Drakes Island holiday rentals

We found 1,288 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:13 Nov - 20 Nov

Living Area
Breakfast Bar
65 in. OLED with Cable
View of Living Area
Exceptional
(28 reviews)

Cozy home 1mi. to beaches/shops/dining, Hot tub, big PATIO, Pvt yard, fire pit

Kennebunk

8% off
AU$5,759
for 7 nights, 1 home
AU$823 per night
includes taxes & fees
Cozy home 1mi. to beaches/shops/dining, Hot tub, big PATIO, Pvt yard, fire pit
View from dining room.
Front of house facing the Beach and Ocean.
Dining table on left and bar overlooking the kitchen.
King Bedroom with ocean view.
Exceptional
(15 reviews)

Beach House On Private Moody Beach

Wells

9% off
AU$15,947
for 7 nights, 1 home
AU$2,278 per night
includes taxes & fees
Beach House On Private Moody Beach
Living area
Marina
Pool
Exterior
Exceptional
(17 reviews)

Seaglass Village Wells #426.Near Clubhouse. Same Time Next Year Promotion, NOW!

Wells

8% off
AU$5,118
for 7 nights, 1 cottage
AU$731 per night
includes taxes & fees
Seaglass Village Wells #426.Near Clubhouse. Same Time Next Year Promotion, NOW!
Private kitchen
Living area
Dining
Terrace/patio
Exceptional
(18 reviews)

Historic Charm & Modern Comfort, Beach Vacation Awaits.

Wells

8% off
AU$3,603
for 7 nights, 1 home
AU$515 per night
includes taxes & fees
Historic Charm & Modern Comfort, Beach Vacation Awaits.
Terrace/patio
Marina
Living area
Property grounds
Exceptional
(76 reviews)

Steps to Perkins Cove, Ogunquit, ME

Cape Neddick

8% off
AU$2,338
for 7 nights, 1 apartment
AU$334 per night
includes taxes & fees
Steps to Perkins Cove, Ogunquit, ME
Interior
Private kitchen
Exterior
Room
Exceptional
(20 reviews)

2 Bedroom Condo steps to beautiful Wells Beach!!!

Wells

8% off
AU$4,697
for 7 nights, 1 apartment
AU$671 per night
includes taxes & fees
2 Bedroom Condo steps to beautiful Wells Beach!!!
Sunset at the Marsh Connection
Property grounds
Fitness facility
Pool
Exceptional
(12 reviews)

Sunset Views over Rachel Carson Preserve. Relax steps from Wells Beach.

Wells

8% off
AU$5,631
for 7 nights, 1 home
AU$804 per night
includes taxes & fees
Sunset Views over Rachel Carson Preserve. Relax steps from Wells Beach.
Kitchen table, seats 8 comfortably.
Beautiful, large home with all the amenities you’ll need for your vacation.
Kitchen
Back deck with large table & gas as well as charcoal grills.
Exceptional
(35 reviews)

Spacious, Well-Appointed Home for Large Groups Close to Beaches and Restaurants!

Wells

8% off
AU$6,257
for 7 nights, 1 home
AU$894 per night
includes taxes & fees
Spacious, Well-Appointed Home for Large Groups Close to Beaches and Restaurants!
Back Deck with Grill
Perkins Cove
Private kitchen
Private kitchen
Exceptional
(45 reviews)

Located Steps From Perkins Cove, Enjoy Shopping, Dining, & Beach--Full A/C!

Ogunquit

8% off
AU$3,026
for 7 nights, 1 apartment
AU$432 per night
includes taxes & fees
Located Steps From Perkins Cove, Enjoy Shopping, Dining, & Beach--Full A/C!
Master Bedroom - 1 Queen Bed and 1 crib
Counter Seating
Sunset at Wells Beach
Living Area
Exceptional
(51 reviews)

Bright And Airy Renovated House 1 Block To Sandy Wells Beach

Wells

8% off
AU$5,572
for 7 nights, 1 home
AU$796 per night
includes taxes & fees
Bright And Airy Renovated House 1 Block To Sandy Wells Beach
House is a few hundred feet from this sign, up Frazier Pasture Road,
Perkins Cove
New front door with screen/storm door
Newly renovated with all new furnishings late May 2016
Exceptional
(116 reviews)

Ideal location close to Marginal Way/Perkins Cove

Ogunquit

8% off
AU$6,424
for 7 nights, 1 home
AU$918 per night
includes taxes & fees
Ideal location close to Marginal Way/Perkins Cove
House Driveway and Entrance
Partial Ocean Views from the living space.
Ocean view from the 2nd Floor Deck
Kitchen with counter bar seating in the Open Living Space.
Exceptional
(129 reviews)

Steps to Wells beach-3 BR, 2 Bath House - Ocean and Marsh Views!

Wells

8% off
AU$3,355
for 7 nights, 1 home
AU$479 per night
includes taxes & fees
Steps to Wells beach-3 BR, 2 Bath House - Ocean and Marsh Views!
Exterior
Marina
Interior
The deck with grill
Exceptional
(91 reviews)

Historic Kennebunkport home only 0.3 miles to Dock Square

Kennebunkport

8% off
AU$5,088
for 7 nights, 1 home
AU$727 per night
includes taxes & fees
Historic Kennebunkport home only 0.3 miles to Dock Square
come and relax
Interior
Private kitchen
This beach has the best waves to play in!
Wonderful
(12 reviews)

Romantic Oceanfront Cottage Get-Away Right on The Beach!!

Ogunquit

8% off
AU$6,097
for 7 nights, 1 apartment
AU$871 per night
includes taxes & fees
Romantic Oceanfront Cottage Get-Away Right on The Beach!!
Living area
Exterior
Property grounds
Exterior detail
Exceptional
(47 reviews)

The Farm Loft, on an organic farm - 10 min from beaches!

Kennebunkport

8% off
AU$1,766
for 7 nights, 1 apartment
AU$252 per night
includes taxes & fees
The Farm Loft, on an organic farm - 10 min from beaches!
Kennebunk
COMPASS POINTE ALONG THE OGUNQUIT RIVER
Living area
Interior
Exceptional
(51 reviews)

"NOT YOUR AVERAGE BEACH HOUSE" walk to Moody Beach to Footbridge ,distance Views

Wells

8% off
AU$3,566
for 7 nights, 1 apartment
AU$509 per night
includes taxes & fees
"NOT YOUR AVERAGE BEACH HOUSE" walk to Moody Beach to Footbridge ,distance Views
Private kitchen
Property grounds
Interior
Private kitchen
Exceptional
(154 reviews)

Fantastic Beach House! 4 bedroom across the Ocean.

Wells

7% off
AU$3,394
for 7 nights, 1 home
AU$485 per night
includes taxes & fees
Fantastic Beach House! 4 bedroom across the Ocean.
Bar Area and Formal Living Room
Exterior
Second Living Room - First Floor
Chef's Kitchen
Exceptional
(152 reviews)

Spectacular Oceanfront Beach House on Gooch's Beach

Kennebunk

8% off
AU$7,781
for 7 nights, 1 home
AU$1,112 per night
includes taxes & fees
Spectacular Oceanfront Beach House on Gooch's Beach
Another beautiful sunset at Moody Beach
Bedroom
Sunrise in Wells
Kitchen and 1/2 Bath
Exceptional
(137 reviews)

Surfers, Cyclists, Paddleboarders, Kayakers! Close to everything in town

Wells

20% off
AU$1,369
for 7 nights, 1 apartment
AU$196 per night
includes taxes & fees
Surfers, Cyclists, Paddleboarders, Kayakers! Close to everything in town
Living area
Terrace/patio
Dining
Exterior
Exceptional
(25 reviews)

A Modern Antique Home - steps to Dock Square and harbor

Kennebunkport

8% off
AU$10,697
for 7 nights, 1 home
AU$1,528 per night
includes taxes & fees
A Modern Antique Home - steps to Dock Square and harbor
Fully stocked kitchen.
Plenty of room for relaxing.
Open kitchen/dining with French doors out to the deck.
Views of Cape Arundel Golf Course and established gardens.
Exceptional
(29 reviews)

Kennebunkport Beauty!!

Kennebunkport

8% off
AU$4,229
for 7 nights, 1 apartment
AU$604 per night
includes taxes & fees
Kennebunkport Beauty!!
Exterior
Property grounds
Private kitchen
Property grounds
Exceptional
(65 reviews)

Cozy condo with harbor views. Walk to Dock Square and Beach.

Kennebunk

8% off
AU$2,977
for 7 nights, 1 apartment
AU$425 per night
includes taxes & fees
Cozy condo with harbor views. Walk to Dock Square and Beach.
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    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Book a holiday rental for your Drakes Island getaway

Learn about the unique charm of Drakes Island with a stay in a holiday home rental. This city has something for everyone. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in Drakes Island

Are you looking for attractions to see while you're in the area? Venture out of your cosy holiday rental and experience everything that makes Drakes Island a one-of-a-kind holiday spot. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Old Orchard Beach Parasail (12.9 mi / 20.7 km)
  • Funtown Splashtown USA (15.3 mi / 24.6 km)
  • Pirate's Cove (15.6 mi / 25.1 km)
  • Wonder Mountain Fun Park (3.8 mi / 6.1 km)
  • Old Marsh Country Club (3.9 mi / 6.2 km)
  • Cape Arundel Golf Club (5.1 mi / 8.1 km)

Exploring the natural features in Drakes Island

Whether you're an outdoor enthusiast or just want to take in the scenery, Drakes Island is a great place to spend some time outside. Here are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Ogunquit Beach (5.6 mi / 9 km)
  • Wells Beach (1.3 mi / 2 km)
  • Rachel Carson National Wildlife Refuge (1.5 mi / 2.5 km)
  • Kennebunk Beach (2.8 mi / 4.5 km)
  • Mother's Beach (3 mi / 4.8 km)
  • Moody Beach (3.7 mi / 5.9 km)

More holiday ideas