
Holiday houses in Drakes Island Beach
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Top-rated holiday rentals in Drakes Island Beach
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Luxury Year-round Hobbit House w/ private hot tub
Fern Hollow is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.
LocationFamilyHeating
4.92 out of 5 average rating, 132 reviews
Newly renovated beach house steps from Wells Beach
Relax with the whole family at this peaceful place to stay. Bright, spacious and packed with family-friendly amenities, this updated 3-bedroom, 1-bath vacation rental is the perfect retreat for you and your loved ones! Start your morning with breakfast in the fully equipped kitchen, then spend the day at Wells Beach steps away. Relax with views, light up the gas grill for dinner and unwind by the fire pit. Start planning your memorable and fun-filled trip at this recently renovated home today!
LocationFamilyKitchen
4.96 out of 5 average rating, 23 reviews
Stunning Oceanfront Home. Directly on Wells Beach
Front row. If you know the feeling at a concert or ballgame, you'll have that same feeling here. Our home features 180 degree ocean & beach views from the deck & living room. Sip your cocktail as the sun sets and your coffee as that same sun rises the next morning. Ample parking for 2 cars & convenient access to the best restaurants in Wells. (All stays contingent on acceptance of rental agreement). All areas of this unit were recently renovated. Enjoy a circa 1924 home with 2021 renovations.
FamilyLocationComfort
4.74 out of 5 average rating, 31 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
LocationFamilyBiking
4.96 out of 5 average rating, 129 reviews
Brand-New 2BR Beach Retreat with marsh views
Located just a stone throw away from Wells Beach in Southern Maine, Paddle Inn is a brand-new cottage built in 2024, that blends modern design with a beachy vibe. This charming blue retreat invites you to bring your bikes and paddle boards to explore. The marsh is right in front of the cottage for your enjoyment. The second story deck offers a tranquil escape. You are close to local restaurants or enjoy local music. Explore the seacoast. Inside you will find it peaceful and relaxing.
LocationFamilyCleanliness
5.0 out of 5 average rating, 77 reviews
Four Story Townhouse With Ocean View 55
Our newly re-done townhouse is available year-round featuring a beautiful kitchen/living area with gas fireplace and relaxing balconies. This townhouse is equipped with gas heat, central air conditioning, ceiling fans, a fully equipped kitchen with a dishwasher, a gas grill, cable TV, Wi-Fi, and more! The 3-bedroom townhouses come with an additional Bedroom on the 4th floor. Feature 2-1/2 bathrooms and a washer and dryer. Private parking for 2 vehicles. Pools/hot tub are seasonal.
FamilyLocationBeach
4.97 out of 5 average rating, 34 reviews
The Granite Harbor
This beautifully renovated beach house on Atlantic Avenue in Wells, Maine, offers the ultimate coastal getaway just steps from the ocean. Located directly across from public beach access, it provides an unbeatable location for families looking to enjoy sun, sand, and surf within moments of stepping outside the door. With five spacious bedrooms and two full kitchens located on different floors, this home comfortably accommodates large groups or two families vacationing together.
LocationFamilyAccess
5.0 out of 5 average rating, 11 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.
LocationFamilyView
4.94 out of 5 average rating, 117 reviews
Romantic Mirror cabin in the woods
Stay at Hidden Pines Cabins. The Mirror cabin is Maines only 3 sided floor to ceiling mirrored glass cabin. Unwind in the hot tub while looking up at the sky full of stars. Take a sauna while surrounded by nature all around. Located in the majestic forest of mount Agamenticus, the extensive trail system is off of our road. Short drive to the Ogunquit/York beaches, Outlets at Kittery and near Portsmouth, Dover and Portland restaurant scenes.
ValueLocationIndoor spaces
5.0 out of 5 average rating, 149 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.
LocationFamilyCondition
4.81 out of 5 average rating, 114 reviews
Minnow Cottage waterfront, in-town Kennebunkport
This quaint Maine cottage in the heart of Kennebunkport village is just steps from great shopping, cafes, gift shops, antiquing, fantastic dining, whale watching & sailing excursions. Perched literally over the Kennebunk River on wooden piers! You can't get any closer to the water. Take advantage of a great opportunity to stay in Dock Square in a truly unique waterfront home.
LocationFamilyGetting around
4.98 out of 5 average rating, 93 reviews
HotTub+Firepit/5 min to DockSquare, Dining, Beach
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."
LocationValueDecor
4.96 out of 5 average rating, 229 reviewsPopular amenities for Drakes Island Beach holiday rentals
Other great holiday rentals in Drakes Island Beach

Charming Beach Front Cottage
ValueLocationBathroom
4.84 out of 5 average rating, 38 reviews
Steps from Crescent Beach • Beach Gear Included
LocationFamilySleep quality
5.0 out of 5 average rating, 6 reviews
Oceanfront Sunrise and Set with Waterfront Hot Tub
FamilyLocationDecor
4.94 out of 5 average rating, 70 reviews
Seaside Serenity 1 - Oceanfront
LocationFamilyAmenities
4.96 out of 5 average rating, 23 reviews
Adorable 3 bedroom cottage in Wells, ME
FamilyValueQuiet
4.98 out of 5 average rating, 57 reviews
Moody beach cabin by the sea
FamilyLocationKitchen
4.97 out of 5 average rating, 67 reviews
Seaz the wave 🌊
FamilyLocationAmenities
4.83 out of 5 average rating, 29 reviews
Seaworthy
LocationFamilyQuiet
5.0 out of 5 average rating, 15 reviewsDestinations to explore
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