39 Oak Court | Island Rentals of Hilton Head

Location

Description

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.”

Availability Calendar

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Unavailable

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February 2026

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March 2026

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April 2026

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June 2026

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August 2026

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September 2026

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October 2026

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November 2026

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December 2026

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January 2027

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Amenities 48

Away From It All
Beach Chairs
Bicycles
Blender
Cable TV
Ceiling Fans
Central Air
Coffee Maker
Cooktop
Cookware
Deck
Deck / Patio
Dining Area
Dining Table
Dishes & Utensils
Dishwasher
Fireplace (Decorative Only)
Free Wifi
Full Kitchen
Garage
Gas Grill
High Speed Internet
Hot Tub
Ice Maker
Ironing Board
Keurig
Linens
Living Room
Microwave
Near Beach
Near Harbour Town
Near The Ocean
Outdoor Shower
Oven
Patio
Private Pool
Refrigerator
Resort
Stove
Tennis
Toaster
Towels
Washer & Dryer
Air Conditioning
Combination tub/shower
Digital Deadbolt
Non Smoking Only
Wheelchair inaccessible

Reviews 5 (26)

Awesome place to stay!
Anonymous - Posted: 9/15/2025

Thanks for your review, Nicholas! We're glad you enjoyed your stay. We hope to welcome you back to Island Rentals of Hilton Head soon!
Island Rentals of Hilton Head staff

Rare for an Airbnb to live up to its photos. We were blown away!
Anonymous - Posted: 9/1/2025

Thanks for your review, Tom! We're glad the property exceeded your expectations and matched the photos. We appreciate your feedback and hope to host you again with Island Rentals of Hilton Head!
Island Rentals of Hilton Head staff

Perfect Setup

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.
Anonymous - Posted: 8/25/2025

Thank you so much for the kind words! We’re thrilled to hear the house worked out perfectly for your fantasy football draft — even with the rainy weather. It’s great to know that the outdoor space, accommodations, and amenities helped make your stay enjoyable and comfortable. We truly appreciate your recommendation and hope to welcome you and your group back for another memorable trip (hopefully with a little more sunshine next time!).
Island Rentals of Hilton Head staff

Paradise on Oak Court

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!
Anonymous - Posted: 8/3/2025

Thank you so much for your thoughtful and detailed review! We're truly honored to hear that our home ranks among your top stays in Sea Pines—it means a lot coming from seasoned visitors like your group. We're especially glad the layout, pool area, and privacy made your trip comfortable and memorable. While the beach isn't right outside the door, we're glad you found the quick drive to the Beach Club convenient and worthwhile for the comfort and amenities of the home. We’d love to welcome you back for your next HHI getaway!
Island Rentals of Hilton Head staff

Perfection

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
Anonymous - Posted: 7/27/2025

Thanks for your review, John! We hope to host you again!
Island Rentals of Hilton Head staff

Anonymous - Posted: 7/27/2025

Thanks for your review, Michelle! We’re glad you had a great stay and hope to welcome you back soon!
Island Rentals of Hilton Head staff

Great house & outdoor space! Perfect vacation!

My family (6 adults and 5 kids) had such a great vacation staying at this property. We loved the outside space and the pool! It was perfect to come back to after a few hours at the beach. We also really enjoyed the large, open kitchen and family space. Everyone slept well and it was clean, extremely relaxing and the perfect way to enjoy some family and friend time. We will definitely book this house again! Thanks for a great vacation!
Anonymous from New Jersey - Posted: 7/20/2025

This property was absolutely amazing—truly a home away from home! Everything we needed was already provided, from beach chairs and toys to bikes, board games, and pool floaties. It made packing and planning so much easier, especially with kids in tow. The house was spotless, felt very safe, and had more than enough room for our group of 10 (5 adults and 5 kids). Everyone had space to relax without feeling crowded. The neighborhood was peaceful and family-friendly, with kind neighbors and a calm atmosphere. We loved being just a short walk from a few restaurants and only a quick 10-minute drive to the beach. The location was perfect for balancing relaxation with easy access to local fun. We had such a great stay—I’d absolutely book this property again in a heartbeat! Highly recommend for families or larger groups looking for comfort, convenience, and a touch of luxury.
Anonymous - Posted: 7/7/2025

Thanks for your review, Tiffany! We're glad the amenities and spaciousness helped make your family trip easier and more enjoyable. It’s great to hear you appreciated the peaceful neighborhood and convenient location. We look forward to hosting you and your group again!
Island Rentals of Hilton Head staff

This property was absolutely amazing—truly a home away from home! Everything we needed was already provided, from beach chairs and toys to bikes, board games, and pool floaties. It made packing and planning so much easier, especially with kids in tow.
The house was spotless, felt very safe, and had more than enough room for our group of 10 (5 adults and 5 kids). Everyone had space to relax without feeling crowded.
The neighborhood was peaceful and family-friendly, with kind neighbors and a calm atmosphere. We loved being just a short walk from a few restaurants and only a quick 10-minute drive to the beach. The location was perfect for balancing relaxation with easy access to local fun.
We had such a great stay—I’d absolutely book this property again in a heartbeat! Highly recommend for families or larger groups looking for comfort, convenience, and a touch of luxury.
Anonymous - Posted: 7/5/2025

Thanks for your review, Tiffany! We're glad the home felt like a perfect fit for your group and that the amenities made your stay easier, especially with kids. It’s great to hear you enjoyed the peaceful neighborhood and convenient location. We’d love to host you again!
Island Rentals of Hilton Head staff

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!
Anonymous - Posted: 6/23/2025

Thanks for your review, Thomas! We're pleased to hear you enjoyed the beautiful home, the amenities, and the outdoor spaces. It sounds like you had a fantastic vacation, and we appreciate your recommendation. We look forward to welcoming you back to Island Rentals of Hilton Head!
Island Rentals of Hilton Head staff

Wonderful Vacation Retreat!

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!
Anonymous - Posted: 6/23/2025

Thanks for your review, Thomas! We hope to be able to host you again!
Island Rentals of Hilton Head staff

Stayed here with the whole family including two young kids… House was great. We loved the pool and outdoor seating areas. Also great to jump on bikes and ride to parks or beach close by. Would highly recommend this house to those that are looking for a relaxing stay in Hilton Head.
Anonymous - Posted: 6/16/2025

Thank you for your review, Chad! We're glad to hear that you and your family enjoyed your stay and took advantage of the pool and outdoor seating areas. It’s great that you found the location convenient for biking to parks and the beach. We appreciate your recommendation and hope to welcome you back to Island Rentals of Hilton Head!
Island Rentals of Hilton Head staff

The house was better than described! Very clean and well cared for. When we arrived our house had no hot water but the owner was very quick and diligent in getting it resolved for us. Other than that the stay was wonderful and I would definitely stay here again!
Anonymous - Posted: 5/29/2025

Thank you for your review, Christopher! We’re glad the house exceeded your expectations and that you found it clean and well cared for. We appreciate your understanding regarding the hot water issue, and it’s great to know it was resolved quickly. We would be happy to welcome you back to Island Rentals of Hilton Head anytime!
Island Rentals of Hilton Head staff

The home and location was beautiful and what we needed for a wonderful weekend away
Anonymous - Posted: 5/11/2025

Thank you for your review, Meghan! We're pleased to know that you found the home and location beautiful for your weekend getaway. We hope to welcome you back for another wonderful stay!
Island Rentals of Hilton Head staff

Had 12 guys stay in the house for our yearly golf trip. House was excellent and comfortable. Great communication throughout the trip. House is located in a great spot close to restaurants, grocery, and golf courses. The only thing that was a little disappointing was the temperature of the pool even with the heater on. Would definitely stay here again.
Anonymous - Posted: 4/28/2025

Thanks for your review, Brad! So glad the space worked for your group. We hope you rent with us again!
Island Rentals of Hilton Head staff

We loved our stay here! The pool was the perfect size for our kids. Each room of every kind was clean, comfortable, and cozy. We would absolutely go back here. The outdoor space was absolutely perfect and our favorite part of the home.
Anonymous - Posted: 4/11/2025

Thanks for your review, Andrew! We look forward to hosting your family again!
Island Rentals of Hilton Head staff

This house was beautiful! Spacious, clean and very responsive host. We had a great stay and would come back again for sure. Kids and adults all loved our stay!
Anonymous - Posted: 4/2/2025

Thank you for your review, Lori! We hope you come back and rent with us again!
Island Rentals of Hilton Head staff

Luxury!

We loved our stay at this property! It was very clean and felt new. Each room was exceptionally well appointed with amenities which created private escapes for people who needed space to unwind. The gathering areas provided ample space for relaxing, playing games and watching movies together. Dinners were easy and the number of restaurants and local bars, each with their own vibe, kept dining interesting even for a large group so much so that the hardest decision was if people wanted to ride bikes to our destinations. We enjoyed the hot tub and sunny backyard, even in January! Our family is looking forward to coming back again!
Anonymous from Indianapolis - Posted: 3/27/2025

The location was awesome. Very clean and comfortable. The pool heater was broken while we were there so we treated jumping in the pool like a cold plunge :-)
Anonymous - Posted: 3/23/2025

Thank you so much for this review, Matthew! And truly thank you for your understanding and humorous attitude about the pool heater. We sincerely hope you come back and rent with us again!
Island Rentals of Hilton Head staff

Great house great stay, we also really appreciated the owners hospitality with a gift they left. Would stay again.
Anonymous - Posted: 1/1/2025

Thank you for your review, David! We always love hearing that our guests enjoyed their time here. We hope you come back and rent with us again!
Island Rentals of Hilton Head staff

Exceptional

Our stay in Hilton Head was nothing short of exceptional. The house itself was spacious and tastefully decorated. The amenities exceeded our expectations. The pictures do not do the house justice. It is gorgeous! The attention to detail was evident throughout our stay. The proximity to the walking / biking trail was super convenient. It truly felt like a home away from home. Overall, our weekend was a rejuvenating experience filled with relaxation and cherished memories. We can’t wait to return to this tranquil retreat in the future.
Anonymous from Huntersville - Posted: 12/5/2024

Amazing place!

We had a great time staying at this property! Our entire family and friends (adults + kids) loved the family room / kitchen and outdoor space. The house feels new and clean. The pool and hot tub are awesome! There’s even a cool room in the pool area with a TV that has sofas, a bar, kitchenette and another fridge. It was great to have so many bedrooms and bathrooms, and super convenient to have 2 sets of washers and dryers. The kitchen is huge, modern and well stocked, and it was nice to have the gas grill on the back deck. We used the 4 bikes that came with the house to take the bike path to get to beaches and restaurants. The Property Management was great and checkin was easy. We will definitely rebook!
Anonymous from North Carolina - Posted: 11/13/2024

Beautiful Place Very well appointed

Loved the neighborhood and the house
Anonymous - Posted: 10/18/2024

Thanks for the review, Ed! Glad to hear that you enjoyed your visit. We hope you'll come stay again!
Island Rentals of Hilton Head staff

Great House

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.
Anonymous - Posted: 10/14/2024

Thanks for your review, Aaron! So glad you enjoyed your time there. We hope you'll come back and stay again!
Island Rentals of Hilton Head staff

We loved the place so much we asked to stay an extra day. It’s a great place for families and/or a group of friends The house is very spacious, open and bright but also has spaces to get away from others The host has thought of so many things to make one’s stay very enjoyable including beach chairs and bikes. It’s very easy to ride bikes to restaurants and stores. We spent a lot of time in the very private outdoor area around the pool. It’s a wonderful place that we look forward to staying in again.
Anonymous - Posted: 10/14/2024

Thanks for your review, Donna! So happy to hear that you enjoyed your stay, especially that pool area! It's such a great hang out spot. We hope you'll come back and rent with us again!
Island Rentals of Hilton Head staff

What a great place.

Where to begin. The owner obviously put so much attention to detail in this home. Each room is so well thought out, with top of the line finishes. The outdoor kitchen, pool, and hot tub area are the perfect area to relax, we ended up spending most of our time outside. The free bikes and beach chairs were a great added amenity as well. The rental agency had great communication, with texts alerting us to early check in being available on our arrival day. Everything was so smooth and convenient from start to finish. Will definitely be renting again.
Anonymous - Posted: 10/9/2024

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