Family-friendly holiday rentals in Brooksville

Tiny House at Wooded Bliss Homestead

On the edge of our family homestead overlooking meadow & forest, this tiny house offers a quiet, cozy refuge only 40 minutes from Acadia National Park. There's a twin daybed on the ground floor & a double futon in the loft. Full kitchen & tiny bathroom with shower too. A heat pump keeps the place toasty warm or nice and cool. The tiny house and meadow are very private on the edge of the property, and just for you. Our family's gazebo, fire pit, hammock, trail & garden are shared with guests.

The Sailors Retreat - Waterfront Home with Kayaks!

Retreat to your own coastal oceanfront paradise, where each day begins with breathtaking views. A private boardwalk leads to your secluded beach — perfect for morning strolls, exploring tidal pools, or launching kayaks into sparkling waters. Evenings bring fireside marshmallows under the stars with waves as your soundtrack. Whether you seek adventure with scenic drives to Acadia National Park or quiet mornings with coffee, sea breezes, and seabirds, this is where comfort meets Maine’s coast.

Exquisitely Modern Maine Cottage @Diagonair

Romantic and secluded, this 2,000-sq-ft modern luxury cottage nestled on 12 private acres is a favorite of honeymooners and lovers of modern design * 1 hour to Acadia National Park & Bar Harbor; 15 min to shopping, hiking, swimming * 2 full baths, one with a steam shower * Fully equipped kitchen with Wolf stove and under-counter Sub-Zero fridge * Two gas fireplaces, one indoors, one on a covered deck * Queen bed with luxurious linens and pillows * WIFI, streaming TV, grill, bar * EV charger

Sea Pearl

This is a Water Front property, unique and tranquil getaway. Newly renovated 2025, this is a perfect spot for your serious fun. Located on water in Penobscot. Bird watchers take notice, watch the eagles soar over head out your door, visit the many islands & see the Puffins, Whale watch. Lots to do kayaking, hiking and lot more! Or just relax in a stunning natural setting on the hammock under the apple trees. Just a short drive to Acadia National Park & Bar Harbor. See you soon.

Blue Hill Bungalow with open, natural light

Newly finished single-floor home close to everything in Blue Hill. Open floor concept, large windows and view of Blue Hill itself from the front porch make this a comfortable place to hang out or base out of for day trips. Everything is within reach with either a short drive, a lovely walk or bike ride, including hiking trails, the ocean, Blue Hill mountain, restaurants, a coffee shop, and boutique shops, as well as the Blue Hill Co-Op and Tradewinds for your grocery needs.

Tiny house with AC!!

A tiny guest house (450 sq ft) overlooking the Benjamin River. AC!!. Enjoy a cup of coffee on your private porch. Living area has a smart tv (no cable, but internet available to access your streaming account). DVD's also available. Kitchenette comes with Keurig with k-cups included, mini fridge, coffee maker/filters, toaster oven, microwave, 2 burner hot plate (no oven), dishes/pots and pans. There is a loft with an army cot. Not suitable for children under age 5.

Penobscot River Views - Two Room Suite!

Two room suite on the first floor of my home with an en-suite private bathroom and views of the Penobscot River/Bay! ***Just under an hour drive to Acadia.*** Convenient access right on Route 1. A short walk to the Sandy Point beach park. Comfortable queen bed and sleep sofa. Two 40” HD TVs with Roku. Mini fridge, microwave, toaster oven and induction burner in room. Almost 400 SF of space! If you need more beds, please see my listing for the room upstairs.

Starry Artsy Garage Loft

Put your feet up and enjoy a cool refreshment on the deck after a long journey! This newly renovated, artsy 2-bedroom above garage apartment is a perfect spot for relaxation. It has its private entrance and dedicated parking. Our family and friends have created many wonderful memories here. We welcome you with our whole heart and hope you can also enjoy this little apartment as much as we do!

Sea Breeze Cottage in idyllic Castine Maine!

Sea Breeze Cottage, Castine, Maine Experience quintessential New England charm in this cozy Castine cottage. Freshly and tastefully renovated and only a short stroll from beautiful Fort Madison beach. Recharge your batteries and relax to the sound of the nearby bellbuoy! Discover all coastal Maine has to offer from the comfort of Sea Breeze Cottage!