2026 Ocracoke Sailing Guide

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Events
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Firehouse Boil Delivery

DIY Seafood Boil Don’t Just Make Dinner, Make An Experience! We Deliver on the Outer Banks! Same Day Delivery! Make lasting memories by doing something new with friends and family. Why wait in line at a grocery store or restaurant? Our Low...

Klein Cottage

This is a Blue Standard Bedding Property. Learn more about our hospitality bedding program here.Bring your family to this classically beautiful oceanfront property with panoramic ocean views from inside and out! Historic properties have been...

  • Southern Shores
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
Brindley Beach Vacations

Brindley Beach Vacations offers premier Real Estate and Property Management services across the entire Outer Banks. Representing more than 450 vacation rental homes, we proudly serve every region—from the southern beaches of Hatteras Island...

BLUE SKIES

Bright, spacious, lovingly-furnished and well-equipped home (with gourmet kitchen) on a quiet, beach side street, near lifeguards. Sunny, custom pool (very private) in the trees with generous lounging and dining area, pool bar (with sink...

  • Southern Shores
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 8
9/4 - 9/11
$2,420  $2,679
$259 off
9/18 - 9/25
$2,186  $2,378
$192 off
9/25 - 10/2
$2,090  $2,378
$288 off
10/2 - 10/9
$2,145  $2,378
$233 off
10/16 - 10/23
$1,876  $1,950
$74 off
10/23 - 10/30
$1,876  $1,950
$74 off
Miss Oregon Inlet

Oregon Inlet Fishing Center is the home of the largest and most modern charter boat fishing fleet on the eastern seaboard. A full service marina in Nags Head NC, Oregon Inlet offers a comprehensive charter boat fishing experience for the "old salt...

5416 - Dragonfly

BEACH GEAR RENTAL INCLUDED IN 2027! Always Included, complimentary linens and made beds! NEW FOR 2026: Level 3 hardwood flooring, and pool decking & fencing. NEW FOR 2025: Hot Tub, 2 HVAC Units...

  • Nags Head
  • 5 Bedrooms
  • 5.5 Bathrooms
Paradise Fun Park

Off the beach, one of the best activities for groups to enjoy in the Outer Banks is mini golf, bumper cars or Go-Karts. Thankfully, Paradise Fun Park offers all three activities! Paradise Fun Park offers exciting outdoor activities that kids and...

Dolphin Watch

Located in Corolla / 4 Bedrooms / 2 Full BathroomsAccessible by 4x4 car only! Dolphin Watch is charmingly located just 3 1/2 miles from the end of the paved road in the Swan Beach area. You will savor unobstructed ocean vistas from both levels...

  • Corolla
  • 4 Bedrooms
  • 2 Bathrooms
8/13 - 8/20
$3,240  $3,555
$315 off
8/23 - 8/30
$3,240  $3,555
$315 off
9/1 - 9/8
$2,876  $3,150
$274 off
Flip Flop Shops

Free Your Toes!®Live, work and play with your toes exposed® and the freedom of flip flops on your feet. 



Grand Banks

SOUNDSIDE Salvo - Sunset Drive - Life sure is GRAND at this soundside delight. The lockable watersports storage and the fact that the home is just steps away from the shared boardwalk to the sound makes GRAND BANKS a marvelous home for watersports...

  • Salvo
  • 6 Bedrooms
  • 5 Bathrooms
KEES Vacations

KEES Vacations offers the best Outer Banks rentals for family vacations, romantic weekend getaways and groups of all sizes looking for the perfect OBX rental for their stay. When booking with KEES Vacations, travelers can expect excellence in...

PEACHY PLOVER

An outstanding and tastefully decorated home only 240 yards from the ocean with easy beach access. The top level of this well-appointed home has ocean views from all public areas. A six bedroom comfortable home, featuring a game room with...

  • Duck
  • 6 Bedrooms
  • 6.5 Bathrooms
  • Sleeps 14
7/12 - 7/19
$5,907  $8,042
$2,135 off
8/9 - 8/16
$5,795  $6,709
$914 off
8/30 - 9/6
$3,999  $4,629
$630 off
9/6 - 9/13
$3,934  $4,332
$398 off
9/13 - 9/20
$3,527  $3,872
$345 off
9/20 - 9/27
$3,470  $3,872
$402 off
9/27 - 10/4
$3,470  $3,872
$402 off
Kitty Hawk Kites

Looking to fly a kite on the beach or atop the spectacular dunes of Jockey’s Ridge State Park? Kitty Hawk Kites offers the largest selection of kites, wind art, flags, games, and toys on the Outer Banks, with experts on staff to get you flying...

5592 - Windjammer

BEACH GEAR RENTAL INCLUDED! Always Included, complimentary linens and made beds! Welcome to Windjammer, where soundside beauty and Outer Banks bliss await. Nestled in the picturesque neighborhood of...

  • Nags Head
  • 4 Bedrooms
  • 4 Bathrooms
Kitty Hawk Kites

Kitty Hawk Kites has been Teaching the World to Fly since 1974 and is home to the world’s largest hang gliding school. As the Outer Banks leader in quality outdoor recreation and adventure, Kitty Hawk Kites offers more than 30 activities to choose from, so get out that pen and start crossing things off your OBX bucket list today! Visit KittyHawk.com or call 1.877.FLY.THIS to book your Kitty Hawk Kites adventure today.