
Holiday rentals with a kayak in Portland
Find and book unique kayak rentals on Airbnb
Top-rated rentals with kayak in Portland
Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

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

Moss House: A Modern Waterfront Cabin in the Woods
Featured in VOGUE and Maine Home + Design, this modern, handcrafted cabin offers calm Atlantic views, 150 feet of shoreline, and a private dock, perfect for morning coffee, launching a kayak, or watching seals, seabirds, and passing boats. Set among tall pines, it blends Nordic and Japanese influences in a space that is calm and composed. Interiors of wood, stone, lime plaster, and concrete form a grounded, quietly expressive, and sustainably built retreat. 1hr from Portland, but a world apart.

Peaceful Cottage on Maine Flower Farm
Maine’s Peaceful Off-Season 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.

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.

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.

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!

Romantic New England Historic Schoolhouse c1866
Winner of Maine Homes Small Space Design Award 2023 We are located on the private 80-acre Shapleigh Pond in the Southern Maine, an hour from Portland and two hours from Boston. Experience a bygone era in this restored Schoolhouse circa 1866 with many original details such as oversized glass-paned windows, wood plank floors, chalkboards, tin ceiling and more. Modern amenities such as fireplace, private hot tub, fire pit, gas BBQ and access to our pool (June-Sept), pond and tennis court.

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.

Cozy log cabin on private pond, near Reid St Park!
Winter or summer, the Little River Retreat will help you step away from the world - but still be minutes from Reid State Park, Five Islands Lobster, the Georgetown General Store, and the rugged beauty of Midcoast Maine. This is our family camp, with our own books, games, and “vibe”. It is not a hotel, and some things may not be “industry standard”. We love the unique charm of this space and place, and many repeat guests do too. We hope you will treasure (and care for it) as we do!

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 kayak rentals in Portland
House rentals with a kayak

Hall Bay Haven

Mirror Pond Cottage

Oceanfront Luxury Estate in Mid-Coast Maine

Forest Lake Cottage

Luxury 6 bedroom Beach House 50 ft from beach

Kayak to the Causeway-50s cottage with modern vibe

Lakehouse on Highland Lake

Cozy Lakefront Cabin Near Portland
Cottage rentals with a kayak

Tranquil waterfront cottage

Coastal Waterfront Cottage in West Bath

Cozy camp near highland lake

Cozy waterfront home on Merrymeeting Bay.

RK North : All season Waterfront cottage with dock

The Loon's Nest Cottage

Covered Bridge Cottage - Maine woods and river

The Great Escape - Picturesque Sebago Lake
Cabin rentals with a kayak

McKeen's Riverside Retreat

Private pond | Sebago Lake Region | Romantic

Thompson Lake, No Cleaning Fee Pine Point Cottage,

Get away at Crystal Lake

Private cabin w hot tub,skiing,firepit & mountains

Peaceful & private waterfront cabin

Peaceful and Rustic Lakeside Cabin

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

Total holiday rentals
Explore 20 holiday rentals in Portland

Nightly prices starting at
Portland holiday rentals start at £75 per night before taxes and fees

Verified guest reviews
Over 1,320 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Wifi availability
10 of Portland holiday rentals include wifi access

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

4.8 Average rating
Portland stays are highly rated by guests – averaging 4.8 out of 5!

Nearby attractions
Portland’s top spots include Peaks Island, Portland Museum of Art and Crescent Beach State Park
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Montreal Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Québec City Holiday rentals
- The Hamptons Holiday rentals
- Capital District, New York Holiday rentals
- Island of Montreal Holiday rentals
- Jersey City Holiday rentals
- Flat rentals Portland
- Rentals with a patio Portland
- Cottage rentals Portland
- Private suite rentals Portland
- Rentals with a washing machine and dryer Portland
- Mansion rentals Portland
- Rentals with a firepit Portland
- Pet-friendly rentals Portland
- Beach house rentals Portland
- Rentals with a sauna Portland
- Villa rentals Portland
- Rentals with an EV charger Portland
- Fitness-friendly rentals Portland
- Cabin rentals Portland
- Boutique hotels Portland
- Family-friendly rentals Portland
- Rentals with outdoor seating Portland
- Rentals with pools Portland
- Beachfront rentals Portland
- Rentals with a fireplace Portland
- Apartment rentals Portland
- Townhouse rentals Portland
- Rentals with a hot tub Portland
- Rentals with beach access Portland
- House rentals Portland
- Rentals with breakfast Portland
- Waterfront rentals Portland
- Hotel rooms Portland
- Rentals with a kayak Cumberland County
- Rentals with a kayak Maine
- Rentals with a kayak United States
- Ogunquit Beach
- Sebago Lake
- Wells Beach
- Scarborough Beach
- Long Sands Beach
- York Harbor Beach
- Popham Beach State Park
- Popham Beach, Phippsburg
- Pemaquid Beach
- King Pine Ski Area
- Cranmore Mountain Resort
- East End Beach
- Pemaquid Point Lighthouse
- Willard Beach
- Short Sands Beach
- Gooch's Beach
- Coastal Maine Botanical Gardens
- Funtown Splashtown USA
- Wolfe's Neck Woods State Park
- Cape Neddick Beach
- Crescent Beach State Park
- Conway Scenic Railroad
- Palace Playland
- Bradbury Mountain State Park
- Things to do Portland
- Tours Portland
- Things to do Cumberland County
- Sports activities Cumberland County
- Sightseeing Cumberland County
- Food and drink Cumberland County
- Things to do Maine
- Tours Maine
- Nature and outdoors Maine
- Sports activities Maine
- Food and drink Maine
- Things to do United States
- Food and drink United States
- Sightseeing United States
- Sports activities United States
- Wellness United States
- Tours United States
- Nature and outdoors United States
- Art and culture United States
- Entertainment United States






