Holiday houses in Seaside

Anchors Away Beachfront *Pet Friendly

Custom Oceanfront Retreat with 2 Kitchens & Beach + Bay Access Location, location, location! This coastal gem is tucked away in the quiet, cozy northern end of Seaside, offering the perfect balance of secluded relaxation and easy accessibility to local attractions and adventures. Boasting "front row" access to breathtaking ocean views, you can enjoy whale watching, dramatic storm watching, and amazing sunsets right from your window. Whether you’re capitalizing on a sunny day in your "beach backyard" or cozying up by the fire to watch the clouds roll in, the shoreline is always at your fingertips. Adventure starts at your doorstep with direct trails leading to the beach, the boardwalk, or the bay. Clamming is popular on this stretch of beach, just steps away on the ocean shore. A quick 2–3 minute stroll brings you to the estuary—known to locals as “the end of the world”—where you can explore, kayak, crab, or catch a sunrise. For a change of pace, take a 8–10 minute walk to the iconic Seaside boardwalk which will lead you into the heart of town to explore the local shops, restaurants, and attractions that make this Oregon Coast destination so beloved. Anchors Away is your one-of-a-kind coastal escape in Seaside. This custom-designed oceanfront home blends upscale comfort with unforgettable character. From the moment you arrive, you’ll notice the thoughtful craftsmanship and distinctive maritime charm woven throughout, including authentic ship-inspired accents like vintage porthole windows and a striking captain’s wheel that pays homage to the sea just steps away. This spacious retreat comfortably sleeps up to 14 guests, with additional sleeping options including rollaway beds and a sleeper sofa, making it an ideal setting for large groups, multi-family vacations, or special gatherings. Inside, the home is designed with both comfort and flexibility in mind. Two kitchens allow for easy meal prep and entertaining, whether you’re cooking together or dividing responsibilities between groups. Two separate family rooms create inviting spaces to gather, relax, or enjoy a movie night, while still offering enough room for everyone to spread out and unwind. A modern combo washer/dryer unit adds everyday convenience, especially for longer stays or beach-filled days. Throughout the home, expansive windows showcase sweeping ocean views, filling the space with natural light and the calming presence of the Pacific. Upstairs, the home opens into a bright and airy main living space featuring a full kitchen and sweeping, panoramic views of both the ocean and the bay. This level includes two bedrooms—one with a king bed and a clever pocket door that can be closed off from the front room for added privacy, and another with a full/queen bunk bed and a full bathroom. A cozy fireplace adds warmth and ambiance, while a rolling big-screen TV provides flexible entertainment that can be enjoyed from anywhere in the upstairs living space. The downstairs level is truly a standout feature of the home, offering a unique and versatile gathering space with a king bedroom, a queen bedroom, a sleeper sofa, two roll away beds and a full bathroom. At the center is a one-of-a-kind game table that transforms seamlessly between a pool table, ping pong table, and a custom dining table—an exceptional amenity that brings everyone together for games, meals, and shared experiences. Whether you’re hosting a friendly tournament or sitting down for a family dinner, this space is designed to create lasting memories. In this space, you’ll also find a stunning custom wood-burning fireplace that serves as a warm and inviting centerpiece for the space. From here, step directly out onto the lower deck and enjoy immediate access to the beach, making it effortless to transition from indoor fun to oceanfront relaxation. Outdoor living is just as impressive as the interior. The outdoor amenities are designed for gathering and enjoyment, including a fire pit perfect for s’mores under the stars, an outdoor tabletop fire for cozy conversations, and a full barbecue setup for classic coastal cookouts. Whether you're planning a lively gathering, a family reunion, or a relaxing getaway by the ocean, this extraordinary home offers the space, amenities, and location to make your stay truly unforgettable. Notes: Up to 2 Dogs allowed in our home with a flat $200 pet fee 3 vehicles allowed in the driveway with additional parking at the end of the street *Save this home :❤️: to easily find it later* We strongly encourage all guests to purchase travel insurance to protect against unexpected cancellations, travel disruptions, illness, weather events, or other unforeseen circumstances. Refunds are issued in accordance with the cancellation policy selected at the time of booking.

Family · Location · Cleanliness

Pond View At The Commons 08 - Dog Friendly

Nestled along the serene Mill Pond, this brand-new 2-bedroom, 2-bathroom home is your perfect retreat to the Oregon coast. With space to accommodate up to six guests, this home offers the ideal setting for relaxation, fun, and making lasting memories. We are a unique collection of 24 homes designed with fun in mind. Step outside to enjoy the communal outdoor space, complete with corn hole boards, BBQ grills, and cozy fire pits. Rainy day? Head to the game room and keep the good times rolling.

Family · Value · Barbecue

Oceanfront #102 1 bdrm Condo

Located in a small condo- co op of 15 units at the quiet north end of Seaside's famous Prom, our 1 bdrm unit features a full kitchen, e-center, Queen sofa sleeper, separate bdrm & bath areas & all the kitchenware needed for those sunset meals at the dining Table. Pet fees: 2 Pets maximum. $50 per trip Self check-in, After receiving your car information, color, model/make, and plate number, Your Key Lockbox code will be provided on check-in day, when your Unit is ready for your arrival.

Location · Family · Nearby

The Sweetheart Cottage, Dreamy Stay Steps to Beach

Explore Seaside from our charming cottage, situated at the northern end of the iconic Seaside Promenade. This prime location offers you a tranquil retreat just steps from a quiet stretch of beach. A short stroll down the Promenade leads you to the heart of town, where you can enjoy a variety of restaurants and enjoy local attractions. Ideal for families and couples alike, the cottage boasts stylish, cozy interiors, comfortable beds with luxurious Brooklinen sheets, and an inviting fireplace.

Value · Family · Indoor spaces

OB:}A+View of Waterfront/Mt/River/Ocean~Hottub~Dog

Ocean Breeze is a magnificent home nestled in the quaint and quiet neighborhood of Gearhart. Our home overlooks the Necanuim River and boasts amazing views of the River, the North Pacific Ocean, Tillamook Head Mountains, and the City of Seaside through the wall to wall windows and has direct access to the shores of the estuary. Ocean Breeze is a perfect getaway for fun, rest, relaxation, doing activities, and gathering with loved ones. 1 mile from Locals favorite McMenamins Restaurant & Pub

Family · Location · Nearby

#210 Amazing Tradewinds Condo Beach Studio-

Beautiful large studio with a king bed and a pullout couch that turns into a king size bed is located at the north end of the Prom in Seaside. There is 1 free parking space onsite per unit. Pet fees: 2 Pets maximum. $50 per trip Pets may not be left unattended in your Unit, crate, or your vehicle. Self check-in, After receiving your car information, color, model/make, and plate number, Your Key Lockbox code will be provided on check-in day, when your Unit is ready for your arrival.

Value · Family · Sleep quality

Seaside Saltbox, 2 blocks 2 sand

Welcome to Seaside, OR. This 1950's home sits 1.5 blocks from the promenade and sand. Home features updated kitchen with quartz counter top and stainless appliances. 3 bedrooms, 2 petite bathrooms, and laundry room. Back yard is fenced with hot tub, deck, basketball hoop, small put-put, and space for dining. Close to annual: Soccer In The Sand, 4th of July Beach Fireworks, Hood 2 Coast finish line, Beach Volleyball, Oregon Beach Kites, Spotlight Dance Cup, Chalk It, Ride The Dirt Waves.

Location · Family · Pets

The Beachy Brothel (aka The Seaside Retreat)

Relax and recharge in Seaside's crown jewel. Enjoy this fully renovated, 120 year old beauty that's filled with charm (Seaside's original brothel). Sip coffee in the sunroom, enjoy conversation with family & friends in the gorgeous custom kitchen or retreat to one of the cozy high design bedrooms for some quiet time. This home has everything you need to unplug and relax. Steps away from the beach and an easy walk to downtown, you won't find another place quite like this on the N. Coast!

Value · Location · Bathroom

160) The Tides by the Sea

Relax in this bright and airy second-floor, 2 BR condo. The boho-chic living room features panoramic views of the ocean, electric fireplace, and vaulted ceilings. Full kitchen for preparing meals, and a large dining table for game nights. Bedroom 1 has a king bed with Sleep Number mattress for your perfect firmness; Bedroom 2 features queen-size bunk beds and a peek-a-boo ocean view. Walk the beach, swim in the pool, walk to shops and restaurants, or just take in our glorious sunsets.

Value · Family · Pool

Ocean's Daughter Seaside Retreat

Escape to coastal luxury in this custom golf course home, just half a block from The Cove, Seaside's premier surfing and beachcombing beach. This elegant single-level retreat features three king suites, sun-filled open living spaces, ocean-inspired décor, a gourmet kitchen, and a cozy gas fireplace. Relax in the private hot tub, dine on the patio, unwind in the fenced backyard, or enjoy the game room. Thoughtfully designed for comfort, style, and memorable coastal getaways.

Value · Location · Backyard

Beautiful updated oceanfront condo

Welcome to Ocean Breeze, an oceanfront Seaside Getaway. Escape to the beauty of the Oregon Coast and experience true beachfront living in this cozy oceanfront retreat in Seaside. With breathtaking views of the Pacific Ocean and direct beach access just steps away, Whether you're seeking a romantic weekend, a family beach vacation, or a peaceful retreat from everyday life, this oceanfront haven offers the perfect blend of comfort, convenience, and natural beauty.

Family · Location · Decor

Sea Glass Inn - Suite #10

This two-story suite includes a living area on the lower level and a sleeping area on the upper level, making it our only two-bedroom unit. Each bedroom is equipped with a queen-size bed dressed in luxurious linens. The main floor features a cozy living room with comfortable seating and a smart TV. The kitchenette and dining area are located near the entryway and adjacent to the living room. This room does not allow pets.

Family · Location · Decor