Vacation rentals in Bend, OR

3745 available vacation rental offers

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Bend, OR vacation rentals
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Best Vacation rentals and Airbnb offers in Bend, OR

Best family friendly Bend, OR vacation rentals

Among the 3745 accommodations in Bend, OR, here are the 4 best family friendly rentals

57 M² Condo ∙ 1 Bedroom ∙ 3 Guests - Bend, OR
10 2 reviews

57 M² Condo ∙ 1 Bedroom ∙ 3 Guests

apartment, Bend
This condo in Ski House 3 at Mt. Bachelor Village Resort offers direct access to the Deschutes River Trail and is located within a 5-minute drive of Downtown Bend and the Old Mill District, with Mt. Bachelor Ski Resort approximately 25 miles away.
This 610 sq ft, 1-bedroom, 1-bathroom condominium accommodates up to 3 guests and features a full kitchen, complimentary coffee, a swimming pool, hot tub, tennis court, and fitness center.
The French Farmhouse At Midtown Manor - Hot Tub! - Bend, OR
9.9 147 reviews

The French Farmhouse At Midtown Manor - Hot Tub!

apartment, Bend
This fully renovated 1940s French Provincial-style apartment is located in Bend's Midtown, offering easy access to local attractions, though specific distances aren't provided.
The three-bedroom, two-bathroom rental sleeps six guests comfortably, boasting a fully equipped kitchen, a private patio with a hot tub, and an EV charging station; a queen sofa bed in a second bedroom adds extra sleeping space.
~Large Westside Home~ Walk To Everything! Welcome To Kingston House - Bend, OR
10 158 reviews

~Large Westside Home~ Walk To Everything! Welcome To Kingston House

apartment, Bend
This Bend vacation home, located on a mountainside, is a 15-minute walk from the Deschutes River, Drake Park, and Westside Church, and under a mile from Bend Whitewater Park and the Deschutes Historical Museum.
This 2,690-square-foot house sleeps up to 10 guests, offering five bedrooms, three bathrooms, a fully equipped kitchen, a private fenced yard, on-site amenities including an arcade/game room and barbecue grills, and free Wi-Fi.
Spacious Two Story 2 Bed 2 Bath West Side Condo - Bend, OR
9.9 154 reviews

Spacious Two Story 2 Bed 2 Bath West Side Condo

house, Bend
This family-friendly condo is located in Century West, just a short distance from the Deschutes River, Old Mill District, and Hayden Homes Amphitheater. The condo has received excellent ratings for user experience, location, and cleanliness.
The 1420 square foot condo has 2 bedrooms and 2 bathrooms, comfortably accommodating up to 6 guests. Enjoy amenities like a private patio with barbecue grills, a spa tub, a fireplace, and a fully equipped kitchen.

Best Bend, OR vacation rentals with a fireplace

Wanderlust Condo Bend - Fully Remodeled! - Bend, OR
10 22 reviews

Wanderlust Condo Bend - Fully Remodeled!

apartment, Bend
Wanderlust Condo Bend, located in Mt. Bachelor Village, offers easy walking access to the Old Mill District, the Deschutes River Trail, and Mt. Bachelor Ski Resort.
This newly remodeled 840-square-foot condo features two bedrooms, two bathrooms, sleeps four, and includes a fully equipped kitchen, in-unit laundry, a private patio, and access to a pool, hot tub, and BBQs.
Live/play/work In Midtown Bend With Central A/c - Bend, OR
10 2 reviews

Live/play/work In Midtown Bend With Central A/c

apartment, Bend
This two-bedroom, one-bathroom rental is situated in Midtown Bend, offering convenient walkability to local parks, coffee shops, and restaurants, and is less than a mile from Downtown Bend.
This pet-friendly apartment accommodates up to four guests and features a fully equipped kitchen, air conditioning, a garden, parking in an attached garage, and dedicated office space with high-speed WiFi.
Downtown, Modern Nostalgia--walk To Shops, Cafes - Bend, OR
9.8 536 reviews

Downtown, Modern Nostalgia--walk To Shops, Cafes

apartment, Bend
This charming Bend cottage is located on the Westside, just a five-minute walk from the Deschutes River and a ten-minute walk to downtown, making it easy to explore the city's attractions and enjoy the beautiful natural surroundings. Guests consistently rate this property excellent for location, cleanliness, and overall experience.
This 1000-square-foot cottage comfortably sleeps six guests in its two bedrooms and two bathrooms. Enjoy modern amenities like free Wi-Fi, cable TV, a fully equipped kitchen, and a private terrace, perfect for relaxing after a day of exploring Bend's breweries, hiking trails, and outdoor activities.
Cozy Condo Near Deschutes River And Pioneer Park - Bend, OR
8.8 24 reviews

Cozy Condo Near Deschutes River And Pioneer Park

apartment, Bend
This condo offers a prime location on the edge of downtown Bend, just an 8.5-minute walk to the city center and adjacent to Pioneer Park and the Deschutes River Trail.
This 650 sq ft apartment accommodates up to 2 guests with 1 bedroom and 2 bathrooms, featuring a full kitchen, two balconies, air conditioning, and on-site staff for assistance.

Frequently Asked Questions about vacation rentals in Bend, OR

  • What should a first-time visitor not miss in Bend, OR?

    Bend is known for its outdoor adventures. You can't miss a hike up Pilot Butte for panoramic views of the city and Cascade Mountains. For a more challenging hike, try the Smith Rock State Park, famous for its rock climbing. And don't forget to visit the Old Mill District for shopping, dining, and the Deschutes River.
  • What are the best Airbnb and vacation rentals in Bend, OR?

    Private Apt - 1bdrm/1bath - With Kitchen - In Town, Kathy's Westside Perch and The Garden Apt-hot Tub Fireplace Ac 250+ Mbps are the most popular Airbnb and vacation rentals in Bend, OR among travelers.

  • Which neighborhood in Bend, OR should you consider for a vacation rental?

    The Old Mill District is a popular choice, with its proximity to restaurants, shops, and the Deschutes River. If you're looking for a quieter stay, consider the Westside, close to the Cascade Lakes Highway and offering easy access to hiking trails and lakes. The downtown area is also a good option, offering a vibrant nightlife and a central location.
  • What are the most popular Airbnbs in Bend, OR?

  • What are the top family-friendly attractions in Bend, OR?

    The High Desert Museum is a must-visit for families, showcasing the natural history and wildlife of the region. For a fun day out, head to the Sunriver Nature Center & Observatory for a guided tour of the night sky. The Pilot Butte State Scenic Viewpoint is a great spot for kids to run around and enjoy the views.
  • What are the best vacation rentals with a pool in Bend, OR?

  • When is the best time to book a vacation rental in Bend, OR?

    Peak season in Bend runs from June to September, so it's best to book your vacation rental well in advance, especially if you're traveling during summer holidays. You'll find better deals and more availability during the shoulder seasons, like spring and fall.
  • What are the best rentals for families and kids in Bend, OR?

  • What are the best budget-friendly activities in Bend, OR?

    Bend is full of free and low-cost activities. Take a stroll along the Deschutes River Trail, enjoy a picnic at Drake Park, or explore the many free art galleries in the downtown area. You can also check out the free events at the Les Schwab Amphitheater, like outdoor concerts and movies.
  • What are the best rentals or Airbnbs with a jacuzzi in Bend, OR?

  • What are the best restaurants with local dishes in Bend, OR?

    For a taste of Bend, try the classic Bend Brewing Co. for their craft beers and pub fare. Anthony's at the Old Mill offers fresh seafood with a beautiful view of the Deschutes River. And for a casual dining experience, head to the popular 10 Barrel Brewing Co. for their craft beers and delicious burgers.
  • What are the best walking or cycling routes in Bend, OR?

    The Deschutes River Trail is a scenic and easy walk or bike ride, offering views of the river and the Cascade Mountains. For a more challenging ride, try the Century Drive, a 40-mile loop around Bend that takes you through forests, meadows, and past the Cascade Lakes.
  • Are there pet-friendly attractions in Bend, OR?

    Many parks and trails in Bend are dog-friendly, including the Deschutes River Trail and Drake Park. The High Desert Museum also welcomes well-behaved dogs on leash. Many restaurants offer outdoor seating where you can bring your furry friend.
  • What are the benefits of choosing a vacation rental in Bend, OR?

    Vacation rentals offer more space and privacy than hotels, often with kitchens and laundry facilities. They can also be a more affordable option, especially for families or groups. Many rentals are located in desirable neighborhoods, offering easy access to attractions and activities.
  • What are the top sports attractions and facilities in Bend, OR?

    Bend is a popular destination for outdoor sports. The area offers world-class skiing and snowboarding at Mount Bachelor in the winter. In the summer, you can enjoy hiking, biking, kayaking, and fishing. The Bend Golf Club is a public course with stunning views of the Cascade Mountains.

Popular destinations

Choose the Perfect Vacation Rentals with a Hot Tub in Bend, OR

Experience the ultimate recovery after a long active day with a private hot tub at these premier Bend, OR vacation rentals.

Park Place- Private Bend Retreat With Hot Tub Under The Stars - Bend, OR
10 2 reviews

Park Place- Private Bend Retreat With Hot Tub Under The Stars

apartment, Bend
This Southwest Bend condo is a 5-minute drive from the Old Mill District and a 7-minute drive from the Les Schwab Amphitheater, offering proximity to outdoor activities like snowboarding and snowmobiling.
This 1100 sq ft, 3-bedroom, 2-bathroom apartment accommodates up to 6 guests and features a full kitchen, air conditioning, complimentary Wi-Fi, a private terrace with a hot tub and barbecue, and on-site parking.
New Listing! River Views | Hot Tub | Near Mt. Bachelor - Bend, OR
9.4 18 reviews

New Listing! River Views | Hot Tub | Near Mt. Bachelor

apartment, Bend
This ground-floor condo in Bend's Century West neighborhood offers direct Deschutes River Trail access, a short walk to Hayden Homes Amphitheater and Drake Park, and is just 5 miles from Downtown Bend and the Old Mill District.
This 1190 sq ft apartment accommodates up to 6 guests with 3 bedrooms and 2 bathrooms, featuring a fully remodeled kitchen, a wood-burning fireplace, a private deck with a hot tub, and access to community amenities including a seasonal swimming pool.
Ghost Tree Management - Bend, OR
10 9 reviews

Ghost Tree Management

apartment, Bend
This family-friendly apartment in Bend is located a short walk from a neighborhood park and minutes from Costco and Trader Joe's, with downtown and the Hayden Amphitheater a 10-minute drive away.
This 3-bedroom, 2-bathroom house accommodates up to 6 guests and features a full kitchen, air conditioning, a hot tub, and is equipped with a pack n' play and highchair for families with young children.
Riverfront Condo Next To Park And Downtown Bend - Bend, OR
8.6 34 reviews

Riverfront Condo Next To Park And Downtown Bend

apartment, Bend
This second-story condo in Bend's River West neighborhood offers river views and is a 10-minute walk to downtown attractions.
This 640 sq ft condo accommodates up to 4 guests with two queen beds, features a full kitchen, indoor pool, hot tub, and is pet-friendly for up to two pets with an additional fee.

Best Bend, OR vacation rentals with parking

Shasta House Near Downtown And Hayden Amphitheater - Bend, OR
9.9 70 reviews

Shasta House Near Downtown And Hayden Amphitheater

apartment, Bend
This three-bedroom, two-bathroom house in Bend's Historic Old Bend district is an eight-minute walk from Downtown Bend, Drake Park, and the Old Mill District.
The 1300-square-foot home features a fully equipped kitchen, in-house laundry, a private courtyard with a BBQ, a Tesla charger, and comfortably sleeps six guests, with easy access to restaurants, breweries, and the Les Schwab Amphitheatre.
Third-floor Riverfront Condo Near Downtown Bend - Bend, OR
9.3 150 reviews

Third-floor Riverfront Condo Near Downtown Bend

apartment, Bend
This one-bedroom, two-bathroom apartment is located in the heart of Bend, within easy walking distance of the Deschutes River and other popular attractions. It has an excellent user rating, location rating, and cleanliness rating.
The apartment is fully equipped with a kitchen, two bathrooms, a balcony, and access to an indoor pool and spa tub. It is also pet-friendly, family-friendly, and has air conditioning. The apartment can accommodate up to two guests and is perfect for a couple or a small family.
Bluebird Day - Casa Sol, Pet Friendly, Hot Tub! - Bend, OR
9.9 67 reviews

Bluebird Day - Casa Sol, Pet Friendly, Hot Tub!

apartment, Bend
Casa Sol, a modern stucco home in Bend's westside, is located blocks from downtown and Newport Avenue, offering easy access to restaurants like Spork, Chow, Nancy P's, and the Newport Market.
This pet-friendly house features two bedrooms with king beds, a full-size sleeper sofa, a fully equipped gourmet kitchen, a private salt-system hot tub, and four cruiser bikes for exploring Bend, accommodating up to six guests.
Urban Roundabout - Bend, OR
9.6 160 reviews

Urban Roundabout

house, Bend
This 2-bedroom vacation home is located in Bend's desirable Westside neighborhood, within walking distance of the Deschutes River, Drake Park, and Westside Church. It has been given excellent ratings for its location, cleanliness, and user experience.
With 1160 square feet of living space, this home has a kitchen, two bathrooms, a washing machine, a TV, and free WiFi. Guests can also enjoy access to an on-site fitness center, barbecue grills, and a laundry facility. The home also features a swimming pool, a Jacuzzi, a terrace/balcony, a garden, a spa, and a restaurant.

Top 5-Star Vacation Rentals in Bend, OR

These upscale vacation rentals in Bend, OR offer premium amenities and refined service for an unforgettable stay.

Drake Cottage 311 - Bend, OR
9.3 170 reviews

Drake Cottage 311

house, Bend

Guest-Favorite Pet-Friendly Vacation Rentals in Bend, OR

Bring the whole family to Bend, OR with pet-friendly vacation rentals that offer comfort for your dog.

Spacious Midtown 3 Bedroom Home! Easy Access! - Bend, OR
10 10 reviews

Spacious Midtown 3 Bedroom Home! Easy Access!

apartment, Bend
Ponderosa Cabin  Modern Home & Amazing Location! - Bend, OR
10 45 reviews

Ponderosa Cabin Modern Home & Amazing Location!

house, Bend
Cheerful 3 Bdrm Hm. Hot Tub,firepit. Bike2oldmill - Bend, OR
9.6 22 reviews

Cheerful 3 Bdrm Hm. Hot Tub,firepit. Bike2oldmill

apartment, Bend
Best Bet For Bend! - Bend, OR
No reviews

Best Bet For Bend!

apartment, Bend

Browse Vacation Rentals with Swimming Pool in Bend, OR

Enjoy a swim whenever you like; these Bend, OR vacation rentals come with an on-site swimming pool.

Upper-level Condo With Mt. Bachelor Village Amenities! - Bend, OR
10 1 review

Upper-level Condo With Mt. Bachelor Village Amenities!

apartment, Bend
Luxury In Bend, Or  | Deluxe Queen Close To Nature - Bend, OR
9.0 12 reviews

Luxury In Bend, Or | Deluxe Queen Close To Nature

apartment, Bend
Premiere Room Near Trails, Rapids, Hiking, Golf - Bend, OR
10 1 review

Premiere Room Near Trails, Rapids, Hiking, Golf

apartment, Bend
Bend Basecamp! Condo W/ Pool Near Deschutes River - Bend, OR
9.6 4 reviews

Bend Basecamp! Condo W/ Pool Near Deschutes River

apartment, Bend
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