Holiday rentals in Drakes Island

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Drakes Island

Guests agree: these stays are highly rated for location, cleanliness and more.

%{current} / %{total}1 / 1
Top guest favourite
The exterior of a private entrance features a charming blue door framed by natural wood shingles. Flowering plants and greenery line the pathway, enhancing the inviting atmosphere. A trellis with climbing vines is visible beside the door, contributing to the tranquil setting.
Flat in Kennebunk
4.99 out of 5 average rating, 173 reviews

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!

Top guest favourite
A modern beach house is positioned along a serene shoreline, featuring large windows that reflect the colorful sunset. The exterior showcases a blend of natural materials and white accents, with a deck that offers expansive ocean views. Rocky shores frame the property, enhancing the coastal setting.
Home in Saco
5 out of 5 average rating, 216 reviews

Oceanfront w/ Stunning views and Private Deck☀️🏖

Welcome to the Beach House on the Rocks, your very own oceanfront retreat! This beautiful, 1350 sq ft house is nestled right next to the ocean. With panoramic views and the ocean just steps away, you won’t forget this one of a kind experience. Tucked away in the hidden gem of Camp Ellis, you’ll enjoy a lively beach scene in the summer and a tranquil retreat in the off season. Just a short trip away to Old Orchard Beach and 30 min to Portland you’ll never be in need of fun activities.

Guest favourite
A vibrant sunset casts shades of orange and pink across the sky, framed by the silhouette of trees. The edge of a white deck is visible in the foreground, creating a serene backdrop for outdoor gatherings.
Home in Wells
4.92 out of 5 average rating, 157 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

Top guest favourite
The exterior of a multi-level beach house is visible, featuring a spacious deck with railings and steps leading to the sandy area by the water. The house is painted white with green accents, and tall windows allow for natural light to enter. A brick chimney is located at one end.
Home in Wells
4.97 out of 5 average rating, 118 reviews

Family Beach House, Wells Beach, Maine

Family Beach House on the Harbor/River of Wells Beach. House Sleeps 8 adults, plus 3 - 4 children. Full kitchen, 4 bedrooms plus Sleeping Loft, 3 baths, Dining Room, large deck, patio, laundry, outdoor shower, fire pit. Private access back beach. Bring your kayaks, paddle boards, surf boards, or boat. Water behind house at High Tide. Approx. 100 yard walk across Atlantic Ave to beach. Parking for 5 cars Max. Optional in-law apartment available, sleeps 5, for $115 per night/$800 per week

Top guest favourite
A bright kitchen area features modern white cabinetry and a spacious countertop. Barstools with woven seats are positioned at the counter. Natural light floods in through a nearby door, illuminating the polished wooden floor and light blue walls.
Cottage in Wells
4.95 out of 5 average rating, 166 reviews

Cozy Cottage with Ocean Views, Wells Maine

Ocean breezes, panoramic views of the Atlantic, comfortable cottage to relax & enjoy your time in Maine, what more could you ask for on a getaway?! This cozy cottage for 6 boasts near panoramic views of the Rachel Carlson preserve and the Atlantic Ocean. Tastefully decorated and newly updated, our cottage offers AC/heat, ceiling fans, fully equipped kitchen with dishwasher, outdoor gas grill, cable TV in all rooms, WiFi, cabled phone, skylights, in unit W/D & a large screened in porch.

Top guest favourite
A cozy living area features two patterned armchairs and a neutral-colored sofa, creating a welcoming seating arrangement. A light-colored coffee table is centered on an area rug, with decorative items and reading materials arranged on it. Natural light enters through the window, enhancing the space.
Farm stay in Kennebunk
4.95 out of 5 average rating, 101 reviews

1760 Morrill Farm House-5 Minutes to Kennebunkport

Welcome to the 1760 Morrill Farm House, your idyllic sanctuary for your iconic Vacationland experience. Just a 5 minute drive to Kennebunk and Kennebunkport villages, Mother’s, Middle and Gooch’s beaches. Free beach pass provided. PLEASE NOTE: This unique space has very low ceilings and may not accommodate people over 6 feet tall comfortably. PLEASE NOTE: Unit 2 only has one designated parking spot. Any extra cars in your party must park on the side of the road next to the bushes.

Guest favourite
The barn house features a rustic design with large, welcoming doors framed by vibrant greenery and colorful flower beds. Two red chairs are positioned invitingly on a pebble pathway leading to the entrance. A soft pink and purple sky complements the charming exterior.
Farm stay in Kennebunkport
4.92 out of 5 average rating, 132 reviews

Farmhouse Experience in a Beachside Community

2025 Summer Rentals: 7 night min requirement (Friday Check-in) / Inquire for alternative dates. Enjoy being equidistant between Dock Square and Cape Porpoise, where you be immersed in a world of top chefs, fine wines, beautiful homes, acclaimed artists, and the quintessential oceanfront charm of Kennebunkport. Relax in this inspired barn house restored design with modern touches in a farm to table community. Weather the storm with our newly installed generator.

Superhost
The exterior entrance of the property features a paved pathway leading to a dark blue front door, flanked by two windows. A small bench is positioned nearby, and an American flag is displayed on the ground. Lush greenery surrounds the area.
Home in Wells
4.92 out of 5 average rating, 262 reviews

3-Bed | 2-Bedroom | Hot Tub | Close To Beach

If you've never stayed in Wells before, make your first stay at the oldest established property in Wells, dating back to 1604, but updated for today's modern needs with wifi, streaming, jacuzzi, grill, outdoor furniture, and hammock all within a short drive to Wells beach in a peaceful neighborhood on a dead end street. Let the Webhannet Falls and River lull you to sleep as they flow through the backyard and see the foundation of the historic gristmill and sawmill.

Top guest favourite
An aerial view shows a classic multi-story home positioned near the beach, surrounded by lush greenery. The coastline is visible, along with gentle waves and neighboring houses, highlighting the inviting ocean setting.
Home in Kennebunk
4.93 out of 5 average rating, 106 reviews

Ocean/Beach Unique Views: THE New England !

QUIET NEIGHBORHOOD, WELCOME TO FAMILIES! GAS FIREPLACE ! Classic architectural details all sited on an enviable ocean/beach location. An alluring home, lovingly maintained for 110 years, encompasses the true understated elegance of the era in which it was created. Amidst the 3,500 sq ft+, find 6 gracious bedrooms accented by 4 and a half baths, updated granite kitchen, pantry, glassed in front porch with mesmerizing views of the ever-changing sea.

Superhost
A serene view of the beach stretches before a grassy path leading to the shoreline. Waves gently lap at the sandy beach under a clear sky, where soft clouds drift above. The outdoor space is bordered by tall grass, providing a natural frame.
Home in Wells
4.81 out of 5 average rating, 104 reviews

Private home on the beach with 360 degree views!

Directly on the beach with views of the water on both sides. This 4 bed/2 bath house has a modern feel with lots of windows and natural light. Very white, bright, and clean and can sleep up to 12 people. Amazing views and location, and it's one of a kind. The sunrises and sunsets can be seen on both sides of the home. The kitchen is stocked with everything from a microwave to a blender...you'll have what you need...and parking for 4 cars.

Top guest favourite
The exterior of the bunkhouse is shown, featuring a grey clapboard siding and a welcoming front porch with white railings. A bright blue door contrasts the muted tones, while greenery surrounds the property, creating a natural, serene setting.
Home in Wells
4.99 out of 5 average rating, 175 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!

Guest favourite
A cozy bedroom features a spacious bed covered with a patterned blanket. Natural light filters in through large windows, highlighting the wooden walls and carpeted floor. A mini fridge is positioned beside the bed, while curtains provide options for light control and privacy.
Flat in Wells
4.8 out of 5 average rating, 294 reviews

The Oasis

This is a one bedroom unit with its own private bathroom close to Wells Beach, and Route 1 Shopping, restaurants , etc. High-speed WiFi, AC/Heat, comfy queen sized bed, mini fridge, microwave, small table with 2 chairs, ceiling fan, first aid kit, iron, and blow dryer. I don't do long term rentals for the summer but please message me if you'd like to do a long term rental from October to May.

Popular amenities for Drakes Island holiday rentals

  1. Airbnb
  2. United States
  3. Maine
  4. York County
  5. Wells
  6. Drakes Island