Holiday rentals with outdoor seating in Downtown Anchorage

Downtown Garden Apt. Great Location!

Location! Location! Private, one bedroom apartment. Great neighborhood. Walking distance to downtown restaurants, breweries, shopping, museums, cultural events, railroad & Anchorage’s trail system. Only fifteen minute drive from the airport! Grocery store, coffee bar & deli across the street. Bakery cafe, gourmet wine shop & an organic produce shop nearby. Easy access to Alaskan outdoor adventures-or relax on the patio & enjoy the garden. Unlimited high speed wifi for work & entertainment.

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.

Downtown Historic Attic Suite

This upstairs suite is in an historic 1917 cottage, in downtown Anchorage, and is a rare find! Steps away from restaurants, bars, convention center, bus station, museum, bike trails, parks and pubs. It shares the building with a hair salon on the main level. With a private entrance, it is upstairs under the attic eaves, so the bathroom ceiling is slanted (FYI super tall people!) quality towels & linens, a full-sized pull out sofa bed in the living room, the queen bed is cool gel memory foam!

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.

Cupples Cottage #2: 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.

* Private 5 -Star Apt in City Center *

A 1200 sq ft. downtown gem! Remodeled~beautiful, modern, open concept. Across the street from downtown's hippest market, bakery and coffee shop. Convenient for morning coffee and pastries or fresh salmon for the BBQ. 5 minute walk to trail access for Westchester Lagoon, the Coastal trail and the Chester Creek trail. 15 min easy walk to downtown; shopping, bike rentals, museums, town square restaurants and nightlife. Off street covered parking. 10 minute drive to the airport.

Elephants on 11th - Close to Downtown-Kitchenette

Maggie's suite at Elephants on 11th is a one bedroom, one bath apartment on the lower level within a 1940s era duplex one block from the Park Strip in Anchorage. This charming space was upgraded within the last five years and includes a compact bedroom with queen size bed, full bath and sitting area with sleeper sofa and kitchenette that includes a small refrigerator, microwave and Keurig coffeemaker. Walking distance to parks, trails and all downtown Anchorage offers.

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.

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.