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Drakes Island Holiday Rentals

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Our top choices for Drakes Island holiday rentals

1. Elmwood Resort Hotel

Elmwood Resort Hotel
3.0 star property
Wells
9.4 out of 10, Exceptional, (469 reviews)
"Loved the pool, great atmosphere and check-in was so smooth and easy"
United States
Dawna
The price is NZ$321
includes taxes & fees
26 Oct - 27 Oct
Elmwood Resort Hotel

2. Village by the Sea

Village by the Sea
3.5 star property
Wells
9.0 out of 10, Wonderful, (561 reviews)
"Friendly staff,clean rooms will definitely book again"
United States
Dylan
The price is NZ$345
includes taxes & fees
20 Oct - 21 Oct
Village by the Sea

3. Coastal Condo with Pool at Wells Beach

Coastal Condo with Pool at Wells Beach
Wells Beach
10.0 out of 10, Exceptional, (6 reviews)
"Great space, clean and easy check in and out. Highly recommend!"
United States
Rachael B.
The price is NZ$810
includes taxes & fees
18 Oct - 19 Oct
Coastal Condo with Pool at Wells Beach

4. The Cottages at Cabot Cove

The Cottages at Cabot Cove
3.5 star property
Kennebunkport
9.6 out of 10, Exceptional, (50 reviews)
"Loved the accommodation and all the little touches such as a breakfast bag hung outside the cottage and evening treat each day. The owner checked us in and gave us some excellent ideas of things to do"
United Kingdom
patrick
The price is NZ$750
includes taxes & fees
18 Oct - 19 Oct
The Cottages at Cabot Cove

5. Generic Two Bedroom- Stair access only

Generic Two Bedroom- Stair access only
Wells
9.0 out of 10, Wonderful, (6 reviews)
"So much space and amenities for an incredible price. Nice and quiet, family friendly."
United States
Shawna B.
The price is NZ$400
includes taxes & fees
18 Oct - 19 Oct
Generic Two Bedroom- Stair access only

6. Studio condo with furnished patio, sauna, & pool - near beaches

Studio condo with furnished patio, sauna, & pool - near beaches
Wells
9.4 out of 10, Exceptional, (9 reviews)
"The place was small but highly effective to stay. Great little kitchen full of utensils, table to eat, light and air via windows, the bed was comfortable and so were the chairs. The bathroom had two sinks and a roomy shower. Parking was ample and location close to things. And if you have friends in the area, great place to invite over for a meal or to hang in the clubhouse for a game of billiards or a swim. Would definitely stay here again. The one downside was a musty smell, but that tends to...
United States
Scott F.
The price is NZ$662
includes taxes & fees
16 Oct - 17 Oct
Studio condo with furnished patio, sauna, & pool - near beaches

7. Pink Blossom Family Resort

Pink Blossom Family Resort
3.0 star property
Ogunquit
9.6 out of 10, Exceptional, (329 reviews)
"It was great and a great location."
United States
Robert
The price is NZ$272
includes taxes & fees
19 Oct - 20 Oct
Pink Blossom Family Resort

8. Salt Box by the Sea: Water View - Charming 3-bedroom Cottage in Wells!

Salt Box by the Sea: Water View - Charming 3-bedroom Cottage in Wells!
Wells
9.6 out of 10, Exceptional, (39 reviews)
The price is NZ$880
includes taxes & fees
9 Nov - 10 Nov
Salt Box by the Sea: Water View - Charming 3-bedroom Cottage in Wells!

9. The Apex at Moody: Beach, Hot Tub, Fireside Nights

The Apex at Moody: Beach, Hot Tub, Fireside Nights
Moody Beach
9.6 out of 10, Exceptional, (10 reviews)
"We absolutely loved this home! The beach front patio and beautiful interior was perfection. We loved every minute. What an amazing property! Highly recommend!"
United States
Kama C.
The Apex at Moody: Beach, Hot Tub, Fireside Nights

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

Cozy home 1mi. to beaches/shops/dining, Hot tub, big PATIO, Pvt yard, fire pit
Kennebunk
9.8 out of 10, Exceptional, (29 reviews)
The price is NZ$1,675
includes taxes & fees
18 Oct - 19 Oct
Cozy home 1mi. to beaches/shops/dining, Hot tub, big PATIO, Pvt yard, fire pit

11. Tiny home steps from the beach.

Tiny home steps from the beach.
Wells
9.6 out of 10, Exceptional, (56 reviews)
"It was nice staying at this peaceful small cabin on the beach. "
United States
christopher b.
The price is NZ$928
includes taxes & fees
22 Oct - 23 Oct
Tiny home steps from the beach.

12. Summer Village fully furnished 2 BR cottage, heated pools, wifi

Summer Village fully furnished 2 BR cottage, heated pools, wifi
Summer Village
The price is NZ$926
includes taxes & fees
18 Oct - 19 Oct
Summer Village fully furnished 2 BR cottage, heated pools, wifi

13. Kennebunk - Kennebunkport Beach House with Heated Swimming Pool!

Kennebunk - Kennebunkport Beach House with Heated Swimming Pool!
Kennebunk
9.4 out of 10, Exceptional, (69 reviews)
"The pool was great fun. We have dogs, and they loved the side yard...lots of room to run. They also had fun at the dog park. The house is perfectly situated; only minutes from beach, town, grocery stores and yet you feel like you're out in the country when you're inside or by the pool. Very quiet area. Had a wonderful time."
United States
Patricia M.
The price is NZ$1,479
includes taxes & fees
18 Oct - 19 Oct
Kennebunk - Kennebunkport Beach House with Heated Swimming Pool!

14. Charming Kennebunk Cape - Walk to Dock Square!

Charming Kennebunk Cape - Walk to Dock Square!
Kennebunk
9.8 out of 10, Exceptional, (43 reviews)
"Perfect location and the home was larger than expected! Plenty of space for several families, comfortable beds, extra (comfy) cots and everything you need for a great stay!"
United States
Hilary C.
The price is NZ$1,681
includes taxes & fees
26 Oct - 27 Oct
Charming Kennebunk Cape - Walk to Dock Square!

15. Chic cottage with pool and hot tub, mins to the beach!

Chic cottage with pool and hot tub, mins to the beach!
Wells
7.8 out of 10, Good, (17 reviews)
"Other than the dirty rugs and floors, it was nice!"
United States
Anonymous traveller
The price is NZ$567
includes taxes & fees
28 Oct - 29 Oct
Chic cottage with pool and hot tub, mins to the beach!

16. Ideal location close to Marginal Way/Perkins Cove

Ideal location close to Marginal Way/Perkins Cove
Oguquit
10.0 out of 10, Exceptional, (120 reviews)
"Amazing home in an amazing location!"
United States
Shannon H.
The price is NZ$1,948
includes taxes & fees
21 Oct - 22 Oct
Ideal location close to Marginal Way/Perkins Cove

17. Walk to Dock Square, 1.2 Mi to Gooch's Beach, Hot Tub -- Pine Tree Place

Walk to Dock Square, 1.2 Mi to Gooch's Beach, Hot Tub -- Pine Tree Place
Kennebunk
10.0 out of 10, Exceptional, (7 reviews)
"Very nice property - extremely neat, clean and comfortable. "
United States
Amy
The price is NZ$1,159
includes taxes & fees
19 Oct - 20 Oct
Walk to Dock Square, 1.2 Mi to Gooch's Beach, Hot Tub -- Pine Tree Place

18. Historic Kennebunkport home only 0.3 miles to Dock Square

Historic Kennebunkport home only 0.3 miles to Dock Square
Kennebunkport
10.0 out of 10, Exceptional, (95 reviews)
"Wonderful stay , pet friendly was a plus !! "
United States
Aimee S.
The price is NZ$1,081
includes taxes & fees
18 Oct - 19 Oct
Historic Kennebunkport home only 0.3 miles to Dock Square

19. Shamrock by the Sea Hot Tub Arcade Basketball Court & Beach Fun

Shamrock by the Sea Hot Tub Arcade Basketball Court & Beach Fun
Moody
10.0 out of 10, Exceptional, (18 reviews)
"The property is beautifully decorated, clean, well supplied & in excellent condition. The kids thoroughly enjoyed the game room & we all loved sitting around the fire pit & several used the hot tub. We definitely recommend Walking the Marginal Way, (the scenery is spectacular) & shopping in Ogunquit & Kennebunkport. It was an excellent choice for a family reunion!"
United States
Patricia A.
Shamrock by the Sea Hot Tub Arcade Basketball Court & Beach Fun

20. Seaside Serenity 2 Oceanfront Cottage with private beach Perkins Cove Ogunquit

Seaside Serenity 2 Oceanfront Cottage with private beach Perkins Cove Ogunquit
Ogunquit
10.0 out of 10, Exceptional, (7 reviews)
"The accommodations, views and overall experience was first rate. Would highly recommend staying at this beautiful property in Perkins Cove."
United States
John P.
The price is NZ$1,139
includes taxes & fees
26 Oct - 27 Oct
Seaside Serenity 2 Oceanfront Cottage with private beach Perkins Cove Ogunquit
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.
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Top Drakes Island Hotel Reviews

Find out more about Drakes Island

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Drakes Island holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Drakes Island. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Drakes Island. Seeing all the best attractions is bound to make you fall in love with Drakes Island. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Drakes Island short-term rentals, that won’t be hard to do.