Holiday rentals with outdoor seating in Anchorage

Denali View! Sauna! 1 mile to Glen Alps/Flattop TH

Lone Pine Cottage is nestled against the Chugach State Park. Walk out the front door and explore the meadow of wildflowers below, or the forest next to the cottage which leads directly into the Chugach. The Glen Alps/Flattop Trailhead is 1 mile up the road and provides easy access to amazing hiking, mountain biking, snow shoeing, climbing, and skiing adventures. Enjoy the unobstructed views of Denali/Mt. McKinley, “Sleeping Lady” (Mount Susitna), and the Anchorage skyline from 1600ft elev.

Tiny home on wheels

"Bentley the Bus " has running water, electricity, heat, AC, WIFI, kitchen , shower and a regular toilet. Our floor plan allows to keep work and play separate as you are able to cook, lounge and enjoy yourself in the front of the bus, a private separated bedroom in the back where sweet dreams await. Two sofas in the front of the invite to be comfy with a movie - Bring Fido( no cats) who is welcome to stay with you for a small fee. Parking available. NOTE: BUS CAN'T BE DRIVEN BY GUESTS

Forest Floor Apartment

The lower level of our Jewel Lake Home with a separate entry, and fun backyard. This is a recent remodel; an eclectic space with vintage wood ceilings and a blend of industrial+ modern detailing. We are 5 minute drive from the airport, and guests can enjoy Alaskan wilderness right from this space. A forested trail system lies right behind our house for walking and biking. Guests may collect eggs from our chickens, use our forest-side hot tub, stoke the firepit, or use the canoe at Sand Lake.

Cupples Cottage #4: Downtown!

Welcome to the award winning Cupples Cottages! This 600sf flat was recently renovated and is beautifully furnished. When built in 1952 by my late grandfather these units were offered fully furnished providing temporary housing primarily to the construction workers living away from their families working on my grandfather's construction crew. Fast forward over 70 years and 3 generations and the property has been reimagined as Cupples Cottages Vacation Rentals, operating since 2017.

5 min walk to Flattop Trailhead! Aurora! Sauna!

Nestled in a forest of Mountain Hemlocks hundreds of years old, the home is located in a quiet neighborhood only a 5-6 minute walk from the Glen Alps/Flattop Trailhead providing the most direct and easy access to Chugach State Park. There are endless possibilities for hiking, climbing, and skiing from the house. Or, if you prefer to sit and relax and read a book, the view from the deck or living room couch of the Anchorage skyline and Denali/Mt. McKinley is spectacular.

Waterfront View of Denali, Alaska Range and Ocean.

Nestled within a private corner of Bootleggers Villa is a Brand New Private Suite with a personal entrance and private patio. Located near downtown offices, and suffused with the feeling of privacy and security. Our location is a short stroll to downtown Anchorage, and an easy drive to adventurous Alaska. Outdoor comfort with sunset-facing private patio. Enjoy, barbecues and relax with a view of Cook Inlet, the Alaska Range all from charming Bootlegger’s Cove.

Amazing Alaskan Retreat In U-Med District!

Visiting Alaska for Work or Fun? This immaculate 1-bedroom home is centrally located walking distance to Providence Hospital and UAA and many nearby restaurants. The bathroom has spa quality toiletries. Smart TV, high speed internet, fully equipped kitchen with a Keurig Coffee Maker, microwave, and gas range. Washer and Dryer in home. This property has no shared walls and we would love to host you and your furry friends on approval too!

Hillside Haven - Cozy & Bright!

Convenient, calm and spacious 1 bedroom, 1 bathroom apartment on the Anchorage hillside. Just a few minutes from all of the conveniences of the city, but tucked away in a quiet neighborhood close to trails, parks, Hilltop Ski Area, the Alaska Zoo, and lots of other fun adventures! Features include fully equipped laundry room and kitchen, Smart TV, and super fast WiFi. Settle in and enjoy a quiet, cozy, hillside retreat.

The Carriage House *Downtown Elegance* SUNNY Deck

Your own elegant house in the best downtown neighborhood. Built in 2020. Radiant-floor heat throughout. Perfect for executive rental or WFH. Stroll 3 blocks to City Market/coffee bar/deli. 3 blocks to Denna’ina Convention Center. Short jog to Lagoon and Coastal Trail. Huge deck with gas grill. Well-equipped kitchen with coffee maker, pots, pans and pantry essentials. Fast WiFi, 50" smart TV, heated garage parking.