Holiday rentals in Drakes Island

4.99 out of 5 average rating, 148 reviews

Flat in Kennebunk

Birch Sea

This new, very private apartment attached to our home is in a quiet and picturesque environment minutes away from Dock Square. It's great for couples, solo adventurers and families with one child. If you are seeking to spend the day at one of the beautiful Kennebunk beaches they are just minutes away. We are committed to environmental sustainability and the apartment is powered by solar energy. A new outdoor hot tub was recently installed in February, 2024! We look forward to your visit!

5 out of 5 average rating, 8 reviews

Everything's "Well Ashore"- 1 mile to Wells Beach!

Welcome to 'Well Ashore', a charming 1-bedroom, 1-bathroom condo just 1 mile from the breathtaking Wells Beach- One of Maine's 7 -mile pristine sandy beaches. Ideal for couples or small families, this cozy retreat features a serene, nautical-inspired ambiance perfect for relaxation. Our condo is 4 miles from The Marginal Way, one of New England's most cherished coastal walks. This 1.25 mile scenic path offers stunning ocean views, plentiful benches, and an easy access to downtown Ogunquit.

4.92 out of 5 average rating, 108 reviews

Boho Farmhouse by the Fields

Your Maine Boho Farmhouse awaits you! You’ll be tucked into the farm fields of Wells and just four miles to Drakes Island Beach. You’ll have everything you need and more at this coastal oasis. 7 miles to Wells Beach 7 miles to Kennebunk Beach 8 miles to Kennebunkport 10 miles to Ogunquit Beach Grocery stores within 4 miles: Spillers Farm Store, Wells IGA, Wells Hannaford Emergency Walk In: 2.5 miles 2 miles to closest gas station 5 miles to Wells Police Station/Wells Fire Department

Superhost

Apartment in Wells

4.76 out of 5 average rating, 134 reviews

Generic Two Bedroom - Stair access only

Our two-bedroom units are located on the first, second or third floor in our all-stair property. All of our two-bedroom units have two bedrooms, with a varying number of beds, two bathrooms, full kitchen, living room, dining room and patio/balcony. They have a washer and dryer too! All kitchens come equipped with standard dishes, baking and cooking supplies, as well as full size appliances! Best for larger families to spread out! Room requests are accepted but not guaranteed.

5 out of 5 average rating, 206 reviews

Cabin in South Berwick

Romantic A-Frame cabin in the woods

Modern cabin tucked privately in the forest. Loaded with modern amenities make it perfect for a romantic getaway. Unwind in the hot tub looking up at the sky full of stars. Take a Sauna while being surrounded by nature all around. Relax by the fire pit. Located in the majestic forest of mount agamenticus, the extensive trail system is off our road. Short drive to the Ogunquit/ york beaches, outlets at Kittery and near Portsmouth, Dover and Portland restaurant scenes.

5 out of 5 average rating, 8 reviews

Historic Charm & Modern Comfort, Beach Vaca awaits

This captivating 3-bedroom retreat, lovingly restored, offers the perfect blend of yesteryear's warmth and today's conveniences. Ideally located near Drake's Island (1.6 mi) and Wells Beach (2.9 mi), it's the perfect getaway for families up to 7. The master suite features a king & ensuite BR. The second room offers a queen, & the 3rd room a bunk bed provides sleeping for 3. This unique vacation rental promises an unforgettable stay in beautiful Wells, ME!

4.99 out of 5 average rating, 155 reviews

Charming Wells Bunkhouse near Drakes Island Beach

This 675 sq ft bunkhouse is the perfect spot for your next beach stay! Situated on an oversized lot with plenty of parking, outdoor grill, and outdoor furniture. It has been designed and decorated with loads of Maine charm. It boasts a full kitchen, smart tv with cable and WiFi. Keyless entry will allow you to check yourself in, at your own convenience. Let me know if you need beach chairs or a cooler to complete your trip!

4.97 out of 5 average rating, 175 reviews

Bright 1 Bd w/full kitchen, quick drive to beaches

Located in the peaceful coastal town of Wells, this private suite is the perfect place to come home to after embracing all the amenities of nearby beaches, restaurants, and shops in the charming towns of Wells, Kennebunk, Kennebunkport, and Ogunquit. Sleep in comfort in your spacious king bed, enjoy a home-cooked meal in your full-sized kitchen, and relax while listening to the birds on your private deck that overlooks the garden.

4.93 out of 5 average rating, 263 reviews

Guest house in Kennebunk

Intimate Ocean View Cottage Near the Mousam River

A newly renovated 700+ sqft one-bedroom, two story cottage, with a beautiful ocean view, is less than one mile from Parson’s Beach. The Mousam River access is less than ¼ of a mile away. A cozy Maine living space with a private backyard and fire pit for your enjoyment. Interested in biking or walking trails? We are less than 500' to the bridal path that can take you to nearby Mother’s Beach or into downtown Kennebunk.

4.87 out of 5 average rating, 119 reviews

Drakes Island Beach Front Breathtaking Property !

Ocean views from Kennebunkport to Cape Neddick and a gorgeous half mile sandy beach right outside your door! Watch the sunrise and the sunset over the sandy Drakes Island shores. Enjoy daily walks on the beach or take a walk on the peaceful trails nearby alongside the Rachel Carson Wildlife Refuge & Laudholm Farm, and go to town for restaurants, arcades and more fun. It doesn’t get better than this !

4.97 out of 5 average rating, 139 reviews

Cabin in Kennebunk

HotTub/5min to K-port, Pet friendly, @anchorunwind

Follow us on IG @anchorunwind. Escape to a hidden gem nestled in the heart of the Kennebunkport area, where modern comfort meets nature's serenity. Our cabin offers an unforgettable vacation experience. ✭"...A must stay location. The host’s were very helpful and genuine..." ✭"...We’ve travelled all around the world and this is in our top 3 Airbnbs we’ve stayed in."

4.9 out of 5 average rating, 51 reviews

Cozy Coastal Hideaway Near Beaches

Welcome to Cercana Hideaway! Escape to this newly refreshed studio! Centrally located to beaches, nightlife, dining, antique shops, and nature trails - our studio is the perfect home base to your Maine adventure! Dog friendly with prior permission. - Under 2 miles to Drakes Island Beach - Under 3 miles to Wells Beach - Under 6 miles to Kennebunkport or Ogunquit

Holiday rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Hotels

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Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Drakes Island holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Drakes Island

4.81 out of 5 average rating, 93 reviews

Private home on the beach with 360 degree views!

Anne-MarieRating, 5 stars8 months ago

Overall, the Crab House was a great place to spend our week-long vacation. You can't beat the location. It's right on the beach with beautiful views of - and easy access to - the ocean. The house is VERY clean and has a lovely, fresh smell to it. I'm very particular when it comes to cleanliness and often have to spend the first day of our vacations cleaning our rental. But not here!! It's nice and well-appointed, but comfortable/modest enough where I wouldn't have worried about having my grandchildren there. One thing that wasn't problematic for us, but might be for others: The master bedroom suite/top level is visually private, but doesn't have a door to it. So, you can hear everyone on the main level (and they can hear you). It also results in the master bedroom being warmer than the other levels. Our friends staying in the lower-level bedroom were cold and wanted the heat on, but that prevented us from using the A/C. Opening the master suite windows fixed that problem for us.

5 out of 5 average rating, 7 reviews

Guest house in Wells

Dream Catcher at the beach

EricRating, 5 stars7 months ago

We really enjoyed staying at Shelli's Dream Catcher guesthouse. Access to a beautiful beach almost directly across the street, and great views of the marsh directly out of the back windows. The place was clean and well laid out. Shelli was responsive and gave us an unexpected early check-in. Sunsets and sunrises were awesome. We stayed in late October, so I believe some of the restaurants within walking distance were closed at this point. Still, it's a great location in Wells, and only a short drive from area restaurants, shopping and other locations. We would recommend Dream Catcher at the Beach!

Superhost

Cottage in Wells

5 out of 5 average rating, 20 reviews

Cottage Nine, 84 Drakes Island Road, Wells

NancyRating, 5 stars10 months ago

Loved staying at cottage in the lane. It’s a beautifully kept spot. Very homey feeling, wonderful atmosphere. In Maine, everything stays wet so having a laundry center is a bonus. Great pool. Just fabulous.

4.79 out of 5 average rating, 19 reviews

Seaz the wave 🌊

JulieRating, 5 stars10 months ago

This was our second time staying at Seaz the wave and we had a great time. The location is great and the house has everything you need for a great beach vacation. Both the outside and inside spaces are comfortable and can accommodate a good number of people. AC upstairs, a gas BBQ grill to cook on, and a lounging deck out back are great additions.Hope to be back next year!

4.96 out of 5 average rating, 27 reviews

Cottage in Wells

Sleeps 10, 1.1 mi. to Beach, Fully Renovated 2025

RachelRating, 5 stars7 months ago

Check in was a breeze, the house was clean and the beds were very comfortable. Close to Moody Beach and just a short drive to Ogunquit village. Would recommend staying here!

5 out of 5 average rating, 52 reviews

Cottage in Kennebunk

*River Rose Cottage* River I Tub I Fireplace

KathrynRating, 5 stars3 weeks ago

My friend and I stayed here for a girls weekend, and the place was so cute, spotless, and the hosts were so friendly and responsive. The location was also great and centrally located. We had a blast and would for sure stay here again!

5 out of 5 average rating, 41 reviews

Flat in Kennebunk

Lower Village Lofts •South• Steps to Dock Square

RobertRating, 5 stars1 week ago

The lofts are incredibly convenient, decorated well and local to everything you’d want in downtown KPT. The hosts are very responsive making it feel like a home away from home. Will be back and would highly recommend.