! Bright, and newly furnished 2 BR.
9.49.4 out of 10 rating
Exceptional
(17 reviews)
Down the road from Bayview Beach on Ferry Rd! Bright, and newly furnished 2 BR.
Saco, ME
10% off
Price is CA $310
CA $310
CA $2,825 total
CA $2,825 total
includes taxes & fees
Image gallery for Classic Maine home in quiet tree-lined street neighborhood with fenced in yard
9.69.6 out of 10 rating
Exceptional
(24 reviews)
Classic Maine home in quiet tree-lined street neighborhood with fenced in yard
Portland, ME
10% off
Price is CA $287
CA $287
CA $2,561 total
CA $2,561 total
includes taxes & fees
Image gallery for Dome Home on 42 Acres! Close to the Beach and Downtown Kennebunkport
1010 out of 10 rating
Exceptional
(15 reviews)
Dome Home on 42 Acres! Close to the Beach and Downtown Kennebunkport
Kennebunkport, ME
10% off
Price is CA $460
CA $460
CA $4,259 total
CA $4,259 total
includes taxes & fees
Image gallery for Full sized home
9.89.8 out of 10 rating
Exceptional
(32 reviews)
Full sized home
Harpswell, ME
10% off
Price is CA $302
CA $302
CA $2,663 total
CA $2,663 total
includes taxes & fees
Image gallery for Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland
1010 out of 10 rating
Exceptional
(5 reviews)
Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland
Scarborough, ME
10% off
Price is CA $414
CA $414
CA $3,905 total
CA $3,905 total
includes taxes & fees
Image gallery for Wonderful Portland Waterfront Home
9.69.6 out of 10 rating
Exceptional
(30 reviews)
Wonderful Portland Waterfront Home
Portland, ME
10% off
Price is CA $811
CA $811
CA $7,114 total
CA $7,114 total
includes taxes & fees
Image gallery for Ocean Front at Fortunes Rocks
1010 out of 10 rating
Exceptional
(72 reviews)
Ocean Front at Fortunes Rocks
Biddeford, ME
5% off
Price is CA $719
CA $719
CA $6,616 total
CA $6,616 total
includes taxes & fees
Image gallery for Historic Munjoy Hill Retreat-Rooftop Water Views!
1010 out of 10 rating
Exceptional
(25 reviews)
Historic Munjoy Hill Retreat-Rooftop Water Views!
Portland, ME
10% off
Price is CA $439
CA $439
CA $3,950 total
CA $3,950 total
includes taxes & fees
Image gallery for Serenity between the lakes and seashore
9.89.8 out of 10 rating
Exceptional
(21 reviews)
Serenity between the lakes and seashore
Westbrook, ME
5% off
Price is CA $168
CA $168
CA $1,696 total
CA $1,696 total
includes taxes & fees
Image gallery for Ocean front cottage with private beach.
9.89.8 out of 10 rating
Exceptional
(19 reviews)
Ocean front cottage with private beach.
Peaks Island, ME
5% off
Price is CA $556
CA $556
CA $4,952 total
CA $4,952 total
includes taxes & fees
Image gallery for Beautifully built Cape Elizabeth home nestled in the woods on 2.5 acres
1010 out of 10 rating
Exceptional
(20 reviews)
Beautifully built Cape Elizabeth home nestled in the woods on 2.5 acres
Cape Elizabeth, ME
19% off
Price is CA $1,059
CA $1,059
CA $9,445 total
CA $9,445 total
includes taxes & fees
Image gallery for Cozy, Pet Friendly, Home In A Quiet Family Oriented, Beach Neighborhood
1010 out of 10 rating
Exceptional
(24 reviews)
Cozy, Pet Friendly, Home In A Quiet Family Oriented, Beach Neighborhood
South Portland, ME
25% off
Price is CA $325
CA $325
CA $2,987 total
CA $2,987 total
includes taxes & fees
Image gallery for Rustic Charm close to Portland
1010 out of 10 rating
Exceptional
(44 reviews)
Rustic Charm close to Portland
Cumberland Center, ME
5% off
Price is CA $285
CA $285
CA $2,627 total
CA $2,627 total
includes taxes & fees
Image gallery for The Anchorage Cottage, Pine Point Maine, offers a wonderful vacation experience.
1010 out of 10 rating
Exceptional
(11 reviews)
The Anchorage Cottage, Pine Point Maine, offers a wonderful vacation experience.
Scarborough, ME
10% off
Price is CA $548
CA $548
CA $4,589 total
CA $4,589 total
includes taxes & fees
Image gallery for The Beach House Bailey Island Maine
1010 out of 10 rating
Exceptional
(34 reviews)
The Beach House Bailey Island Maine
Bailey Island, ME
10% off
Price is CA $371
CA $371
CA $3,257 total
CA $3,257 total
includes taxes & fees
Image gallery for New Listing! AmongstTheAspens - Off Grid Tiny House in a Serene Location
9.09.0 out of 10 rating
Wonderful
(6 reviews)
New Listing! AmongstTheAspens - Off Grid Tiny House in a Serene Location
Saco, ME
15% off
Price is CA $338
CA $338
CA $2,815 total
CA $2,815 total
includes taxes & fees
Image gallery for Adorable, Bright and By the Bay!
9.09.0 out of 10 rating
Wonderful
(14 reviews)
Adorable, Bright and By the Bay!
Falmouth, ME
20% off
Price is CA $615
CA $615
CA $5,791 total
CA $5,791 total
includes taxes & fees
Image gallery for Direct Oceanfront/Beachfront Home in Saco, ME. Family Retreat sleeps 19
9.89.8 out of 10 rating
Exceptional
(37 reviews)
Direct Oceanfront/Beachfront Home in Saco, ME. Family Retreat sleeps 19
Saco, ME
10% off
Price is CA $1,108
CA $1,108
CA $9,851 total
CA $9,851 total
includes taxes & fees
Image gallery for 2026 summer weeks are on hold for returning guests—join the waitlist today.
1010 out of 10 rating
Exceptional
(29 reviews)
2026 summer weeks are on hold for returning guests—join the waitlist today.
Kennebunkport, ME
10% off
Price is CA $1,362
CA $1,362
CA $11,515 total
CA $11,515 total
includes taxes & fees
Image gallery for Beautiful, single story ranch. Next to city park with ocean view!
9.09.0 out of 10 rating
Wonderful
(13 reviews)
Beautiful, single story ranch. Next to city park with ocean view!
Portland, ME
10% off
Price is CA $991
CA $991
CA $8,673 total
CA $8,673 total
includes taxes & fees
Image gallery for New 3BR Home for Hitting Birdies and the Beach in Old Orchard - ADA Friendly!
1010 out of 10 rating
Exceptional
(5 reviews)
New 3BR Home for Hitting Birdies and the Beach in Old Orchard - ADA Friendly!
Old Orchard Beach, ME
10% off
Price is CA $310
CA $310
CA $2,989 total
CA $2,989 total
includes taxes & fees
Image gallery for A Waterfront Retreat with Private Deep Water Dock. Dogs allowed upon request
1010 out of 10 rating
Exceptional
(81 reviews)
A Waterfront Retreat with Private Deep Water Dock. Dogs allowed upon request
Yarmouth, ME
10% off
Price is CA $712
CA $712
CA $6,444 total
CA $6,444 total
includes taxes & fees
Image gallery for Waterfront home on Forest Lake in Gray, Maine. Perfect for 1 or 2 couples.
1010 out of 10 rating
Exceptional
(31 reviews)
Waterfront home on Forest Lake in Gray, Maine. Perfect for 1 or 2 couples.
Gray, ME
10% off
Price is CA $425
CA $425
CA $3,718 total
CA $3,718 total
includes taxes & fees
Image gallery for Entire House - three suites - conferences, reunions, retreats
9.69.6 out of 10 rating
Exceptional
(17 reviews)
Entire House - three suites - conferences, reunions, retreats
Westbrook, ME
10% off
Price is CA $1,114
CA $1,114
CA $9,729 total
CA $9,729 total
includes taxes & fees
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Find the best place to stay - Portland Head Light
Swim, Kayak & Relax in Coastal Comfort from this Charming, Pet-Friendly Home
Sleeps 6 · 3 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Sleeps 4 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
50 reviews(50 reviews)
Modern, Spacious Guest Suite Near the Ocean
Sleeps 4 · 2 bedrooms
1010 out of 10
Exceptionalexceptional
51 reviews(51 reviews)
Beachfront and only 30 Steps To Beach!
Sleeps 8 · 4 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
New Listing! AmongstTheAspens - Off Grid Tiny House in a Serene Location
Sleeps 5 · 3 bedrooms · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
6 reviews(6 reviews)
Beautiful ocean views and spectacular sunsets at this modern beachfront home
Sleeps 7 · 3 bedrooms · 1+ bathroom
9.89.8 out of 10
Exceptionalexceptional
25 reviews(25 reviews)
Top rated rentals - Portland Head Light
Great location .
1010 out of 10
Exceptionalexceptional
44 reviews(44 reviews)
Great location. House was clean.
Karen D.
Stayed May 2025
Perfect in every way
1010 out of 10
Exceptionalexceptional
126 reviews(126 reviews)
It was truly wonderful, amazing location with everything you could hope for. Indeed, the ceilings are low so be aware if you are more than 6 feet tall! ☺️
Stephanie P.
Stayed Oct 2024
Outstanding!
1010 out of 10
Exceptionalexceptional
64 reviews(64 reviews)
Beautiful house, well thought out with bedrooms downstairs and living areas upstairs. Amazing views anywhere you look. Front of house is looking at the marshes and back is overlooking ocean. Quiet neighbourhood minutes way from downtown. Easy communication with owner, very responsive.
Manon B.
Stayed Jun 2024
Love the place
1010 out of 10
Exceptionalexceptional
101 reviews(101 reviews)
Great location
Luc D.
Stayed Nov 2023
Paradise
1010 out of 10
Exceptionalexceptional
94 reviews(94 reviews)
We had the most wonderful stay in this house that is just perfect. Very well equiped. Waking up right by the water was amazing. Definetly coming back.
Mariane D.
Stayed Oct 2023
Beautiful week!
1010 out of 10
Exceptionalexceptional
52 reviews(52 reviews)
Our stay was just wonderful!
Isabelle T.
Stayed Sep 2023
Beautiful view excellent property.
1010 out of 10
Exceptionalexceptional
78 reviews(78 reviews)
Alfred is an excellent host. The property is well cared for md well stocked with amazing views. The location is in the heart of the action of Old Orchard Beach and even though we were there in the.off season it was a dream. This property gets a 10/10!
Dawn D.
Stayed Mar 2022
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
More for lessMore space, more privacy, more amenities — more value