Family-friendly vacation rentals in Drakes Island Beach

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Top-rated family-friendly rentals in Drakes Island Beach

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Guest favorite

A two-story apartment building is situated near the beach, featuring spacious decks on both levels. Bright white railings and chairs are visible on the decks, creating an open and inviting outdoor space. Lush greenery and decorative elements surround the base of the structure.

Apartment in Wells

4.92 out of 5 average rating, 133 reviews

Wells Beach - Baywatch North

North Side 2 story apartment on 2nd and 3rd floors. Large deck with Weber gas grill and patio table and chairs. Large deck off of master bedroom with king size bed. There are 1 1/2 baths with a washer and dryer. Both decks overlook the bay with amazing sunsets. The bay has striped bass, seals, Egrets, Great Blue Herons and many other birds. Mitsubishi heat pumps for heat and air conditioning. Kayaks are available for use in the bay. Enjoy a short walk across the street to the beach (100 yards)

Superhost

A dedicated office space features a custom-built desk with an ergonomic chair and a computer monitor. Natural light fills the room through two large windows with subtle shades. A vacuum cleaner is positioned near the entrance, while the open layout allows views of the adjoining living area.

Apartment in Ogunquit

4.94 out of 5 average rating, 150 reviews

Step to Perkins Cove From The Loft in Ogunquit

Architect-designed loft just steps from the Marginal Way& Perkins Cove with the best in relaxation, comfort and finishes. Two guest suites meet with open and spacious living. Enjoy a bright and open living space with gourmet kitchen. The outdoor space is perfect for grilling out or just welcoming the morning sun with a cup of coffee, or ending the night with a great glass of wine. With private parking for up to two cars, leave them and walk to any of the attractions Ogunquit is known for.

Top guest favorite

A modern building with a light-colored exterior features large windows and a steeply pitched roof. A set of stairs leads to an upper entry, while two wooden garage doors are present at ground level. Surrounding greenery enhances the serene setting.

Guest suite in Cape Neddick

4.97 out of 5 average rating, 366 reviews

Peaceful Coastal Retreat

Tucked away in the woods along a stretch of rocky coastline, this hidden retreat is the perfect place to truly get away. Located midway between Ogunquit and York, guests can enjoy all the amenities of the towns, yet return to the quiet and peaceful seclusion of the Peaceful Coastal Retreat. Listen to the wind blow and the birds chirp as you gaze into the surrounding forrest or the star speckled sky; there is no place more perfect to relax and experience the magnificent Maine coastline.

Guest favorite

A cozy seating area features a dark leather sofa adorned with a colorful throw and red accent pillows. A small wooden table and a soft rug complement the space, where a light stands beside a vibrant orange wall. Natural light enters through a window dressed with light curtains.

Guest suite in Kennebunk

4.85 out of 5 average rating, 283 reviews

We welcome Canadian guests with 20 % off

CANADIAN RESIDENTS: inquire with dates for a special offer to include the discount. Our spacious suite with private bath is comfortable, well appointed, close to everything. 1 mile to the beach. Many extras included ! The suite consists of a large studio, with private bath. The second room rents for $55 per night for a second or third person in the group and shares the bath. Free amenities include use of beach parking pass, chairs, pack-n-play, kayaks, gas grill, picnic table, fire pit

Top guest favorite

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, 110 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

Guest favorite

A wide sandy beach stretches along the coastline, with gentle waves breaking at the shore. Two figures walk along the water's edge, while a clear blue sky enhances the tranquil atmosphere of the scene.

Condo in Old Orchard Beach

4.9 out of 5 average rating, 105 reviews

Oceanfront Condo with Awesome Views

Wake up to a full ocean view on a seven mile sandy beach! Enjoy this one bedroom condo's great views, private balcony, and fully furnished decorated living space, along with a full kitchen with dishwasher, and even including a washer and dryer! Walk to everything downtown Old Orchard Beach has to offer: Amusement park, restaurants, clubs, shopping, and the famous Pier. Downstairs is a bar/restaurant that features live bands seven days a week in summer. Enjoy the fireworks every Thursday!

Top guest favorite

A cozy outdoor seating area features two wooden chairs arranged around a circular stone fire pit. The space is surrounded by landscaped mulch and bordered by a winding pathway. Lush greenery and a home can be seen in the background, contributing to a serene atmosphere.

Loft in Barrington

4.96 out of 5 average rating, 534 reviews

Sunny, secluded studio loft apartment

Fully furnished studio apartment above home owners' garage with private entrance. Secluded 5.5 acre lot of land surrounded by beautiful woods. Vaulted ceilings with ladder to loft with queen bed. Big, sunny south-facing windows overlooking back yard and gardens. Homeowners are a laid-back, married gay couple, living in the main house with their 5 year old daughter. LGBTQ friendly home that welcomes kind guests of any race, religion, gender, and orientation. A minute from Route 125.

Top guest favorite

A tranquil water view is captured from a balcony, showcasing calm reflections on the surface of the estuary. Lush greenery lines the waterfront, and the distant tree line is visible against a softly clouded sky.

Guest suite in Kittery

4.97 out of 5 average rating, 275 reviews

Coastal home on the water

A nautical look and feel is what this coastal home away from home offers. A detached from the main house in-law apartment is the perfect get away. Located directly on the water, on an estuary called Spinney Creek, part of the Piscataqua River. Bring your kayak, fishing rod, or sit back enjoy a cold beverage and watch the sunsets by the fire pit. Best water views ever. It is 1.5 miles to downtown Portsmouth, NH and less then 1 mile to the beautiful rejuvenated downtown Kittery.

Guest favorite

The entryway features a blend of natural wood and modern design elements. A staircase with a wooden railing leads to an upper level. A vibrant area rug lies beneath a plant and a bar cart, while large windows allow natural light to brighten the space.

Farm stay in Kennebunkport

4.96 out of 5 average rating, 114 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.

Top guest favorite

The Birch Ledge Guest House is a two-story structure nestled among trees, featuring a rustic exterior with a metal roof. A small patio with two chairs is positioned at the entrance, and a staircase leads to the loft area. Lush greenery surrounds the home.

Home in Hollis

4.99 out of 5 average rating, 429 reviews

Birch Ledge Guesthouse--Four Season Maine Getaway

Both rustic and elegant, the Birch Ledge Guest House offers a cozy place to relax and recharge, whatever the season. The first floor features a spacious living room (with queen sized pull-out-couch), dining area, and small kitchen. The bathroom has a walk-in shower. The second floor is a loft accessible by a spiral staircase and has a comfy queen and two twin sized beds. The guesthouse is surrounded by quiet forest and is an easy 30 minute drive to Portland.

Guest favorite

A light-filled living area is highlighted by exposed wooden beams overhead, complemented by modern furnishings. An open kitchen features a gray countertop and red barstools. A comfortable sectional sofa offers a cozy seating option, with a flat-screen TV mounted on the wall.

Apartment in Kennebunk

4.96 out of 5 average rating, 212 reviews

Dock Square Pied-A-Terre Loft Beachy Vibes!

The Sail Loft Unit is a brand new (since 2018) 2nd floor 1 bedroom, 1 full bathroom Suite. Our Property has 5 apartments and we are proud to say we have over 1000 5 Star Reviews!! Discover the delightful town of Kennebunk and enjoy your ideal seaside retreat in our snug 1-bedroom holiday house. Situated just a short walk from the vibrant Dock Square, you'll be immersed in the heart of the local community, with easy to all beaches and attractions!

Top guest favorite

A spacious bedroom features two beds: a queen bed and a full-size bed, with colorful bedding and cushions. A small desk and a television are positioned against the wall. Natural light filters in through a large window adorned with blue curtains, illuminating the warm peach walls.

Guest suite in Biddeford

4.97 out of 5 average rating, 403 reviews

Private, spacious, colorful, fun & unique space

Large private comfortable annex with a SEPARATE entrance, your own bathroom. A "kitchenette" located within one of the 2 bedrooms for our guests to enjoy in a farmhouse style family home built in 1850. Located on a quiet street 3 miles from Biddeford Pool Beach. 1 mile to the UNE Biddeford campus. 10 minutes to Saco train station. 15 minutes to Old Orchard Beach and 25 Minutes to the city of Portland and the Jetport.