Holiday rentals with outdoor seating in Anchorage

Cupples Cottage #3: Downtown, On-Site Car Rental!

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 2 generations and the property has been reimagined as Cupples Cottages Vacation & Vehicle Rentals, operating since 2017.

Downtown Portside Hideaway

This newly renovated cottage is in a downtown setting yet out of the bustle of busy city streets. It has a great view of the inlet and port, ands sits above the railyard. The bedroom has a KING size cool foam mattress and full bathroom with shower. On chilly nights enjoy an electric fireplace while cooking in the fully equipped kitchen. The large backyard has a deck with table and chairs, as well as a firepit. There is a desk to work at and high-speed wifi internet, plus a free parking space.

Alpenglow Loft ~ 1Br/Ba W&D Radiant Charmer

Unique modern loft 1 bedroom/1 bathroom apartment. Cool A/C in bedroom, spiral staircase, sunny floor-to-ceiling windows and live plants. Comfortably furnished, conveniently located between Midtown and Downtown Anchorage. This charming home base is perfect for embarking on your Alaskan getaway. The unit is equipped with a full-size washer/dryer, 43” Smart TV, stocked kitchen, and fast Wi-Fi for your convenience. However, due to the spiral staircase, we do not recommend this unit for children.

Sunny & Spotless: Walk to Prov/UAA/ANMC

Quiet & clean, compact & cozy, large south windows brighten this 1-BR remodel with sunshine all day. Complete modern kitchen with gas range, vaulted ceilings and bamboo floors. One mile to Providence, UAA. 5-minutes to the Seward Hwy and Moose's Tooth, 10 minutes to downtown. 2nd-story unit with no shared-walls and small deck above a quiet street. Private parking and south balcony for sunrises and sunsets. Keycode lock, no check-in required. Washer/dryer. Fast wifi, hot water Stairs.

New Guest Apartment on the Coastal Trail

Located near the Airport and on the world famous Coastal Trail right on the water of the Cook Inlet, the location boasts a super fast (fastest) internet connection and unlimited downloads for business traveler’s needs. We are in a quiet and safe neighborhood and have free dedicated parking for our guests. Literally 5 minutes to the airport, 5 minutes to downtown and midtown Anchorage by car. We also provide two Bikes and Tennis equipment for your enjoyment during summer months.

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.

A-Frame Cabin 2: Hot tub & view!

This newly constructed modern A-Frame offers a unique and luxurious accommodation opportunity. It features a comfortable king bed with crisp linens, keyless entry, washer & dryer, gas fireplace, TV, WiFi, hot tub, and large windows so you can soak up beautiful Alaskan views while surrounded by a tranquil forest. The kitchen and bathroom are stocked with everything you need to feel right at home. Enjoy the cozy and comfortable atmosphere during your private escape.

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!