
Vacation rentals with a kayak in Scarborough
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Top-rated kayak rentals in Scarborough
Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.

Privacy, River, Pond, A frame Hot Tub EPIC Views,
14 Acres Secluded A-frame nestled along Clean Crooked River, Hot tub with breathtaking VIEWS and world-class fishing. Swim in the river, private pond or explore hiking trails right from your door. Central AC - Gas Fireplace - Modern Kitchen. Just minutes from pristine lakes, primo golf courses, and thrilling ski slopes, this charming private oasis offers an ideal mix of tranquil relaxation and outdoor adventure. Invite a private chef, florist or yoga teacher to fully unwind. Heated bath floors.

Luxury Year-round Hobbit House w/ private hot tub
Fern Hollow 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.

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

Cozy waterfront home on Merrymeeting Bay.
Our cozy cottage is the perfect romantic getaway or quiet retreat in any season. Located on a private rd with scenic waterfront view. Guests can enjoy sitting on the dock (May- October) or the jetty, watch the eagles and Osprey, use our kayaks, do some fishing, walking or biking. Sit by the propane fueled fireplace on a chilly night. Brunswick, home of Bowdoin College and a # of great restaurants and unique shops is just 5 mi. Travel by bus or train to/from Boston. Portland is @ 30 min away.

Beautiful lakehouse 2.5 hours from Boston, 40 minutes from Portland
Beautiful lake living: 2.5 hours from Boston, 40 min. from Portland. This cozy 2-bedroom home on Lake Sabattus with 110 feet of private lake frontage, sleeps four. All the amenities of home incl. a SS kitchen with newer appliances, air conditioning. Minutes to Lewiston/Auburn - close to dining and stores. Spend your days swimming, canoeing, kayaking and fishing, use our grills or lobster pot to prepare your dinner and relax by the fire pit, toasting s'mores while watching the gorgeous sunsets.

Maine A-Frame with Hot Tub, Game Room, Lake Access
Escape the city and relax at Camp Merryweather. Our A-Frame is perfect for a romantic getaway or a family retreat with the kids and dogs welcome! If you’re a work from home professional looking to escape your normal routine, we’ve got you covered! With a fully equipped work space and reliable high speed internet you can break free from the pressures of the city while still staying connected. Enjoy our hot tub and game room Come experience our slice of heaven for yourself, you won’t regret it!

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.

Waterfront Gem walkable to Restaurants!
Waterfront Oasis on Pettingill Pond. You couldn't get any closer to the water, it's steps away. There are 3 Kayaks, and a paddleboat, firepit and dock for guest use! This a great spot for swimming and watersports! This home has been newly renovated, the effect results in a simple, stylish, comfortable space for guests to enjoy. Walk to Franco's Bistro for from Scratch Italian food, or Bob's Seafood for a fish taco! This is a piece of paradise on sweet Pettingill Pond in the heart of Windham.

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.

Beautiful lake-side home close to Portland Maine
A peaceful & charming renovated old home with private dock on Highland Lake, Falmouth Maine, 20 mins from Portland. *Contact us for longer winter availability! **June/July/Aug, Sat-Sat 7 day min Enjoy beautiful sunsets, canoeing, kayaking, paddle-boarding or fishing on the lake. Or take a short drive to downtown Portland, visit Old Port restaurants & bars, local breweries, Freeport outlet shopping, ski resorts, hiking and walking trails, golf courses, indoor/outdoor cinemas, and more!

Beautiful Kettle Cove Apt Steps to Beaches
Enjoy some of the Portland area’s finest 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.

Birch Ledge Guesthouse--Four Season Maine Getaway
Both rustic and elegant, the Birch Ledge Guest House offers a cozy place to relax and recharge, whatever the season. The first floor features a spacious living room (with queen sized pull-out-couch), dining area, and small kitchen. The bathroom has a walk-in shower. The second floor is a loft accessible by a spiral staircase and has a comfy queen and two twin sized beds. The guesthouse is surrounded by quiet forest and is an easy 30 minute drive to Portland.
Popular amenities for Scarborough kayak rentals
House rentals with a kayak

Mirror Pond Cottage

Lakefront Getaway

Rising Tide Times - quintessential Maine cottage

Fish Tales Cabin

Waterfront| Outdoor Sauna| Ski| Mountains| Firepit

Lakefront Home-Stunning Views-Hot Tub, 3100 sqft!

Historic Kennebunkport home .3 mile to Dock Square

Cozy Lakefront Cabin Near Portland
Cottage rentals with a kayak

Gorgeous Romantic Lakefront Getaway

Tranquil waterfront cottage

Cozy camp near highland lake

The Cozy Cottage at Loon Pond, Netflix

RK North : All season Waterfront cottage with dock

The Loon's Nest Cottage

Covered Bridge Cottage - Maine woods and river

Peaceful Cottage on Maine Flower Farm
Cabin rentals with a kayak

Cozy cottage near the lake

Lakefront Getaway Cabin/Private Sandy Beach!

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

Thompson Lake, No Cleaning Fee Pine Point Cottage,

Get away at Crystal Lake

Private cabin w hot tub,skiing,firepit & mountains

Peaceful and Rustic Lakeside Cabin

Barrett’s Cabin-Ski Pleasant Mountain
Quick stats about vacation rentals with a kayak in Scarborough

Total vacation rentals
Explore 20 vacation rentals in Scarborough

Nightly prices starting at
Scarborough vacation rentals start at ﺩ.ﺇ257 per night before taxes and fees

Verified guest reviews
Over 1,920 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Scarborough vacation rentals include wi-fi access

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

4.9 Average rating
Scarborough stays are highly rated by guests—averaging 4.9 out of 5!
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- Rentals with a kayak Cumberland County
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- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Long Sands Beach
- Scarborough Beach
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- Pemaquid Point Lighthouse
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- Funtown Splashtown USA
- Crescent Beach State Park
- Coastal Maine Botanical Gardens
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- Pleasant Mountain Ski Area
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- Palace Playland
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