Family-friendly holiday rentals in Dennis Port

4.98 out of 5 average rating, 103 reviews

A backyard space is equipped with a fire pit surrounded by four white Adirondack chairs, providing a cozy gathering area. String lights hang overhead, illuminating the outdoor dining table set for a meal. A charming cottage is visible in the background, enhancing the inviting atmosphere.

Home in West Dennis

Sunset Sabbatical Cape Cod

**Newly updated Bathroom for 2026 Season!** Put your feet up and enjoy yourself! Just a 5 minute walk to South Village Beach, you will enjoy everything Cape Cod has to offer. A backyard oasis, complete with Outdoor Shower, beautiful lights, fire pit and grill - you will create family memories here for a lifetime. Updated kitchen with new gas stove, dishwasher and microwave. High-speed WiFi, Roku TVs, luxury pottery barn linens & towels. Small Hypoallergenic Dog(s) allowed with a $50 pet fee.

KitchenFamilyComfort

A charming beach house is showcased, featuring a stone-paved driveway and a well-maintained garden with vibrant pink flowers. The exterior reveals a traditional design with light-colored siding and dark green shutters, complemented by grassy areas and trees in the background.

4.96 out of 5 average rating, 106 reviews

ONE Minute walk to BEACH! High end home special!

ONE Minute walk to the BEACH! High End, newly remodeled beach house SPECIAL! Walk to great bars, restaurants, breakfast spots, shopping and more! 3br, 2bath (1 full ba + 1 half ba + 1 enclosed outdoor shower) with high end granite kitchen. SPACIOUS living area and bonus sun porch & office! Newly landscaped yard, high end patio/driveway/walkways and built in fire pit next to a fully furnished outdoor lounge! Dishwasher, washer/dryer, Central AC, fully applianced kitchen w/ cookware and more!

FamilyIndoor spacesCheck-in

4.82 out of 5 average rating, 129 reviews

Cottage in Harwich Port

2BR Directly on Pleasant Beach – 30 Steps to Ocean

You are not near the beach- You are on it! Only 30 steps from your door to the ocean! Fall asleep to waves. This is a true beachfront cottage located directly on Pleasant Beach. Drink your morning coffee watching the tide roll in. This adorable cottage is reflective of old Cape Cod and is part of a direct beachfront triplex property in the heart of Cape Cod with panoramic views of Pleasant Beach. You'll never feel like you need to leave the cottage but it is close to the quaint Harwich village.

Indoor spacesKitchenLaundry

The living area features a cozy arrangement of blue sofas surrounding a coffee table, with artwork on the walls and soft lighting. A fire pit shines brightly in the backyard, where guests gather under string lights, creating a welcoming atmosphere. A spacious bedroom includes a neatly made bed with beach-themed decor and a fan overhead. A storage area displays bicycles, demonstrating available amenities for outdoor activities.

4.92 out of 5 average rating, 425 reviews

★ 0.4mi Beach &Village ★Firepit & Fireplace★ Bikes

✅4 adult bikes / helmets / beach chairs ✅Woodburning FPL in LR w/65” ROKU TV ✅Located at end private cul-de-sac, 0.4mi to ocean beach & 1/2mi to Village ✅Steps to restaurants & Sundae School Ice-Cream ✅Enjoy the backyard w/plenty of seating, fire-pit, outdoor shower & hammock ✅Large eat-in kitchen w/Island ✅2 Queen BR’s downstairs & 2 twin + rollaway in loft plus 1/2 bath ✅Pet Fee $30/day ✅1200 Mbps FastWiFi ✅Washer/Dryer ✅ Full A/C ✅All linens included & beds made Locally managed

KitchenFamilyLaundry

5.0 out of 5 average rating, 251 reviews

A charming colonial home is framed by vibrant yellow blooms. The front porch features a welcoming entrance with a dark door and white trim, flanked by two large windows. Lush greenery surrounds the property, creating a serene atmosphere.

Home in Harwich Port

Harwich Retreat on Cape Cod - Relax or explore!

Enjoy the tranquility of Cape Cod in all seasons. Short walk to the beach. Sleeps 8. Comfortable colonial with open living, dining & kitchen floor plan. 1st floor: full bath with large custom shower & laundry, 4th bedroom/study with picture window overlooking beautiful English-styled gardens. Dining room opens through french doors to a small deck & extensive outdoor living areas with pond, fire pit & outdoor shower. 2nd floor: 3 bedrooms (King, Queen & Twin), luxurious bath w/ deep soaker tub.

Indoor spacesFamilyAccuracy

The exterior of a charming two-story home is presented, featuring a sloped roof and light blue shutters. Well-maintained greenery surrounds the entrance, which is framed by a modest walkway and bordered by vibrant hydrangeas. A fenced yard offers a sense of privacy.

4.96 out of 5 average rating, 206 reviews

4 Minute Walk to Beach, Cape Cod Serenity

Located on a quiet corner with lots of privacy, 2 full baths, 4 bedrooms, outdoor shower, and a quick stroll to the beach. Activities, great restaurants and shopping are moments away! Fully equipped kitchen, linens included, outdoor seating, a grill and beach accessories will make your trip great. 1 full bath down with two bedrooms, 1 full bath up with two bedrooms. AC/Heating units installed to make your stay more enjoyable! June, July and Aug are 7 day stays w/ Friday as arrival day!

KitchenFamilyGetting around

A cozy living room features a large, light-colored sectional sofa adorned with various decorative pillows. A neutral coffee table sits centrally on a woven area rug. Natural light enters through multiple windows, and a wall-mounted flat-screen TV is visible, enhancing the inviting atmosphere.

4.93 out of 5 average rating, 301 reviews

Walk to Beach - Experience Dennis Beach House - AC

A quaint, cozy, well-decorated & well-equipped Cape Cod cottage located .2 miles away from Sea St Beach and a variety of other bars/restaurants, coffee shops and more. The house sleeps 5 people comfortably and has 1 small bathroom. Kitchen is fully stocked. 4-6 bath towels will be provided. The house has many smart home tech amenities, central air, Temperpedic mattresses, and a lovely & large outdoor space/back deck. First time booking on Airbnb? Save using link: www.airbnb.com/c/brianm30025

KitchenFamilyCleanliness

4.97 out of 5 average rating, 300 reviews

Pet Friendly - Walk to Downtown Dennis Port!

Newly renovated - cozy, clean and bright! PET FRIENDLY! (PRE APPROVAL required) All amenities provided for an enjoyable and relaxing family vacation or quick get-a-way! Three car driveway and private outdoor shower. Five minute walk to Dennis Port Main Street shopping, restaurants, yoga, Pet Salon, and Town playground. South Side Beaches and Ponds just 1 mile away as well as Cape Cod Bike Trail minutes away! Pet friendly beaches in Dennis after Labor Day and before Memorial Day weekends.

Indoor spacesFamilyTV

A tranquil scene captures a couple seated on a dock, surrounded by tall green grasses. The calm water reflects soft hues of pink and blue from the sunset, creating a serene backdrop of trees across the pond.

4.96 out of 5 average rating, 239 reviews

Lakefront House/Private Dock/Year Round Hot Tub/AC

Beautiful cottage nestled on a half-acre of waterfront property on Swan Pond. The dock offers direct water access. Available are two kayaks, a canoe and two paddleboards. The kitchen offers beautiful views of the water while you enjoy your morning coffee. Local beaches are just minutes away. Enjoy the hammock, swings, hot tub, grill, outdoor fire pits and cocktails on the deck. Wanderers' Rest is located close to bike trails, boat rentals, movie theaters, restaurants, and bars.

KitchenFamilyValue

A charming Cape Cod house is presented, featuring a light grey exterior and a sloped roof. A white picket fence surrounds the front yard, adorned with neatly trimmed bushes. A stone pathway leads to the front door, framed by windows and a symmetrical layout.

4.86 out of 5 average rating, 228 reviews

Lovely! 4Bed 3baths Walk to Beach DennisPort

Dennisport! Excellent location! Great for groups and families! Easy walk to 3 public Beaches with the warm waters of Nantucket sound! This lovely home is fully equipped, comfortably sleeps 8 with 4 bedrooms, 3 baths, outdoor shower and al fresco dining on deck or porch. A mile to downtown where you'll find great restaurants and cafes. The space is designed for comfort and convenience and exploring the Cape from this Dennisport home is easy due to it's central location.

Indoor spacesKitchenCondition

The cottage's exterior features a welcoming entrance with a white door and blue shutters. A well-maintained lawn stretches in front, bordered by a gravel path. Two Adirondack chairs are positioned on the lawn, inviting relaxation under the clear blue sky.

5.0 out of 5 average rating, 135 reviews

@TheCapeSummerHouse - 2bdrm Cottage in Dennisport

Explore Cape Cod from a Beautiful Cottage in Dennisport Village Freshly updated and sunny! This cozy cottage exudes coastal charm. It has a large yard perfect for the kids to play & located just .2 miles to Glendon Beach on Nantucket Sound. It’s a great place to get away for a Cape Cod vacation: central AC, fenced-in backyard with a Weber gas Grill & fire-pit, quintessential outdoor shower, WiFi, Smart TV’s, updated kitchen including a dishwasher, washer & dryer.

FamilyKitchenBackyard

A charming home features a light grey exterior with a dark shingled roof and two dormer windows. A front yard with green grass is accented by a wooden fence. Two black Adirondack chairs are positioned invitingly on the lawn.

4.78 out of 5 average rating, 111 reviews

Sandy Feet Retreat

Located on highly desirable Oak Street in Dennisport, you will relax and unwind in a newly updated 3BR/ 2 BA home. 2021 updates included a fully fenced in backyard and central air conditioning! Exterior renovations will be done Spring 2022! Updated master bedroom with a master bathroom including Electrolux washer and dryer. Less than 1000/ft walk to private Oak Street Beach and located in a family friendly neighborhood with many restaurants within walking distance.

Indoor spacesFamilyOutdoor spaces

Popular amenities for Dennis Port family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Superhost

Home in West Dennis

Walk2Beach, HotTub, FirePit, PetsOk

FamilyIndoor spacesLaundry

4.8 out of 5 average rating, 214 reviews

4.96 out of 5 average rating, 169 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*

KitchenIndoor spacesComfort

4.95 out of 5 average rating, 321 reviews

A spacious dining area features a long white table adorned with a runner and decorative centerpiece. Overhead, a chandelier adds elegance, while large windows frame views of the water. Natural light brightens the room, complemented by charcoal slate flooring and a cozy seating arrangement nearby.

Home in Chatham

Slate House - a modern waterfront getaway

FamilyKitchenHospitality

4.92 out of 5 average rating, 319 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 spacesParking

4.94 out of 5 average rating, 121 reviews

An outdoor area showcases a gas firepit surrounded by several chairs on a stone patio, under a pergola. In the background, a deck with outdoor furniture and a hot tub is visible, complemented by a fenced yard and lush trees. Sunlight brightens this inviting space.

Home in West Yarmouth

Awesome Cottage near Beach, Backyard Bar & Hot Tub

Indoor spacesKitchenHot tub

4.97 out of 5 average rating, 126 reviews

A covered outdoor seating area features a comfortable sectional sofa with neutral cushions and a round coffee table. A dining table with several chairs is positioned nearby, alongside an outdoor kitchen equipped with a grill. Sunlight casts distinct shadows across the space.

Home in East Falmouth

Seacoast Shores Oasis-Steps From Private Beach Bay

FamilyIndoor spacesCheck-in

5.0 out of 5 average rating, 104 reviews

An open living area features large glass doors that provide views of the golf course. A comfortable seating arrangement includes a recliner and a sectional sofa. A spiral staircase leads to the loft above, and a mounted television is positioned above a modern fireplace.

Condo in Brewster

Ocean Edge Resort/Pool access/2bedroom-2bath Condo

Indoor spacesKitchenGetting around

4.9 out of 5 average rating, 332 reviews

A hot tub is situated under a wooden pergola, surrounded by trees reflecting natural greenery. Soft lighting is arranged along the structure, creating a calm ambiance. The tub is partially covered, with jets visible, inviting relaxation after a day at the beach.

Home in West Dennis

Sun Sand & Sea House- Fenced Yard and Hot Tub!

FamilyKitchenBeach

Family- and pet-friendly home rentals

A cozy living area is equipped with comfortable seating, including a gray couch and armchair. A nautical-themed rug anchors the space, while a wall clock and decorative items add character. A fireplace against the light-colored wall enhances the welcoming atmosphere, with a view of the kitchen beyond.

4.94 out of 5 average rating, 246 reviews

Walk to beach - firepit - fireplace

Indoor spacesKitchenWalkability

4.99 out of 5 average rating, 148 reviews

A circular stone fire pit is surrounded by four white Adirondack chairs, offering a cozy gathering spot. Flames flicker above a bed of decorative stones, casting a warm glow. A smooth patio surface extends around the area, enhancing the outdoor experience.

Cottage in West Dennis

5 min walk to beach w/modern amenities

Indoor spacesKitchenCleanliness

A loft space features three full beds and three twin beds, suspended from the ceiling by thick manila rope. Blue bedding adds a coastal touch, while the light wood floor complements the airy atmosphere. Large windows provide natural light, enhancing the open design.

5.0 out of 5 average rating, 104 reviews

Cozy Family Retreat Sleeps 14 Pets Fire Pit

FamilyKitchenBarbecue

4.99 out of 5 average rating, 136 reviews

A spacious, modern kitchen area features a large island with a dark base and white countertops, accented by pendant lights above. To the side, an open concept living space includes a comfortable seating arrangement and dining area, with natural light streaming in through large windows.

Home in Harwich

Spacious cottage beach Wychmere < 4 min Central AC

Indoor spacesFamilyCheck-in

4.99 out of 5 average rating, 337 reviews

A private waterfront deck offers a serene view of Flax Pond, surrounded by lush greenery. Adirondack chairs are positioned for relaxation, providing a perfect spot to enjoy the tranquil waters and natural surroundings.

Home in Dennis

Stunning Waterfront with Serene Sunrise Views!

FamilyKitchenOutdoor spaces

4.99 out of 5 average rating, 133 reviews

Home in Yarmouth Port

Sauna · Fireplace · Waterfront · 2 Kings · DogsYes

Indoor spacesFamilyView

4.99 out of 5 average rating, 156 reviews

A cozy studio space showcases a grey sofa with decorative cushions, positioned beside a small table featuring a fan. The kitchenette is visible in the background, equipped with white cabinetry and essential appliances. Natural light filters through a window, illuminating the warm and welcoming interior.

Apartment in West Dennis

The Cape Cod Perch at West Dennis Beach Studio Apt

FamilyIndoor spacesWalkability

4.98 out of 5 average rating, 159 reviews

A cozy living area is highlighted by a stone fireplace, contributing to the room's warmth. A light-colored sofa and a decorative throw are arranged atop a patterned rug. Natural light enters through windows, enhancing the inviting space with a relaxed atmosphere.

Cottage in West Yarmouth

Charming cape cod cottage

Indoor spacesKitchenValue

Family-friendly home rentals with a pool

4.93 out of 5 average rating, 134 reviews

A communal pool area features a clear blue pool surrounded by concrete decking. Lounge chairs are arranged neatly on the sides, with greenery visible in the background. A wooden fence encloses the area, providing a private atmosphere.

Condo in Dennis Port

Sea Salt Studio - Steps to Glendon Rd Beach

FamilyKitchenSolo travel

5.0 out of 5 average rating, 13 reviews

Home in South Dennis

Modern Oasis, Heated Saltwater Pool, Beach, Golf

KitchenFamilyQuiet

4.91 out of 5 average rating, 11 reviews

Apartment in Dennis Port

Deluxe Double Room | Full Studio w/ Kitchenette

HospitalityNearbyValue

4.97 out of 5 average rating, 33 reviews

A cozy living area features light wood paneling and large windows allowing natural light. A gray sofa is paired with a wicker rocking chair, and a white TV console sits opposite. A decorative sign displaying 'COTTAGE' adds a charming touch.

Tiny home in Dennis Port

Cozy cottage steps to the beach!

FamilyIndoor spacesView

The exterior of a contemporary cottage is seen, featuring a light-colored wooden facade and a circular window. An American flag is displayed proudly from the front. A fenced yard surrounds the property, complemented by greenery and a gravel pathway.

4.9 out of 5 average rating, 93 reviews

Bright and Lovely Cottage With Community Pool

Indoor spacesKitchenValue

A bright studio unit features a queen-sized bed with a comfortable pull-out sofa nearby. Natural light floods the space through large windows. A small dining table with two chairs is positioned next to the seating area, providing a functional living space.

4.96 out of 5 average rating, 92 reviews

Walk to the beach or sit poolside! Updated studio!

FamilyKitchenAccess

4.83 out of 5 average rating, 6 reviews

Home in West Yarmouth

Coastal Luxury Oasis - Ag2 Luxury Home

FamilyKitchenPool