Vacation rentals with a kayak in Scarborough

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Top-rated kayak rentals in Scarborough

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Guest favorite

The cabin's exterior is captured through a flickering flame, showcasing large glass windows that invite natural light. Surrounded by lush trees, the cozy structure features a modern design, blending seamlessly with the serene outdoors.

Home in Naples

4.99 out of 5 average rating, 146 reviews

LUX Designer Private Waterfront

Waterfront GLASS cabin with privacy professionally designed, escape to somewhere really special. Crooked river acres surrounding the house with the river wrapping around the property. Dock with direct access to Sebago lake and state park just minutes away, Outdoor shower, hot tub, hammocks, BIG walk-in shower w/ window. Heated bath floors, ac. See through Fireplace. The property has its own sandy swimming beach, pets are welcome. Come enjoy privacy and the space to run around seconds to Sebago.

Guest favorite

The three-story beach house features a prominent grey exterior with multiple large windows allowing natural light. A spacious patio is surrounded by landscaped greenery, offering seating areas with chairs and sun beds. Balconies extend from the upper levels, providing outdoor spaces with relaxing views.

Home in Old Orchard Beach

4.96 out of 5 average rating, 154 reviews

Luxury 6 bedroom Beach House 50 ft from beach

This has to be the Best looking house in Old Orchard Beach! Our Beach house is so close to the Ocean you can smell the salty air see & hear the small waves crashing. This 3 story home is ideal for families and friends reuniting & spending either a long weekend together off-season or a week together during the summer season. Located on a quiet, serene cul-de-sac street that leads on to Maine's best hidden treasure The beach! 15 min drive to Downtown Portland. Sleeps up to a maximum of 25 guests.

Top guest favorite

A single-story cottage is shown with a white wooden exterior and a grey roof. Multiple windows with a dark trim allow natural light in. A gravel pathway leads to the entrance, where a door is framed by steps. A dog rests on the grass nearby.

Cottage in Buxton

4.97 out of 5 average rating, 156 reviews

Peaceful Cottage on Maine Flower Farm

Overlooking the gardens at Ferris Farm, our family-owned specialty cut flower farm, this charming cottage offers a peaceful retreat to relax and reconnect with nature. Take in garden views, sip coffee on the deck, wander through the flowers, kayak the river, and end your day with a cozy bonfire under the stars. Use the cottage as your home base to explore beaches, or head into Portland for breweries, coffee shops, and great dining. Perfect for a solo retreat, romantic escape, or work getaway.

Guest favorite

A cozy living and dining area features comfortable seating, including a pair of light-colored armchairs and a round dining table. Soft lighting illuminates the space, and decorative accents, such as art and plants, create a welcoming atmosphere.

Apartment in Cape Elizabeth

4.92 out of 5 average rating, 652 reviews

Portland + Cape Elizabeth + Beaches + luxurious!

Permit210780 •Luxurious 3 rm apt with 1322 5* reviews! Only a mi to the beach & 4.4 mi to Portlnd - Location! •1st flr Great Rm to dine & relax: microwave, fridge, toaster, Keurig, TV, cooktop •2nd flr huge bathrm & bedrm for 2 w/ another sitting rm + a 2nd bdrm w/ 1 Q & 2 twins •More than 2 people? Alter reservation #’s for additional cost •2 people wanting 2 bedrms? Only add a $50 cleaning fee for 2nd bdrm •luxurious furnishings & superior bedding! •I am known for thinking of EvErYtHiNg ;-l

Top guest favorite

A wooden dock extends into the calm waters of Littlefield Pond, surrounded by lush greenery. The still surface of the water reflects the blue sky and trees, creating a serene atmosphere. Delicate plants can be seen in the water near the dock, enhancing the natural beauty.

Treehouse in Sanford

4.9 out of 5 average rating, 539 reviews

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.

Guest favorite

A modern kitchen is presented with light green cabinetry and a dark countertop. A wooden table with stools is set for dining, adorned with decorative elements. Stainless steel appliances, including a refrigerator and stove, are visible. Natural light enters through a nearby window, enhancing the vibrant space.

Guest suite in Scarborough

4.88 out of 5 average rating, 162 reviews

Moose Creek Lodge & Cabin

Located 5 mi. from Pine Point Beach in Scarborough near kayaking and Frith Farm with fresh food & pick-your-own flowers. Close to Portland, Portland Head Light, L.L. Bean, or Kittery outlets; 3-hrs to Acadia National Park. Hosts live in an upper Suite in the house with separate entrances. Lower Suite includes (kitchen, 1 bath), salt-water Hot Tub, picnic table, Cabin, & parking next to the house surrounded by beautiful gardens & woods. VACATIONLAND! Dogs allowed but not cats due to allergies.

Top guest favorite

A serene waterfront scene features a small boat gliding across calm waters, reflecting the surrounding buildings. A cluster of white cottages stands on pilings, with a dock visible, under a soft pastel sky as day transitions to evening.

Cottage in Brunswick

5 out of 5 average rating, 180 reviews

Lobstermen's ocean-front cottage

Be our guests & experience the life & beauty of Midcoast Maine. Relax & enjoy the views, warm up in the sauna or go for a refreshing dip. The cottage is part of an over 100 year old working lobstering, and now oyster farming property we call, Gurnet Village. Located right on historic Route 24, we are conveniently situated between Brunswick & the islands of Harpswell. All rooms have ocean views. The tidal beach & the floating dock (May-Dec) is ideal for seasonal fishing, lounging & swimming.

Top guest favorite

An aerial view captures a custom-built home nestled within a dense wooded landscape. Surrounding trees create a natural border, while the waters of Harraseeket Cove are visible, showcasing the blend of forest and coastal scenery.

Guest suite in Freeport

4.97 out of 5 average rating, 245 reviews

Waterfront Private Apartment just 5 min to LLBean!

Guest apartment with private entrances, king bed, pull out sofa, kitchenette, walk-in shower, and porch facing the water providing the perfect relaxing coastal Maine experience! Custom built home on 8 acres tucked away in the woods with waterfront access to Harraseeket Cove & South Freeport Harbor, great for kayaking! Located 5 minutes from LL Bean and Freeport's many shops, restaurants, bars, etc. Wolfes Neck State Park and its stunning coastal trails and forests are less than a mile away.

Guest favorite

Four wooden lounge chairs are arranged around a small table on a grassy lawn, overlooking a rocky shoreline. The calm ocean stretches into the distance, framed by a clear sky with soft clouds.

Home in Harpswell

4.95 out of 5 average rating, 135 reviews

Brand new Scandinavian cottage: dock & kayaks!

Brand new architectural cottage and detached 'boathouse' with sweeping elevated ocean views both east and west, private waterfront lawns and deep water dock with kayaks. This property was built in 2020 so expect a fresh and clean experience on one of Harpswell's most private peninsulas. Watch the sunrise from the cantilevered 2nd floor deck, sit by the campfire on your private lawn oceanside, or walk down to the dock for a paddle in the west facing protected cove. The best of coastal Maine!

Top guest favorite

The modern lakehouse structure is framed by tall trees, featuring large windows that provide ample natural light. A spacious deck is equipped with lounge chairs and picnic tables, while the lower level includes a hot tub. A clear lawn extends towards a serene backdrop.

Home in Oxford

5 out of 5 average rating, 213 reviews

The Modern Lakehouse

This modern lakehouse is situated on Hogan Pond in Oxford Maine. Here you can stay with all the comforts of a beautiful lakehouse built in 2020 while being feet from the water. This is a great place to vacation whether you prefer the private sandy beach, the A/C inside complete with Smart TV cable and Wifi, or the hottub! Sip a drink at the bar while watching the game or use the grill on the deck but be sure to use the built in sound system to play your music throughout the house and deck.

Top guest favorite

A spacious yard features a hammock set up for relaxation, accompanied by a fire pit area. The light yellow house stands in the background, offering multiple levels and direct access to outdoor spaces. Lush greenery surrounds the property, contributing to a serene outdoor setting.

Guest suite in Westbrook

4.93 out of 5 average rating, 248 reviews

Awesome open space in Westbrook near Portland, ME!

Welcome!! We're excited to share our house with you! You'll get the whole ground level of the house - two very large clean modern rooms with a private entrance, bathroom, and direct yard access to the hammock, fire pit, and wildlife. Off-street parking for 2 cars, kitchenette, fast wifi, smart TV, heat or A/C, and much more! We will give you awesome tips on everything in the area and beyond! 15 mins downtown Portland (Uber/Lyft available) 1 mile from I-95 11 mins from the airport

Top guest favorite

A bright living room features a gray sofa with orange accent pillows, paired with an orange armchair and matching ottoman. Natural light streams in through large windows, illuminating the hardwood floor and a circular woven area rug that adds texture to the space.

Apartment in Cape Elizabeth

4.98 out of 5 average rating, 118 reviews

Beautiful Kettle Cove Apt Steps to Beaches

Enjoy some of the Portland area’s best destinations year-round. This sunny, 1 BR ground floor apt in Cape Elizabeth has seasonal water views and is nestled between Kettle Cove, Crescent Beach, and Two Lights State Parks. Fields, forests and ponds are a stroll away while downtown Portland is an easy 15-minute drive. The apartment is a great base to explore Southern Maine from and an equally great location to chill out and soak in coastal Maine’s restorative water and air.