Family-friendly holiday rentals in Drakes Island Beach

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Top-rated family-friendly rentals in Drakes Island Beach

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Guest favourite

Flat 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

Flat 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 favourite

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.

Top guest favourite

Guest suite in Freeport

4.97 out of 5 average rating, 238 reviews

Waterfront Private Apartment only 5 min to LLBean!

Guest apartment with private entrances, king bed, pull out sofa, kitchenette, walk-in shower, and porch facing the water providing the perfect relaxing coastal Maine experience! Custom built home on 8 acres tucked away in the woods with waterfront access to Harraseeket Cove & South Freeport Harbor, great for kayaking! Located 5 minutes from LL Bean and Freeport's many shops, restaurants, bars, etc. Wolfes Neck State Park and its stunning coastal trails and forests are less than a mile away.

Guest favourite

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

Guest favourite

Apartment 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 favourite

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.

Guest favourite

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 favourite

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 favourite

Apartment in Old Orchard Beach

4.91 out of 5 average rating, 434 reviews

Luxury Beach Front Condo! Prime Location!

Condo is directly on the beach! ✨Generally minimum night stay is 2 nights during the week and 3 nights over the weekend. Unless the trip is within the next few weeks, we appreciate it if guests don't book trips that leave a single night open. If you see a 14 day minimum, it’s only to prevent the reservation from leaving a single night open.✨ ✨To simplify things and to be fair to those that instant book, we typically do not negotiate rates. Thank you!✨

Top guest favourite

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.

Guest favourite

Apartment in Wells

4.85 out of 5 average rating, 188 reviews

Two-Bedroom Condo on the Wells/Ogunquit town-line

New condo unit at Compass Pointe Club, located on the Wells/Ogunquit town-line. Only one mile to Footbridge Beach and a quick 3-minute drive to downtown Ogunquit. Short drive to the supermarket and to great restaurants. Beautiful views of the Ogunquit River basin, with the Atlantic ocean peaking out beyond. The location cannot be beat.