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Family-friendly vacation rentals in Raymond

Find and book unique family-friendly homes on Airbnb

Quick stats about vacation rentals that are family-friendly in Raymond

  • Total vacation rentals

    Explore 230 vacation rentals in Raymond

  • Nightly prices starting at

    Raymond vacation rentals start at G$31,380 GYD per night before taxes and fees

  • Verified guest reviews

    Over 6,460 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 90 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    100 properties have a dedicated workspace

  • Wi-Fi availability

    220 of Raymond vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Raymond rentals

  • 4.9 Average rating

    Raymond stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated family-friendly rentals in Raymond

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite
A serene lake view is depicted, showcasing calm waters reflecting the sky and surrounding trees. A private dock is visible at the water’s edge, adding to the tranquil atmosphere. The natural landscape features a variety of green hues from the trees lining the shore.
Cottage in Raymond

Relax by a Quiet Lake

Charming lakeside cottage only 29' from the water on Panther Pond, w/65' of private waterfront. The cottage is a 3-season, classic L.C. Andrews log-sided Maine summer lake home. Cozy atmosphere and a wonderful enclosed porch with amazing waterfront views. Enjoy fishing off the dock, hiking, canoeing, campfire, and exploring surrounding areas. Air conditioning units will ensure your comfort on warm summer nights and high-speed internet will keep your devices connected. Furnishings are family mix.

4.93 out of 5 average rating, 137 reviews
Guest favorite
The master bedroom features a spacious bed with light-colored bedding, complemented by soft pink pillows. Natural light floods the room through sliding glass doors leading to the outdoor area. A rustic barn door adds character and provides access to the adjacent bathroom.
Home in Casco

Fully Updated Lake View Home on Thomas Pond

Full of light and thoughtful touches, this lake view home on Thomas Pond is perfect for your Sebago Lake getaway. Spend your evenings relaxing or entertaining on the spacious deck and days on the water. Enjoy boating, fishing, swimming and kayaking with access to two association beaches and a boat launch across the street. Perfect for family fun and couples' retreats, this home is a fantastic home base to explore the Lake Region. Minutes to North Windham shopping and 30 minutes to Shawnee Peak.

4.87 out of 5 average rating, 106 reviews
Top guest favorite
A serene waterfront scene is presented, showcasing a calm lake framed by trees. In the foreground, a small dock extends into the water alongside a moored boat. Rocky shorelines feature boulders partially submerged, adding to the natural beauty of the landscape.
Guest suite in Raymond

Sebago Lake Waterfront Studio

Beautiful Lakehouse studio apartment located on Sebago Lake. A perfect spot to take in the gorgeous lake view w/sandy beach. The lake is great for swimming, boating, kayaking, and water activities. Backyard to enjoy lawn games, grill, and relax by the outdoor fire-pit. This space has a cozy modern feel, for a perfect summer vacation or fall leaf-peeping. Located within 40 minutes of Portland and the beautiful Maine coast. This space is furnished to sleep 4. Dock available for $100 per stay.

4.96 out of 5 average rating, 105 reviews
Top guest favorite
A bright living space features a comfortable dark sofa facing a small wooden coffee table. A round dining table with two chairs is visible in the background. Large windows allow natural light to fill the room, complemented by pale curtains and wooden flooring.
Cottage in Windham

The Purple House by Pettingill Pond

Welcome to Maine. The way life should be! The Purple House (bc the paint color is a happy shade of light purple) is 2 floor home ACROSS the gravel road from Pettingill Pond. Less than 100 ft away from the dock with SHARED access with two super friendly neighbors in the Summer. As a guest of this house you have access to this pond where it is perfect for swimming, rowing, kayaking, canoeing, paddle boarding, boating, floating, ice skating, & snow shoeing. Quick 5 mins from the city center!

4.9 out of 5 average rating, 102 reviews
Top guest favorite
Home in Oxford

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.

5.0 out of 5 average rating, 248 reviews
Guest favorite
A scenic view of a tranquil lake is captured, with a boat dock extending into the water. A boat is anchored near the dock, surrounded by lush greenery. A picnic table sits on sandy ground nearby, inviting relaxation by the lakeside.
Cottage in Gray

Edgewater Retreat - Lakefront w/Sauna & EV Charger

Welcome to Edgewater Retreat! This custom-built cottage features lakefront views and access to three beaches: secluded pocket beach in front of cottage, boaters beach with docks, and a full sun sandy bottom swim beach. Enjoy an unforgettable Maine vacation. Paddlecraft on the water, lounge in the hammocks, S'mores by the campfire, canoe to nearby island for offshore yoga, and gril with friends & family. In winter, enjoy ice fishing and kids enjoy snow sledding on adjacent hill.

4.81 out of 5 average rating, 120 reviews
Guest favorite
Home in Naples

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!

4.98 out of 5 average rating, 200 reviews
Top guest favorite
Treehouse in Pownal

The Copper Fox Treehouse

Named the 10th most spectacular tree house in the world by the BBC Featured in the book: Modern Tree Houses by Taschen Airbnb's Most wishlisted property in Maine in 2025! Come experience the whimsy and craftsmanship of this red fox head shaped treehouse for yourself. The magic of this wild adventure awaits you in the treetops... Come to relax, explore and make lasting memories your family and friends will talk about for years. Follow our journey on IG at @thecopperfoxtreehouse

4.99 out of 5 average rating, 199 reviews
Top guest favorite
Two wooden chairs are situated on a dock overlooking a calm pond surrounded by dense trees. The water reflects the sky and greenery, creating a serene backdrop. A sense of tranquility is conveyed through the peaceful atmosphere of the natural setting.
Home in Oxford

Mirror Pond Cottage

A sweet space on a pond, this cottage is perfect for those looking for a quiet getaway. We offer swimming, kayaks and a canoe, life jackets along with a raft to float on. Endless fun in the water, with no motors to be heard. This is a quiet spot and we would hate to be responsible for ruining that. We are family friendly and kids are welcome, but please leave the party at the casino (5 minutes away)! The waterfront is sandy and shallow, perfect for young ones to splash around in.

4.92 out of 5 average rating, 150 reviews
Top guest favorite
A serene lakeside view reveals a wooden dock with a reclining chair near the water's edge. Vibrant autumn leaves frame the scene, contrasting with the clear blue sky and calm lake. Rocky terrain adds natural texture to the tranquil environment, inviting relaxation.
Cabin in Raymond

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.

4.93 out of 5 average rating, 184 reviews
Guest favorite
The living area features high, wooden ceilings with exposed beams and large windows, allowing natural light to flood the space. A stone fireplace serves as a focal point, while a cozy seating area is complemented by a dining table surrounded by red chairs.
Home in Naples

Best Ski & Lake House

Spectacular, expansive, state-of-the-art log cabin—your ultimate four-season escape. Winter ski trips (just 25 minutes to Pleasant Mountain, formerly Shawnee Peak), summer fun (beaches & watersports galore), & unforgettable year-round gatherings. Chef’s kitchen with two ovens, dining for eight + bar seating, sleeps up to 12 (with 2 king beds), two living rooms, and abundant outdoor dining & lounge space, including a playground - designed to make lasting memories!

4.94 out of 5 average rating, 140 reviews
Guest favorite
A charming waterfront cottage is presented with a bright blue door and two red chairs on a stone patio. Lush greenery surrounds the property, enhancing its inviting exterior. The tranquil waters of Pettingill Pond can be seen in the background, reflecting the sky.
Home in Windham

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 Lakeside Tavern, or Bob's Seafood for a fish taco! This is a piece of paradise on sweet Pettingill Pond in the heart of Windham.

4.95 out of 5 average rating, 204 reviews

Popular amenities for Raymond family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top guest favorite
A spacious deck is shown, featuring a hot tub and a dining table surrounded by several chairs. An umbrella provides shade over the seating area, while comfortable outdoor furniture is arranged for relaxation. Lush green trees are visible in the background.
Vacation home in Windham

Sebago Lakehouse: Hot Tub and Private Beach Access

4.99 out of 5 average rating, 108 reviews
Top guest favorite
The exterior of a red barn-style home is surrounded by lush greenery and colorful flower beds. A patio setup includes comfortable seating, a dining table with an umbrella, and a fire pit on a pebbled area, providing an inviting outdoor space.
Home in New Gloucester

The Barnhouse with hot tub

4.97 out of 5 average rating, 208 reviews
Top guest favorite
Tiny home in New Gloucester

Tiny house in the Birch Grove with private HOT TUB

4.94 out of 5 average rating, 287 reviews
Top guest favorite
An open space features a vaulted wooden ceiling with beams and skylights. A cozy seating area includes a brown sofa and a modern coffee table. A wood stove adds warmth, while a well-equipped kitchen with dark green cabinets is visible in the background.
Tiny home in Freeport

Cozy Rock Cabin #thewaylifeshouldbe

4.99 out of 5 average rating, 394 reviews
Guest favorite
Two houses are positioned near the water, showcasing a floating dock and a water trampoline. The exterior features a large deck with seating beneath trees, while lights illuminate the windows of the main house, hinting at a cozy interior with a welcoming atmosphere.
Home in Casco

Exceptional Private Lakefront Retreat | Hot Tub, S

4.92 out of 5 average rating, 108 reviews
Top guest favorite
A hot tub is positioned on a spacious deck, offering a stunning view of a mountain during sunset. The scenery features a blend of warm hues in the sky, with gentle slopes visible in the background. Steps lead up to the hot tub, enhancing accessibility.
Home in Bridgton

*1MMview*Bar,Hot Tub,3mins2Pleasant Mnt, Pool tab.

4.95 out of 5 average rating, 174 reviews
Guest favorite
The modern cabin features a sleek design surrounded by lush greenery. Soft bistro lights create a warm glow, illuminating the outdoor seating area with two Adirondack chairs. The deck can be seen in the background, enhancing the inviting atmosphere of the natural setting.
Cabin in Freeport

Romantic hideaway cabin w/ access to spa - 26

4.96 out of 5 average rating, 125 reviews
Top guest favorite
A hobbit house is nestled among lush green trees, with a sloping earth-covered roof adorned with grass and ferns. The rounded front features a large window framed in white, complemented by a natural stone border, emphasizing the home's connection with its woodland surroundings.
Earthen home in Sanford

Luxury Year-round Hobbit House w/ private hot tub

4.92 out of 5 average rating, 132 reviews

Family- and pet-friendly home rentals

Top guest favorite
A modern kitchen is equipped with a stainless-steel microwave and stove beneath a stylish backsplash. The countertop features a sink and invites meal preparation. A comfortable nook with a raised twin bed can be seen in the background, surrounded by decorative plants.
Guest suite in Freeport

Studio Apartment in Freeport

4.97 out of 5 average rating, 148 reviews
Top guest favorite
A wooden dock extends toward calm water, with a gentle sloping pathway leading down from the boathouse. The clear water reveals stones at the bottom, while green trees frame the picturesque lakeside view.
Guesthouse in New Gloucester

On the water Boathouse!

4.9 out of 5 average rating, 178 reviews
Top guest favorite
A relaxing outdoor area is shown, featuring several seating options around a fire pit. Two cabins can be seen, with one situated on a hill and the other by the water. A sun umbrella provides shade, surrounded by trees and nature.
Chalet in Standish

Blueberry Hill

4.96 out of 5 average rating, 263 reviews
Top guest favorite
A rustic white barn with a grey roof is nestled within a field of tall grasses and wildflowers. Autumn foliage in shades of red and gold decorates the surrounding trees, offering a tranquil rural landscape. A separate red cottage is visible in close proximity.
Guesthouse in Denmark

Red Shed Cottage at Pickett Hill Farm

4.96 out of 5 average rating, 105 reviews
Top guest favorite
A welcoming living area is furnished with two dark sofas adorned with vibrant orange cushions. A rustic coffee table is centered on a colorful area rug, while large windows allow natural light to fill the space, highlighting the wall art above.
Home in Portland

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

4.96 out of 5 average rating, 179 reviews
Guest favorite
Cabin in Oxford

3BR Lake View Cabin~Fire Pit~Deck~Casino Nearby

4.96 out of 5 average rating, 114 reviews
Top guest favorite
The modern two-story home is surrounded by lush greenery, featuring large windows that invite natural light. A covered porch with comfortable seating offers a relaxing view of the expansive lawn. Tall trees provide shade, enhancing the serene outdoor atmosphere.
Home in Raymond

37(A) Shore Rd, Raymond ME

4.97 out of 5 average rating, 30 reviews
Guest favorite
A charming home nestled among trees, with a spacious deck extending from the front. Large windows offer views of the serene surroundings, while a pathway leads from the house to the water's edge. The exterior features a mix of natural elements and a carefully maintained yard.
Cottage in Raymond

The Great Escape - Picturesque Sebago Lake

4.91 out of 5 average rating, 67 reviews

Family-friendly home rentals with a pool

Guest favorite
The spacious loft is highlighted by 16-foot ceilings and multiple skylights. A queen bed is positioned near a cozy seating area, complemented by a wooden dining table. Eye-catching artwork adorns the walls, and natural light fills the room through large windows.
Loft in Falmouth

Loft Apartment on Tree-Lined Street in Falmouth

4.95 out of 5 average rating, 702 reviews
Top guest favorite
A spacious suite is showcased with large windows allowing natural light. A comfortable couch faces a marble-topped coffee table, and a custom-built king bed is nestled against a natural pine headboard. The decor reflects minimalism, offering a peaceful setting for relaxation.
Apartment in Portland

Luxury Retreat In Back Cove | 10 Min to Downtown

5.0 out of 5 average rating, 116 reviews
Top guest favorite
The living area is highlighted by a spacious sectional sofa and a wooden spiral staircase leading to the upper level. Natural light fills the space, accentuating the wooden flooring and cozy decor. A coffee table sits centrally, complementing the overall inviting atmosphere.
Condo in Bartlett

An Amazing Mountain Getaway!

4.94 out of 5 average rating, 341 reviews
Top guest favorite
Place to stay in Shapleigh

Historic Schoolhouse c1866 + Pool + Lake + Hot tub

5.0 out of 5 average rating, 145 reviews
Top guest favorite
The outdoor area features a circular pool surrounded by reclining lounge chairs with blue and white stripes. A stone patio is adorned with a wooden table and chairs, while lush greenery and flowering shrubs frame the scene under a clear blue sky.
Guest suite in Portland

Resort-like 2 bed/1 bath - seasonal pool/hot tub

4.93 out of 5 average rating, 147 reviews
Guest favorite
A welcoming living area features warm wood flooring and natural light from multiple windows. Comfortable seating includes a sofa and chairs arranged around a central table. A ceiling fan provides gentle airflow, while double French doors lead to an outdoor space.
Guest suite in Standish

Steep Falls Escape, river & falls just steps away

4.92 out of 5 average rating, 125 reviews
Top guest favorite
Apartment in Portland

Apt in Victorian Mansion w/ Hot Tub & Parking

4.98 out of 5 average rating, 525 reviews
Guest favorite
A warm living and dining area features a wooden dining table surrounded by five chairs, a stone fireplace, and a comfortable seating arrangement with a brown sofa. Large windows allow ample natural light, complemented by a rustic chandelier overhead.
Condo in Conway

Elevate Your Adventure: Book Slope side Now!

4.84 out of 5 average rating, 122 reviews

When is the best time to visit Raymond?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$68,199 GYDG$67,990 GYDG$71,965 GYDG$67,990 GYDG$67,781 GYDG$71,546 GYDG$80,542 GYDG$81,588 GYDG$63,806 GYDG$60,668 GYDG$66,525 GYDG$66,735 GYD
Avg. temp-6°C-4°C1°C6°C12°C18°C21°C20°C16°C10°C4°C-2°C

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