Holiday rentals in Dennis 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.

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.

Breezy home with easy beach access and ocean views

Across the street from Glendon Beach on Nantucket Sound, this spacious home with views of the ocean will help you create beautiful memories with family and friends. The home is fully furnished with kitchen supplies, beach items, games, books, kayaks, an electric Tesla car charger and more to make your time off comfortable and rejuvenating. Enjoy the ocean breeze in the large grassy yard with firepit. 4-6 car parking in the driveway. Sleeps 8 comfortably, perfect for a small family or friends.

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.

Expansive Ocean Views

Welcome to Dunes Edge! Embrace the charm of coastal living at our unique private beach cottage. Perched on a sand dune just a step from the beach. Awake to the sweet salty air & the soothing sounds of suttle waves. Immerse yourself w/the tranquil ocean views. 1 queen bed, 2 twin mattresses in the loft, & a pull-out sofa. Full kitchen, bath & an outdoor shower. Step back in time by enjoying a community that was built in the 1950's. The last of its kind. A place where memories are made.

Walk to beach/Pelham House, dog friendly, sleeps 6

With ample parking, get here and leave your keys! Walk to summer musts within 10 minutes including the BEACH, restaurants, resorts, ice cream, mini golf, coffee and more. Unwind in this open, bright, 2bd(+bonus room), 1bath home. LINENS provided, children/adult books&games, kitchen cooking/grilling needs, beach chairs and wagon. Outside is where the memories are made. Fenced-in, large yard for kids & dog, outdoor shower, dining w/ lights for ambiance, and a comfortable lounge section.

Cozy Summer Cottage w/ Water Access

Welcome to your cozy summer cottage. Whether it’s a Netflix night in or an Adventurous day Kayaking to the beach, we got you covered. You can head straight to Swan Pond right in the neighborhood and paddle to the beach! You won’t have to pay or fight for parking! You can also easily bike around scenic trails next door. Located in Dennis Port, you can bike to the Beach (about 10 min) and spend the day at the beach or head to Main St. Just bring your own bike/kayak or rent them close by.

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!

Luxury Waterfront - Hot Tub, Deck & Waterviews

Welcome to Aunt Laura’s Retreat, a newly renovated waterfront home ideal for families and groups seeking a relaxing Cape Cod getaway. Enjoy beautiful water views from every room, direct access to Swan Pond for kayaking and beautiful sunsets to end the day. Unwind in the hot tub, dine on the deck overlooking the water, or relax on the lower patio with a grill and cozy seating. - Direct access to Swan Pond - 5 min drive to Sea Street Beach - Close to Cape Cod Rail Trail & dining

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

Modern & Coastal Cape Cottage + Steps to Beach

Newly remodeled in 2025! Just 200 steps from Haigis Beach, Surfcamp Cottage mixes beachy charm with modern comfort. This sunny 2BR features an open layout, A/C, full kitchen with ice maker, dishwasher, large outdoor shower, and a deck where you can hear the waves. Bikes, beach gear, and BBQ grill included! Walk or bike to beaches, dining, and fun. Centrally located near Hyannis & ferries. This unforgettable spot is anything but ordinary.

Salt Cottage

Make unforgettable family memories at this charming, kid-friendly cottage just a short walk from the beach and an even shorter walk from a playground! Stay cool and comfortable with mini-split A/C units in the living room and both bedrooms. The fully equipped kitchen features a fridge, full-size stove and oven, microwave, and a compact dishwasher—perfect for easy, stress-free meals after a day in the sun.