Welcome to 'Happy Hour' at Oak Island, NC
Welcome to 'Happy Hour' at Oak Island, NC
Walking distance to the sandy shores of OKI !
Walking distance to the sandy shores of OKI !
Heated Pool waiting for you and your family to start your vacation!

Happy Hour at Oak Island, NC

3 bedrooms·2½ baths
Oak Island • North Carolina
4.89(83 reviews)

$1,536.93 USD total for 3 nights

Oct 13 – 16, 2026

The open living space has a smooth transition to the kitchen and dining room.
Welcome to Winnimere, a newly built coastal farmhouse in the Historic District of Downtown Wilmington!
The living room is a comfortable space featuring a Hydeline leather sofa, Castlery performance fabric sofa, and World Market swivel chair to watch the Samsung 65" SmartTV from.
The living room is a comfortable space featuring a Hydeline leather sofa, Castlery performance fabric sofa, and World Market swivel chair to watch the Samsung 65" SmartTV from.
There's plenty of prep space in the kitchen with quartz countertops and a large island with space for prep and dining.

Winnimere

4 bedrooms·2½ baths
Wilmington • North Carolina

$1,090.32 USD total for 3 nights

Oct 18 – 21, 2026

Sunny Daze Main Entrance and 6-Seater Golf Cart
Cute OKI Cottage: Walk to Beach, Town + Golf Cart image 2
Fully Equipped Gourmet Kitchen with Breakfast Bar for Your Cooking Experience
King Bed - Sea Life Themed Bedroom, Bright Airy Design with Colors of Blues and Vibrant Coral
Sip Morning or afternoon refreshment in a sunny, flower-filled veranda retreat.

SunnyDaze Cottage: Walk to Beach, Town + Golf Cart

4 bedrooms·3 baths
Oak Island • North Carolina
5(15 reviews)

$1,385.00 USD total for 3 nights

Oct 13 – 16, 2026

Our Home is your home. Welcome!
The Naked Bean
Spacious open kitchen
A new kitchen with everything you would need on vacation.
Table for 4 in the kitchen, 3 more bar stools and an extendable table for 6 on the screened porch.

The Naked Bean

3 bedrooms·3 baths
Oak Island • North Carolina
5(92 reviews)

$661.96 USD total for 3 nights

Oct 13 – 16, 2026

That 70s Bungalow - Pet Friendly!
Queen bed with comfy linens. Peep the vintage bed skirt!
Full kitchen with retro supplies
That 70s Bungalow - Pet Friendly!
That 70s Bungalow - Pet Friendly!

That 70s Bungalow - Pet Friendly!

1 bedroom·1 bath
Wilmington • North Carolina

$532.00 USD total for 3 nights

Oct 16 – 19, 2026

55 Inch TV and extremely comfortable sofa to relax and unwind after a day exploring historic Wilmington. Log into your favorite streaming account and catch up on your favorite shows.
Anchors Aweigh ILM
Anchors Aweigh ILM
Anchors Aweigh ILM
Enjoy your mornings, evenings or any time of day on our covered patio in our quiet and private backyard. Enjoy the warmest days with cool breeze from the patio ceiling fan.

Anchors Aweigh ILM

3 bedrooms·2½ baths
Wilmington • North Carolina
4.97(117 reviews)

$829.43 USD total for 3 nights

Oct 18 – 21, 2026

Living room with plenty of seating and open floor plan.
Lots of natural light and bright open floor plan!
Plenty of storage and little extras including books for adults and kids.
Livingroom Smart TV includes Netflix, Hulu, Disney + and HBO
1st Bedroom- Full sized bed

Stylish ranch home near Middleton Park

3 bedrooms·2 baths
Oak Island • North Carolina
4.94(18 reviews)

$1,127.50 USD total for 3 nights

Nov 1 – 4, 2026

Palmbrook One: Coastal Retreat on Oak Island
Palmbrook One: Coastal Retreat on Oak Island
Palmbrook One: Coastal Retreat on Oak Island
Palmbrook One: Coastal Retreat on Oak Island
Palmbrook One: Coastal Retreat on Oak Island

Palmbrook One: Coastal Retreat on Oak Island

3 bedrooms·2 baths
Oak Island • North Carolina
5(2 reviews)

$1,005.00 USD total for 4 nights

Oct 13 – 17, 2026

Resort style pool
Resort style outdoor space
View of the decks and screened lounge areas
Aerial view of pool
Front porch

The Salty Oak - OKI

3 bedrooms·2 baths
Oak Island • North Carolina
$450 – $750/ night(excl. fees & taxes)
Steps to the Sea: Newly built in Fall 2021
Relaxing porch for morning coffee
Large Living Area with open plan: Living room, dining area, and kitchen.
Steps to the Sea ~Walk to the Beach~
Large open living area

Steps to the Sea ~Walk to the Beach~

3 bedrooms·2 baths
Oak Island • North Carolina
5(28 reviews)

$1,018.71 USD total for 3 nights

Oct 15 – 18, 2026

Hot tub -Open March thru October
Our Happy Place
La-z-Boy leather recliner.
Open floor plan with vaulted ceilings. Large Smart tv.
Record player with vinyl and cds.

Our Happy Place

2 bedrooms·2 baths
Oak Island • North Carolina
5(11 reviews)

$1,936.11 USD total for 5 nights

Jan 24 – 29, 2027

Charming Beachside Cottage with Spacious Interiors and Stylish Homey Decor.
15-min drive to Wrightsville Beach
Cottage close to the Beach
Elegant Dining Space with Seating for Six, Seamlessly Connected to a Fully Equipped Kitchen.
Bedroom #1- Queen Sized Bed

Cottage by the Beach: Best Suited for Large Groups

4 bedrooms·2 baths
Wilmington • North Carolina

$1,620.15 USD total for 3 nights

Oct 13 – 16, 2026

Long Beach Cottage
Rocking chair front porch
Long Beach Cottage
Long Beach Cottage
Long Beach Cottage

Long Beach Cottage

4 bedrooms·2 baths
Oak Island • North Carolina
5(30 reviews)

$1,274.31 USD total for 3 nights

Oct 13 – 16, 2026

The living room seats seven comfortably, with additional seating at the high table and counter.
The living room includes two full size couches and one corner chair, with additional seating available at the table and counter. The high table includes cables for charging iPhone and Android phones.
The Roku tv provides access to all your Netflix, Prime, and Hulu streaming. Local channels (NBC, CBS, ABC, FOX, etc) are available via antenna-connected live TV.
With the blinds open there is plenty of natural light.
The counter chairs are a great place to stay out of the way of whoever is preparing dinner. :-)

Pet-Friendly Oak Island Home Rental - Monthly Stay

3 bedrooms·2 baths
Oak Island • North Carolina
4.94(36 reviews)

$11,269.50 USD $6,849.70 USD total for 28 nights

May 1 – 29, 2027

West end, great views, steps to beach, new rental! image 1
West end, great views, steps to beach, new rental! image 2
West end, great views, steps to beach, new rental! image 3
West end, great views, steps to beach, new rental! image 4
West end, great views, steps to beach, new rental! image 5

West end, great views, steps to beach, new rental!

4 bedrooms·2 baths
Oak Island • North Carolina
4.86(7 reviews)

$1,135.00 USD $1,090.75 USD total for 3 nights

Oct 13 – 16, 2026

This open-concept floor plan with ceiling fans, large windows with blinds, and a sky-blue ceiling induces calm.
Living area with peek-a-boo views of the ocean.
This living space includes a large smart TV, cabinet with games, whole house wifi, and seating for nine.
There is no reason to go out. The kitchen-dining area has full-sized appliances, a table with six chairs, and extras like an air fryer, electric pressure cooker, and crock pot.
Beach House! Views! Steps to Ocean! Amenities!

Steps to Beach! Sunset Views! Kayaks & Games!

3 bedrooms·2 baths
Oak Island • North Carolina
4.88(43 reviews)

$3,190.00 USD total for 7 nights

Oct 17 – 24, 2026

Welcome to The C's By The Sea - your pool awaits your arrival
Nigh time swim anyone?
Rocking your cares away looking at over the beach!
Welcome to The C's By The Sea
Front porch sitting area looking over ocean

The C's By The Sea

5 bedrooms·4½ baths
Holden Beach • North Carolina
5(18 reviews)

$2,590.50 USD total for 3 nights

Oct 13 – 16, 2026

Welcome to Anchor's Away
Come sit and relax on our front porch
5 minute walk to public beach access and fishing pier
Quick boat/kayak ride to the intercoastal waterway
Master Bedroom w/ Ensuite

Anchor's Away Canal Home- Private Dock

3 bedrooms·2½ baths
Holden Beach • North Carolina
5(44 reviews)

$1,272.84 USD total for 3 nights

Oct 13 – 16, 2026

House From The Oceanfront
Oceanfront strand
Tanning Ledges On The Sides
House From The Streetside
Picnic Table on Oceanside Porch

Wind Beneath My Wings-Upstairs Unit

3 bedrooms·2 baths
Holden Beach • North Carolina
4.95(116 reviews)

$4,062.38 USD $3,866.62 USD total for 7 nights

Oct 19 – 26, 2026

Wind Beneath My Wings-Downstairs Unit
Wind Beneath My Wings-Downstairs Unit
Wind Beneath My Wings-Downstairs Unit
Wind Beneath My Wings-Downstairs Unit
Wind Beneath My Wings-Downstairs Unit

Wind Beneath My Wings-Downstairs Unit

2 bedrooms·1 bath
Holden Beach • North Carolina
4.76(82 reviews)

$2,590.50 USD total for 7 nights

Oct 24 – 31, 2026

Tanning Ledges On The Sides
Pool
House From Oceanfront
Beach Strand
House From The Streetside

Wind Beneath My Wings

5 bedrooms·3 baths
Holden Beach • North Carolina
4.93(56 reviews)

$5,504.81 USD total for 7 nights

Oct 24 – 31, 2026

Come Find Contentment On The Beach
Private Oceanfront Pool
Home From Oceanfront
Home From Street
Rocking Chair Row

Contentment On The Beach

6 bedrooms·4 baths
Holden Beach • North Carolina
4.98(95 reviews)

$5,740.31 USD $5,348.81 USD total for 7 nights

Oct 13 – 20, 2026

Welcome to Carolina Views - 4bed, 4bath home surrounded by views/nature.
Brand-new larger windows in 2026, delivering the BEST views in all of Holden.
Ocean views from the front decks with a 2-minute walk to the sand.
Numerous 5-star reviews.
Tranquil marsh views off the back deck bedrooms.

Carolina Views

4 bedrooms·3½ baths
Holden Beach • North Carolina

$1,392.46 USD total for 3 nights

Oct 25 – 28, 2026

Sunset and new dock - boat lift and boat NOT included
Main level balcony with great rocking chairs to enjoy the sunset
Main floor balcony outdoor dining area
Main level living, dining and kitchen
Canterbury Soundcastle

Canterbury Soundcastle

4 bedrooms·3½ baths
Topsail Beach • North Carolina
5(4 reviews)

$3,514.98 USD total for 5 nights

Oct 13 – 18, 2026