Family-friendly vacation rentals in Plymouth

4.96 out of 5 average rating, 136 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.

Indoor spacesKitchenComfort

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, 165 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 spacesFamilyWalkability

4.94 out of 5 average rating, 104 reviews

The image captures a serene seascape at twilight, showcasing a vibrant sky filled with shades of pink and purple. Gentle waves lap against the shore, while a distant landmass is visible on the horizon, creating a calming backdrop to the tranquil waters.

Cottage in Kingston

Quiet Luxe Water Front Oasis

Amazing ocean views from nearly every spot in the house. Open layout on first floor with kitchen, dining room, living room, and sunroom with deck to ocean. Gaze at the water as you work at the desk, cook your meals, or lounge on one of the two first floor couches. There's a half bath downstairs as well, and books and games to enjoy. The second floor features two bedrooms and full bathroom. Both bedrooms have ocean views; the master is your calming tranquil oasis next to the sea.

Indoor spacesKitchenBathroom

4.97 out of 5 average rating, 158 reviews

Apartment in Plymouth

Downtown Backyard Oasis

Enjoy easy access to everything from this perfectly located home base in downtown Plymouth. It is just a five minute walk to the 1620 Hotel, Mayflower, Plymouth Rock, beach, waterfront restaurants, Main Street boutiques & coffee shops, etc. Five minute drive to T station (in Kingston) for fun day trips to Boston without the traffic. Easy drive to Cape Cod for day trips as well! This newly renovated, yet charming, 2 bedroom first floor apartment is a perfect get away.

Indoor spacesFamilyLocation

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.

FamilyKitchenCondition

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, 278 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.

Indoor spacesKitchenBiking

4.96 out of 5 average rating, 244 reviews

The kitchen features stainless steel appliances, including a refrigerator and a gas stove. Light grey walls are complemented by granite countertops. Natural light enters through a window above the sink, with kitchen essentials and decor items visible on the counters.

Townhouse in Wareham

The Gateway to Cape Cod townhouse !

Summer of 2027 calendar open BEACH PASS PROVIDED PLEASE CHECK OUT SLEEPING ARRANGEMENTS PRIOR TO BOOKING MAX 6 adults only Ideal for families Parking for 2 vehicles only WELCOME to Wareham! The town with the most coastline out of any town in MA 60 miles! Minutes to Water wizz and TONS of local beaches! Wareham center and a local grocery store are both walking distance away! Great proximity to Boston , providence , Plymouth, Cape and Bourne

Indoor spacesFamilyBeach

4.9 out of 5 average rating, 191 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!

Indoor spacesFamilyCleanliness

4.99 out of 5 average rating, 137 reviews

Condo in Plymouth

Captain's Lodge- #1, Plymouth Water Front Condo

1200 square foot condo. 2 bedrooms plus loft. 1 +1/2 baths with shower in each. Full large eat in kitchen + dinning and living room area. Massive outside deck over looking Plymouth harbor. Located in the heart of the historic Plymouth Water front. Short walk to the rock, Mayflower and beaches and surrounded by resturants , pubs and night life. Location offers access to all that Plymouth has to offer. Off street parking on site.

KitchenIndoor spacesQuiet

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, 177 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.

KitchenFamilyLocation

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, 184 reviews

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

Pond-Front property boasts unparalleled privacy and charm. 5 minutes from shopping and downtown Plymouth. Located on a peninsula of land, water views are plentiful. Both ponds are tested yearly and safe for swimming, fishing, etc. Bring your furry friend to run in the back yard, your kids to play, or simply your friends to relax and catch some sun. Opportunities are endless!

FamilyKitchenOutdoor spaces

4.96 out of 5 average rating, 201 reviews

An oceanfront cottage is positioned prominently on the beach, featuring a wooden deck with stairs leading down to the sand. Surrounding the property, large rocks provide natural protection from the surf, while a clear blue sky complements the serene beach landscape.

Cottage in Plymouth

Stunning ocean views, stairs down to the beach

Welcome! Wilkommen! Bienvenue! Our oceanfront cottage offers stunning panoramic views through wrap-around windows. You will be able to walk directly from the spacious deck down the stairs onto beautiful White Horse Beach. This house has been in our family for generations and we are excited to welcome you as guests into our home.

Indoor spacesKitchenGrill

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, 124 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 spacesKitchenParking

4.94 out of 5 average rating, 160 reviews

An open living space features a comfortable sectional sofa and a wooden dining table with six chairs. Natural light enters through large windows, with light curtains softly framing the views. A television is positioned in the corner, and decorative mirrors adorn the walls.

Condo in Plymouth

John Alden Condo

FamilyIndoor spacesTV

A hot tub emits a soothing green glow, surrounded by softly illuminated string lights. The tranquil outdoor setting features trees in the background and hints of nearby greenery, creating a relaxing atmosphere for evening enjoyment.

4.84 out of 5 average rating, 392 reviews

Historic 1 Bed/In Town/Best Location/Hot tub/deck

KitchenFamilyDecor

4.92 out of 5 average rating, 318 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

Indoor spacesKitchenBathroom

4.87 out of 5 average rating, 125 reviews

Home in Somerset

Campfires & Porch Swings Hot Tub | Pets Welcome

KitchenIndoor spacesOutdoor spaces

4.96 out of 5 average rating, 167 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*

Indoor spacesFamilyBackyard

4.94 out of 5 average rating, 121 reviews

A spacious loft area features a cozy seating arrangement with a dark sofa and a bright yellow armchair. Bookcases lined with books and decorative items occupy the walls, while a large area rug adds warmth to the wooden floor.

Guesthouse in Sandwich

Nautical loft guest house with hot tub and sauna

Indoor spacesKitchenHospitality

5.0 out of 5 average rating, 202 reviews

An outdoor seating area features a light-colored sectional sofa adorned with decorative cushions, positioned around a fire pit table. The lawn is well-manicured, with a rustic fence in the background, and a two-story building is visible beyond the grassy area.

Home in Middletown

Walk to the Beach - Serene Coastal Country Cottage

FamilyKitchenCheck-in

Family- and pet-friendly home rentals

4.99 out of 5 average rating, 117 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

KitchenFamilyValue

4.96 out of 5 average rating, 121 reviews

Home in Buzzards Bay

Oceanfront | Firepit | Gameroom | Pets | Kayaks

Indoor spacesFamilySleep quality

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, 153 reviews

Pet Friendly 🐶 …Walk to White Horse Beach

FamilyIndoor spacesAir conditioning

4.94 out of 5 average rating, 109 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

Indoor spacesFamilySleep quality

4.93 out of 5 average rating, 123 reviews

A historic lighthouse stands beside a renovated white keepers home, both set on a lush green lawn. The Atlantic Ocean stretches out in the background under clear blue skies, offering a serene coastal view.

Lighthouse in Pocasset

Wings Neck Lighthouse

KitchenFamilyBackyard

4.94 out of 5 average rating, 110 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.

Indoor spacesFamilySleep quality

4.97 out of 5 average rating, 216 reviews

An open-concept living space showcases a well-equipped kitchen featuring a retro blue refrigerator and modern appliances. A comfortable sofa with decorative pillows faces the kitchen, with a wooden dining table positioned nearby. Light streams in through a nearby window, complementing the warm tones of the decor.

Apartment in Bourne

A Shore Thing (King Bed, private patio w/ grill)

KitchenIndoor spacesSleep quality

4.93 out of 5 average rating, 130 reviews

The exterior of the cottage features a raised deck with a lattice design, offering a clear view of the entrance. Brightly colored umbrellas and planters add subtle touches to the space. A gravel pathway leads to the stairs, surrounded by greenery.

Cottage in Buzzards Bay

Buzzards Bay - Beach Bungalow

Indoor spacesKitchenPets

Family-friendly home rentals with a pool

4.99 out of 5 average rating, 101 reviews

Home in Sandwich

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

FamilyKitchenBathroom

4.91 out of 5 average rating, 103 reviews

Home in Wareham

Edgewater Retreat | Oceanfront Home | Heated Pool

Indoor spacesFamilyHeating

4.96 out of 5 average rating, 110 reviews

A serene scene is captured as the in-ground saltwater pool reflects the evening sky. Lounge chairs are aligned beside the pool, while the house showcases warm lights glowing through large glass doors, offering a welcoming view of the outdoor entertaining area.

Home in Middletown

Heated Salt Pool | Near Newport, Beaches | Pkg 4 6

KitchenIndoor spacesPool

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!

FamilyIndoor spacesComfort

4.87 out of 5 average rating, 191 reviews

Apartment in Charlestown

Lux 2BR Apt w/ Pool and Gym

Indoor spacesKitchenBathroom

Guest suite in Centerville

4.99 out of 5 average rating, 103 reviews

“The Hideaway”Private Guest Suite/Pool/Beach Pass

Indoor spacesFamilyCondition

4.88 out of 5 average rating, 206 reviews

A cozy living area features a spacious daybed flanked by decorative pillows. Two armchairs are positioned across from a coffee table, enhancing the seating arrangement. A decorative vase adds charm beside the fireplace, while natural light filters through the window, illuminating the wood flooring.

Guest suite in Revere

Amazing studio

FamilyKitchenBeach