Family-friendly holiday rentals in Edgartown

Guest suite in Oak Bluffs

A spacious living room is highlighted by a large grey sectional couch adorned with various throw pillows. A wooden coffee table sits in front, featuring storage compartments. Two abstract paintings in calming blues are displayed above the couch, while soft lighting illuminates the area.

4.95 out of 5 average rating, 434 reviews

Lovely 2 BR Oak Bluffs Apartment

This 100% private apartment is on the first floor of a shared house where owners and their son live upstairs. There are no shared spaces. You have a private entrance and parking. The living room, bedrooms, bathroom, and kitchenette are bright and clean. It is exactly 1 mile from Oak Bluffs Center, a half mile from The Cottages and Farm Neck Golf Course, and a block from Tradewinds walking trails. Across the street is the bike path, & the bus stop is on the corner for easy island transportation!

Indoor spacesKitchenNearby

5 out of 5 average rating, 127 reviews

A private garden patio is showcased, featuring a circular table surrounded by four chairs. Plush cushions in vibrant blue patterns adorn the seating. Nearby, two wooden lounge chairs offer additional relaxation options. Lush greenery and flowers provide a natural backdrop, enhancing the outdoor ambiance.

Apartment in Edgartown

Private Garden Oasis -Outdoor Shower- Walk to town

* Private garden patio: string lights create chill evenings around the propane fire pit. Table & chairs, propane grill, & enclosed outdoor shower * 10 min walk to Edgartown's dining & boutiques * Cable TV, Streaming services, Sonos * High-speed WiFi, comfortable workspace in the bedroom * USB charging ports in the BR & LR * Small but mighty fully stocked kitchen for home-cooked meals * Organic, local bath products * Board games & a small library * HW floors, SS Bosch appliances, DW, W/D, HVAC

KitchenIndoor spacesBathroom

The exterior of a charming house is shown, featuring a gray shingle facade and a welcoming covered porch. Lush greenery and ornamental shrubs frame the entrance, while a gravel driveway leads up to the front door, creating an inviting approach.

4.93 out of 5 average rating, 221 reviews

Spectacular beach & pool combo; beautiful sunsets!

Close to airport, you’ll love backyard beach, water view, pool/grass yard, ambiance and outdoors space. Beach & Pool (POOL HEAT STARTS SUMMER, ENDS 9/1) is a hard to find combination!! Location is private, yet it's close to the 3 largest towns on Martha's Vineyard. Great for couples, families (with kids), and big groups. Enjoy dinner with the indoor/outdoor Sonos music system during a beautiful sunset! NOTE; Rate increase in high season, pool/spa is a combined unit & ONLY heated in summer!

Indoor spacesKitchenHospitality

4.95 out of 5 average rating, 201 reviews

A modern kitchen area is displayed with white cabinetry and granite countertops. Stainless steel appliances, including a refrigerator and microwave, are visible. Natural light filters in through multiple windows above, creating an airy and bright atmosphere.

Apartment in Oak Bluffs

111C Beautiful private condo walk to everything!

This is an incredible property! Renovated and spotless with all the amenities to make your stay feel like home, only better. Downtown Oak Bluffs and her beautiful beaches are within a five-minute walk. There is a local market and deli right next door where you can find anything you need in a pinch, and a great BBQ restaurant across the street. This second floor apartment has one bedroom with a queen-sized bed and a queen pullout couch. Smart TVs, full kitchen and laundry plus much more!

Indoor spacesKitchenCheck-in

4.91 out of 5 average rating, 113 reviews

The interior features a wooden wall with a triangular peak highlighted by a small window, allowing natural light to filter through. A pendant light hangs from the ceiling, complementing the rustic aesthetics of the space.

Guesthouse in Edgartown

Martha’s Vineyard Cottage - A Glamping Experience!

This is your vineyard home, where you can walk or ride a bike less than a mile to the beach or two into town. Get the glamping experience with kitchenette, A/C, an outdoor shower, a composting toilet, a queen bed in the loft and futon couch that can sleep two more in the living room. Enjoy outdoor games, outdoor seating, a Weber grill for bbq, tv, WiFi, cozy indoor space and more, right on the bike path with a bus stop for easy accessibility or free car parking. Whatever you want!

Indoor spacesFamilyBathroom

Cottage in Chappaquiddick

A cozy living area features a lightweight sofa adorned with colorful cushions, complemented by a pink upholstered chair. Large windows reveal ocean views, allowing natural light to fill the space. A small table holds fruit and a book, creating a welcoming setting.

5 out of 5 average rating, 35 reviews

Beachfront Cottage + Studio w. Town Access

Welcome to The Rudder Cottage! Fully renovated 1930's cottage on an ocean front compound, with a picturesque porch overlooking the outer harbor, full basement with washer/dryer and central air. An additional detached studio provides a third bedroom/work space. Stunning views of the Edgartown lighthouse and Cape Poge. Access to private beach. Access town with just a 10 minute walk (or 1 minute drive) to the Chappaquiddick Ferry, and be in downtown Edgartown in 15 minutes or less!

FamilyKitchenView

The front exterior of the house is shown surrounded by lush greenery, featuring a well-maintained lawn. A pathway leads to the entrance, and the porch offers seating. Two sun loungers are positioned on the grass, inviting relaxation in the open space.

4.93 out of 5 average rating, 149 reviews

** Vineyard Vacation Retreat ** with HOT TUB

Gated 2br house with lots of different places to lounge and relax. Drive through the 10’ granite gate onto the shell driveway. The house is filled with art from local artist Alan Whiting, Colin Rule, Kara Taylor and Scott McDowell. There is so much to do and explore. The adventure is just starting so make sure to pack up your swimmers, suntan lotion and get out the door. Kick back and relax, you're home. Updated 7/25/2025 we do not have any more firewood on the property.

KitchenFamilyAmenities

A charming two-story cottage features a shingled exterior with a pitched roof. The inviting front porch is supported by wooden pillars and surrounded by lush greenery. A white picket fence encloses the well-kept lawn, creating a warm curbside appeal.

5 out of 5 average rating, 28 reviews

Martha's Vineyard Cottage: Walk to Town and Beach

Updated 1920s Cottage in Edgartown Village – Walk to Beach, Harbor and Main Street Step into classic Vineyard charm at this fully updated 4-bed, 3-bath craftsman cottage in the heart of Edgartown. Two blocks from Main Street’s restaurants, galleries, and harbor and a quick walk to Fuller St Beach & Lighthouse Beach. Fully winterized + AC, high-speed Wi-Fi, three workstations. Ideal for families, bachelorette parties or anyone craving a New England coastal escape.

FamilyIndoor spacesLayout

The exterior of the yurt showcases a circular wooden structure with large, rounded windows, complemented by a metal roof. A private yard features lush greenery, colorful flora, and outdoor seating arrangements, creating an inviting space for relaxation and outdoor activities.

4.93 out of 5 average rating, 319 reviews

The Luxury Vineyard Yurt

Discover this exceptional Luxury Yurt firsthand! Upon entering, you will be welcomed by a distinctive experience, featuring textured concrete radiant floors and a four-foot circular central skylight. Every aspect has been meticulously designed, allowing you to relax in a generous private yard. Enjoy your evenings under the stars, utilize the complimentary paddling, practice yoga in the spacious loft, and indulge in the beauty of your private island Yurt!

Indoor spacesFamilyLaundry

An inviting in-ground pool is situated within a meticulously maintained grassy area, surrounded by trees. The pool area features slate-like patio stones and is complemented by six lounge chairs organized neatly under a shaded umbrella.

5 out of 5 average rating, 23 reviews

Modern & Spacious Edgartown Home with Pool

Enjoy your vacation in this wonderfully charming three bedroom home with an in-ground heated pool. Head to the beach or stay at home and go for a swim in your own backyard. There is plenty of dining room & deck space to entertain. The bike path and bus shuttle are at the end of the road (a two minute walk away). Downtown Edgartown is less than two miles away for you to enjoy shopping and multiple dining choices.

KitchenFamilyComfort

Guest suite in Oak Bluffs

4.98 out of 5 average rating, 204 reviews

Quiet Hide Away

Lovely efficiency suite with private entrance in a quiet neighborhood. Private space located over attached garage. Plenty of space for two guests. Comfortably appointed with queen bed, dining set, living area with tv and full bath. Enjoy a coffee or cocktail on the private deck. Toaster oven, refrigerator and coffee maker will start your day right before heading to nearby beaches, golf courses or shopping.

Indoor spacesFamilySleep quality

The entrance of a condo is framed by a well-maintained lawn, with vibrant greenery and colorful flowers surrounding the doorway. The front door, featuring a decorative glass panel, opens to a sunlit pathway lined with stone pavers.

4.98 out of 5 average rating, 191 reviews

Close to Edgartown Village Center!

This 1800 square foot Ranch-style Condo with loft was built in 2018 and is set on a large nicely landscaped lot with plenty of room inside and out. It has 3 bedrooms and a loft and sleeps 9. It’s a 20-minute walk to the Edgartown village center, a 10-minute walk to Morning Glory Farm, and just a 10-minute drive to South Beach! All updated furnishings, beds, linens, appliances. Read our reviews! Immaculate!

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Popular amenities for Edgartown family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A modern kitchen features a spacious island with four bar stools and stylish pendant lighting above. Sleek white cabinetry complements the elegant quartz countertop. Large windows provide natural light, and stainless steel appliances, including a gas range and refrigerator, are visible in the background.

4.95 out of 5 average rating, 44 reviews

Vineyard Vacation, 3-Bedroom, Hot-tub, Golf course

Indoor spacesKitchenLaundry

Guest suite in West Tisbury

The outdoor deck features two loungers with colorful striped cushions, a small white table, and potted plants. A hot tub is positioned nearby, surrounded by greenery that creates a tranquil setting. The home's windows allow for natural light to enhance the spaces.

4.97 out of 5 average rating, 96 reviews

Quiet West Tisbury 2 BDR Suite

FamilyIndoor spacesLaundry

4.97 out of 5 average rating, 61 reviews

A gravel driveway leads to a charming house with a red garage. A wooden pergola, adorned with greenery, provides shade along the entrance. Lush trees and open sky enhance the serene outdoor setting, inviting visitors to explore the surrounding landscape.

Home in West Tisbury

Vineyard Meadow Writer's Cottage with Hot Tub

FamilyIndoor spacesNearby

4.88 out of 5 average rating, 25 reviews

The rear of the house is showcased, featuring a deck with white railings. A grill is present on the deck, and large windows allow natural light to fill the space. Surrounding greenery adds to the peaceful setting.

Home in Falmouth

Falmouth Oasis with Jacuzzi

Indoor spacesFamilyLocation

An inviting living room features a light-colored sofa and a natural wood coffee table. Artwork and plants add warmth, while natural light fills the space through ample windows. A large television is mounted on the wall, providing entertainment options for guests.

4.97 out of 5 average rating, 75 reviews

Valentine's Retreat Hot Tub Fire Pit Trails Beach

KitchenIndoor spacesComfort

4.93 out of 5 average rating, 28 reviews

A bright and airy living room is featured, showcasing white-brick walls and exposed wooden beams. Comfortable sofas are arranged around a central coffee table, with a flatscreen smart TV mounted on the wall. Natural light filters through the windows, creating an inviting atmosphere.

Home in West Tisbury

Top-Rated Island Retreat: Hot Tub, Lamberts Cove!

KitchenFamilyAir conditioning

5 out of 5 average rating, 48 reviews

A custom-built home features a large front porch bordered by well-maintained greenery. The two-story structure is framed by trees, with expansive windows visible. Water views are apparent in the distance, set against a bright blue sky with soft clouds.

Home in Tisbury

Stunning 4/2.5 Water View, Hot Tub, Dogs ok (fee)

KitchenFamilyCleanliness

4.97 out of 5 average rating, 39 reviews

A sandy beach extends toward calm waters bordered by a tree-lined shore, creating a serene natural setting. The gentle curve of the waterway leads to a distant point, where lush greenery enhances the picturesque landscape. The bright blue sky adds to the tranquil atmosphere.

Home in East Falmouth

Renovated ranch with pool access

FamilyKitchenCleanliness

Family- and pet-friendly home rentals

4.95 out of 5 average rating, 19 reviews

Casa Luca| Serene 3BR| SunRm, Outdr Shwr, A/C, BBQ

Indoor spacesKitchenHospitality

Guest suite in Oak Bluffs

A spacious outdoor deck features wooden furniture, including a dining table with chairs and lounge seating. An umbrella provides shade, and potted plants enhance the natural setting. The deck is surrounded by greenery, contributing to a serene outdoor atmosphere.

4.8 out of 5 average rating, 358 reviews

Cottage suite between the harbors: no minimum stay

Indoor spacesKitchenComfort

A charming cottage is framed by a lush garden with vibrant flowers. The front porch features two rocking chairs, inviting relaxation. Soft lighting emanates from inside, through the gothic-style windows, under a welcoming blue roof surrounded by greenery.

4.92 out of 5 average rating, 211 reviews

impeccable cottage STEPS to downtown OB & beach!

FamilyKitchenGetting around

4.9 out of 5 average rating, 61 reviews

Edgartown Cottage By The Pond

KitchenIndoor spacesHospitality

A grassy outdoor space features two blue Adirondack chairs and a small fire pit, surrounded by trees and overlooking a serene pond. A hammock hangs in the distance, while the deck is visible on the right, extending from the house.

4.83 out of 5 average rating, 217 reviews

Waterview, Private, Walk to Beach, Mile to Town

KitchenIndoor spacesBiking

A charming beach house is set on a lush green lawn, featuring a picnic table and two lounge chairs arranged for relaxation. The house has multiple windows, and its exterior is made of wood, harmonizing with the surrounding nature.

4.9 out of 5 average rating, 120 reviews

Katama Barn

FamilyIndoor spacesCheck-in

4.96 out of 5 average rating, 313 reviews

The cottage is adorned with warm, glowing string lights that outline the roof and windows, creating a welcoming ambiance. A lush wreath decorates the front door, while charming wood paneling and multiple windows enhance the inviting exterior.

Cottage in Tisbury

Not Your Great Aunt's Island Cottage

KitchenIndoor spacesComfort

4.92 out of 5 average rating, 133 reviews

The historic property is displayed from the street level, showcasing its architectural charm with a multi-story design. A covered porch is visible, featuring ornate woodwork. Shops line the street, contributing to a lively town atmosphere. Clear skies and bright sunlight enhance the inviting appearance.

Apartment in Oak Bluffs

Absolute Best Location on the Island

Indoor spacesFamilyLocation

Family-friendly home rentals with a pool

4.97 out of 5 average rating, 30 reviews

The exterior of the house is presented, featuring a light-colored facade with a black roof and six front-facing windows. A porch is accessible with seating arranged nearby. A well-maintained lawn with flower beds is visible, complemented by a gravel driveway and American flag displayed.

Home in East Falmouth

Modern Cape Cod home steps to beach; pool access!

Indoor spacesKitchenComfort

5 out of 5 average rating, 23 reviews

Home in Popponesset

Popponesset, Exclusive, 3-Bdrm, 4-Bths, Sleeps 6,

KitchenFamilyPool

4.96 out of 5 average rating, 28 reviews

An aerial view reveals a spacious bay front home surrounded by lush greenery. A large pool is visible in the backyard, with steps leading down to a beach area featuring kayaks. The residence is set in a tranquil, wooded environment.

Home in Cotuit

ShoestringBayHouse, waterfront & pool in Cotuit

Indoor spacesFamilyPets

A spacious colonial house is framed by lush green grass and mature trees. The exterior features dark shingles with multiple windows reflecting natural light. A winding driveway leads to the entrance, while a wooden fence provides privacy at the rear.

4.93 out of 5 average rating, 57 reviews

Beautiful Edgartown 3500 sq ft home, heated pool

KitchenFamilyPool

4.82 out of 5 average rating, 28 reviews

The exterior of a cozy blue condo is shown, surrounded by green grass and trees. A wooden fence and picnic table are visible in the foreground, as well as a large tree with budding leaves. The building features multiple windows with white shutters.

Condo in Tisbury

Martha’s Vineyard Condo * Near Ferry

FamilyKitchenCleanliness

4.8 out of 5 average rating, 5 reviews

Home in Falmouth

Pool Escape in East Falmouth

FamilyPoolLocation

4.94 out of 5 average rating, 50 reviews

An aerial view of a spacious property featuring a uniquely shaped heated saltwater pool surrounded by a stone patio. A large deck is positioned next to the pool, with several lounge chairs arranged nearby and greenery framing the area.

Home in New Seabury

Coastal Charm New Seabury: 5BRs with Private Pool

FamilyKitchenDecor