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Family-friendly vacation rentals in Raymond

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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$31,381 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.

FamilyIndoor spacesPool

4.93 out of 5 average rating, 135 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.

FamilyKitchenLong stay

4.87 out of 5 average rating, 104 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.

KitchenIndoor spacesAccess

4.96 out of 5 average rating, 104 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!

KitchenFamilyCheckout

4.9 out of 5 average rating, 101 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.

Indoor spacesFamilyComfort

4.82 out of 5 average rating, 119 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!

Indoor spacesFamilySleep quality

4.97 out of 5 average rating, 197 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!

In the water! Two story boathouse. Originally built in 1939 and parked boats in until 1972. Converted to living space in the early eighties. The upstairs consist of a bedroom walk in closet and a balcony. The downstairs is a living room, kitchen and bathroom. Walk out the door to the patio , dock , and beach! You won't find anything closer to the water! The balcony is the perfect place to watch the sunset, thunderstorms, or sip your morning coffee. Watch the fish out the window!

FamilyIndoor spacesParks

4.9 out of 5 average rating, 175 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

KitchenIndoor spacesBathroom

4.99 out of 5 average rating, 195 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.

FamilyIndoor spacesCheckout

4.92 out of 5 average rating, 146 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.

KitchenFamilyHospitality

4.93 out of 5 average rating, 182 reviews
Top guest favorite
A cozy fire pit area is situated near the water's edge, surrounded by tall trees. Adjacently, five colorful adirondack chairs offer seating for gatherings. A serene view of the lake and a private dock can be seen in the background, providing a tranquil backdrop.
Chalet in Naples

The Chalet~ 4 bed Lakefront Family Vacation

Welcome to your secluded slice of paradise on the shores of Sebago Lake! Nestled amidst towering pines and overlooking the tranquil waters of Seabgo Cove, our 4-bedroom waterfront chalet promises a serene escape like no other. Whether you're seeking adrenaline-pumping thrills from the local excursions, or peaceful moments surrounded by nature and a book, The Chalet offers endless opportunities for unforgettable experiences and cherished memories in the heart of Naples.

FamilyKitchenCondition

4.96 out of 5 average rating, 124 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!

FamilyIndoor spacesBackyard

4.94 out of 5 average rating, 140 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

Indoor spacesKitchenAir conditioning

4.99 out of 5 average rating, 106 reviews
Top guest favorite
Home in Oxford

The Modern Lakehouse

FamilyKitchenQuiet

5.0 out of 5 average rating, 245 reviews
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

Indoor spacesFamilyLaundry

4.97 out of 5 average rating, 203 reviews
Top guest favorite
Home in Bridgton

Family & Friends Retreat*Hot Tub*Game Room*King Be

FamilyIndoor spacesParking

4.99 out of 5 average rating, 138 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

Indoor spacesFamilyAccess

4.99 out of 5 average rating, 389 reviews
Top guest favorite
Cabin in Norway

Secluded Cabin: Mountain View, Hot Tub + Fireplace

FamilyIndoor spacesBathroom

5.0 out of 5 average rating, 103 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

Indoor spacesFamilyHot tub

4.93 out of 5 average rating, 107 reviews
Guest favorite
Bus in Durham

Solar Powered Bus in Forest | Hot Tub + Wellness

FamilyIndoor spacesAccuracy

4.9 out of 5 average rating, 145 reviews

Family- and pet-friendly home rentals

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

FamilyIndoor spacesHospitality

4.96 out of 5 average rating, 261 reviews
Top guest favorite
A wooden treehouse with large windows and a spiral staircase is surrounded by lush green trees. The structure is elevated, allowing for a view of the forest floor, which is covered in natural earth tones from fallen leaves and pine needles.
Treehouse in Sanford

Luxury Year-round Treehouse with private hot tub

Indoor spacesFamilyLong stay

4.91 out of 5 average rating, 602 reviews
Superhost
A gravel path leads to a charming two-story house surrounded by lush greenery. Three goats are seen walking along the path, accompanied by a person in casual attire, creating a serene rural scene. The lawn features various plants and a few large rocks.
Farm stay in Gray

Great Goat Get-away in Southern Maine!

KitchenFamilyCheckout

4.93 out of 5 average rating, 321 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

KitchenFamilySkiing

4.96 out of 5 average rating, 102 reviews
Top guest favorite
An aerial view captures a secluded log cabin surrounded by lush greenery on a private island. A wooden dock extends over the tranquil water, providing access to the cabin, which is nestled among trees. Sunlight glistens on the lake's surface.
Island in Monmouth

Naughty Dog Private Island Log Cabin

Indoor spacesKitchenSleep quality

4.98 out of 5 average rating, 274 reviews
Top guest favorite
The cottage features a charming exterior with a wrap-around porch, complemented by wooden siding and decorative string lights. Tall trees provide shade around the property, creating a sense of tranquility. The house showcases multiple windows, allowing for natural light to brighten the interior.
Cottage in Bridgton

True Maine Artist Cottage with Outdoor Shower

FamilyIndoor spacesBathroom

4.91 out of 5 average rating, 222 reviews
Top guest favorite
Home in Raymond

Renovated New Waterfront Cottage on Crescent Lake!

FamilyIndoor spacesBathroom

4.89 out of 5 average rating, 9 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

KitchenFamilyCheckout

4.91 out of 5 average rating, 67 reviews

Family-friendly home rentals with a pool

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!

Indoor spacesKitchenValue

4.97 out of 5 average rating, 174 reviews
Top guest favorite
Home in Old Orchard Beach

OOB Oasis: 6BR Home w/ Private Pool Near Beach

FamilyIndoor spacesLaundry

4.95 out of 5 average rating, 155 reviews
Guest favorite
Cabin in Freeport

A-frame w/ huge window, half-bath, and deck - 16

Indoor spacesFamilyLocation

4.96 out of 5 average rating, 117 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

Indoor spacesKitchenNearby

5.0 out of 5 average rating, 113 reviews
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

Indoor spacesFamilyCheck-in

4.95 out of 5 average rating, 700 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

Indoor spacesFamilyLong stay

4.92 out of 5 average rating, 125 reviews
Top guest favorite
Place to stay in Shapleigh

Historic Schoolhouse c1866 + Pool + Lake + Hot tub

KitchenFamilyHiking

5.0 out of 5 average rating, 140 reviews
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

Indoor spacesKitchenAmenities

4.93 out of 5 average rating, 146 reviews

When is the best time to visit Raymond?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$68,200 GYDG$67,991 GYDG$71,966 GYDG$67,991 GYDG$67,782 GYDG$71,548 GYDG$80,544 GYDG$81,590 GYDG$63,807 GYDG$60,669 GYDG$66,527 GYDG$66,736 GYD
Avg. temp-6°C-4°C1°C6°C12°C18°C21°C20°C16°C10°C4°C-2°C

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