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

Guesthouse in Portland

4.95 out of 5 average rating, 281 reviews

Beautiful large studio on the ocean.

Our large, light, 2nd floor studio is airy and modern with a deck overlooking the garden, ocean and sunrise. We love to welcome guests to share our beautiful property so if you'd like to book please introduce yourselves and let us know about who is coming and some hopes for your trip. We are caring, unobtrusive hosts who value getting to know our guests a little beforehand. We think we have the best of both worlds here - the peace and beauty of Casco Bay, yet 5 minutes to the center of town.

May 27 – Jun 3

R2,799 ZAR per night

Guest favorite

Apartment in Wells

4.93 out of 5 average rating, 124 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)

Sep 22 – 29

R7,510 ZAR per night

Guest favorite

Loft in Barrington

4.96 out of 5 average rating, 490 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 2 year old daughter and a dog. LGBTQ friendly home that welcomes kind guests of any race, religion, gender, and orientation. A minute from Route 125.

Dec 12 – 19

R1,781 ZAR per night

Guest favorite

Guesthouse in Harpswell

4.95 out of 5 average rating, 431 reviews

Harpswell Studio on Waterview Property! Lobster!

Attached Cottage Style Studio! Clean, comfy, spacious, colorful and bright! Easy access to Harpswell’s 216 miles of coastline via coastal trails, lovely side roads, small beaches and preserves. Too many trails to count in the surrounding area! Fresh lobster and seafood! Two spectacular state parks with expansive beaches within a scenic 35 minute drive! Just 45 minutes (33 miles) to Coastal Maine Botanical Gardens! Saturday check-in may be available before mid June. Please message us.

Oct 22 – 29

R2,579 ZAR per night

Guest favorite

Guest suite in Cape Neddick

4.97 out of 5 average rating, 288 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.

Sep 18 – 25

R3,146 ZAR per night

Guest favorite

Guest suite in Kennebunk

4.84 out of 5 average rating, 263 reviews

Beautiful Spacious Studio, 1 mile to beaches.

Our spacious suite with private bath is comfortable, well appointed and close to everything. 1 mile to the beach. Lots of extras included ! The suite consists of a large studio, with private bath. The bathroom is shared with a second bedroom which is only rented in conjunction with the suite. The second room rents for $55 per night for a second or third person in the group. Free amenities include use of beach parking pass, chairs, pack-n-play, kayaks, gas grill, picnic table, fire pit

Mar 7 – 14

R2,594 ZAR per night

Guest favorite

Guest suite in Kennebunkport

4.99 out of 5 average rating, 168 reviews

Get back to nature in this new woodsy retreat.

Perfect for "leaf peeping". Brand new rental! Beautiful 2nd floor two bedroom apartment with great light, nestled in the woods. Listen to the owls at night and wake to the birds chirping. Comfortably sleeps 5 in two queen beds and a twin XL bunk. Easy access to Goose Rocks Beach as well as Smith Preserve conservation trails for biking, hiking, trail running, snow shoeing and cross-country skiing. Located 6 miles from the center of Kennebunkport and 3 1/2 miles from Cape Porpoise.

Feb 20 – 27

R3,811 ZAR per night

Guest favorite

Guest suite in Lee

4.98 out of 5 average rating, 128 reviews

Farm setting. In-house suite with own entrance.

This lovely 3-room suite in our home has a private entrance. Rooms include bedroom, private bathroom, and sitting room/art studio with a sofa bed. 10 minutes from University of New Hampshire, and 30 minutes from Portsmouth. Small refrigerator, coffee maker and electric kettle. Nearby hiking, pickle-ball, tennis. In winter, 1 hour to downhill ski, cross country nearby. This property is a working farm and greenhouse business, with CSA vegetable gardens. All are welcome.

Oct 14 – 21

R2,433 ZAR per night

Guest favorite

Home in Kennebunk

4.98 out of 5 average rating, 165 reviews

Kennebunk Cottage

A renovated Maine cottage, our home is just a 1/4 mile to the beautiful Bridal Path that runs along the Mousam River. The Mousam River leads you to Parsons Beach and is great for Stand up Paddleboarding, kayaking and is a hot spot for fishing. The home is also just one mile to Mothers Beach, which is a favorite for families and just 1.5 miles to the shops and restaurants of Kennebunkport. Come overlook the marsh in our spacious backyard perfect for grilling and family time!

Jan 5 – 12

R5,569 ZAR per night

Guest favorite

Home in Hollis

4.98 out of 5 average rating, 359 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.

Sep 26 – Oct 3

R3,433 ZAR per night

Guest favorite

Home in Kennebunk

4.97 out of 5 average rating, 157 reviews

350 Steps to Gooch’s Beach! Water Views

Ideal location 350 steps to beautiful Gooch’s beach. Easy walk or short drive to Kennebunkport's Dock Square with shops and restaurants. This is the upper floor of a 2 floor, 2 unit building. Sunny and cheerful w/open floor plan, gas fireplace, and large back deck. WiFi and live streaming tv are included. Outdoor shower. Beach chairs/towels provided. Walk to beach & town. 7 day minimum, Saturday check in/check out June 29 through August 31., 2024

Nov 25 – Dec 2

R15,115 ZAR per night

Guest favorite

Home in Biddeford

4.97 out of 5 average rating, 381 reviews

Private, spacious, colorful, fun & unique space

Large private comfortable annex with a SEPARATE entrance, bathroom and dining nook 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.

Nov 2 – 9

R1,850 ZAR per night