Vacation rentals with outdoor seating 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.

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.

Cozy Bluff Getaway with Hot Tub

Escape to a beautiful Alaska retreat nestled on a bluff overlooking the majestic Talkeetna Mountains. This 2-acre property features a large deck with a 4-person hot tub and fire pit, perfect for unwinding at the end of the day. There are two comfortable bedrooms, each equipped with its own TV, and a spa-like bathroom for relaxation. There's a washer and dryer, so you’ll have all the comforts of home. Located near outdoor recreational spots like Hatcher Pass, this place is ideal for everyone.

Private backyard, firepit, mtn views, full kitchen

Quiet guest suite of a family home outside the city with private backyard: •Full kitchen and private entrance •Fire pit and gas grill •On-site laundry (shared) •20 minutes to the airport/5-15 minutes to the best hiking trails •Mountain views and sounds of Rabbit creek from the valley below One review: "...amazing find in Anchorage...extremely clean, convenient and in a beautiful location. Hosts were well organized...Impressed with the professionalism exhibited by these property owners."

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.

Amazing views! Deck with hot tub & barrel sauna.

One-of-a-kind property in a one-of-a-kind place. This cozy, detached guesthouse that overlooks the Mat-Su Valley from iconic Lazy Mountain. Includes a huge new covered deck where you can enjoy the unobstructed views from the barrel sauna and hot-tub while protected from the elements. 2 bedrooms, 1 bathroom, steam shower, full kitchen, open living room. Pull-out queen couch can sleep additional two guests. *Winter months, AWD is a must. Garage is not for guest use.

Modern A-Frame Cabin 1: 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.

Flattop Mtn Flat

Cute, comfortable upper level unit located close to hospitals, University of Alaska Anchorage, and the military base. It is also a short and convenient drive to downtown shopping areas, or can be a great home base for exploring beyond city limits. You will love its rustic charm, quiet neighborhood, privacy, and extra space. Features private patio, fenced yard, washer/dryer. 2 bedroom/1 bathroom. It is perfect for short or long term stays.

Magnificent View Chalet

Cozy, family friendly Chalet in the beautiful South Fork Valley of Eagle River. This serene and peaceful home is close to JBER and thirty minutes from downtown Anchorage. Our home offers sweeping Mountain View’s, wildlife, Northern Lights, easy access to South Fork Trail System and Symphony Lake, hiking, and back country skiing.