2026 Nags Head Sailing Tours Guide

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Sun Realty

Sun Realty offers the Best Selection of Vacation Rentals on the Outer Banks. Our large selection of Outer Banks rentals means you can choose from a wide range of amenities, including private swimming pools, hot tubs, theater rooms, game rooms, pet...

THE TREEHOUSE

Nestled among oak trees at the end of a quiet cul-de-sac, this cozy oceanside beach house will deliver the vacation of your dreams. This 4 bedroom, 2.5 bath beach house sits up high on an elevated lot just steps from the Atlantic Ocean. The serenity...

  • Corolla
  • 4 Bedrooms
  • 2.5 Bathrooms
  • Sleeps 8
8/23 - 8/30
$1,874  $2,213
$339 off
8/30 - 9/6
$1,706  $1,952
$246 off
9/6 - 9/13
$1,626  $1,822
$196 off
9/13 - 9/20
$1,372  $1,521
$149 off
9/27 - 10/4
$1,389  $1,521
$132 off
10/4 - 10/11
$1,389  $1,521
$132 off
10/11 - 10/18
$1,389  $1,521
$132 off
Flip Flop Shops

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



Casey's Place

Located in Salvo | 8 Bedrooms | 8 Full Bathrooms | 2 Half Bath | 8 Master SuitesCasey's Place, located in the heart of heaven, is really one of a kind.  When your family and friends come together here, you’ll discover an opulent oceanfront escape...

  • Salvo
  • 8 Bedrooms
  • 8 Bathrooms
OBX Ghost Tours

OBX Ghost tours is something your family will be talking about the rest of the summer! You'll be entertained as a guide leads you through down town Manteo by lantern telling the spooky stories that makes The Outer Banks one of the most haunted...

5330 - Margarita Mix

BEACH GEAR INCLUDED FOR 2027! Always Included, complimentary linens and made beds! Vacation Caribbean Style! Start your vacation in this beautifully decorated, comfortable cottage located in the...

  • Kill Devil Hills
  • 4 Bedrooms
  • 4.5 Bathrooms
Twiddy & Company

Twiddy & Company is here to provide all the help and southern hospitality you've come to anticipate when planning your beach vacation. We invite you to let us share our unique understanding of this coastal landscape; unlike any place in the...

Point of View

Introducing 'Point of View,' an Oceanfront paradise nestled in the charming Village of Nags Head. This meticulously maintained gem stands as a beacon of luxury, boasting a rare availability that promises exclusivity. Perched on a high lot, this...

  • Nags Head
  • 6 Bedrooms
  • 5 Bathrooms
Jumpmasters OBX

Now with Axe Throwing! Jumpmasters OBX is the ultimate trampoline park on the Outer Banks with attractions the entire family will enjoy. From open jump trampolines to the dodgeball court, 3-D climbing wall, a foam pit, an epic ninja obstacle course...

Privasea Beach

SOUNDFRONT Avon - Kinnakeet Shores - There are plenty of private deck spaces to savor the best vacation at PRIVASEA BEACH. Ease back into the hot tub on the pool deck while your family splashes in the pool. The glistening Pamlico Sound is visible...

  • Avon
  • 7 Bedrooms
  • 7.5 Bathrooms
ZoomAround Street Legal Golf Cart Rentals

ZoomAround Street Legal Golf Cart Rentals provides our communities and our visitors with fun, safe and convenient access to innovative transportation while providing an unparalleled customer experience. Don’t carry all of your beach gear...

Anchored at Last

Whether you want a relaxing and restful experience, fun-filled vacation, or a family reunion, you have found the perfect rental! With its twist on classic modern style and amenities and amazing proximity to the ocean, "Anchored at Last" has a style...

  • Nags Head
  • 7 Bedrooms
  • 5 Bathrooms
8/16 - 8/23
$8,423  $9,623
$1,200 off
8/23 - 8/30
$7,268  $7,968
$700 off
Ben Franklin

Stop by Nags Head's Ben Franklin at Mile Post 10 on the Bypass where you will find everything you need for the beach! From Clothing, T-shirts and Swimwear to Boards, Chairs, Umbrellas and Tackle. You'll find it all…and of course, we have the...

KOHLER COTTAGE

Experience breathtaking ocean views from this charming Outer Banks rental. Kohler Cottage is a delightful oceanfront home in Southern Shores. You’ll want to sit back and watch the waves all day on its spacious sun and dune decks. Not only does...

  • Southern Shores
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
10/10 - 10/17
$1,991  $2,252
$261 off
10/17 - 10/24
$1,816  $1,847
$31 off
10/24 - 10/31
$1,776  $1,847
$71 off
11/7 - 11/14
$1,625  $1,696
$71 off
11/14 - 11/21
$1,666  $1,696
$30 off
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.