Southern Crossing holiday rentals

We found 499 holiday rentals — enter your dates for availability
Discover a selection of 65 homes and other holiday rentals in Southern Crossing that are perfect for your trip. Holiday homes offer the best amenities for you and your friends, family or even pets, such as a hot tub and a washer and dryer. No matter what you're looking for, you'll be sure to find a property to rent for everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Southern Crossing

Showing deals for:11 Dec - 18 Dec

Home viewed from backyard with fire pit. Hot tub is not shown, on left
Beautifully appointed living spaces
Breakfast bar and kitchen
New Chef's kitchen with quartz counters, high-end applicances,
Excellent
(8 reviews)

Location! Historical District Downtown - Walk everywhere, new 4 Bedroom, 3 Bath

Bend

8% off
S$6,798
for 7 nights, 1 home
S$971 per night
includes taxes & fees
Location! Historical District Downtown - Walk everywhere, new 4 Bedroom, 3 Bath
Living area
Exterior
Outdoor dining
Private kitchen
Exceptional
(318 reviews)

Great Downtown Location And House

Bend

7% off
S$1,693
for 7 nights, 1 home
S$242 per night
includes taxes & fees
Great Downtown Location And House
Complete kitchen with 4 burner stove, Microwave and Bosh dishwasher
While relaxing on the cottage patio, guests are often enticed to see more
Tranquil setting - hidden gem in the heart of Bend
Secluded, quiet, and peaceful luxury in a retreat like setting
Exceptional
(222 reviews)

Immaculate Downtown Cottage Retreat- EV charger. Walk downtown in 4 minutes

Bend

6% off
S$2,473
for 7 nights, 1 cottage
S$353 per night
includes taxes & fees
Immaculate Downtown Cottage Retreat- EV charger. Walk downtown in 4 minutes
Comfy spacious living room. Has a sleeper sofa.
Easy access to the river from the back yard. Put in kayaks, SUP's or floats.
Love the granite we choose.
Desk for you to connect for laptop to our WiFi, if you have to work on vacation.
Exceptional
(198 reviews)

RIVERFRONT COTTAGE EPIC WALKABLE LOCATION ON RIVER

Bend

8% off
S$8,247
for 7 nights, 1 home
S$1,178 per night
includes taxes & fees
RIVERFRONT COTTAGE EPIC WALKABLE LOCATION ON RIVER
New stainless appliances and fully stocked kitchen.
Property grounds
Terrace/patio
Morning coffee on the porch of this original 110-year-old Bend classic.
Exceptional
(95 reviews)

Historic 1917 cottage by the river, walkable to all of downtown Bend!

Bend

7% off
S$2,123
for 7 nights, 1 home
S$303 per night
includes taxes & fees
Historic 1917 cottage by the river, walkable to all of downtown Bend!
Back bedroom w/ queen bed and two closets
The Bend Bungalow awaits! Set up high off street level is your quiet retreat.
New fridge and vintage (awesome!) stove with oven.
Dining
Exceptional
(138 reviews)

Bend Bungalow - a Walk in the Park to Downtown and River!

Bend

6% off
S$1,521
for 7 nights, 1 home
S$217 per night
includes taxes & fees
Bend Bungalow - a Walk in the Park to Downtown and River!
Living area
More than 25 golf courses to choose from in the area including Tetherow shown here.
Kitchen
Entry View!
Exceptional
(159 reviews)

Spectacular Luxury Old Mill District Townhouse Walking Distance To River Walk

Bend

6% off
S$2,152
for 7 nights, 1 home
S$307 per night
includes taxes & fees
Spectacular Luxury Old Mill District Townhouse Walking Distance To River Walk
View of river from back deck
Summer on the river
Living area
Living room
Exceptional
(197 reviews)

Riverfront Cottage -Near Drake Park, Walk to Town.

Bend

23% off
S$1,737
for 7 nights, 1 home
S$248 per night
includes taxes & fees
Riverfront Cottage -Near Drake Park, Walk to Town.
Exterior
Interior
Property grounds
Living area
Exceptional
(5 reviews)

Modern Nordic Nest: Sauna & Stroll to Galveston Ave

Bend

8% off
S$3,012
for 7 nights, 1 home
S$430 per night
includes taxes & fees
Modern Nordic Nest: Sauna & Stroll to Galveston Ave
95A36747-1443-4A2F-91A2-1421C79A0E72.jpeg
475278F8-70B1-4570-9F9F-26ECCC39D838.jpeg
Exterior
782E5D86-B7D6-4BE7-B9FE-B6A6A96EF4E2.jpeg
Exceptional
(44 reviews)

Downtown Craftsman with King Bed and Private Yard - Walk Everywhere

Bend

12% off
S$1,852
for 7 nights, 1 home
S$265 per night
includes taxes & fees
Downtown Craftsman with King Bed and Private Yard - Walk Everywhere
Terrace/patio
Living area
Interior
Exterior detail
Exceptional
(7 reviews)

Dog friendly~Hot Tub~King Bed~Modern Construction

Bend

7% off
S$2,450
for 7 nights, 1 home
S$350 per night
includes taxes & fees
Dog friendly~Hot Tub~King Bed~Modern Construction
Private kitchen
Terrace/patio
Exterior
Dining
Exceptional
(14 reviews)

Downtown cottage with hot tub and fenced yard

Bend

8% off
S$4,289
for 7 nights, 1 home
S$613 per night
includes taxes & fees
Downtown cottage with hot tub and fenced yard
Interior
Evening relaxation on the private back patio
Living Room
Take the Cruiser bikes for a spin around town
Exceptional
(17 reviews)

Mckay Getaway, between Drake Park/Miller's Landing

Bend

7% off
S$1,856
for 7 nights, 1 home
S$265 per night
includes taxes & fees
Mckay Getaway, between Drake Park/Miller's Landing
Interior
Private kitchen
Dining
Living area
Exceptional
(11 reviews)

2 Bedrooms Home Retreat Old Mill Bend Near Downtown

Bend

7% off
S$1,770
for 7 nights, 1 home
S$253 per night
includes taxes & fees
2 Bedrooms Home Retreat Old Mill Bend Near Downtown
Backyard BBQ Spot.
Wrens Nest with front yard.
Large kitchen with ample counter space allows group feasts.
Tiny dining table can still seat four.
Exceptional
(118 reviews)

Wren's Nest Updated Historic Home In The Heart Of Bend.

Bend

5% off
S$1,552
for 7 nights, 1 home
S$222 per night
includes taxes & fees
Wren's Nest Updated Historic Home In The Heart Of Bend.
View downstairs from loft bedroom
Dining
Loft area features a full sized bed as well as a twin daybed with trundle
View of living room from stairs to loft
Exceptional
(163 reviews)

Upgraded Mt.Bachelor Village Loft Condo + includes IKON pass holder offer

Bend

11% off
S$1,716
for 7 nights, 1 apartment
S$245 per night
includes taxes & fees
Upgraded Mt.Bachelor Village Loft Condo + includes IKON pass holder offer
Living area
Property grounds
Living area
Terrace/patio
Exceptional
(38 reviews)

Top 5% - Finnish Sauna - Near Old Mill - No Pets - Fully Remodeled - Quiet

Bend

12% off
S$1,630
for 7 nights, 1 home
S$233 per night
includes taxes & fees
Top 5% - Finnish Sauna - Near Old Mill - No Pets - Fully Remodeled - Quiet
Living area
Private kitchen
Dining
Living area
Exceptional
(15 reviews)

Home Centrally Located Near Old Mill Downtown

Bend

7% off
S$1,548
for 7 nights, 1 home
S$221 per night
includes taxes & fees
Home Centrally Located Near Old Mill Downtown
Interior
Lake
Exterior
Room
Exceptional
(63 reviews)

Executive suite in Mount Bachelor Village - great for a couple

Bend

7% off
S$1,308
for 7 nights, 1 apartment
S$187 per night
includes taxes & fees
Executive suite in Mount Bachelor Village - great for a couple

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

What is the most popular type of holiday rental accommodation in Southern Crossing?
According to our research, houses are the most in-demand property type in Southern Crossing. But that goes without saying, everyone's idea of an awesome trip can vary. Vrbo has holiday rentals of all sizes, shapes and budgets, and we'll help you discover the best fit for your needs.
How much does it cost to rent a holiday rental in Southern Crossing?
The average price for a holiday rental in Southern Crossing is determined by several factors, like season, property type and length of stay. Whether you're in search of a sprawling villa with room to move around or a quaint cabin just for the two of you, just add your dates of travel to find stays with amazing value.
How much does it cost to rent a beach house in Southern Crossing?
When you travel and the style and size of the property will influence how much you'll pay for your beachside stay. Type in your Southern Crossing travel dates to see all your options on Vrbo. Looking for a backyard so the kids can run around, or a pool to keep them busy? Use our filters to choose the features and amenities you want in your rental.
Are there pet-friendly holiday rentals in Southern Crossing?
With 54 properties that welcome four-legged guests, your furry friend can also come along on your Southern Crossing break. Use our filter tool to search our pet-friendly holiday rentals and find the pawfect pad on Vrbo.
Can I rent a house with a pool in Southern Crossing?
Mark the "pool" box in our filter tool and take your pick of two houses with private pools in Southern Crossing on Vrbo. Morning swim, sunset soak or midnight dip? Leisure time is up to you when your holiday home has a swimming pool.
What are popular rental amenities in Southern Crossing?
A nearby waterfront, a sauna and a fireplace are rated the most popular rental amenities in Southern Crossing. Whether you're taking a trip on your own, with your significant other or a group of best friends, Vrbo can help you find a holiday home that matches your style with all the features you'll enjoy.
Are there large group holiday rentals in Southern Crossing?
With two properties that can sleep 10 guests or more in Southern Crossing, you don't have to limit the invite list. From fun family holidays to special events like anniversary parties and weddings, Vrbo can help you find a large group rental to suit the occasion.
Are there holiday rentals in Southern Crossing that welcome kids?
With 54 family-friendly holiday properties to select from in Southern Crossing, now is the perfect time to introduce the kids to the excitement of travel. Simply click on our "Properties good for families" filter box to view stays loaded with amenities ideal for holidaying families, such as multiple bedrooms, outdoor spaces, bunk beds and hot tubs.
What are the top attractions for families in Southern Crossing?
Keeping the kids occupied during your holiday in Southern Crossing is simple with these leading family-friendly attractions:
  • High Desert Museum
  • Sun Mountain Fun Centre
  • Des Chutes Historical Museum
Are there one-bedroom holiday rentals in Southern Crossing?
Southern Crossing has four one-bedroom rentals on offer. Typically located in prime spots due to their smaller size, a one-bedroom holiday property is ideal if you're travelling with a friend or your partner. And with home comforts such as full kitchens and more privacy than a standard hotel, you'll be able to kick back and relax while sightseeing around this top destination.
Can I find two-bedroom holiday rentals in Southern Crossing?
Southern Crossing has 11 two-bedroom holiday properties that you can choose from. Enjoy a holiday home with all the comfort and space you need at an attractive price on Vrbo.
Are there holiday rentals with WiFi in Southern Crossing?
Southern Crossing has 15 holiday rentals with WiFi, so you can stay connected while you're travelling. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming TV shows with the family to sending emails, these Vrbo homes make it a cinch to go online.
How can I find holiday rentals with air conditioning in Southern Crossing?
You'll have a choice of 49 holiday homes with air conditioning in Southern Crossing providing that cooling breeze and extra touch of comfort. Simply enter your travel dates and then use our handy filter tool to help you locate properties with air conditioning.
How old do you have to be to rent a holiday rental in Southern Crossing?
You should check with the Southern Crossing holiday rental you're considering on Vrbo as the age limit varies. However, typically it's 16, 18 or 21.
How long can I rent a holiday rental in Southern Crossing for?
How long you can rent a holiday rental in Southern Crossing is down to the property. Simply enter your chosen dates to view a list of options offering extended stays. With tons of creature comforts such as air conditioning and full kitchens, as well as some offering weekly or monthly discounts, you're sure to get someplace just right to call your home away from home in Southern Crossing.

More holiday ideas