Holiday rentals with a kayak in Scarborough

Luxurious 5 bedroom on the ocean, w/ dock & kayaks

Historic 1735 home on a spacious one-acre property overlooking the ocean. Enjoy swimming from the dock in Cape Porpoise’s protected cove. Two kayaks provided for exploring the lighthouse & picnicking on nearby islands. Stroll past picturesque lobster boats to the town pier, where restaurants serve fresh local lobster & drinks. Walk to morning coffee, pastries, a local grocery store, athe renowned Nunan’s Lobster Hut. Just two miles from Kennebunkport and a nine-minute drive to Goose Rocks Beach.

Value · Outdoor spaces · Nearby

Portland & Beach & Lighthouses! Romantic! Lovely

Location! You get the BEACH + Portland in minutes! HUGE BEDRM Romantic canopy bed w/ lux linens Chaise lounge couch turns into twin bed TV Giant mirror for weddings etc 35’ Great Rm w/ TV Kitchen *quality pots etc New Q Sofa Bed Priv entrance Beachy Light filled tall ceilings Spacious for 2-can fit 5 pond/bridge firepit 2 decks+patio Teak Furniture Open views New bthrm A/C Parking No stairs/Garden Level All in Cape: Crescent Beach 2 Lights State Pk Portland Headlight Prtlnd 8 min! 210780

Outdoor spaces · Location · Parking

Historic Kennebunkport home .3 mile to Dock Square

Under 10 min walk to Dock Square, 2 min walk to Kennebunk River. Luxury linens, Casper pillows, SandCloud towels, Malin + Goetz toiletries, well-appointed kitchen and beach chairs included in your stay. 2 bikes & 2 kayaks available. Walk to Colony Beach, bike to Kennebunk Beach. 2 min walk to Perkins Park on the River, steps down to water for launching kayaks. Dock Square is a vacationer’s dream. Stroll along Ocean Ave on the water or grill fresh seafood on the cozy porch. 420 friendly outside

Outdoor spaces · Value · Bathroom

Luxury Year-round Treehouse with private hot tub

The Canopy is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

Value · Outdoor spaces · River

Beautiful Kettle Cove Apt Steps to Beaches

This sunny, 1 BR ground-floor apartment in Cape Elizabeth has seasonal water views and is nestled between Kettle Cove, Crescent Beach, and Two Lights State Parks. Fields, forests, beaches and ponds are a stroll away, while downtown Portland is an easy 15-minute drive. The apartment is a great base for exploring Southern Maine and an equally great place to simply soak in the restorative water and air of coastal Maine. Get one free sauna session in Kettle Cove Sauna, subject to availability.

Location · Outdoor spaces · Decor

Charming Historic Freeport House

Bring the whole family to this historic house just minutes from downtown Freeport and the LL Bean flagship stores. The cozy central kitchen and dining are flanked by two separate living rooms making plenty of room for fun and relaxation! With two twin beds, toddler bed and full-sized crib we can accomodate any family. Catch glimpses of the Harraseeket River from this updated 1840s home on a half acre. A wonderful jumping off point for both Portland and the natural beauty of Mid-coast Maine!

Location · Outdoor spaces · Access

#2Marsh Views, Cozy quiet spot on river&preserve

Enjoy this 2nd floor getaway in this totally quiet & cozy spot with beautiful sunrises and awesome views off the back deck. Close to beaches and town but far enough away to be secluded from the hecticness. Lots of nature trails very close by. Roads have bike/ walking lanes. Many fresh seafood restaurants & eateries close by. Kayaks & bikes for use are available. Free parking on site. Enjoy a complimentary bottle of wine when you visit. **(Waivers must be signed for kayak & bike usage)

Outdoor spaces · Value · Cleanliness

LUX Designer Private Waterfront Hot Tub - Secluded

Escape to a luxurious, privately designed glass-walled waterfront cabin on 3+ secluded acres along the Crooked River in Naples, Maine. The river wraps around, offering total privacy, your own sandy beach, dock with direct Sebago Lake access, and state park minutes away. Unwind in the year-round hot tub, outdoor shower, hammocks, or by the see-through fireplace. Luxe bath with heated floors, huge walk-in shower w/ scenic window. AC, pets welcome. Perfect peaceful retreat—come recharge!

Value · Location · Layout

The Loon's Nest Cottage

Located only 30 minutes from Portland this adorable and cozy cottage sits 10 feet from Watchic Lake. Listen to the loons all day, paddle to an island, stare at the glassy lake from the breakfast nook, swim forever, read a book in the screened-in porch or toast marshmallows in the firepit, whichever it may be you'll simply enjoy the peace and tranquility of this very private Maine lake house nestled in the woods. If you’re feeling like a hike, a dinner out there are options a plenty!

Location · Outdoor spaces · Comfort

Lakefront Getaway

Looking for a quiet peaceful getaway? Our Maine post and beam home is set on 7 acres of lake front. Great getaway to enjoy marshmallows and a roaring fire, kayaking, canoeing, swimming, boating or enjoy a great movie. For downhill skiers proximity to King Pine, Sunday River, Shawnee Peak and Black Mountain. Cross country and snow shoeing on property and on the lake. If you have a snow mobile- great trails available. Finally, great shopping in nearby North Conway at the outlets.

Outdoor spaces · Value · Cleanliness

Peaceful Cottage on Maine Flower Farm

Maine’s Peaceful Escape Nestled next door to Ferris Farm, our family-run flower farm, this charming cottage offers a private place to rest and recharge. Enjoy slow, coffee-filled mornings, quiet walks, and cozy evenings by the fire pit. Use the cottage as your home base to explore nearby beaches (30 minutes) or head into Portland (35 minutes) for breweries, coffee shops, and great dining. Perfect for a couple retreat, solo escape, or remote work getaway, with dedicated workspace.

Value · Outdoor spaces · Hiking

Rustic, cozy cabin on Sebago Lake. A hidden gem.

Step out of the screened in patio to lakeside relaxation. Dive into crystal waters, snorkel or float with a cool beverage. Kayak or canoe out to Turtle Cove and enjoy the wildlife in this natural waterway teeming with birds to include our resident Blue Heron, ducks, geese, and loons who make this place their home. We have the fortune of bald eagles in several tall pines. Turtles sunning on doting rocks and lily pads in bloom greet us each day. It is a natural water landscape.

Location · Outdoor spaces · Wi-Fi