Holiday rentals in Skagway

Rainbow Country Lodge Ocean Front w/ Glacier Views

The views from this 2800 sq. foot home in Haines, AK are sure to impress the most well traveled explorer. Eagles, whales, sea lions, & moose are seen occasionally. Whether you're a single family, several families, or group of friends, this home is well suited to fit your needs. The yard has a fire pit, treehouse, & lawn chairs. A perfect place, 12 minutes from town, to spread out & enjoy vacation. A charge of $100 per guest after 5 guests will apply per night. Hot tub is no longer available

Forest Hideaway: Central, private guest apartment

Great basecamp to explore Haines! A one-bedroom private apartment 15-minute walk to downtown. Enter the suite by walking up a set of stairs a small private deck and entrance. Set overlooking the forest, the apartment has a bathroom, a fully equipped kitchen, and a bedroom. The bedroom has a queen-sized bed, and there is a maximum of two people. There is nearby parking and walking access to local trails. Fiber WIFI. Owners live in the cabin next door. Dogs on property. Dog friendly upon approval

Front Street #1, 2 BR, water view, w/d, downtown

Nestled along the shores of the spectacular Lynn Canal, Front Street Condos offer the perfect blend of comfort, convenience, and breathtaking scenery. Located just one block from the boat harbor and within easy walking distance to downtown Haines, these new vacation rentals provide an ideal home base for exploring all that Southeast Alaska has to offer. Designed with travelers in mind, each condo is bright, airy, and spacious—perfect for families, couples, or friends.

Perfect Downtown Skagway Apt, Walk Everywhere

Step into your charming downtown hideaway in Skagway, Alaska! An inviting one-bedroom apartment mixing comfort with convenience, it’s perfect for quiet getaways or intrepid explorers. Just minutes from lively Skagway, this delightful space offers a serene base to explore historic treasures, natural beauty, and vibrant culture. Perfect for an active Alaskan adventure or a relaxing stay with your furry friend, this prime location is your ideal Alaska Airbnb.

Skagway Lily Pad/ 3 bedrooms

You are renting three bedrooms with a shared bath, living room and kitchen. You'll only be sharing with the others who you have in the three bedrooms. The location of the LilyPad is within a three block walking distance to Broadway and downtown. There are hiking trails and the Lynn Canal all within walking distance also.

Cozy Skagway Home

Older 3 bedroom home in Skagway, AK within walking distance to grocery store, restaurants, and hiking trails. You will have the main floor of the house and a porch with outdoor eating area that includes a grill and fire pit. The bottom floor is a separate apartment housing Pure Connection Massage Therapy, LMT.

The Nest

Our sunny little cottage sits 2.3 miles from town. There are many options for adventure just minutes away! Lots of beaches within walking distance of cottage. Wonderful trail system 1/2 mile away. Wake up to the sound of birds! Our place is good for couples, couples with small child and solo adventurers.

Apartment Dolphin House

Secluded three room vacation rental apartment suite with private entrance and private bath. It includes a fully equipped and stocked kitchen and comfortable living room. It overlooks the scenic Lynn Canal. The bedroom has a queen sized bed and has one queen sized sleeper sofa in the living room.

3 bedroom yurt with amazing view

Our cozy yurt overlooking the Chilkat River and mountains isn't your average yurt! It has 3 bedrooms, a bathroom, kitchen, loft space, and hot tub. We also provide wireless internet and direct TV. The yurt shares the property with our family home, 2 miles outside of scenic Haines, Alaska.

Suite 2 beds at Bakery (5)

Your cozy retreat is convenient to all amenities yet peaceful and quiet when it should be. Enjoy breathtaking mountain vistas on your short walk to the Waterfront, Fort Seward, Bald Eagle Center, The Brewery or Distillery, groceries, and much more.

Midtown Skagway (Upstairs Apartment)

Located smack-dab in the middle of Skagway, you will be close to everything at this cozy apartment. Walking distance to all the fun "downtown" Skagway has to offer, yet nestled in the mid-town neighborhood offering mountain views and quiet escape.

Skagway Studio Suite

Charming second floor studio apartment nestled in the heart of Skagway, Alaska. Located a few short blocks from the downtown historic business district, you will find this location ideal and within walking distance to Skagway valley highlights.