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Family-friendly vacation rentals in Orland

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Orland

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Apartment in Searsport

4.82 out of 5 average rating, 293 reviews

Lakefront Vacation Apartment in Searsport ME

All season private top floor apartment. Hammock, loungers, floats. Acadia/State parks close. Canoe, kayaks, hot tub/wood floating dock (seasonal use), fire pit, grill, swim, fish. Modern/Antique furnished: queen bed plus loveseat twin. Massage/lounger. 2nd queen, twin inflatables. Fully equipped kitchen. Families w/kids, business guests welcome. Wifi smart TV. Great hikes, mountain bike rentals close. Snow shoes/sled included, skiing close. Separate entrance/apt above home not full home.

Oct 25 – Nov 1

R2,136 ZAR per night

Home in Holden

4.96 out of 5 average rating, 208 reviews

Chalet Central

This is a great central location for many of Maine's greatest attractions and places to visit as well as events to attend. We are only 21 miles from the University of Maine, Orono (UMO), 36 mi to great destinations like Bar Harbor, Acadia National Park and 7 miles from Interstate 95. We are 2 hr drive from Portland ME (Maine's largest city) filled with 100's of restaurants, pubs, Shopping, lighthouse, Botanical Gardens, art district...thatres and museums. Old Port, The Maine Mall, Foodie Tours

Jan 15 – 22

R3,218 ZAR per night

Home in Surry

4.93 out of 5 average rating, 132 reviews

Gran Den Lakefront Home Near Acadia

Gran Den is a large, contemporary, kid-friendly home on the sunset side of a 9 mi lake (Toddy Pond). Enjoy privacy, stunning elevated sunsets, a dock, raft, canoe, big yard and a tennis court! Deck spans the length of the home - great for grilling, sunbathing, meals, drinks, naps and stargazing. Waterfront and tennis ct only 100 ft from deck. Enjoy all nature offers, loons, bald eagles, humming birds – on a lake that you’ll feel like you own. Close to Acadia National Park, Deer Isle & Blue Hill.

Oct 17 – 24

R12,839 ZAR per night

Guesthouse in South Bristol

4.98 out of 5 average rating, 345 reviews

Waterfront Guest House on the Maine Coast

Bright open four-season guest house with fantastic view of Jones Cove and the open ocean in beautiful South Bristol, Maine. The guest house offers privacy and independence. The top floor has an open space with kitchen, sleeping area with queen bed, bathroom. The ground floor has a desk, Smart TV, seating area and French doors that open onto a stone patio. Includes Kohler generator, fiber optic wifi, outdoor grill & fire pit. The water is tidal Owner lives on property (150 ft from guest house)

Nov 19 – 26

R2,907 ZAR per night

Cottage in Glenburn

4.94 out of 5 average rating, 196 reviews

Your own private getaway on Pushaw Lake!

Welcome to Pushaw Lake! You’ll find all the comforts of home here! :-) Come for the weekend! Save 25% for a week, or 35% for a month stay! :-) Jump in the lake or go on an adventure in a kayak or canoe this summer! Bring snowmobiles, snowshoes, skis, or go ice-fishing this winter! :-) Relax... Read a book and listen to the Loons, or sit around the fire pit and say goodbye to stress! :-) You’re less than 20 minutes from Bangor International Airport, Downtown Bangor, and UMO! :-)

Apr 11 – 18

R2,921 ZAR per night

Chalet in Prospect

4.9 out of 5 average rating, 138 reviews

The Penobscot River Ranch House

This unique four season property is located on the Penobscot River close to Rt 1/1A and Fort Knox State Park. The Ranch House is cozy, clean, eclectic and spacious. I try to lovingly up cycle. It is conveniently located 5 miles to Bucksport which has a grocery, restaurants, cool shops and a lovely downtown theater; 18 miles to Belfast, Castine, Ellsworth, and Hampden; less than an hour to Camden, Bangor and an hour to Acadia National Park. I truly love sharing this special place with others.

Aug 5 – 12

R4,074 ZAR per night

Home in Frankfort

4.95 out of 5 average rating, 155 reviews

Relaxing lodge in the woods

Rustic lodge nestled in the woods, on 60+ acres. Close to Bangor, coastline, and 50 miles to Bar Harbor. Large eat in dining area with plenty of room for family and friends. Outdoor fields for games, grilling, access to Maine wildlife, with plenty of parking. Private master bedroom w/bath. Large community areas to enjoy time with friends and family. At night spend time by the campfire and take in the stunning night sky. Party and events are not allowed at this time due to COVID-19 policies.

Oct 4 – 11

R3,971 ZAR per night

Apartment in Blue Hill

4.94 out of 5 average rating, 162 reviews

Coastal Maine Barn Apartment

Light airy upstairs apartment with exterior stairs offers quiet retreat for friends or family exploring the Blue Hill Peninsula. Play croquet on the lawn while you grill up your dinner or relax on the deck. Cozy living room with gas-fired heater is perfect for playing games, watching movies or catching up on your email. Great hiking (5-minute walk to Blue Hill Mountain trailhead), kayaking, swimming and biking. 1.5 miles to center of Blue Hill, with great restaurants, shops and galleries.

Oct 19 – 26

R2,690 ZAR per night

Cottage in Sullivan

4.94 out of 5 average rating, 106 reviews

Edgewater Cabins

Edgewater is centrally located off of Route 1 (Schoodic Scenic By-way) in Sullivan Harbor. You can enjoy our beach and picnic tables on the wharf while surrounded by amazing views. You will find a tennis court just a short walk up our driveway. Nearby there are restaurants and dining, local hiking trails, and Acadia National Park. There are 2 other small cabins plus larger ones available that can accommodate families. In July and August there is a 7 night minimum stay from Sat. to Sat.

Jun 4 – 11

R2,280 ZAR per night

Cabin in Freedom

4.9 out of 5 average rating, 288 reviews

Cozy Lakefront Cabin in Freedom, ME

Our secluded, very quiet and private two bedroom cabin with loft features a bug-free screened-in porch on its large deck. The cabin overlooks peaceul Sandy Pond, inhabited by bald eagles, loons, and herons. Watch beautiful sunrises and sunsets, and swim, fish and kayak from our dock. We're close to coastal Belfast, Unity, MOFGA (annual Common Ground Fair), Waterville, Acadia and Camden. Eat at The Lost Kitchen, visit the Amish, hike the Hills to Sea Trail.

Dec 10 – 17

R1,545 ZAR per night

Apartment in Ellsworth

4.94 out of 5 average rating, 254 reviews

Coastal Studio in Ellsworth

This comfortable, furnished, studio apartment is located close to Acadia National Park. Come enjoy a peaceful destination with beautiful, distant views of the mountains. Includes some outdoor living with your own fire pit area, a bundle of wood, and a propane grill. Sleeping arrangements include 2 queen size beds and/or Pack N Play. We are pet friendly, but ask that you notify us if you are bringing your pet.

Nov 2 – 9

R2,058 ZAR per night

Campsite in Penobscot

4.98 out of 5 average rating, 107 reviews

Private Lakeside Camping in Penobscot, Maine

Private lakeside camping on Toddy pond in Penobscot, Maine 50 min. from Acadia and Bar Harbor. This 400 foot private wooded lakeside lot is available for camping. This rental is close to Acadia, Ellsworth, Bucksport and the Blue Hill Peninsula. Go out and explore the area attractions or stay put and swim, fish, and kayak on one of Downeast Maine's most popular lakes; Toddy Pond.

Jan 7 – 14

R2,341 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Popular amenities for Orland family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Treehouse in Georgetown

4.98 out of 5 average rating, 404 reviews

Modern Tree Dwelling w/Water Views+Cedar Hot Tub

Dec 14 – 21

R6,371 ZAR per night

Cottage in Verona Island

4.88 out of 5 average rating, 154 reviews

Nashport on the Penobscot

Mar 5 – 12

R5,990 ZAR per night

Home in Surry

4.89 out of 5 average rating, 168 reviews

Peaceful retreat on Newbury Neck

Apr 15 – 22

R5,727 ZAR per night

Cabin in Appleton

4.88 out of 5 average rating, 276 reviews

Raven's Crossing - Kate's Cottage

Oct 8 – 15

R1,705 ZAR per night

Guest suite in Lincolnville

4.95 out of 5 average rating, 44 reviews

Waterfront Loft w/ Bold Ocean Views

Oct 10 – 17

R5,947 ZAR per night

Farm stay in Searsport

4.92 out of 5 average rating, 105 reviews

Latham Blueberry Farm for up to 6 guests.

Dec 21 – 28

R4,753 ZAR per night

Cottage in Penobscot

4.88 out of 5 average rating, 41 reviews

Beach cottage on Penobscot Bay

Apr 6 – 13

R5,650 ZAR per night

Cabin in Bucksport

4.82 out of 5 average rating, 178 reviews

BUCKET LIST! 100+Yr.Old Bonnie Lass Cabin in Maine

Oct 20 – 25

R3,716 ZAR per night

Family- and pet-friendly home rentals

Guest suite in Brooksville

4.83 out of 5 average rating, 117 reviews

Waterfront at Tapley Farms Apartment, Acadia, Pets

Oct 26 – Nov 2

R3,081 ZAR per night

Cabin in Deer Isle

4.89 out of 5 average rating, 129 reviews

Long Cove Artist Cottage

May 12 – 19

R2,098 ZAR per night

Dome in Tremont

4.82 out of 5 average rating, 198 reviews

Little Frog at The Howling Woods

Mar 5 – 12

R1,396 ZAR per night

Cottage in Trenton

4.88 out of 5 average rating, 189 reviews

The Float Cottage

May 1 – 8

R2,550 ZAR per night

Treehouse in Hancock

4.95 out of 5 average rating, 493 reviews

Treehouse near Bar Harbor. Luxurious and private!

Jul 12 – 19

R15,454 ZAR per night

Home in Stetson

4.96 out of 5 average rating, 151 reviews

Lakefront Log Cabin on Pleasant Lake

Dec 3 – 10

R4,879 ZAR per night

Apartment in Belfast

4.96 out of 5 average rating, 341 reviews

Belfast Harbor Loft

Dec 23 – 30

R4,009 ZAR per night

Home in sullivan

5.0 out of 5 average rating, 138 reviews

Plovers Cottage, Waterfront

Dec 8 – 15

R5,431 ZAR per night

Family-friendly home rentals with a pool

Apartment in Cornville

4.85 out of 5 average rating, 123 reviews

Large Home with Great View next to horse farm

Sep 29 – Oct 6

R3,322 ZAR per night

Apartment in Boothbay Harbor

5.0 out of 5 average rating, 27 reviews

Luxury Condo on Water's Edge in Boothbay Harbor

Mar 19 – 26

R5,756 ZAR per night

Cottage in Belfast

4.58 out of 5 average rating, 12 reviews

Shore Cottage

Feb 23 – Mar 2

R4,916 ZAR per night

Home in South Thomaston

4.95 out of 5 average rating, 83 reviews

Large private area, close to Rockland

Aug 22 – 29

R10,206 ZAR per night

Home in Benton

5.0 out of 5 average rating, 13 reviews

Riverside home in Central Maine near Colleges

Sep 6 – 13

R4,347 ZAR per night

Apartment in Stonington

4.92 out of 5 average rating, 12 reviews

The Carriage House at Spruce Harbor

Jun 12 – 19

R3,494 ZAR per night

Home in Tremont

5.0 out of 5 average rating, 5 reviews

Tremont, ME. Shorefront compound for 7-12

Sep 9 – 16

R12,236 ZAR per night

Apartment in Rockland

Heart of Rockland Maine

Nov 28 – Dec 5

R5,181 ZAR per night

Quick stats about vacation rentals that are family-friendly in Orland

Total rentals
60 properties
Wifi availability
50 properties include access to wifi
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Total number of reviews
1.7K reviews
Nightly prices starting at
R1,693 ZAR before taxes and fees

Destinations to explore