2026 Nags Head Sailing Tours Guide

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Carolina Designs

Plan your Outer Banks vacation with us! Browse our inventory of 350+ premier Outer Banks vacation rentals, including houses in Duck, Corolla, Southern Shores, Kill Devil Hills, Kitty Hawk, and Nags Head!

135 | Sunflower

This Outstanding Kitty Hawk Vacation Home is Located in a Quiet, Peaceful Area, offers Good Ocean Views, and is a Short Walk from the Beach (Just 1 Block w/Direct Access). Thoughtfully Designed w/Many Unexpected Touches including Hardwood Floors...

  • Kitty Hawk
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
Poke Box

PokeBox offers fresh, quick, simple, healthy poke bowls in Nags Head. Choose your items and build your bowl. Tuna, salmon, chicken, steak, shrimp and tofu options available. Mix in your favorite veggies, sauces and toppings for the perfect poke...

Shor-Ten-Sweet

2025 upgrades supplied: sink and min refrigerator added to the pool bar area and a half bathroom by the pool.Located in Southern Shores / 4 Bedrooms/ 3 Full Bathrooms/ 1 Half BathroomShore-Ten-Sweet is a striking, well equipped 4-bedroom home...

  • Southern Shores
  • 4 Bedrooms
  • 3 Bathrooms
5/8 - 5/15
$1,405  $1,653
$248 off
5/12 - 5/19
$1,571  $1,849
$278 off
Black Pelican

Black Pelican oceanfront restaurant is one of the Outer Banks’ premier restaurants serving lunch and dinner daily. Black Pelican is where you can enjoy fresh seafood, steaks, vegetarian dishes, sandwiches and some of the barrier island’s...

Casa Lala SS-159

Relax in luxury at Casa Lala, an incredibly designed and professionally decorated home. This exceptional five-bedroom, custom-built, Sun Select oceanfront home is in the heart of Southern Shores and features curated art, high-end furniture, and...

  • Southern Shores
  • 5 Bedrooms
  • 5 Bathrooms
4/17 - 4/24
$4,802  $5,302
$500 off
5/22 - 5/29
$8,165  $9,165
$1,000 off
10/9 - 10/16
$6,157  $6,457
$300 off
10/16 - 10/23
$6,181  $6,481
$300 off
10/23 - 10/30
$5,019  $5,319
$300 off
10/30 - 11/6
$4,241  $4,541
$300 off
11/6 - 11/13
$4,584  $4,884
$300 off
11/13 - 11/20
$4,241  $4,541
$300 off
11/20 - 11/27
$6,597  $6,897
$300 off
11/27 - 12/4
$4,593  $4,893
$300 off
12/4 - 12/11
$4,286  $4,586
$300 off
12/11 - 12/18
$4,261  $4,561
$300 off
12/18 - 12/25
$5,884  $6,184
$300 off
Pigman's Bar-B-Que

You haven’t experienced North Carolina until you’ve experienced North Carolina BBQ, and Pigman’s Bar-B-Que offers excellent North Carolina BBQ meals served with southern hospitality. Pigman’s offers traditional eastern...

See Blue Sea

OCEANSIDE Hatteras — Sand Rd. — Not only do you have a clear view of the ocean from SEE BLUE SEA, but alluring sound vistas enhance the experience of staying in this appealing three-bedroom/two-full- and one-half-bath home located just a short...

  • Hatteras
  • 3 Bedrooms
  • 2.5 Bathrooms
TRiO Restaurant & Market

Wine, beer and cheese lovers will love TRiO, an exciting retail and tasting destination in Kitty Hawk. Both a gourmet retail wine, beer and cheese shop as well as a bistro with a wine bar and tap house, TRiO offers the best of the worlds of...

Breaking Winds

This is a Blue Standard Bedding Property. Learn more about our hospitality bedding program here.Panoramic ocean views await you from the rooftop deck of this charming property in Southern Shores. Well maintained, your family will love their week in...

  • Southern Shores
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 12
Flip Flop Shops

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



Parrot'dise

OCEANVIEW Avon - Angelfish Road -Painless access to the beach is just steps away as PARROT'DISE is only 2 tons back from the beach. You'll appreciate the mesmerizing oceanfront view right from the living room or while calming in an Adirondack chair...

  • Avon
  • 3 Bedrooms
  • 2.5 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...

Dot's Dream 436-A

Dot's Dream in Nags Head is a spacious, six-bedroom, semi-oceanfront home featuring a private pool, hot tub, and game room. With beach access practically across the street, ocean views to the east, and Jockey’s Ridge National Park to the west...

  • Nags Head
  • 6 Bedrooms
  • 5.5 Bathrooms

Kitty Hawk Kites’ Whalebone Watersports Center is your one-stop shop for Outer Banks water adventures. Located on the Nags Head-Manteo Causeway right on Roanoke Sound, this location offers it all – dolphin watching cruises with a marine...