Drakes Island holiday rentals

We found 1,274 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:25 Dec - 1 Jan

Kitchen
Beautiful, large home with all the amenities you’ll need for your vacation.
Back deck with large table & gas as well as charcoal grills.
Kitchen table, seats 8 comfortably.
Exceptional
(36 reviews)

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

Wells

8% off
AU$8,619
for 7 nights, 1 home
AU$1,231 per night
includes taxes & fees
Spacious, Well-Appointed Home for Large Groups Close to Beaches and Restaurants!
Sunset at the Marsh Connection
Property grounds
Pool
Dining
Exceptional
(13 reviews)

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

Wells

8% off
AU$5,776
for 7 nights, 1 home
AU$825 per night
includes taxes & fees
Sunset Views over Rachel Carson Preserve. Relax steps from Wells Beach.
Living Area
Counter Seating
Sunset at Wells Beach
Dining Area
Exceptional
(54 reviews)

Bright And Airy Renovated House 1 Block To Sandy Wells Beach

Wells

8% off
AU$5,716
for 7 nights, 1 home
AU$817 per night
includes taxes & fees
Bright And Airy Renovated House 1 Block To Sandy Wells Beach
Interior
Private kitchen
Room
Living area
Exceptional
(20 reviews)

2 Bedroom Condo steps to beautiful Wells Beach!!!

Wells

8% off
AU$4,819
for 7 nights, 1 apartment
AU$688 per night
includes taxes & fees
2 Bedroom Condo steps to beautiful Wells Beach!!!
Living area
Dining
Exterior
Outdoor dining
Exceptional
(5 reviews)

Spacious 6 BR Condo – Ten minutes to the beaches

Kennebunk

8% off
AU$10,160
for 7 nights, 1 apartment
AU$1,451 per night
includes taxes & fees
Spacious 6 BR Condo – Ten minutes to the beaches
Kitchen with counter bar seating in the Open Living Space.
Partial Ocean Views from the living space.
House Driveway and Entrance
Ocean view from the 2nd Floor Deck
Exceptional
(134 reviews)

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

Wells

8% off
AU$3,443
for 7 nights, 1 home
AU$492 per night
includes taxes & fees
Steps to Wells beach-3 BR, 2 Bath House - Ocean and Marsh Views!
Dining
Living area
Private kitchen
Terrace/patio
Exceptional
(19 reviews)

Historic Charm & Modern Comfort, Beach Vacation Awaits.

Wells

8% off
AU$3,818
for 7 nights, 1 home
AU$545 per night
includes taxes & fees
Historic Charm & Modern Comfort, Beach Vacation Awaits.
Exterior
Interior
Exterior detail
Swanky ! Great Porch for People Watching!
Exceptional
(11 reviews)

Swanky Flat in the Heart of Dock Square, SUPER CLEAN! WALK TO EVERYTHING!

Kennebunk

8% off
AU$5,873
for 7 nights, 1 home
AU$839 per night
includes taxes & fees
Swanky Flat in the Heart of Dock Square, SUPER CLEAN! WALK TO EVERYTHING!
This beach has the best waves to play in!
Interior
Private kitchen
view from inside cottage
Wonderful
(12 reviews)

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

Ogunquit

8% off
AU$6,132
for 7 nights, 1 apartment
AU$876 per night
includes taxes & fees
Romantic Oceanfront Cottage Get-Away Right on The Beach!!
Property grounds
Marina
Beach
Terrace/patio
Exceptional
(84 reviews)

Steps to Perkins Cove, Ogunquit, ME

Cape Neddick

8% off
AU$2,351
for 7 nights, 1 apartment
AU$336 per night
includes taxes & fees
Steps to Perkins Cove, Ogunquit, ME
Private kitchen
Perkins Cove
The Famous Ogunquit Playhouse
Private kitchen
Exceptional
(46 reviews)

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

Ogunquit

8% off
AU$3,389
for 7 nights, 1 apartment
AU$484 per night
includes taxes & fees
Located Steps From Perkins Cove, Enjoy Shopping, Dining, & Beach--Full A/C!
Open kitchen/dining with French doors out to the deck.
Plenty of room for relaxing.
Plenty of beautiful views.
Fully stocked kitchen.
Exceptional
(31 reviews)

Kennebunkport Beauty!!

Kennebunkport

8% off
AU$4,254
for 7 nights, 1 apartment
AU$608 per night
includes taxes & fees
Kennebunkport Beauty!!
Living area
COMPASS POINTE ALONG THE OGUNQUIT RIVER
Kennebunk
Living area
Exceptional
(53 reviews)

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

Wells

8% off
AU$3,587
for 7 nights, 1 apartment
AU$512 per night
includes taxes & fees
"NOT YOUR AVERAGE BEACH HOUSE" walk to Moody Beach to Footbridge ,distance Views
Living area
Marina
Property grounds
Exterior
Exceptional
(19 reviews)

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

Wells

8% off
AU$5,148
for 7 nights, 1 cottage
AU$735 per night
includes taxes & fees
Seaglass Village Wells #426.Near Clubhouse. Same Time Next Year Promotion, NOW!
Exterior detail
Exterior
Living area
Interior
Exceptional
(48 reviews)

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

Kennebunkport

8% off
AU$2,033
for 7 nights, 1 apartment
AU$290 per night
includes taxes & fees
The Farm Loft, on an organic farm - 10 min from beaches!
Private kitchen
Interior
Our Best Loft!
Room
Exceptional
(5 reviews)

Coastal Elegance in Historic Dock Sq Breath Again

Kennebunk

8% off
AU$5,672
for 7 nights, 1 apartment
AU$810 per night
includes taxes & fees
Coastal Elegance in Historic Dock Sq Breath Again
The deck with grill
Marina
Room
Interior
Exceptional
(94 reviews)

Historic Kennebunkport home only 0.3 miles to Dock Square

Kennebunkport

8% off
AU$5,647
for 7 nights, 1 home
AU$807 per night
includes taxes & fees
Historic Kennebunkport home only 0.3 miles to Dock Square
Kitchen!
Exterior
Living area
Have your meals and snacks while looking out at the salt marsh and ocean!
Exceptional
(13 reviews)

Ocean View Dog Friendly Cottage 4-min to Kennebunkport

Kennebunk

8% off
AU$3,099
for 7 nights, 1 home
AU$443 per night
includes taxes & fees
Ocean View Dog Friendly Cottage 4-min to Kennebunkport
Table seats 12.
Perkins Cove
New front door with screen/storm door
Newly renovated with all new furnishings late May 2016
Exceptional
(117 reviews)

Ideal location close to Marginal Way/Perkins Cove

Ogunquit

8% off
AU$9,121
for 7 nights, 1 home
AU$1,303 per night
includes taxes & fees
Ideal location close to Marginal Way/Perkins Cove
Exterior
Property grounds
Living area
Private kitchen
Exceptional
(70 reviews)

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

Kennebunk

7% off
AU$2,486
for 7 nights, 1 apartment
AU$355 per night
includes taxes & fees
Cozy condo with harbor views. Walk to Dock Square and Beach.
Interior
Exterior
Room
Interior
Exceptional
(14 reviews)

One Minute Walk to Dock Square! Better than a hotel room!!

Kennebunk

8% off
AU$4,038
for 7 nights, 1 apartment
AU$577 per night
includes taxes & fees
One Minute Walk to Dock Square! Better than a hotel room!!

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    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:

  • Funtown Splashtown USA (15.3 mi / 24.6 km)
  • Pirate's Cove (15.6 mi / 25.1 km)
  • Dunegrass Golf Club (15.9 mi / 25.6 km)
  • Old Orchard Beach Parasail (12.9 mi / 20.7 km)
  • The Links at Outlook (13.5 mi / 21.8 km)
  • York Golf and Tennis Club (14 mi / 22.5 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:

  • 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)
  • Gooch's Beach (3.9 mi / 6.3 km)

Frequently asked questions

What are the best holiday rentals near Drakes Island?
The best holiday rentals near Drakes Island are primarily located along the coastline of Wells, Maine, offering convenient access to the island and its surroundings. You will find a wide array of private holiday houses and charming cottages, many with direct beach access or scenic views of the ocean. If you are willing to drive a bit further, renting in nearby areas can be an affordable option for finding larger properties. These best holiday rentals near Drakes Island are superb for experiencing the coastal charm.Many of these properties offer desirable amenities such as a deck or patio for outdoor enjoyment, and laundry facilities for a comfortable stay. This area is ideal for families and guests who enjoy beach activities and the convenience of having home comforts during their stay.
Are there any cheap holiday rentals near Drakes Island?
There are several affordable holiday rentals near Drakes Island, especially if you are flexible with location and travel dates. Budget-friendly stays are typically around AU$300 per night. Some stays even drop below this price in February and March during the early spring, making it a great option for guests looking to experience the area without overspending. These rentals often include amenities such as WiFi, toiletries, and self-parking, and can range from cosy cottages to modest private homes, providing a clean, comfortable base for adventure.To get the best value, consider staying slightly outside major hubs. If you're willing to drive a bit further, renting around nearby areas can be an affordable option. With a little planning, it is absolutely possible to find a comfortable stay near Drakes Island while keeping costs down.*Pricing data are based on past 12 months data.
What are the best pet-friendly holiday rentals near Drakes Island?
There are over 90 pet-friendly holiday rentals near Drakes Island, primarily private holiday houses and cottages in the surrounding areas. These properties often feature private outdoor spaces, ensuring your pet has room to roam, alongside essential comforts like fully equipped kitchens and comfortable living areas for guests. Many specifically welcome dogs and cats, making it easy to find a suitable stay for your companions.When searching for the best pet-friendly holiday rentals near Drakes Island, always verify the specific house rules regarding pet size or breed restrictions, and any additional fees. Drakes Island itself is very accommodating, offering pet-friendly beaches and open green areas where pets can enjoy the outdoors.
What are the top holiday rentals with pools near Drakes Island?
There are approximately 180 holiday rentals with pools near Drakes Island, offering a variety of options including private, shared, outdoor, and indoor pools. Many of these properties are cottages and condos, frequently found in areas close to the coast and within Wells. Guests can expect homes equipped with standard amenities such as full kitchens, Wi-Fi, and comfortable living spaces, making them suitable for families or groups seeking a relaxing stay.When selecting your ideal property, consider whether a private pool for seclusion or a shared pool with potential access to other facilities like hot tubs better suits your needs. For stays during cooler months, properties with heated or indoor pools are excellent choices.
What are the best family holiday rentals near Drakes Island?
There are over 347 family-friendly holiday homes available near Drakes Island, predominantly private holiday houses and charming cottages. These properties offer ample space with multiple bedrooms and bathrooms, ideal for groups. Families will particularly appreciate the inclusion of full kitchens for preparing meals, outdoor play areas like yards and gardens, and amenities such as highchairs and cribs for younger children. Many homes also feature patios and various games or books for entertainment.When selecting your family's ideal home, consider properties that offer distinct sleeping areas for adults and children, and look for those with practical features such as laundry facilities, which are invaluable during a longer stay. Staying close to Drakes Island means less travel time and more opportunities to enjoy the area's attractions.
Are there any luxury holiday rentals near Drakes Island?
Near Drakes Island, guests can find several luxury holiday rentals that offer natural scenery and modern comfort. These properties often feature amenities such as heated private pools, deep soaking bathtubs, and the option of a private chef, alongside various views.These homes are ideal for families or larger groups, providing conveniences like air conditioning and entertainment options. Many of these top-tier stays are managed by highly rated Stayz hosts, ensuring a professional and premium experience.
How much is a holiday rental near Drakes Island?
Holiday rentals near Drakes Island offer a wide range of options to suit different budgets, making it easy for guests to enjoy a memorable stay. Budget-friendly properties, such as simple apartments, typically start around AU$300 per night, providing an affordable way to experience the area. Mid-range rentals, including private homes with standard amenities, are generally around AU$605 per night, offering more comfort and privacy. For those seeking a more luxurious experience, upscale options can cost AU$955 or more per night, especially during the busy summer months.Enter your destination, travel dates, and number of guests on search to see the best options. You can use filters to set a minimum and maximum nightly price range along with other preferences. Rates may vary based on the season and specific amenities, but with a little planning, guests can find a rental that perfectly balances convenience and value.*Pricing data are based on past 12 months data.
Where should I stay when visiting Drakes Island?
When visiting Drakes Island, several areas offer excellent holiday rental options. The Wells Beach area is a popular choice, providing easy access to the sandy shores and the natural beauty of the coastline. Properties here are well-suited for those who enjoy beach activities and scenic walks.Alternatively, the Moody Beach area, just north of Wells Beach, offers a slightly more secluded experience with private beach access opportunities. These rentals are a short drive from Drakes Island, providing a tranquil base whilst still being close to local attractions.For a more central location with a wider array of dining and shopping, the main Wells area, slightly inland, features various homes and apartments. These properties are a convenient drive from Drakes Island, allowing guests to explore the broader region with ease.
What is the cheapest month to stay near Drakes Island?
The cheapest time to find holiday rentals near Drakes Island is typically during the late Winter to early Spring (February to March), excluding any major local festivals or school holidays that might occur. March is frequently the cheapest month, often providing lower rates on properties compared to the peak summer season. Guests can often find better deals and more availability during these months.
Are there any top beachfront holiday rentals near Drakes Island
Beachfront holiday rentals near Drakes Island are primarily found along the coastal stretches of Wells Beach and Drakes Island Road, offering guests direct access to the sand and breathtaking ocean views. These properties allow for easy strolls along the shore, with many offering ocean-view balconies. While the immediate area around Drakes Island offers a more relaxed environment, a short drive connects guests to the lively dining, nightlife, and shopping options in Wells and Ogunquit.Guests can often enjoy amenities such as beach chairs, beach towels, and private walkways to the water. Accommodation types range from charming cottages to multi-bedroom private homes, many featuring ocean-facing rooms and additional living space, ideal for families or groups.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Stayz customer service and Stayz™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare customer service is available 24/7 to support you every step of the way.Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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