Holiday rentals near Drakes Island
We found 1,260 holiday rentals — enter your dates for availability
If you'd like to stay close to Drakes Island, take a look at holiday rentals to find the perfect one for your trip. Whether you’re staying in a holiday home with your children or with friends, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a garden. At the end of the day, you'll be able to choose a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Drakes Island
Showing deals for:21 Nov - 28 Nov
Image gallery for Kennebunk/Kennebunkport Beach House with Swimming Pool!
9.49.4 out of 10 rating
Exceptional
(56 reviews)
Kennebunk/Kennebunkport Beach House with Swimming Pool!
Kennebunk, ME
8% off
Price is AU$7,066
AU$7,066
AU$1,009 per night
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
8% off
Price is AU$5,505
AU$5,505
AU$786 per night
includes taxes & fees
Image gallery for Kennebunk 5 Bedroom 3.5 Bathroom Cottage and Bunkhouse— Walk to Beach and Town!
1010 out of 10 rating
Exceptional
(9 reviews)
Kennebunk 5 Bedroom 3.5 Bathroom Cottage and Bunkhouse— Walk to Beach and Town!
Kennebunk, ME
8% off
Price is AU$15,120
AU$15,120
AU$2,160 per night
includes taxes & fees
Image gallery for Beautiful, Oceanfront Home, Perfect Location near Downtown KPT!
9.89.8 out of 10 rating
Exceptional
(8 reviews)
Beautiful, Oceanfront Home, Perfect Location near Downtown KPT!
Kennebunk, ME
8% off
Price is AU$12,538
AU$12,538
AU$1,791 per night
includes taxes & fees
Image gallery for Kennebunk's Charming Beach Home
9.89.8 out of 10 rating
Exceptional
(16 reviews)
Kennebunk's Charming Beach Home
Kennebunk, ME
8% off
Price is AU$6,200
AU$6,200
AU$886 per night
includes taxes & fees
Image gallery for If you want privacy, look no further!
1010 out of 10 rating
Exceptional
(40 reviews)
If you want privacy, look no further!
Kennebunkport, ME
8% off
Price is AU$4,755
AU$4,755
AU$679 per night
includes taxes & fees
Image gallery for Spacious Beach Villa - Ocean Views - 3 Minute Walk to Shore - Available All Year
9.69.6 out of 10 rating
Exceptional
(57 reviews)
Spacious Beach Villa - Ocean Views - 3 Minute Walk to Shore - Available All Year
Wells, ME
8% off
Price is AU$10,885
AU$10,885
AU$1,555 per night
includes taxes & fees
Image gallery for In-Town Kennebunk - walk to mult cafes/restaurants/shops! Beaches 6 mins away!
1010 out of 10 rating
Exceptional
(22 reviews)
In-Town Kennebunk - walk to mult cafes/restaurants/shops! Beaches 6 mins away!
Kennebunk, ME
8% off
Price is AU$3,742
AU$3,742
AU$535 per night
includes taxes & fees
Image gallery for Salty but Sweet - 3 min walk to Beach - Newly Renovated - Video!
9.89.8 out of 10 rating
Exceptional
(18 reviews)
Salty but Sweet - 3 min walk to Beach - Newly Renovated - Video!
Wells, ME
8% off
Price is AU$8,534
AU$8,534
AU$1,219 per night
includes taxes & fees
Image gallery for Ocean Views & Just Steps to Beach!
9.69.6 out of 10 rating
Exceptional
(47 reviews)
Ocean Views & Just Steps to Beach!
Kennebunk, ME
8% off
Price is AU$9,645
AU$9,645
AU$1,378 per night
includes taxes & fees
Image gallery for Beautiful Family Beach House, just a few short steps to Wells Beach!
1010 out of 10 rating
Exceptional
(33 reviews)
Beautiful Family Beach House, just a few short steps to Wells Beach!
Wells, ME
16% off
Price is AU$7,782
AU$7,782
AU$1,112 per night
includes taxes & fees
Image gallery for This sweet, cozy, and relaxing beach cottage is ready for you in 2024! Sleeps 6!
9.89.8 out of 10 rating
Exceptional
(16 reviews)
This sweet, cozy, and relaxing beach cottage is ready for you in 2024! Sleeps 6!
Wells, ME
8% off
Price is AU$3,120
AU$3,120
AU$446 per night
includes taxes & fees
Image gallery for WELLS BEACH HOUSE: "THE GULL"
8.68.6 out of 10 rating
Excellent
(27 reviews)
WELLS BEACH HOUSE: "THE GULL"
Wells, ME
8% off
Price is AU$6,090
AU$6,090
AU$870 per night
includes taxes & fees
Image gallery for Historic Charm & Modern Comfort, Beach Vacation Awaits.
1010 out of 10 rating
Exceptional
(10 reviews)
Historic Charm & Modern Comfort, Beach Vacation Awaits.
Wells, ME
8% off
Price is AU$4,243
AU$4,243
AU$606 per night
includes taxes & fees
Image gallery for Modern Victorian House with Beautiful Pool in the Heart of Ogunquit
9.89.8 out of 10 rating
Exceptional
(49 reviews)
Modern Victorian House with Beautiful Pool in the Heart of Ogunquit
Ogunquit, ME
8% off
Price is AU$9,927
AU$9,927
AU$1,418 per night
includes taxes & fees
Image gallery for Winter Renovation for 2025 Waterfront The Heart Of Kennebunkport Dock Square!
1010 out of 10 rating
Exceptional
(31 reviews)
Winter Renovation for 2025 Waterfront The Heart Of Kennebunkport Dock Square!
Kennebunkport, ME
8% off
Price is AU$13,099
AU$13,099
AU$1,871 per night
includes taxes & fees
Image gallery for Seabreeze Cottage, steps to Kennebunk's Beaches
9.89.8 out of 10 rating
Exceptional
(30 reviews)
Seabreeze Cottage, steps to Kennebunk's Beaches
Kennebunk, ME
8% off
Price is AU$5,555
AU$5,555
AU$794 per night
includes taxes & fees
Image gallery for Brand New Build 4 bed/2 bath w/private beach access-On Atlantic Ave!
8.28.2 out of 10 rating
Very good
(31 reviews)
Brand New Build 4 bed/2 bath w/private beach access-On Atlantic Ave!
Wells, ME
8% off
Price is AU$6,425
AU$6,425
AU$918 per night
includes taxes & fees
Image gallery for Large Ocean View House Steps to Beach w/Amenities Galore!
1010 out of 10 rating
Exceptional
(13 reviews)
Large Ocean View House Steps to Beach w/Amenities Galore!
Wells, ME
8% off
Price is AU$6,793
AU$6,793
AU$970 per night
includes taxes & fees
Image gallery for Perfect Maine Getaway – Walk to Downtown, Cozy for All - Flexible Cancellation.
1010 out of 10 rating
Exceptional
(72 reviews)
Perfect Maine Getaway – Walk to Downtown, Cozy for All - Flexible Cancellation.
Kennebunk, ME
8% off
Price is AU$5,865
AU$5,865
AU$838 per night
includes taxes & fees
Image gallery for Updated and charming Vacationland home less than a mile to Wells beaches!
1010 out of 10 rating
Exceptional
(7 reviews)
Updated and charming Vacationland home less than a mile to Wells beaches!
Wells, ME
8% off
Price is AU$3,666
AU$3,666
AU$524 per night
includes taxes & fees
Image gallery for Historic Kennebunkport home only 0.3 miles to Dock Square
1010 out of 10 rating
Exceptional
(72 reviews)
Historic Kennebunkport home only 0.3 miles to Dock Square
Kennebunkport, ME
8% off
Price is AU$5,037
AU$5,037
AU$720 per night
includes taxes & fees
Image gallery for Updated 5 Bedroom, 3.5 Bathroom, Walk to Dock Square & 3/4 mile to Goochs Beach!
1010 out of 10 rating
Exceptional
(16 reviews)
Updated 5 Bedroom, 3.5 Bathroom, Walk to Dock Square & 3/4 mile to Goochs Beach!
Kennebunk, ME
13% off
Price is AU$10,431
AU$10,431
AU$1,490 per night
includes taxes & fees
Image gallery for Great Spot! Moody Beach, PRIVATE BEACH!!
1010 out of 10 rating
Exceptional
(65 reviews)
Great Spot! Moody Beach, PRIVATE BEACH!!
Wells, ME
8% off
Price is AU$3,834
AU$3,834
AU$548 per night
includes taxes & fees
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Find the best place to stay - Drakes Island
Drakes Island Beach Front Breathtaking Property : Oceanviews and Sandy Beach !
Sleeps 15 · 5 bedrooms · 4 bathrooms
1010 out of 10
Exceptionalexceptional
46 reviews(46 reviews)
Private Beach House - Steps from Drakes Island Beach!
Sleeps 8 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
26 reviews(26 reviews)
Drakes Island-Renovated!-tidal water views!
Sleeps 10 · 5 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
18 reviews(18 reviews)
Relax in this comfy Log Cabin after your short walk back from the beach
Sleeps 10 · 4 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
7 reviews(7 reviews)
Drakes Island Oceanfront 6 Bedroom/3 Bath DISCOUNT for October dates
Sleeps 12 · 6 bedrooms · 3 bathrooms
Beachfront Drakes Island Cottage
Sleeps 10 · 5 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
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, gardens and more
More for lessMore space, more privacy, more amenities — more value