Family-friendly vacation rentals in Dennis Port

4.96 out of 5 average rating, 164 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*

Welcome to the Bayside Retreat! Enjoy the real Cape Cod in this Quintessential Beach Rental Featuring: Private hot tub, outdoor patio & sofa set in a peaceful backyard 🕊️ 2️⃣ Kayaks- Outdoor Shower- Gas Grill 🔥 Indoor Gas Fireplace ❄️ Mini Splits ✔️Games ✔️Washer/Dryer 📺 55” Sony TV w/ Apps & DirectTV 🛋️ Comfy Furnishings➕Stocked Kitchen 🛁New Bathroom 🕊️Relax out back in peace & privacy or go explore! 📍 Centrally located ❌NO FEES ⛱️ Year Round Beach Vacation ➡️Bayside_Retreat_Capecod

4.97 out of 5 average rating, 295 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.

4.83 out of 5 average rating, 528 reviews

The image displays four sections of the cottage. A cozy sleeping area features a full-size bed with soft linens. A bright kitchen with marble counters is visible, alongside a comfortable living space with seating. An outdoor deck with furniture showcases a partially fenced yard.

Tiny home in Dennis Port

★TINY HOUSE★4/10mi Beach & Village★Pet OK★2 Bikes

Welcome to SAND PEBBLE COTTAGE! We are PET FRIENDLY! ($25/nt) This 300sq.ft "TINY HOUSE" walk to ocean beach, dog park & Dennisport village At the end of a cul-de-sac, this tiny cottage has everything you need ✅ 4/10mi to beach & village ✅ Kitchen w/marble counter ✅ 2 Bike w helmets ✅ Deck w/furniture & charcoal BBQ ✅ Parking-2 cars ✅ Separate bedroom ✅ Full A/C ✅ Bring your sheets/towels- or our cleaners can provide for a charge ✅ Pet friendly-only 1 pet $25/nt

4.93 out of 5 average rating, 103 reviews

Cottage in Dennis Port

Oceanview Cottage, Million $ View Sea Street Beach

Oceanview Cottage! Everything you will need for your Cape Cod stay including the best view. Wake up to the scent of the ocean, see and hear the waves, make your way down to the sand to sink your toes right in. We have fully updated everything in this home. Newer furnishings, including a full kitchen, bath, central AC, outdoor shower for your stay! You won't believe your eyes and the changes we made! Cape Cod decor, homey, and warm! Quick stroll to The Pelham Rooftop Restaurant!

4.99 out of 5 average rating, 144 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

Welcome to west_dennis_rental! Just 5 minutes from the beach, this updated Cape Cod home is perfect for small families seeking a relaxing getaway. Inside, enjoy a remodeled space with modern comforts and cozy charm. Out back, unwind on the patio with a lush lawn and easy-start gas fire pit—great for dinners or s’mores under the stars. Stocked with linens, beach gear, toys, games, Wi-Fi, AC, full kitchen, and grill. Close to Holiday Hill mini golf, ice cream, and seafood shacks!

A single-story home is positioned on a large corner lot, surrounded by a well-maintained lawn. A covered front porch enhances the entrance, while landscaping features add visual interest. The semi-private driveway leads to a spacious backyard with trees in the distance.

4.92 out of 5 average rating, 215 reviews

SUMMERS OFF CAPE HOUSE

All new paver patio and landscaping with enormous back yard. Spacious home on large corner lot just 5 minute walk to downtown Dennis Port or Inman Beach. Fully stocked kitchen. Huge LR w/ 2 couches, large fireplace and TV/DVD. BD#1 has a queen bed with a 1/2 bath ensuite. BD#2 has a queen bed. BD#3 has 2 twin over full bunk beds as well as pack n'play for infants. Covered front porch, screened in side porch, gas and charcoal grill, horseshoe pit and spacious outdoor shower.

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, 221 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.

5 out of 5 average rating, 131 reviews

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.

Cottage in Dennis Port

@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.

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.

4.99 out of 5 average rating, 148 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

Take it easy at this unique and tranquil getaway just a short walk from three Nantucket Sound beaches. This 300-square-foot studio apartment on the second floor of our home. With a brand new Weber grill, picnic table, and fire pit, there is plenty of outside living. Trotting Park, South Village, and West Dennis Beaches are all walkable. Enjoy food from Sandbar, Swan River Seafood, Chapin's, Cleat & Anchor, & Bandera's Market in the summer. Call off season.

4.97 out of 5 average rating, 202 reviews

A compact studio space features a queen bed with a blue blanket and a decorative pillow. A kitchenette with yellow cabinetry includes a stove, refrigerator, and microwave. Natural light fills the area, complemented by a small dining table and a television mounted on the wall.

Condo in Dennis Port

#3 Seashore Studio, 300 yards to Glendon Beach

Newly renovated 250 square ft studio at Near Beach Rentals. 300 yards to Glendon Beach. Fully furnished studio waits for your Cape Cod getaway. Head to the beach in the morning and you're close enough to walk back for lunch. Studio comes with a queen bed, a twin bed, kitchenette with stove, fridge, coffee maker and microwave, air conditioning, 40" smart TV, newly renovated bathroom, Wifi, and access to the shared courtyard with grills and furniture.

4.86 out of 5 average rating, 600 reviews

An open living area features a comfortable gray sofa facing a round dining table and chairs. A full kitchen is equipped with modern appliances, including a stainless steel refrigerator. Natural light brightens the space through large windows, complemented by light-colored wooden flooring.

Cottage in South Dennis

Beachfront Cottage on White Pond (Marshmallow)

Our Cottage sits directly on White Pond tucked away on acres of private property. Our cottage offers a private beach, deck, outdoor shower, outdoor dining area all while enjoying Cape Cod. White Pond is ideal for swimming, boating and fishing. The bike path and well known beaches are less than 2 miles and near to many delicious restaurants. There is another cottage on this property that sleeps four if you have other guest wanting to join

Popular amenities for Dennis Port 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, 317 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

4.55 out of 5 average rating, 11 reviews

Dennis Port House BeachHot Tub & Fire Pit Fun!

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

4.81 out of 5 average rating, 208 reviews

Home in West Dennis

Walk2Beach, HotTub, FirePit, PetsOk

4.94 out of 5 average rating, 114 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

Home in Centerville, Barnstable

The exterior of the house is surrounded by well-maintained greenery and tall, lush trees. A welcoming front entrance is framed by neatly trimmed hedges, leading to a slate pathway and steps. Large windows allow natural light to brighten the façade.

4.98 out of 5 average rating, 170 reviews

Luxury House 0.25 mi from Craigville Beach

4.9 out of 5 average rating, 330 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!

5 out of 5 average rating, 10 reviews

Luxury Waterfront - Hot Tub, Deck & Waterviews

Family- and pet-friendly home rentals

4.97 out of 5 average rating, 239 reviews

A bright bedroom features a spacious bed with colorful blankets and decorative pillows. A variety of sun hats are displayed on the wall, providing a cheerful accent. Natural light enters through the window, illuminating the cozy interior.

Cottage in Dennis

★Waterview ★Pet Friendly ★Kayaks ★Trails ★

4.95 out of 5 average rating, 20 reviews

Ship Cottage | 5-Min Walk to Beach & Dining

4.96 out of 5 average rating, 128 reviews

An outdoor dining area is presented, featuring a rectangular wooden table surrounded by six rattan chairs. A large striped umbrella provides shade. In the background, a mural of an octopus and the words 'Cape Cod' adorns the cottage wall, enhancing the vibrant atmosphere.

Cottage in Yarmouth

Charming Cape Near Beaches + Dog Friendly

4.99 out of 5 average rating, 330 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!

4.92 out of 5 average rating, 103 reviews

Home in East Dennis

** East Dennis - Perfect Spot - Historic Rte 6A **

5 out of 5 average rating, 129 reviews

Home in Yarmouth Port

Sauna · Fireplace · Waterfront · 2 Kings · DogsYes

Guest suite in West Harwich

A cozy living area features a brown sofa set, complemented by a rustic wooden coffee table at its center. A flat-screen TV is positioned on a white stand against the wall, while a rocking chair is visible in the corner. Soft natural lighting illuminates the space.

4.92 out of 5 average rating, 337 reviews

Cape Hideaway

4.94 out of 5 average rating, 242 reviews

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.

Cottage in Dennis Port

Walk to beach - firepit - fireplace

Family-friendly home rentals with a pool

4.83 out of 5 average rating, 40 reviews

The image showcases a heated fresh-water pool surrounded by white lounge chairs, with a fenced area providing a sense of privacy. In the background, the calm waters of Nantucket Sound are visible, alongside a portion of the condominium's exterior, creating a serene poolside environment.

Apartment in Dennis Port

Beachside Condo with Balcony - Oceanside Condos

4.76 out of 5 average rating, 38 reviews

A bright bedroom features blue walls and a floral accent wall. A spacious bed with a textured quilt is positioned prominently. Natural light enters through a skylight, and a flat-screen TV is mounted on the wall. Storage units in warm wood tones complement the space.

Apartment in Dennis Port

King Bed Suite (Pet Friendly) in a great location

4.97 out of 5 average rating, 31 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!

4.96 out of 5 average rating, 77 reviews

Condo in West Dennis

Steps from Bass River Marina · Private Balcony

4.96 out of 5 average rating, 140 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

4.92 out of 5 average rating, 127 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

4.82 out of 5 average rating, 11 reviews

A covered walkway leads to a grassy area with well-maintained landscaping. Lounge chairs are arranged around a heated pool, with ocean views visible beyond a fenced area. The building's exterior features a wooden overhang, providing shade along the path.

Apartment in Dennis Port

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