Book Holiday Homes in Kennebunkport

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Kennebunkport

Gorgeous 6 Bedroom Ocean Front Home steps from Short Sands

Gorgeous 6 Bedroom Ocean Front Home steps from Short Sands

York
When you stay at this vacation home in York Beach, you'll be on the waterfront, within a 15-minute drive of Ogunquit Beach and Perkins Cove.
Gorgeous 6 Bedroom Ocean Front Home steps from Short Sands
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough

Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough

2 out of 5
Scarborough
With a stay at this vacation home in Scarborough (Grand Beach), you'll be within a 15-minute drive of Engine and Grand Beach.
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough
Stille Wasser, Quiet, secluded spot on Saco River with Dock (Boat lift option)

Stille Wasser, Quiet, secluded spot on Saco River with Dock (Boat lift option)

Buxton
When you stay at this vacation home in Buxton, you'll be on the waterfront and 8 minutes by car from Saco River.
Stille Wasser, Quiet, secluded spot on Saco River with Dock (Boat lift option)
Save an average of 15% on thousands of hotels when you're signed in
The Moonglow! A beautiful ocean view house in Biddeford!

The Moonglow! A beautiful ocean view house in Biddeford!

Biddeford
With a stay at this vacation home in Biddeford, you'll be near the beach, within a 15-minute drive of Engine and Fortunes Rock Beach.
The Moonglow! A beautiful ocean view house in Biddeford!
Beach House ∆ Prime Location ∆ Steps to the Ocean

Beach House ∆ Prime Location ∆ Steps to the Ocean

Old Orchard Beach
With a stay at this vacation home in Old Orchard Beach, you'll be on the beach, within a 10-minute drive of Engine and Old Orchard Beach.
Beach House ∆ Prime Location ∆ Steps to the Ocean
Amazing Beach House! 5 Bedroom across the Ocean!

Amazing Beach House! 5 Bedroom across the Ocean!

Wells
With a stay at this vacation home in Wells, you'll be near the beach, within a 10-minute drive of Ogunquit Beach and Wells Beach.
Amazing Beach House! 5 Bedroom across the Ocean!
Historic Kennebunkport home only 0.3 miles to Dock Square

Historic Kennebunkport home only 0.3 miles to Dock Square

Kennebunkport
The price is AU$800 per night from 23 Dec to 24 Dec
AU$800
includes taxes & fees
23 Dec - 24 Dec
A stay at this vacation home places you in the heart of Kennebunkport, steps from Kennebunkport Village Green and 5 minutes by foot from Mast Cove ...
Historic Kennebunkport home only 0.3 miles to Dock Square
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub

Spacious & Sunny 4 Bedroom Close to Downtown, hot tub

Portland
With a stay at this vacation home, you'll be centrally located in Portland, within a 10-minute drive of Maine Mall and Casco Bay.
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
7-bedroom home that sleeps 14.  5-minute walk to Moody Beach

7-bedroom home that sleeps 14. 5-minute walk to Moody Beach

Wells
With a stay at this vacation home in Wells, you'll be within a 15-minute drive of Ogunquit Beach and Perkins Cove.
7-bedroom home that sleeps 14. 5-minute walk to Moody Beach
Don't see what you're looking for?
See all available properties in Kennebunkport
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Kennebunkport Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Kennebunkport vacation homes are the perfect way for you to wing it.

Holiday houses in Kennebunkport let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Kennebunkport in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Kennebunkport adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Kennebunkport with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Kennebunkport vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Kennebunkport Holiday Homes essential information

Accommodation
933 Holiday Homes
Lowest Price
AU$250
Highest Price
AU$800
Popular accommodation
Gorgeous 6 Bedroom Ocean Front Home steps from Short Sands, Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough, Stille Wasser, Quiet, secluded spot on Saco River with Dock (Boat lift option), The Moonglow! A beautiful ocean view house in Biddeford!, Beach House ∆ Prime Location ∆ Steps to the Ocean, Amazing Beach House! 5 Bedroom across the Ocean!, Historic Kennebunkport home only 0.3 miles to Dock Square, Spacious & Sunny 4 Bedroom Close to Downtown, hot tub, 7-bedroom home that sleeps 14. 5-minute walk to Moody Beach

Top trending hotels in Kennebunkport

The Breakwater Inn and Spa

The Breakwater Inn and Spa

4.5 out of 5
127 Ocean Avenue, Kennebunkport, ME
The price is AU$250 per night from 1 Jan to 2 Jan
AU$250
includes taxes & fees
1 Jan - 2 Jan 2025
With a stay at The Breakwater Inn and Spa in Kennebunkport, you'll be by the ocean, just a 4-minute walk from Colony Beach and 7 minutes by foot from St. Ann’s ...
The Breakwater Inn and Spa
The Boathouse Waterfront Hotel & Marina

The Boathouse Waterfront Hotel & Marina

3 out of 5
21 Ocean Ave, Kennebunkport, ME
The price is AU$347 per night from 1 Jan to 2 Jan
AU$347
includes taxes & fees
1 Jan - 2 Jan 2025
When you stay at The Boathouse Waterfront Hotel & Marina in Kennebunkport, you'll be on the waterfront, just steps from Dock Square and 4 minutes by foot from ...
The Boathouse Waterfront Hotel & Marina
Kennebunkport Inn

Kennebunkport Inn

3 out of 5
One Dock Square, Kennebunkport, ME
The price is AU$311 per night from 5 Jan to 6 Jan
AU$311
includes taxes & fees
5 Jan - 6 Jan 2025
With a stay at Kennebunkport Inn, you'll be centrally located in Kennebunkport, steps from Dock Square and within a 5-minute walk of Kennebunkport Harbor.
Kennebunkport Inn
Save an average of 15% on thousands of hotels when you're signed in
Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
6 Pleasant Street, Kennebunkport, ME
The price is AU$364 per night from 5 Jan to 6 Jan
AU$364
includes taxes & fees
5 Jan - 6 Jan 2025
Located in Kennebunkport, Kennebunkport Captains Collection is by the ocean, within a 10-minute drive of Walker's Point and Mother's Beach.
Kennebunkport Captains Collection
Don't see what you're looking for?
See all available properties in Kennebunkport
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.