Family-friendly holiday rentals in Dennis Port

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, 103 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!

A serene beach scene captures the sun setting over calm waters, casting soft pink and orange hues across the sky. Gentle waves lap against the sandy shore, and distant silhouettes of homes can be seen along the coastline, surrounded by lush grass.

4.93 out of 5 average rating, 100 reviews

Salt Cottage Dennis Port, Cape Cod, MA

Two bedroom cottage that is merely a few steps to a private beach. **Can be booked with it’s adjacent sister properties, ‘Seabbatical (Sea) Cottage and Shore Thing (Shore) Cottage,’ for larger groups. Views of the ocean from front windows & deck. Salty breezes to breathe in and the sound of waves to put you to sleep nightly. Everything you need for a summer vacation. Perfect beach for families-close enough to hop back to the cottage for whatever you need. Relax, unwind & enjoy Cape Cod.

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

4.98 out of 5 average rating, 238 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 ★

Welcome to SEAGLASS COTTAGE! 🔸 200 MBPS WIFI 🔸 Steps to sandy beach on a crystal clear pond 🔸 Pet friendly 🔸 Linens & towels are included. Beds will be made 🔸 Swim, fish or use our 2 kayaks & 2 SUP’s 🔸 Bluestone private patio w/waterviews+charcoal BBQ 🔸 Outdoor shower 🔸 Sunroom w waterview 🔸 Washer+dryer 🔸 Fully equipped kitchen w/Carrera marble counter 🔸Gas firepit 🔸Ductless A/C & Heat 🔸Small library of books, didn't finish the book? Take it! 🔸Pet fee $25/day

4.97 out of 5 average rating, 294 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, 526 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

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 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.

4.97 out of 5 average rating, 235 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.

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, 131 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.

4.99 out of 5 average rating, 145 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.

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

4.81 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

4.95 out of 5 average rating, 316 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

4.91 out of 5 average rating, 182 reviews

A private hot tub is set beneath a wooden pergola, surrounded by vertical slatted fencing. Natural light filters through the structure, casting patterns on the spa surface. Green foliage is visible in the background, creating a serene outdoor retreat.

Home in West Dennis

Violet’s Place- king bed- pet friendly- hot tub!

4.92 out of 5 average rating, 316 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

4.92 out of 5 average rating, 106 reviews

An outdoor entertainment area features a hot tub surrounded by a wooden deck, flanked by comfortable seating with bright cushions. A large umbrella provides shade, and a cooler displays refreshments. Colorful flowers and lush greenery enhance the tranquil ambiance of the space.

Home in Chatham

Great Chatham Location w/ Hot Tub, Near Beach!

4.98 out of 5 average rating, 170 reviews

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.

Home in Centerville

Luxury House 0.25 mi from Craigville Beach

5.0 out of 5 average rating, 10 reviews

Luxury Waterfront - Hot Tub, Deck & Waterviews

Family- and pet-friendly home rentals

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

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

A spacious backyard is highlighted, featuring a deck furnished with seating and an umbrella for shade. A well-maintained lawn surrounds the area, complemented by a fenced perimeter. Various seating arrangements, including Adirondack chairs, are positioned for relaxation in the outdoor space.

4.97 out of 5 average rating, 146 reviews

Cape Escape

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, 242 reviews

Walk to beach - firepit - fireplace

5.0 out of 5 average rating, 129 reviews

Home in Yarmouth Port

Sauna · Fireplace · Waterfront · 2 Kings · DogsYes

4.99 out of 5 average rating, 387 reviews

A serene outdoor seating area is set by the waterfront, featuring two chairs with teal cushions and a white table. Lush greenery surrounds the area, enhancing the view of the calm waters and trees beyond. Lanterns add a subtle decorative touch to the space.

Home in Yarmouth Port

Fabulous Waterfront with Spectacular Sunset Views!

4.92 out of 5 average rating, 103 reviews

Home in East Dennis

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

4.96 out of 5 average rating, 127 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

Family-friendly home rentals with a pool

4.92 out of 5 average rating, 126 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

4.92 out of 5 average rating, 105 reviews

The exterior of the cottage features a well-maintained lawn with lush green trees in the background. A wooden deck extends from the house, along with patio chairs overlooking a tranquil pond surrounded by vibrant flowers and plants.

Cottage in Centerville

The Holly Cottage

4.87 out of 5 average rating, 119 reviews

The exterior of the Cape Cod cottage is shown, featuring a light-colored siding and a unique turret-like structure. Lush green landscaping surrounds the home, which is set back from a gently curved pathway. Tall trees provide natural shade in the area.

Townhouse in Brewster

Ocean Edge Cape House with Beach, Pool, and AC

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!

The living area is furnished with two striped sofas and a white coffee table, creating a casual setting. Natural light is provided by a large window with light drapes. A decorative round tray rests on the coffee table, and a lamp stands on an adjacent side table.

4.96 out of 5 average rating, 55 reviews

Poolside studio home! A walk to the beach!

5.0 out of 5 average rating, 7 reviews

Home in South Dennis

Modern Oasis, Heated Saltwater Pool, Beach, Golf

4.81 out of 5 average rating, 90 reviews

The spacious living area features a queen-sized bed and a comfortable sofa. A dining table with two chairs sits near the window, allowing natural light to brighten the room. Simple decor includes star-shaped wall accents, enhancing the relaxed coastal ambiance.

Condo in Dennis Port

Comfy Cape Escape! Spacious, Cozy, Close to Beach!