Holiday rentals in Anchorage

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.

Lovely 1 bedroom unit, centrally-located (3)

Enjoy a stylish experience at this centrally-located place. Equipped with amenities and a Roku TV, this renovated apartment has everything you need to make your stay comfortable. This spot is located 9 minutes from the airport, 6 minutes from downtown, and is in walking distance to restaurants and stores. We look forward to hosting you! *Before booking, please read the entire listing description to get an understanding of the pros/cons, sleeping arrangements, house rules, and more.*

Wooded hillside studio apartment

Our place is located in south anchorage up on the hillside surrounded by beautiful trees and right by the hillside park , it’s a very safe and private neighborhood. You will have you own studio apartment to yourself. We are 3.1 miles from the closest grocery store (7 mins). We are 5.5 miles from the alaska native hospital (11 mins). We are 0.8 of a mile from hilltop skii area and hillside park (3 mins) and about a 5 min. walk. We are 2.4 miles from the alaska zoo (5mins).

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.

Cozy 2-Bedroom Home Near Airport

Close to airport and Kincaid Park trails, use this a landing pad for your Alaskan adventure or bring your mountain bike and enjoy the trails. The main level features a full kitchen, living & dining areas, and a half bath. The upper level has one bedroom with a king bed, an additional bedroom with an extra long twin bed, and a bathroom w/ walk-in shower. Full washer and dryer, occasional airplane noise, parking for two vehicles in driveway, no street parking.

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!

Cozy Riverside Retreat

Welcome to The Riverside! Nestled on the bank of the Matanuska River this cozy riverfront property is the epitome of relaxation and comfort. Boasting south facing views over the water, you will be watching Alaska’s world class sunsets from the hot tub on the deck while enjoying the sounds of the river below.

King Bed Suite w/Alaskan Charm & washer/dryer

- Onsite free parking - A private entrance - Fully stocked kitchen (including coffee) - King bed - Smart TV with Roku (no streaming service provided) - Shared washer and dryer in entryway Military friendly: ~16 min from JBER gate. We can provide invoices for reimbursement

Modern Studio Located in the Center of Downtown

Enjoy a king-sized bed, cozy seating, and a fully equipped kitchen in this newly remodeled space. Relax with high-speed WiFi, a flat-screen TV, and modern amenities. Located steps from dining, shopping, and the Coastal Trail, this space blends comfort and convenience.