
Family-friendly holiday rentals in Raymond
Find and book unique family-friendly homes on Airbnb
Quick stats about holiday rentals that are family-friendly in Raymond

Total holiday rentals
Explore 230 holiday rentals in Raymond

Nightly prices starting at
Raymond holiday rentals start at $256 NZD per night before taxes and fees

Verified guest reviews
Over 6,460 verified reviews to help you choose

Pet-friendly accommodation
Find 90 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
100 properties have a dedicated workspace

Wi-Fi availability
220 of Raymond holiday 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.

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.
Indoor spacesKitchenCleanliness

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.
Indoor spacesKitchenAir conditioning

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.
KitchenFamilyCheck-in

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.
KitchenIndoor spacesCheckout

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!
Indoor spacesKitchenBathroom

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!
FamilyKitchenNearby

Crow’s Nest Tiny House at Old Crow Ranch
The Crow's Nest Tiny House sits nestled on Old Crow Ranch, a 70-acre working livestock farm, a true example of thriving Maine farmland. You'll be surrounded by fields and pine woods in Durham, Maine. Just outside Freeport and only 30 minutes from Portland, this cozy space makes a calming retreat away from the city - for a night or for a week. Fall asleep listening to the peepers and gazing at the stars, drink your morning coffee while looking out at the cattle grazing in the fields.
FamilyIndoor spacesAccuracy

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
Indoor spacesFamilyBathroom

The Maine Frame | Modern A-Frame Cabin in Freeport
• Perfect for small families or couples, our signature A-Frame cabin features a modern interior gas burning fireplace, soaring ceilings, huge windows, stylish interiors, and all the comforts of home. • This cozy 1,100 square foot space comfortably accommodates up to four guests in two bedrooms (one with a King-size bed and the other with a Queen-size bed) and a shared bathroom. • 7 minute drive to downtown Freeport. • Proud to be ranked in the top 1% and voted Guest Favorite!
Indoor spacesKitchenBreakfast

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.
KitchenIndoor spacesSleep quality

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.
Indoor spacesFamilyTV

Cozy Lakefront Cabin-Private Dock-Kayaks-Firepit
Welcome to Salmon Point Cottage a 1,000 sq. ft. cabin on stunning Panther Pond. Deck sits less than 10’ from the water with direct dock access. Open concept living with high-end kitchen. Cozy up by the gas stove. Swim, kayak, or relax by the firepit—your private lakeside retreat awaits. This property has it all including: -Private Dock -Fire Pit -Complementary Kayaks -BBQ Grill -Gas burning fireplace -Washer & Dryer -Fully Equipped Kitchen
KitchenIndoor spacesOutdoor spaces
Popular amenities for Raymond family-friendly rentals
Family-friendly home rentals with a hot tub

LuxuryTreehouse w/ Hot Tub Near Sunday River
KitchenFamilyAir conditioning

Cozy romantic A-frame by a woodland stream - 25
Indoor spacesFamilyHot tub

Luxe Lodge in the Woods! With Sauna & Hot tub
Indoor spacesKitchenSleep quality

Dreamy Mountain Home w/ Hot Tub, Firepit, + Views!
Indoor spacesFamilyTV

Cozy Library Tiny Home *Private Hot Tub* King Bed
Indoor spacesFamilyHeating

Sebago Lakehouse: Hot Tub and Private Beach Access
Indoor spacesKitchenBathroom

Solar Powered Bus in Forest | Hot Tub + Wellness
Indoor spacesFamilyAmenities

Cozy Rock Cabin #thewaylifeshouldbe
FamilyKitchenCleanliness
Family- and pet-friendly home rentals

Studio Apartment in Freeport
Indoor spacesFamilyHiking

Naughty Dog Private Island Log Cabin
Indoor spacesKitchenQuiet

THE LILLIPAD.Off-grid A frame. Sebago lake region!
Indoor spacesKitchenCheck-in

True Maine Artist Cottage with Outdoor Shower
KitchenIndoor spacesCheck-in

Beautiful Lakefront View, on Sebago Lake
FamilyKitchenAmenities

Renovated New Waterfront Cottage on Crescent Lake!
Indoor spacesFamilyGetting around

Lake front home on Little Sebago
Indoor spacesFamilyHospitality

Best Ski & Lake House
FamilyKitchenParks
Family-friendly home rentals with a pool

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

A Riot of Color at an Artist's Retreat on the Port
KitchenFamilyLocation

Spacious Condo-Attitash Ski-Storyland-Saco & More!
FamilyKitchenComfort

"Good Vibes" 4 Wonderful Seasons @ Portland Home!
Indoor spacesKitchenAccess

Large Historic 7 Bedroom home with Pool & Hot Tub
KitchenIndoor spacesBackyard

Cozy Fireplaced Mountain King Suite w/Hot Tubs & P
KitchenFamilyValue

Historic Schoolhouse c1866 + Pool + Lake + Hot tub
FamilyKitchenBackyard

Stunning 2BR with Mountain Views | Nordic Village
FamilyKitchenSkiing
When is the best time to visit Raymond?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $557 NZD | $555 NZD | $588 NZD | $555 NZD | $554 NZD | $584 NZD | $658 NZD | $666 NZD | $521 NZD | $495 NZD | $543 NZD | $545 NZD |
| Avg. temp | -6°C | -4°C | 1°C | 6°C | 12°C | 18°C | 21°C | 20°C | 16°C | 10°C | 4°C | -2°C |
Destinations to explore
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- Rentals with beach access Raymond
- Rentals with a kayak Raymond
- House rentals Raymond
- Cottage rentals Raymond
- Cabin rentals Raymond
- Rentals with lake access Raymond
- Pet-friendly rentals Raymond
- Beachfront rentals Raymond
- Waterfront rentals Raymond
- Family-friendly rentals Cumberland County
- Family-friendly rentals Maine
- Family-friendly rentals United States
- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Story Land
- Popham Beach, Phippsburg
- Sunday River Resort
- Willard Beach
- Scarborough Beach
- Footbridge Beach
- Cape Neddick Beach
- Pemaquid Beach
- Pemaquid Point Lighthouse
- Coastal Maine Botanical Gardens
- East End Beach
- Gooch's Beach
- Cranmore Mountain Resort
- Hills Beach
- Fortunes Rocks Beach
- King Pine Ski Area
- Conway Scenic Railroad
- Pleasant Mountain Ski Area
- Popham Beach State Park
- Crescent Beach State Park
- Wolfe's Neck Woods State Park





