
Family-friendly vacation rentals in Oakland
Find and book unique family-friendly homes on Airbnb
Quick stats about vacation rentals that are family-friendly in Oakland

Total vacation rentals
Explore 50 vacation rentals in Oakland

Nightly prices starting at
Oakland vacation rentals start at G$25,097 GYD per night before taxes and fees

Verified guest reviews
Over 1,470 verified reviews to help you choose

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
50 of Oakland vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Oakland rentals

4.9 Average rating
Oakland stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated family-friendly rentals in Oakland
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Off-Grid Cabin with Wood Fired Hot Tub. 4 Kayaks
Relax at this off-grid modern A-Frame cabin on 90 acres in Maine's Lakes Region. The cabin is tucked deep in the woods, far away from everything. 4 kayaks and firewood included. Separate bunk cabin increases sleeping capacity to 10 Wood-Fired Cedar Hot Tub - a relaxing, very unique experience 5+ lakes nearby- beautiful swimming and kayaking Cedar throughout cabin, concrete countertops, cedar/concrete shower. Outdoor firepit. Hiking trails. Beaver Pond. Property has private airstrip (51ME)
KitchenIndoor spacesGetting around

Farm house, River, Island, animals & private Chef.
MARCH-APRIL DAILY. Medicine Hill is a 136 acre farm on the Sandy River complete with a swimming hole and an entire island to explore. We grow vegetables, herbs & flowers. Our animals include sheep, chickens & rabbits. You will have full access to all areas of the farm! Spend time fishing or relaxing on the river. Or literally just sitting on the porch unwinding and taking it all in. 4 private bedrooms have stunning views surrounded by trees or fields. And if the Chef is available..EAT!!!
KitchenFamilyDecor

Quaint Little Cottage
Clean, quiet, cozy, and includes extras that will make your stay a comfortable one. We host short or long term. Located in the Belgrade Lakes region this home is nearby Colby and Thomas College, Maine General Hospital, centrally located between Waterville and Augusta, and 1 hour to the Maine coast as well as ski mountains. Enjoy hiking, fishing, exploring Maine, and more! For great dining options your commute is 5-10 minutes, or you can stay in and have delivery from one of our local eateries.
Indoor spacesKitchenSkiing

Sister a-frame in Woods (A)
Escape to one of our two sister A frames. These cozy cottages are nestled in the Oakland, Maine woods. Close proximity to I-95, Messalonskee and prestigious Belgrade Lakes you will find home to a wide variety of wildlife and nature. Boating, fishing and ATV riding close by! The campus includes a loft with a view, walking trail, free/overflow parking. A luxury, campy feel makes this a perfect getaway for you and your family. Check out our other listings managed by Hall’s Homes RE online!
Indoor spacesKitchenTV

Home away from home cozy new Apartment in Oakland
Escape to this newly built apartment in Oakland for a relaxing and peaceful getaway. Unwind on the porch while enjoying Maine’s beautiful wildlife, breathtaking sunsets, and star-filled skies. Conveniently located just minutes from Colby College, Thomas College, Snow Pond public beach/boat landing, Bowl in the Pines, and many local restaurants, shops, and outdoor attractions. Perfect for a vacation exploring beautiful Central Maine, visiting family, college visits, or business travel.
FamilyKitchenSleep quality

Cozy House in Waterville
Our private Cozy House has just been renovated! We put in a new kitchen, bathroom, laundry room, and a big 4k smart tv/Apple TV. It's in a friendly neighborhood located in the heart of Waterville only five minutes from Colby College, Thomas College (by car) and just a few minutes from downtown Waterville. Everything is very close to our location. There's a Hannafords nearby, Maine General Hospital and many restaurants, schools and stores. We are located on a private dead-end driveway .
Indoor spacesFamilyDecor

The Copper Fox Treehouse
Named the 10th most spectacular tree house in the world by the BBC Featured in the book: Modern Tree Houses by Taschen Airbnb's Most wishlisted property in Maine in 2025! Come experience the whimsy and craftsmanship of this red fox head shaped treehouse for yourself. The magic of this wild adventure awaits you in the treetops... Come to relax, explore and make lasting memories your family and friends will talk about for years. Follow our journey on IG at @thecopperfoxtreehouse
FamilyIndoor spacesWifi

Lakeside retreat on quiet cove on Cobbessee Lake!
Nothing beats summer days on the lake in Maine. Not only is this lake home situated on a quiet cove on central Maine's Cobbossee Lake, but it is near amenities in Augusta and close to I-95! Enjoy two large docks, a large lawn and gently sloping swimming area, and a newly renovated five bedroom house with two full bathrooms. This is the Maine vacation home you are looking for! Two of the bedrooms and one bathroom are in the basement, which is still under some small construction.
KitchenIndoor spacesGrill

The Lake House on McGrath Pond | 4BR | Waterfront
Unwind year-round at this stunning lakeside home on McGrath Pond with 100+ ft of private water frontage. Sleeps 10 with 4 spacious bedrooms. Enjoy an open floor plan, fully equipped kitchen, large deck with lake views, WiFi & cable TV. Near Colby College and a short drive to Sugarloaf, Acadia, Bar Harbor & Freeport (LL Bean and outlets). Whether you're kayaking in summer, leaf-peeping in fall, or skiing in winter, this home has everything you need for a memorable Maine escape.
KitchenIndoor spacesGrill

Brook Ridge Retreat
Work, play, & relax at Brook Ridge Retreat! Come visit your Colby or Thomas College student and have the comforts of home. Do some grilling or cook up a favorite meal in the full kitchen. Remotely connect to work or school at our custom-made desk and dedicated office area with wireless printer and available computer monitor. Splash in the brook or in the basin, and sit under the waterfalls. WiFi, firepit, Keurig or french press, electric fireplace, large decks, & big yard.
KitchenFamilyRiver

Lake-House on water, East Lake, Near Waterville
Welcome to the Lake House! 5 bedrooms. Access to a mooring. Full bathroom and kitchen with accessories. Bedrooms have locked doors & Wi-Fi. The house has a Deck and Docks, 8 foot by 10 foot floating Island, BBQ Grill. Lakeside Bon Fire Pit. Full bath, 30 feet from Lake! 2 entrances, 3 Kayaks, Fishing/Swimming. Nice neighbors including Camp Manitou, Matoaka and Somerset. Near Public Boat Landing & country store. I reside nearby, and will help with any issues.
FamilyIndoor spacesComfort

Visit Beautiful Home on Snow Pond
Belgrade Lakes, Maine's premiere lakes region. Beautiful, four season home on 9 mile long, Messalonskee Lake also known as, Snow Pond. Come to experience life the way it should be. Sunrise view, from master bedroom and lakeside deck surrounded by undeveloped wooded shoreline. Swim, canoe and kayak from private dock. Loons, eagles, osprey, and beavers can be your neighbors for a relaxing week at the lake. Open concept kitchen dinning and living room.
Indoor spacesKitchenPool
Popular amenities for Oakland family-friendly rentals
Family-friendly home rentals with a hot tub

Lakefront: Private Hot Tub, Sauna & Free Massages!
KitchenFamilyHiking

Solar Powered Bus in Forest | Hot Tub + Wellness
FamilyIndoor spacesHot tub

Modern Lakefront Home w/ Hot Tub • Summer Vacation
KitchenFamilyAmenities

A comforting sweet off grid cabin near the beach!
Indoor spacesKitchenWifi

Waterfront Tipi Glamping // Phoenix Landing
Indoor spacesKitchenParks

Cozy Rock Cabin #thewaylifeshouldbe
FamilyKitchenAccuracy

Maybelle the Tiny Cabin on 100 acres
FamilyIndoor spacesValue

SkyView Treehouse | Lakefront • Private Hot Tub
FamilyKitchenGrill
Family- and pet-friendly home rentals

Lake Great Pond| Dog Friendly | Boat Launch
FamilyKitchenWalkability

Lakefront Home w/ Dock | Porter Lake | Sugarloaf!
FamilyIndoor spacesGrill

Camp Bai Yuka/Little Camp (Log Cabin on Webb Lake)
FamilyKitchenGetting around

Kate-Ah-Den Cabin, a soul soothing escape.
Indoor spacesFamilyWifi

Charming Cottage With Spectacular Water View
KitchenIndoor spacesSleep quality

Camp at Shale Creek Homestead
KitchenFamilyQuiet

Private tiny cabin on six acres of trees
KitchenIndoor spacesDecor

Little Apple Cabin on 5 acres, amazing stargazing!
Indoor spacesKitchenCheck-in
Family-friendly home rentals with a pool

Large private area, close to Rockland
KitchenIndoor spacesView

the lake house
FamilyIndoor spacesCondition

The heart of the Belgrade lakes
FamilyKitchenCheck-in

Riverway Cottage
KitchenFamilyNearby

Home away from home
Indoor spacesFamilyNearby

Maine Fall Getaway •Grill •Fire Pit •King Bed •EV
Indoor spacesFamilyPool

Angel Mist Retreat Garage Apartment
Indoor spacesKitchenCheck-in

Maine Lakehouse Retreat with pool
KitchenIndoor spacesCondition
When is the best time to visit Oakland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$47,893 GYD | G$50,193 GYD | G$59,395 GYD | G$44,128 GYD | G$51,866 GYD | G$52,494 GYD | G$62,742 GYD | G$60,650 GYD | G$54,376 GYD | G$44,128 GYD | G$41,828 GYD | G$39,527 GYD |
| Avg. temp | -6°C | -5°C | 0°C | 6°C | 12°C | 17°C | 21°C | 20°C | 16°C | 9°C | 3°C | -2°C |
Destinations to explore
- Montreal Vacation rentals
- Boston Vacation rentals
- Quebec City Vacation rentals
- Portland Vacation rentals
- Mont-Tremblant Vacation rentals
- Newport Vacation rentals
- Providence Vacation rentals
- Salem Vacation rentals
- York County Vacation rentals
- Bar Harbor Vacation rentals
- Cambridge Vacation rentals
- New Haven Vacation rentals
- Pemaquid Beach
- Coastal Maine Botanical Gardens
- Saddleback Ski Mountain Maine
- The Camden Snow Bowl
- Maine Maritime Museum
- Rockland Breakwater Light
- Camden Hills State Park
- Farnsworth Art Museum
- Maine Lighthouse Museum
- Cellardoor Winery
- Moose Point State Park
- Hollywood Slots Hotel & Raceway
- Black Mountain of Maine
- Belgrade Lakes Golf Club
- Range Ponds State Park
- Lost Valley Ski Area
- Sugarloaf Golf Club





