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

Alpenglow Vista - Bend, OR
9.7 109 reviews

Alpenglow Vista

apartment, Bend
This modern 3-bedroom farmhouse rental is located in Bend's Old Farm District, a 10-minute drive from the Old Mill District and adjacent to a new park.
The 3-bedroom, 2-bathroom home comfortably sleeps 8 guests and features a fully equipped kitchen, air conditioning, a garden, parking, and internet access, all in a peaceful cul-de-sac setting.
Whole House! Tiny Home On Bend's East Side - Bend, OR
9.8 154 reviews

Whole House! Tiny Home On Bend's East Side

house, Bend
This charming home is located in Bend's Orchard District, just a short distance from attractions like Pilot Butte State Park, St. Charles Bend, and the bustling downtown area. The house consistently receives excellent ratings for location, cleanliness, and overall experience. This cozy rental is perfect for a couple's getaway, with 1 bedroom, 1 bathroom, and a total floor area of 250 square feet. Guests can enjoy a fully equipped kitchen, a private patio, a barbecue grill, and access to a spa, making it easy to relax and unwind after a day of exploring Bend.
Charming East Side House, With Hot Tub. - Bend, OR
9.8 442 reviews

Charming East Side House, With Hot Tub.

apartment, Bend
This Bend, Oregon house, sleeps six guests in three bedrooms and one bathroom, and includes a detached studio apartment.
The property features a fully equipped kitchen, a hot tub, a large backyard, and one off-street parking space; additional details regarding proximity to specific Bend landmarks are unavailable.
Parkridge At Pilot Butte - Warm & Modern Bend Ski/outdoor Basecamp - Bend, OR
10 45 reviews

Parkridge At Pilot Butte - Warm & Modern Bend Ski/outdoor Basecamp

apartment, Bend
This Bend vacation home is located in the Orchard District, less than a mile from downtown Bend, Pilot Butte State Park, and Blockbuster.
The three-bedroom, two-bathroom house sleeps eight guests and features a fully equipped kitchen, Jacuzzi, private garden with barbecue grills, and is perfect for families or groups enjoying hiking and exploring Central Oregon.

Best Bend, OR vacation rentals with a fireplace

New! Diamond Retreat  Peaceful Bend Hideaway Near Old Mill & Trails - Bend, OR
9.8 14 reviews

New! Diamond Retreat Peaceful Bend Hideaway Near Old Mill & Trails

apartment, Bend
This 3-bedroom, 2-bathroom Southwest Bend vacation home is located in a quiet residential neighborhood, 7 minutes from the Old Mill District and 12 minutes from downtown Bend's breweries.
This 1320 sq ft rental accommodates up to 6 guests and features air conditioning, a kitchen with a fridge, microwave, and dishwasher, high-speed Wi-Fi, a private back deck, and is close to hiking, biking, and Mt. Bachelor.
Quiet River - On River, Right In Town! - Bend, OR
9.8 8 reviews

Quiet River - On River, Right In Town!

apartment, Bend
This Bend vacation home sits in the Awbrey Butte neighborhood, a short walk from the Deschutes River and Bend River Promenade, with popular attractions like Sun Mountain Fun Center and River's Edge Golf Course nearby. The property has excellent user, location, and cleanliness ratings, making it a great choice for travelers.
This 4-bedroom house provides 2,200 square feet of space for families and groups. Enjoy a private balcony, barbecue grills, a fireplace, a swimming pool, a spa, a fitness center, and a water park, all within this spacious home.
Stunning High End Craftsman Located Downtown Bend! - Bend, OR
10 138 reviews

Stunning High End Craftsman Located Downtown Bend!

apartment, Bend
This charming Craftsman-style bungalow is located in downtown Bend, just across the street from McMenamins and within walking distance of shops, restaurants, and attractions. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
This three-bedroom, two-bathroom home can comfortably accommodate up to six guests. It features a gourmet kitchen, a formal dining room, two living areas, and a private backyard, perfect for relaxing and enjoying the Bend sunshine.
Bluebird Day - Timber Ridge, A 3-bed Townhome In Broken Top Resort! - Bend, OR
9.6 5 reviews

Bluebird Day - Timber Ridge, A 3-bed Townhome In Broken Top Resort!

apartment, Bend
This four-bedroom, three-bathroom townhome is located in Bend, Oregon's gated Broken Top community, a short drive from Mount Bachelor Ski Resort and the Cascade Lakes, and near the Old Mill District.
The 2190-square-foot property boasts two living areas, a private hot tub, a balcony with a BBQ, in-unit laundry, and accommodates up to eight guests with amenities including a full kitchen, dishwasher, and air conditioning.

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.

2beds - Family-friendly- Mt Bachelor Village - Bend, OR
8.0 1 review

2beds - Family-friendly- Mt Bachelor Village

house, Bend
This Bend vacation home, located in Mount Bachelor Village, is 2.5 miles from Drake Park and 4.6 miles from Hollinshead Park, offering easy access to Bend's outdoor recreation.
The 830-square-foot property features one bedroom, one bathroom, sleeps eleven guests, and includes a fully equipped kitchen, swimming pool, jacuzzi, and on-site parking.
A Stone's Throw - Westside Vibes - Bend, OR
9.8 21 reviews

A Stone's Throw - Westside Vibes

apartment, Bend
This 3-bedroom, 1-bathroom downtown Bend condo is located in the Westside neighborhood, one block from Galveston Street and within walking distance to The Lot food cart pod and the Deschutes River tubing takeout.
This pet-friendly vacation rental accommodates up to 6 guests and features a private saltwater hot tub, a wrap-around patio with outdoor dining, a fully equipped kitchen, central air conditioning, and private off-street parking for 3 vehicles.
28 M² Condo ∙ 1 Bedroom ∙ 2 Guests - Bend, OR
No reviews

28 M² Condo ∙ 1 Bedroom ∙ 2 Guests

apartment, Bend
This studio apartment in Mt. Bachelor Village, Bend, is located minutes from the Deschutes River Trail, downtown Bend, and 19 miles from Mt. Bachelor.
This 290 square feet studio offers a queen bed, mini-fridge, microwave, and coffeemaker, with community access to a seasonal pool, year-round hot tub, and game room for up to 2 guests.
Walk Everywhere, Private Hot Tub, Modern Chic - Bend, OR
9.9 291 reviews

Walk Everywhere, Private Hot Tub, Modern Chic

bungalow, Bend
The Nest is a cozy and modern Bend home located just one block from Columbia Park and the Deschutes River, offering excellent user, location, and cleanliness ratings. This one-bedroom, one-bathroom house with a loft-style layout and 650 square feet of floor space comfortably accommodates two guests.
Amenities include a king-sized bed, a large bathroom with a walk-in shower, a private two-person hot tub on the front deck, an outdoor dining area, a fully equipped kitchen, a coffee bar, and a ductless AC/heating system for year-round comfort.

Best Bend, OR vacation rentals with parking

Gateway To Mt Bachelor - Bend, OR
9.8 178 reviews

Gateway To Mt Bachelor

house, Bend
This Bend vacation home is conveniently located just 2.4 miles from Drake Park and 4.6 miles from Hollinshead Park, making it easy to explore the city's attractions and enjoy the surrounding natural beauty. This property consistently receives excellent ratings for location, cleanliness, and overall guest experience.
The 850 square foot house comfortably accommodates up to 6 guests with two bathrooms. The home is fully equipped with modern amenities like air conditioning, a private pool, a jacuzzi, a terrace, a garden, and free parking, making it an ideal choice for a relaxing and enjoyable stay in Bend.
Private Pine Retreat | Hot Tub | Relax & Reset - Bend, OR
9.9 65 reviews

Private Pine Retreat | Hot Tub | Relax & Reset

apartment, Bend
This two-bedroom apartment in Bend's Westside has an excellent user rating and is a short walk from the scenic Drake Park and Tower Theater. It is also close to Central Oregon Community College and Westside Church.
The apartment has 1800 square feet of floor area and can accommodate up to 4 guests. It has 3 bathrooms, a well-equipped kitchen with modern appliances, a spa tub, a barbecue, a private fenced yard, a terrace/balcony, a garden, a parking space, and free WiFi.
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.
Drake Park Charmer In The Heart Of Bend - Bend, OR
9.7 384 reviews

Drake Park Charmer In The Heart Of Bend

apartment, Bend
This charming apartment is located in Old Bend, just steps from Drake Park, shops, restaurants, and the Deschutes River. It consistently receives excellent ratings for location, cleanliness, and overall user experience.
The apartment features a unique layout with a spiral staircase leading to the bedroom on the third floor, comfortably accommodating up to 3 guests. Enjoy complimentary cruiser bikes and floaties for exploring the river, and relax in the quiet oasis of this historic apartment.

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.

Hot Tub Home Near Old Mill Sleeps 8 - Bend, OR
8.4 9 reviews

Hot Tub Home Near Old Mill Sleeps 8

apartment, 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.

Bluebird Day - Kingfisher Bungalow - Bend, OR
10 2 reviews

Bluebird Day - Kingfisher Bungalow

house, Bend
Huckleberry Cottage - Bend, OR
9.6 223 reviews

Huckleberry Cottage

house, Bend
Old Mill And River Walk Retreat - Bend, OR
9.9 433 reviews

Old Mill And River Walk Retreat

house, Bend
Modern Bend Family-friendly Home W/ Fenced Yard - Bend, OR
No reviews

Modern Bend Family-friendly Home W/ Fenced Yard

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.

170 M² House ∙ 3 Bedrooms ∙ 6 Guests - Bend, OR
9.8 20 reviews

170 M² House ∙ 3 Bedrooms ∙ 6 Guests

house, Bend
Downtown Condo With Riverview & Balcony - Bend, OR
8.0 1 review

Downtown Condo With Riverview & Balcony

house, Bend
River Ridge 322b- Queen Bed, Ground Floor Condo - Bend, OR
10 3 reviews

River Ridge 322b- Queen Bed, Ground Floor Condo

apartment, Bend
Cozy Condo With Private Patio And Resort Amenities - Inviting Retreat - Bend, OR
No reviews

Cozy Condo With Private Patio And Resort Amenities - Inviting Retreat

apartment, Bend
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