39 Oak Court: Sea Pines Luxury! 5 BR, 5.5 BA Private Pool & Spa, Bikes

Hilton Head Island, South Carolina
$1060 avg/night
Bed 5

Bed

Bath 6

Bath

Home Private Vacation Home

Property Type

Sleep 12

Max Sleeps

Welcome to the Sea Pines Escape at 39 Oak Court—an upscale 5-bedroom, 5.5 bathroom retreat in Hilton Head Island's exclusive Sea Pines Resort. This fully renovated luxury home offers the perfect blend of modern coastal design, spacious indoor comfort, and resort-style outdoor living—perfect for your next family vacation or group getaway!

Enjoy a private pool, always-heated standalone spa, Carolina room with bar, custom outdoor shower, elevated tiled dining deck, and rocking-chair front porch, all surrounded by lush tropical landscaping and privacy in a quiet Sea Pines cul-de-sac. You're just minutes from pristine beaches, Harbour Town, Coligny Plaza, South Beach Marina, tennis, pickleball, horseback riding and world-class golf —accessible by bike or trolley.

Meticulously Maintained Cleanliness:
• Guests consistently praise the home's immaculate condition
• It's maintained to the highest standards between every stay

Stylish, Spacious and Comfortable Interiors:
Step into vaulted ceilings, bright open living spaces, and designer furnishings. The main living room offers plush seating and a large Roku Smart TV, seamlessly connected to the dining area and chef’s kitchen. The fully-equipped kitchen features quartz countertops, Café appliances, dual sinks, a gas range, and an oversized island with barstools—great for entertaining! Enjoy a movie or watch the big game in the separate media room upstairs.

Sleeps 12 in Total Comfort:
• 3 King Bedrooms, 1 Queen Bedroom, 1 Room with 4 Twins
• 2 Queen Sleeper Sofas (office + media room)
• 3 ensuite bathrooms, hallway bathroom, 2 half baths, pool bathroom, plus a private outdoor shower

Each bedroom is a cozy, inviting retreat and includes:
• Roku Smart TV, premium linens, plush comforters, pillow-top mattress, ceiling fan, individual A/C and Heat, and ample closet/dresser space

Work-from-Home Friendly:
• Dedicated office with desk, chair, and Roku TV
• Additional desk setup in private upstairs bedroom
• High-speed WiFi

Has a decorative only fireplace.

RESORT-STYLE OUTDOOR LIVING
Guests love the private and fully integrated outdoor areas!

Carolina Room (Covered & Poolside):
• Bar area with seating for 8, sink, full fridge/freezer
• 2 deep seating sofas, outdoor Roku TV, ceiling speakers, fans, and ambient lighting

Private Pool and Heated Spa:
• Underwater bench seating and integrated outdoor Roku TV
• Adirondack chairs and chaise loungers for the sun seekers
• Spa always heated (free), and ready year-round
• Luxury pool bathroom with shower, towels, bench, storage
• Free pool heating June–August, optional Mar–May and Sept–Oct ($50 setup fee + $50/night)

Custom Outdoor Shower:
• Rainfall head, handheld wand, excellent water pressure with instant hot water, fully enclosed

Tiled Dining Deck:
• Dining for 10, Weber gas grill
• Overlooks pool and yard; connected to kitchen for seamless indoor-outdoor flow

Front Porch:
• Rocking chairs, ceiling fans, coastal charm —perfect for morning coffee or evening wine

Bonus Amenities:
• 4 free adult bikes, 10 beach chairs, pool towels/toys/floats
• 9 Roku Smart TVs, free Spectrum cable, free WiFi, 2 full size washer/dryer sets
• Board games, garage and breezeway storage, parking for 3–4 vehicles

Incredible Sea Pines Location:
• Walk or bike to Sea Pines Beach Club, Harbour Town, Coligny Plaza, and more
• Minutes to grocery stores, restaurants, shopping, golf, pickleball and nature trails
• 2 blocks from bike path entrance

Perfect For:
• Family and group vacations
• Golf getaways
• Snowbird retreats
• Remote work trips
• RBC Heritage lodging
• Year-round enjoyment

What Guests Love Most:
• “We loved the outside space and the pool!”
• “Super clean, incredibly comfortable, and beautiful.”
• “Close to everything—beach, golf, dining.”
• “One of the top houses we’ve rented by far!”
• “A home away from home.”

* All Reservations made for a duration of 1 month (28 Days) or longer are non refundable. Travel Insurance is highly recommended.

HHI STR Permit #075146

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Not Reported (host Has Not Indicated Whether There Is A Carbon Monoxide Detector On The Property; Consider Bringing A Portable Detector) Deadbolt Lock Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    5 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 3400 Sq Ft (316 Sq M)
  • KITCHEN

    Cookware/dishes/utensils Dishwasher Ice Maker Kitchen Island Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking Onsite Parking Options Include A Garage
  • INTERNET

    Free WiFi, With Speed Of 100+ Mbps (good For 1–2 People Or Up To 6 Devices)
  • OUTDOORS

    Barbecue Grill Patio
  • POOL/SPA

    Heated Pool Hot Tub Private Pool
  • BATHROOMS

    6 Bathrooms Bathtub Or Shower Hair Dryer Outdoor Shower Towels Provided
  • WORKSPACES

    Desk
  • LANGS SPOKEN

    English Spanish
  • THINGS TO DO

    Bicycle On Site Ecotours Nearby Fishing Nearby Golf Nearby Horse Riding Nearby Marina Nearby Swimming Nearby
  • ENTERTAINMENT

    Smart TV With Cable/satellite Service
  • LIVING SPACES

    Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • LOCATION HIGHLIGHTS

    Near The Sea
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 07:00 PM CheckOut Check-out : 07:00 PM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 12

Map Map

School District Rates & Availability

Review Review

  • Brad M.

    Submitted Aug 25, 2025

    Stayed Aug 21, 2025

    Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We rented this house for a fantasy football draft for 10 middle aged guys and it could’ve not been more perfect. We unfortunately ran into rain the whole time but that did not stop us from fully enjoying ourselves. The house had so much to offer and the outdoor space was perfect for our draft. There were enough beds to accommodate everyone and the house was clean and fully stocked with everything we needed. The property management was very kind and help gf enduring our whole stay. Would definitely recommend.

  • Adele H.

    Submitted Aug 3, 2025

    Stayed Jul 26, 2025

    Rating Details: The property manager was very helpful. The vacation rental was spotless. I was more than happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We've been visiting Sea Pines for years and this is definitely one of our top homes we've rented by far. What a wonderful home for our group to spend our annual HHI trip in. Every single bit of space has been utilized so well and thought out. Our group of 10 had plenty of personal space when needed but the open group spaces were perfect. The pool and covered area were top notch and we loved every minute of our week. Very private backyard area for our group to enjoy. A little bit of a haul to the beach with kids but doable quick drive to the beach club and worth the drive to have such a wonderful house to come back too. This is one we will come back to for sure!

  • John C.

    Submitted Jul 27, 2025

    Stayed Jul 5, 2025

    Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Awesome

  • Linda B.

    Submitted Jun 23, 2025

    Stayed Jun 14, 2025

    Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: House was Beautiful! Clean, had all the amenities and so much space! Loved the pool and outdoor areas. Close drive to restaurants, sights and beach. Had an absolutely lovely vacation!! Would definitely recommend this vacation retreat!

  • Ed H.

    Submitted Oct 18, 2024

    Stayed Oct 15, 2024

    Loved the neighborhood and the house

  • Aaron B.

    Submitted Oct 14, 2024

    Stayed Sep 25, 2024

    Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Awesome house with great amenities! Would recommend this house to anyone.

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Total

Includes taxes and fees
$1,060+
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