Homes -

1097 - FIVE O CLOCK SOMEWHERE


Bedroom 5 bedrooms
Bathroom 5 baths 1 half baths
Guests 12 guests
GUESTS PETS NOT PERMITTED GUESTS PETS NOT PERMITTED

  • TurnDay: Sunday
  • Address: 153 Crooked Back Loop
  • Location: Westside
  • City: Southern Shores
  • Type: Homes
  • Subdivision: Chicahauk

Location and Nearby Properties Location and Nearby Properties

Description Description

Relax and enjoy every special moment that you and your family spend in this 3,600 square foot, five bedroom, upscale home. A beautifully appointed home with wonderful views, Five O’Clock Somewhere sits on a spacious lot (2/3 acre) in one of the most desirable areas of the Outer Banks. Includes home theater room and 2,200 square feet of spacious wrap around decks.

Level 1:

Home theater room with projection screen and theater seating; recreation room with foosball, SmartTV, wet bar, refrigerator, Queen sleep sofa and full bath.

Level 2:

4 bedrooms (1 with King, private bath whirlpool, separate shower, deck access and SmartTV; 1 with Queen, private bath with shower and SmartTV, deck access; bedroom with Twins shares a bath with tub/shower unit with a bedroom with Double over Double bunk set; twin room also has deck access). All have SmartTVs.

Level 3:

Bedroom (with King, private bath with shower, SmartTV); great room has great views, hardwood floors, wet bar, SmartTV and see-through gas fireplace, separating it from the dining room; dining room table seats 10; kitchen has 2 dishwashers, granite counter tops, and breakfast bar with bar chairs; powder room. Crows Nest.

Property Amenities

  • Beds: 2 King, 1 Queen, 2 Twins, 1 Double bunk set, 1 Queen sleep sofa
  • 14 x 30 PRIVATE POOL 
  • HOT TUB (New stand alone for 2025)
  • Smart TVs with Spectrum Streaming Service and Disney Plus
  • Home theater
  • Foosball
  • 2 wet bars, 2 dishwashers, Keurig
  • Books, puzzles, movies, games
  • Whirlpool
  • Crows Nest
  • Screened porch
  • Open and covered decks
  • Wireless internet access
  • Gas grill
  • Basketball goal
  • Approximate distance to beach access: 557 yards
  • NO SMOKING
  • GUESTS' PETS NOT PERMITTED
  • SHEETS, 12 TOWEL SETS, AND TERRY BATH MATS PROVIDED

Community Amenities

  • Chicahauk Tennis
  • SSCA Racquet Club - Tennis & Pickleball
  • Playground with basketball and soccer areas
  • 2 beach parking lots (parking pass provided)

2026 description


Amenities 14 Amenities
  • Screened Porch
  • Theater Room
  • Fireplace
  • Hot Tub
  • Internet
  • Keyless Entry
  • Linens
  • Non Smoking
  • Partial Weeks Allowed
  • Pickleball Courts
  • Private Pool
  • Rec Room
  • TruPlace Floorplan

Beach Gear Included

New for 2026 bookings: Southern Shores Realty guests with reservations of 3-to-21 nights beginning April 1, 2026 and on participating vacation rental homes, will receive a credit towards beach gear rentals during their stay.

This property includes a $35/night rental credit towards select VayKLife beach equipment rentals. For more information, please go to VayKLife Beach Gear Credit*.

*This Special only applies to rentals booked for 2026.


Standard Amenities Standard Amenities

The following items are standard in all properties unless specified in the unit description

  • Central heat & A/C
  • Washer/Dryer
  • Coffee maker, toaster 
  • Pots, pans, dishes, silverware     
  • Refrigerator, range/oven, microwave, dishwasher
  • Television
  • Sheets and Bath Towels

The following Rules apply to Seasonal Amenities

  • Private Pools, if provided at property, are available early May through early October, unless otherwise specified in the property description
  • Fireplaces, if available for tenant use, are available 10/15-4/15.
  • Screened porches, if provided at the property, may not be screened during winter months

Our Cleaning Policies and Procedures follow the standards recommended by OSHA and the CDC.

For our rental policies please visit our Rental Agreement page

Southern Shores Realty cannot guarantee that a non-pet property has not had pets or service animals present on the property at some time.

Errors: Every effort has been made to ensure all descriptions and photos are accurate, however Southern Shores Realty is not responsible for changes or errors in rates, discounts, furnishings, bed arrangements, and equipment, or for down time of inoperative equipment.


Availability Calendar Availability Calendar
Available
Unavailable
Check-In
Check-Out
March 2026
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 7
8 9 10 11 12 13 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30 31        
April 2026
Su Mo Tu We Th Fr Sa
      1 2 3 4
5 6 7 8 9 10 11
12 13 14 15 16 17 18
19 20 21 22 23 24 25
26 27 28 29 30    
May 2026
Su Mo Tu We Th Fr Sa
          1 2
3 4 5 6 7 8 9
10 11 12 13 14 15 16
17 18 19 20 21 22 23
24 25 26 27 28 29 30
31            
June 2026
Su Mo Tu We Th Fr Sa
  1 2 3 4 5 6
7 8 9 10 11 12 13
14 15 16 17 18 19 20
21 22 23 24 25 26 27
28 29 30        
July 2026
Su Mo Tu We Th Fr Sa
      1 2 3 4
5 6 7 8 9 10 11
12 13 14 15 16 17 18
19 20 21 22 23 24 25
26 27 28 29 30 31  
August 2026
Su Mo Tu We Th Fr Sa
            1
2 3 4 5 6 7 8
9 10 11 12 13 14 15
16 17 18 19 20 21 22
23 24 25 26 27 28 29
30 31          
September 2026
Su Mo Tu We Th Fr Sa
    1 2 3 4 5
6 7 8 9 10 11 12
13 14 15 16 17 18 19
20 21 22 23 24 25 26
27 28 29 30      
October 2026
Su Mo Tu We Th Fr Sa
        1 2 3
4 5 6 7 8 9 10
11 12 13 14 15 16 17
18 19 20 21 22 23 24
25 26 27 28 29 30 31
November 2026
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 7
8 9 10 11 12 13 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30          
December 2026
Su Mo Tu We Th Fr Sa
    1 2 3 4 5
6 7 8 9 10 11 12
13 14 15 16 17 18 19
20 21 22 23 24 25 26
27 28 29 30 31    
January 2027
Su Mo Tu We Th Fr Sa
          1 2
3 4 5 6 7 8 9
10 11 12 13 14 15 16
17 18 19 20 21 22 23
24 25 26 27 28 29 30
31            
February 2027
Su Mo Tu We Th Fr Sa
  1 2 3 4 5 6
7 8 9 10 11 12 13
14 15 16 17 18 19 20
21 22 23 24 25 26 27
28            
March 2027
Su Mo Tu We Th Fr Sa
  1 2 3 4 5 6
7 8 9 10 11 12 13
14 15 16 17 18 19 20
21 22 23 24 25 26 27
28 29 30 31      
Swipe Swipe for Availability

Guest Recommendations Reviews
We loved the property! The pool was awesome, the mattresses were comfortable, and we all loved the deck space. Very close proximity to the beach with a parking pass. The house is also very private, even though it is in a neighborhood.
Joseph S - Dates of Stay: 06/15/25 - 06/22/25
This house as always was amazing. This was our fourth summer family vacation in this house and we have reserved it again for next summer. The house is perfect for our group and all of us love staying here.
Sandra M - Dates of Stay: 06/22/25 - 06/29/25

The house was a pleasure to stay in. Everything was very clean and well taken care of. We truly enjoyed the stay. We loved the pool area, but it would have been nice to have an umbrella at the table by the pool. Would like to say - we enjoyed the house and location so much we have already reserved it again for next year.

Sandra M - Dates of Stay: 06/19/22 - 06/26/22

"Great property and location for our large family! We really think that the Sunday to Sunday week helped with traffic."

Michele S - Dates of Stay: 07/14/19 - 07/21/19
Swipe Swipe for More Reviews

Request More Info Request More Info

Want to know specifics? Ask anything in reference to vacationing at this property that you would like to know...

Example: "Are fresh linens provided?"

I agree