Vacation rentals with outdoor seating in Anchorage

Caribou Flat, 2 Bath, Theater, Bar, Firepit & Yard

Unique Alaskan Wilderness themed stay in the "Big City"! Bar & entertainment. Stand Alone House, Not Shared, No Stairs, Ramp to Front door, Pet Friendly & Fenced Yard! Enjoy the chef's kitchen, with high end appliances, Hexclad pots & pans. Sit back & relax with your favorite beverage under the gazebo, around the firepit. Roast hotdogs in the firepit or fire up the BBQ. Movie theater night? We have you covered with the 120 in projector & popcorn bar End the evening with a night cap @ the bar

Cupples Cottage #4: 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.

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.

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.

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.

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!

Sleeping Lady Suite

This bright and sunny space is convenientally located for your vacation needs. It is close to the military base, hospitals, and the University of Alaska. The building is also just a quick drive to downtown Anchorage. You will love its rustic charm, quiet neighborhood, privacy, and extra space. Features private patio, fenced yard, washer/dryer. 2 bedroom/1 bathroom. Perfect whether you are enjoying a quick trip, or a long stay.