Family-friendly vacation rentals in Plymouth

4.96 out of 5 average rating, 134 reviews

A charming cottage features a red front door and a brick chimney. A patio set with an umbrella is positioned outside, surrounded by a lush green lawn and trees. The exterior showcases a mix of horizontal siding and brick accents.

Cottage in Plymouth

Cozy Ladybug Cottage Near Cape Cod Canal

My cozy lil'Ladybug Cottage located on a rustic dead end street w/Great Herring Pond at end of road and tennis/basketball courts w/playground across from the other end of the road-make a perfect spot! Centrally located to major roads, highways &convenient to historic Plymouth/Sandwich. Easy to explore and enjoy the Cape Cod canal, ocean beaches as well as recreational activities nearby. Hike trails @ Ellisville Harbor State Park/picnic at the Herring run or canal, or grab a game of golf nearby.

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The entryway features a wooden staircase with white railings leading to the second floor. A cozy seating nook sits beside a window, adorned with decorative pillows. Light-colored walls complement the hardwood flooring, while a console table with a decorative bowl adds a welcoming touch.

5.0 out of 5 average rating, 161 reviews

Updated Antique in Historic Downtown Plymouth

Updated antique colonial within walking distance to everything historic Downtown Plymouth has to offer- waterfront, boating, shops, restaurants, historic sites, and more. Fenced in backyard with patio overlooking gorgeous, well-maintained garden. Patio has large farm table with umbrella and Weber grill, great for entertaining! This charming in-town location offers you the best of both worlds - walking distance to everything while also being cozy and comfortable to enjoy a day at home to relax.

Indoor spacesKitchenLaundry

4.93 out of 5 average rating, 319 reviews

A serene sunset can be seen over calm waters, with the sun rising behind a lighthouse. The sky transitions from orange to soft pink and light blue, while the lighthouse stands silhouetted against the horizon, creating a peaceful coastal scene.

Cottage in Plymouth

Ocean View Cottage

Charming cottage with an ocean view in a private setting seaside community with updated kitchen that does NOT include a stove there is a cooktop, microwave and toaster oven, 3/4 bathroom w a shower. Firestick/RokuTV. It is ONE room, open concept with a comfortable memory foam easy fold out king couch. The cottage is separate from the house with its own entrance w parking for 2 cars. 1 mile from the beach and 5 miles from downtown. **PLEASE NOTE ONLY 2 PERSON OCCUPANCY / 450 LB LIMIT COUCH

Indoor spacesFamilyBeach

4.92 out of 5 average rating, 190 reviews

Panoramic ocean views 100 ft above Cape Cod Bay

Our 5-bdrm Nantucket style beach house has a new kitchen & open living space, with a new deck, all overlooking the entire shoreline of Cape Cod Bay from a commanding perch atop a 100-foot bluff. Whales and seals can be seen from your deck. Located in a private community with its own rocky beach access about 5 min walk from the house where you can hunt for shells & observe the ocean wildlife. This beach is ideal for kayaking. Plymouth also boasts 4 of top 10 rated public golf courses in MA.

KitchenIndoor spacesAmenities

4.94 out of 5 average rating, 107 reviews

A view of a serene outdoor space featuring a green lawn bordered by a cranberry bog. A fire pit with chairs is situated in the foreground, while a rustic building and tree line create a picturesque backdrop under a cloudy sky.

Guest suite in Duxbury

Guest suite on cranberry bog, 1 mile from beach

Why fight the traffic to Cape Cod when you can enjoy New England's beaches, trails and seafood from beautiful Duxbury - just an hour from Boston! Our home is on a gorgeous cranberry bog surrounded by biking and walking trails and just a mile from the beach. Skylights and french doors to a private patio fill the suite with sunlight. Guests enjoy the fire pit, grill and yard in summer or hit the trails on snow shoes and sleds in winter. The bog freezes over too and is great for ice skating!

FamilyIndoor spacesOutdoor spaces

5.0 out of 5 average rating, 241 reviews

Cottage in Buzzards Bay

140 Steps to Beach with Water Views

This small rustic unique cottage is ready for you to enjoy on Buttermilk Bay. Located within a sought after cape style cottage community. It offers a Pristine Private Association Beach. There are water views from both the living room and deck. Grab the provided beach chairs, cooler and walk a 140 steps from the deck to the beach. Location! Close to Cape Cod Canal, Restaurants, Beaches, Walking Trails, Golf Courses and Cape Cod Bridge. August Last Minute Deals- 25% OFF!

KitchenIndoor spacesLaundry

4.97 out of 5 average rating, 238 reviews

A handcrafted tree house is perched among trees, supported by wooden stilts. The structure features a rustic exterior with a metal roof and large windows, surrounded by greenery and vibrant pink flowers in the foreground, creating a serene and natural setting.

Treehouse in Wareham

Mink Cove Treehouse

A unique adult adventure awaits in this cozy hand crafted tree house! Nestled 12 feet off the ground amongst the chirping birds, red oaks & breathtaking views of Mink Cove in Buzzards Bay. The tree house is accessible by a suspension bridge that leads you to a partially covered porch where you can enjoy a cup of coffee or sit back & take in the sunset with a glass of wine. Step inside to the living space & snuggle up on the couch for an intimate evening.

KitchenFamilyParking

Superhost

A serene pool area is surrounded by lush gardens, featuring vibrant flowers in planters. A pool house is visible in the background, framed by greenery. The clear water of the pool reflects the surrounding natural beauty, inviting relaxation and enjoyment.

4.9 out of 5 average rating, 198 reviews

The Secret Garden 4 Bedroom, 7 Bed 3 Baths

This beautiful 2.5 acre fully fenced in private property has gardens, an in-ground pool & pool house with an outdoor heated shower. Our home offers 2 kitchens, dining room seating 12, a great room, 3 bedrooms with private sitting areas & lower level with 2 bunk beds (bottoms are full beds) & exercise area. Outside are 2 grills & a fire pit. We are 3 miles from the beach, shopping/cafes, 45 minutes from Boston (on a train route) and 20 minutes to Cape Cod.

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A collage showcases various aspects of The Captain's House, including a stylish bedroom with a spacious bed, a modern kitchen equipped with essential amenities, a cozy living room, and a front porch with rocking chairs. Scenic views of Plymouth harbor and historic sites are also featured.

4.95 out of 5 average rating, 277 reviews

The Captain's House - Downtown Plymouth

A true downtown gem. Sparkling clean PRIVATE 1,600 sq ft HOUSE. Unbeatable location with all that Plymouth has to offer literally outside the door - restaurants, the harbor and historic sites (yet on a quiet street). Stylish, renovated 5 bedroom, 2 full bathrooms, laundry, a huge front porch and hidden backyard courtyard. Full kitchen, dining room, and living room. Park 2-3 cars in driveway. Central AC. A guest favorite that rarely disappoints.

KitchenIndoor spacesParks

4.9 out of 5 average rating, 188 reviews

A spacious room features a king-sized bed with a neutral quilt and decorative pillows. French doors open to a view of the outdoor area, allowing natural light to illuminate the space. A patterned area rug enhances the room's aesthetic.

Apartment in Plymouth

Remodeled Studio Apartment in Downtown Plymouth

Come experience the charm and rich history of “America’s Hometown!” Get transported back in time in an 1887 colonial home located in the heart of downtown Plymouth. Enter through the French doors into a recently remodeled studio apartment with a full kitchen, full bath and king-sized bed. All the modern comforts you could ask for in a quaint and cozy rental. Walking distance to restaurants, shopping, Plymouth Rock, the Mayflower and more!

KitchenFamilyDecor

A heated indoor pool is framed by sleek gray walls and illuminated with recessed lighting. Large sliding glass doors offer a view of the outdoor patio. Colorful pool floats and equipment are neatly arranged nearby, providing options for leisure activities.

4.9 out of 5 average rating, 174 reviews

Seaview Summit | Ocean Views, Indoor Pool, Beach

Perched above the coastline with panoramic Atlantic views, Seaview Summit House is Plymouth's premier oceanfront retreat. Designed for discerning travelers seeking serenity, space, and sophistication. With a heated indoor pool, expansive outdoor living areas, and direct beach access just moments away, this stunning property delivers a five-star experience in every season. Book your stay today. You'll be glad you did.

KitchenFamilyParking

4.99 out of 5 average rating, 115 reviews

A serene sunset over a calm body of water reflects vibrant orange and soft blue hues. Lush green grass borders the shore, while silhouettes of distant trees frame the scene. A dock is visible on the left, offering a peaceful spot to enjoy the view.

Home in Wareham

Sunset Cove Beach

This ocean view cottage is perfect for you and your family to relax, unwind and adore the wonderful scenery it has to offer. This charming cottage is on a quiet dead-end street, suitable for a small family or a couple, seeking to appreciate the neighborhood and beaches without the hassle of cape traffic. Come and enjoy the warm water, beautiful sunrises, breathtaking sunsets, and much more.

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Popular amenities for Plymouth family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.95 out of 5 average rating, 122 reviews

An open living area is highlighted by vaulted ceilings and large windows that allow natural light to illuminate the space. A comfortable seating arrangement faces a coffee table, while a dining area with bar stools is situated near the kitchen. A spiral staircase leads to the upper level.

Guest suite in Plymouth

Manomet Boathouse Station #31

Indoor spacesFamilyAccess

4.96 out of 5 average rating, 165 reviews

Two kayaks are stored beside a shed in a natural setting, surrounded by tall grass. A view of the calm water reflects the greenery of the area, while a cozy indoor space showcases a gas fireplace and comfortable furnishings.

Cottage in South Dennis

Local Beach+ Fireplace + Hot Tub Under the *Stars*

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Superhost

Home in Somerset

4.88 out of 5 average rating, 121 reviews

Backyard paradise Pool & Hot Tub | Pets Welcome

Indoor spacesFamilyPets

4.92 out of 5 average rating, 317 reviews

The cottage, surrounded by mature landscaping, is located near a private beach. A sandy expanse is visible in the background, highlighting the close proximity to the shore. Nearby structures exhibit a rustic charm, contributing to the serene beach environment.

Cottage in Sandwich

Hideout at Water's Edge, 131 North Shore Blvd, #4

FamilyIndoor spacesWifi

4.94 out of 5 average rating, 100 reviews

An oceanfront backyard is showcased with comfortable seating arranged around a circular table. A hot tub is visible nearby, and additional seating is provided by lounge chairs. The expansive view of the ocean under a partly cloudy sky enhances the coastal atmosphere.

Home in Scituate

Oceanfront home w/Amazing Views, Hottub! Sleeps 10

Indoor spacesFamilyView

4.99 out of 5 average rating, 189 reviews

A spacious wrap-around porch is shown with comfortable seating, offering panoramic views of the waterfront. The warm glow of sunrise reflects on the water, and a distant bridge is visible under a clear sky. The setting invites relaxation and enjoyment of the serene environment.

Home in Somerset

Beachfront W/ HotTub, Sauna, Pool & Panoramic view

Indoor spacesKitchenValue

4.98 out of 5 average rating, 174 reviews

An outdoor dining area overlooks the tranquil cove. The table is surrounded by six wicker chairs, set against a backdrop of calm blue water and a clear sky dotted with fluffy white clouds.

Cottage in Portsmouth

Waterfront Oasis minutes from Newport w/ hot tub!

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4.94 out of 5 average rating, 267 reviews

A waterfront hot tub is set against a natural backdrop of trees and calm waters. Inside, a dining area features a large window with views of the lake. A cozy living room displays comfortable seating, while an outdoor patio has seating for relaxation and enjoying the scenery.

Home in South Yarmouth

Waterfront•Hot Tub • Kayaks/SUP's • King Bed •Dock

Indoor spacesKitchenAccuracy

Family- and pet-friendly home rentals

4.8 out of 5 average rating, 243 reviews

A view overlooking a serene beach with clear, calm waters. Steps lead down toward the sandy shore, surrounded by greenery. Small boats can be seen in the distance, and the sky is bright with scattered clouds.

Guesthouse in Plymouth

A peaceful retreat on Cape Cod Bay

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4.96 out of 5 average rating, 101 reviews

Stunning Design|7minWalk to Beach|Lg BackYard|Deck

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A serene pond-front view captures a charming green house surrounded by lush trees and a well-maintained yard. Water's smooth surface reflects the structure, enhancing the tranquil atmosphere. Nearby foliage hints at seasonal changes, adding to the picturesque outdoor setting.

4.95 out of 5 average rating, 182 reviews

1 of a Kind Pond-Front Home, Minutes from Downtown

KitchenFamilyGetting around

A well-maintained outdoor space features two blue Adirondack chairs positioned on a grassy area. A large tree with lush green leaves provides shade, while the side of the house, partially visible, presents a welcoming entrance framed by greenery.

4.9 out of 5 average rating, 152 reviews

Pet Friendly 🐶 …Walk to White Horse Beach

FamilyKitchenLaundry

4.88 out of 5 average rating, 153 reviews

A small, red-roofed structure is visible in the foreground, surrounded by a neatly maintained grassy area. A white fence encloses the space, with trees and lush greenery present in the background. Two horses can be seen grazing peacefully, adding to the serene rural setting.

Tiny home in Pembroke

Tiny Farm House on a Horse Farm

FamilyIndoor spacesBathroom

4.97 out of 5 average rating, 118 reviews

Home in Buzzards Bay

Oceanfront | Firepit | Gameroom | Pets | Kayaks

Indoor spacesFamilyDecor

4.93 out of 5 average rating, 107 reviews

A decorative sign featuring the phrase 'Welcome Aboard' is displayed on a light-colored tabletop. An anchor graphic is incorporated into the design. A wooden pelican figurine and a seashell accent piece are also present, adding to the coastal-themed decor.

Condo in Marshfield

Studio suite at Sunrise Beach.

FamilyIndoor spacesGetting around

5.0 out of 5 average rating, 53 reviews

A bright dining nook features a round wooden table placed on tiled flooring. Natural light streams through large glass windows, illuminating a cozy seating area with plush cushions. Lush greenery and colorful flowers are visible outdoors, enhancing the serene atmosphere.

Cottage in Plymouth

Sweet + Sunny 2BR Cottage 5-min Walk to the Beach

FamilyKitchenAmenities

Family-friendly home rentals with a pool

4.95 out of 5 average rating, 100 reviews

Apartment in Everett

Curated Designer Retreat • Pool • Gym • Dining

FamilyIndoor spacesQuiet

4.99 out of 5 average rating, 100 reviews

Home in Sandwich

"Cape Escape" luxury home w/pool & beach access.

KitchenFamilyCleanliness

4.96 out of 5 average rating, 141 reviews

The expansive pool, surrounded by a landscaped yard, features a vibrant blue surface reflecting the clear sky. Comfortable lounge chairs are positioned alongside, inviting relaxation. A floating inflatable adds a playful touch to the tranquil setting.

Home in Cotuit

Private Pool, near beaches, 3 BR/3 BA, Central Air

FamilyKitchenWifi

Guesthouse in West Roxbury

A bright bedroom features a spacious bed with a white coverlet and colorful pillows. Natural light filters through multiple windows, enhancing the wooden accents of the walls and furniture. A television is mounted on the wall above a wooden dresser, creating a comfortable and inviting space.

4.95 out of 5 average rating, 215 reviews

Country Cottage in the City

Indoor spacesKitchenCheckout

4.94 out of 5 average rating, 253 reviews

A spacious outdoor area features a dining table surrounded by chairs, complemented by loungers and a hot tub. An umbrella provides shade over the seating area, while lush greenery and well-maintained landscaping create a peaceful environment. The in-ground pool is visible in the foreground.

Guesthouse in Newton

Charming 2-story private Guesthouse

FamilyKitchenParking

4.87 out of 5 average rating, 113 reviews

A spacious room features a full-sized bed with light bedding. A euro lounger is positioned in front, decorated with a soft throw. Mirrors on the opposite wall reflect the room's layout, and a window offers natural light, contributing to the overall bright atmosphere.

Guest suite in Rockland

Cozy Private Suite halfway between Cape & Boston

FamilyIndoor spacesValue

4.94 out of 5 average rating, 109 reviews

A cozy studio space features sloped ceilings and warm wooden flooring. A spacious bed is dressed in white linens, with accent pillows adding a touch of color. A small kitchenette is visible beside a comfortable chair and a blue rug, offering a relaxed atmosphere.

Guest suite in Dartmouth

The Loft @ Beechwood. Private, comfy, coastal!

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