US $175/Night
7 Nights - US $1,228
Bend Holiday Rentals
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Compare Villas, Resorts, & Rentals in Bend
House
10.0(8 Reviews)
2 Bedrooms
4 Guests
Hot Tub
Internet
Pet Friendly
Child Friendly
US $193/Night
7 Nights - US $1,352
US $328/Night
7 Nights - US $2,296
Resort
6 Guests
- Hot Tub
Pool
Balcony/Terrace
Kitchen
US $248/Night
7 Nights - US $1,735
House
10.0(7 Reviews)
3 Bedrooms
8 Guests
Parking- Pool
- Balcony/Terrace
- Internet
US $290/Night
7 Nights - US $2,030
Cottage
10.0(1 Review)
2 Bedrooms
4 Guests
- Balcony/Terrace
- Kitchen
Air Conditioner- Internet
US $342/Night
7 Nights - US $2,393
House
9.4(6 Reviews)
1 Bedroom
2 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $351/Night
7 Nights - US $2,455
Apartment
9.4(3 Reviews)
1 Bedroom
4 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $299/Night
7 Nights - US $2,093
House
8.0(6 Reviews)
1 Bedroom
4 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $329/Night
7 Nights - US $2,301
Luxury Holiday Rentals in Bend
Over 7876+ Luxury Holiday Rentals in or Near Bend
House
50 Bedrooms
100 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $9,206/Night
7 Nights - US $64,442
US $6,299/Night
7 Nights - US $44,096
House
30 Bedrooms
60 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $5,481/Night
7 Nights - US $38,365
House
10.0(1 Review)
20 Bedrooms
40 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $3,830/Night
7 Nights - US $26,813
House
10.0(78 Reviews)
7 Bedrooms
16 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $3,254/Night
7 Nights - US $22,777
House
5 Bedrooms
10 Guests
- Parking
- Pool
Spa- Balcony/Terrace
US $2,740/Night
7 Nights - US $19,178
House
10.0(2 Reviews)
15 Bedrooms
30 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $2,729/Night
7 Nights - US $19,106
House
15 Bedrooms
30 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $2,729/Night
7 Nights - US $19,106
House
10.0(3 Reviews)
6 Bedrooms
14 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $2,670/Night
7 Nights - US $18,692
Top-Rated Holiday Rentals with a Pool in Bend
Over 3084+ The Best Private Villas and Holiday Rentals in Bend with a Pool
House
10.0(444 Reviews)
3 Bedrooms
8 Guests
- Hot Tub
- Parking
- Pool
Ocean View
US $369/Night
7 Nights - US $2,581
House
10.0(264 Reviews)
3 Bedrooms
8 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $608/Night
7 Nights - US $4,253
House
10.0(248 Reviews)
4 Bedrooms
10 Guests
- Hot Tub
- Parking
- Pool
- Spa
US $594/Night
7 Nights - US $4,160
House
10.0(224 Reviews)
3 Bedrooms
6 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $312/Night
7 Nights - US $2,185
Cabin
10.0(216 Reviews)
6 Bedrooms
14 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $865/Night
7 Nights - US $6,055
House
10.0(182 Reviews)
3 Bedrooms
9 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $370/Night
7 Nights - US $2,591
House
10.0(164 Reviews)
3 Bedrooms
9 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $286/Night
7 Nights - US $2,002
House
10.0(154 Reviews)
3 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $641/Night
7 Nights - US $4,488
House
10.0(145 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $266/Night
7 Nights - US $1,861
Pet-Friendly Holiday Rentals in Bend
Over 3000+ Pet-Friendly Holiday Rentals in or Near Bend
Cabin
10.0(6 Reviews)
5 Bedrooms
10 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $971/Night
7 Nights - US $6,797
US $559/Night
7 Nights - US $3,913
US $869/Night
7 Nights - US $6,085
House
9.0(30 Reviews)
4 Bedrooms
8 Guests
Oceanfront- Parking
- Spa
- Ocean View
US $536/Night
7 Nights - US $3,749
House
10.0(3 Reviews)
4 Bedrooms
8 Guests
- Hot Tub
- Parking
Skiing- Balcony/Terrace
US $531/Night
7 Nights - US $3,717
House
8.0(16 Reviews)
4 Bedrooms
8 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $425/Night
7 Nights - US $2,978
House
4.0(1 Review)
4 Bedrooms
10 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $357/Night
7 Nights - US $2,499
Cottage
10.0(14 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $196/Night
7 Nights - US $1,375
House
10.0(4 Reviews)
2 Bedrooms
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $371/Night
7 Nights - US $2,599
Large Holiday Rentals and Private Villas in Bend
Over 1942+ Large Holiday Rentals and Private Villas in or Near Bend
House
9.2(5 Reviews)
4 Bedrooms
13 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $682/Night
7 Nights - US $4,775
House
10.0(3 Reviews)
4 Bedrooms
12 Guests
- Hot Tub
- Parking
- Skiing
- Air Conditioner
US $520/Night
7 Nights - US $3,639
US $396/Night
7 Nights - US $2,774
House
9.0(6 Reviews)
3 Bedrooms
10 Guests
- Balcony/Terrace
- Kitchen
- Internet
- Child Friendly
US $382/Night
7 Nights - US $2,671
House
10.0(3 Reviews)
4 Bedrooms
11 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $236/Night
7 Nights - US $1,652
House
10.0(84 Reviews)
4 Bedrooms
11 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $376/Night
7 Nights - US $2,631
House
10.0(27 Reviews)
5 Bedrooms
10 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $615/Night
7 Nights - US $4,307
House
10.0(23 Reviews)
5 Bedrooms
10 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $661/Night
7 Nights - US $4,627
House
10.0(15 Reviews)
4 Bedrooms
10 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $522/Night
7 Nights - US $3,653
Wheelchair Accessible Holiday Homes in Bend
Over 269+ Wheelchair Accessible Holiday Homes in or Near Bend
Condo
10.0(21 Reviews)
2 Bedrooms
6 Guests
- Parking
- Skiing
- Balcony/Terrace
- Kitchen
US $330/Night
7 Nights - US $2,307
Resort
10.0(1 Review)
6 Guests
- Hot Tub
- Parking
- Pool
- Internet
US $179/Night
7 Nights - US $1,251
US $346/Night
7 Nights - US $2,420
Condo
10.0(15 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $760/Night
7 Nights - US $5,323
Resort
10.0(1 Review)
5 Guests
- Hot Tub
- Parking
- Pool
- Internet
US $165/Night
7 Nights - US $1,157
Hotel
8.8(6 Reviews)
- Parking
- Kitchen
- Air Conditioner
- Internet
US $154/Night
7 Nights - US $1,075
Hotel
8.8(3 Reviews)
- Parking
- Kitchen
- Air Conditioner
- Internet
US $154/Night
7 Nights - US $1,075
Hotel
8.4(8 Reviews)
- Parking
- Kitchen
- Air Conditioner
- Internet
US $142/Night
7 Nights - US $997
House
10.0(5 Reviews)
4 Bedrooms
10 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $591/Night
7 Nights - US $4,136
Bend Private Villas and Holiday Homes Under $200
Over 1339+ Bend Private Villas and Holiday Homes Under $200
US $117/Night
7 Nights - US $818
House
10.0(4 Reviews)
1 Bedroom
4 Guests
- Parking
- Internet
Security/Safety
Guest Services
US $200/Night
7 Nights - US $1,400
US $188/Night
7 Nights - US $1,316
Cottage
10.0(1 Review)
2 Bedrooms
4 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $195/Night
7 Nights - US $1,366
Ski Chalet
10.0(3 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $110/Night
7 Nights - US $770
House
9.6(65 Reviews)
1 Bedroom
3 Guests
Private Pool- Hot Tub
- Parking
- Pool
US $161/Night
7 Nights - US $1,128
Apartment
9.4(11 Reviews)
1 Bedroom
2 Guests
- Parking
- Kitchen
- Internet
- Pet Friendly
US $107/Night
7 Nights - US $746
House
9.0(21 Reviews)
1 Bedroom
3 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $181/Night
7 Nights - US $1,266
House
2 Bedrooms
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $195/Night
7 Nights - US $1,363
Instantly Bookable Holiday Homes in Bend
Over 4989+ Instantly Bookable Holiday Homes in or Near Bend
New
House
1 Bedroom
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $232/Night
7 Nights - US $1,624
House
10.0(12 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $351/Night
7 Nights - US $2,459
House
10.0(45 Reviews)
3 Bedrooms
8 Guests
- Parking
- Ocean View
- Balcony/Terrace
View
US $461/Night
7 Nights - US $3,225
House
10.0(11 Reviews)
3 Bedrooms
8 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $468/Night
7 Nights - US $3,273
House
10.0(3 Reviews)
3 Bedrooms
8 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $297/Night
7 Nights - US $2,078
House
9.8(11 Reviews)
3 Bedrooms
7 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $600/Night
7 Nights - US $4,203
House
8.8(13 Reviews)
3 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $328/Night
7 Nights - US $2,298
House
10.0(98 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $343/Night
7 Nights - US $2,401
House
10.0(92 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $423/Night
7 Nights - US $2,958
Book a Last Minute Place to Stay in Bend
About Casai's Private Villas and Holiday Rentals in Bend
Discover more than 7885 vacation rentals available in Bend. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Bend.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Bend, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Bend. On average, places to stay near Bend offer 1487.14 ft², with nightly prices averaging US $446.
With Casai, finding and comparing holiday rentals in Bend is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Other places to stay near the Bend, OR
There are 7885 Bend, OR Holiday Rentals
- Prices for a holiday home in Bend start at US $45
- Top rated vacation home in Bend is Central Oregon Escape - Mountain Views - Hot Tub - AC and Fireplace
- Most popular short term in Bend is Valley River Inn
- Cheapest place to stay in Bend is Chalet Motel - Your Cozy Basecamp for Bend Adventures
- Most expensive holiday rental in Bend is Sleeps 100! 20 Modern Units, 50 BDRs, Near DT Bend
Recently Booked Holiday Rentals in Bend
Frequently Asked Questions About Bend?
What are the top holiday rentals in Bend?
With numerous options available in Bend, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Bend:
- Central Oregon Escape - Mountain Views - Hot Tub - AC and Fireplace
- Cozy log cabin with wrap-around porch, Hot tub Loft space, Washer & Dryer
- Great Downtown Location And House
- Amazing West Side - 2 King Suites - Walk Everywhere 8 Person Hot Tub
- BEAUTIFUL HOME OVERLOOKING THE RIVER-MINUTES TO IT ALL-UPDATED KITCHEN!
- Spacious and charming Craftsman retreat.
- Caldera Springs Aug. 16-23 AVAILABLE Happiness Is Just Around The Bend!
- Log cabin, private, hottub, sauna, spa, gardens, featured in national magazine.
- Enjoy Our Family Friendly Home In Tollgate
- Skyline Lodge, Gorgeous Setting, Walk to Downtown!
How many holiday rentals have private pools in Bend?
Discover a selection of holiday rentals with private pools near Bend with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
Which holiday homes in Bend are best for families?
If you're searching for a family-friendly holiday home in Bend, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Bend:
How many Casai.com holiday rentals are available in Bend?
As of 2026, Casai boasts over 7885 properties listed in the Bend area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Bend.
Nearby Neighborhood (16)
| Neighborhood | Property Count |
|---|---|
| Century West Vacation Rentals in Bend, Oregon | 292 |
| Broken Top Vacation Rentals in Bend, Oregon | 242 |
| Oregon Water Wonderland Vacation Rentals in Bend, Oregon | 161 |
| Southern Crossing Vacation Rentals in Bend, Oregon | 109 |
| Overlook Park Vacation Rentals in Bend, Oregon | 100 |
| Old Bend Vacation Rentals in Bend, Oregon | 99 |
| Orchard District Vacation Rentals in Bend, Oregon | 63 |
| Larkspur Vacation Rentals in Bend, Oregon | 55 |
| Mountain View District Vacation Rentals in Bend, Oregon | 41 |
| Mountain View Vacation Rentals in Bend, Oregon | 41 |
| Old Farm District Vacation Rentals in Bend, Oregon | 36 |
| Southwest Bend Vacation Rentals in Bend, Oregon | 33 |
| Deschutes River Woods Vacation Rentals in Bend, Oregon | 26 |
| RiverWild Vacation Rentals in Bend, Oregon | 1997 |
| West Hills Vacation Rentals in Bend, Oregon | 1908 |
| River Terrace Vacation Rentals in Bend, Oregon | 2008 |
