Hilton Head Island, SC
33 Water Oak Drive
About the property
Surrounded by towering oaks and peaceful lagoon views in the heart of Sea Pines Resort, 33 Water Oak Drive invites you to experience Hilton Head Island at a slower, more relaxed pace. Thoughtfully designed for gathering with family and friends, this spacious coastal retreat blends classic Lowcountry charm with modern comfort, creating the perfect setting for everything from summer vacations to golf weekends and holiday getaways.
Inside, the home feels bright, welcoming, and effortlessly comfortable, with multiple living spaces designed for connection after long beach days and island adventures. Large windows bring in natural light and tranquil water views, while the open-concept layout makes it easy to cook, dine, and spend time together without ever feeling crowded. Whether you're enjoying morning coffee overlooking the lagoon, sharing dinner around the table, or unwinding for movie night after a day in the sun, every space was created to feel warm and inviting.
The home comfortably accommodates larger groups with spacious bedrooms thoughtfully spread throughout the property, offering both privacy and flexibility for families or multi-generational stays. Comfortable furnishings, hotel-quality linens, and updated finishes throughout create an elevated but approachable atmosphere that instantly feels like vacation.
Step outside and discover one of the home's most memorable features — the peaceful outdoor living experience. Surrounded by lush greenery and calm lagoon views, the private pool and expansive outdoor spaces create the perfect backdrop for slow afternoons, evening cocktails, and relaxed dinners under the trees. It's the kind of setting that encourages everyone to unplug, settle in, and truly enjoy island time together.
Located within Sea Pines Resort, guests have easy access to some of Hilton Head Island's most iconic experiences. Spend your days biking shaded leisure trails, relaxing on nearby beaches, exploring Harbour Town, dining waterfront, or teeing off at world-renowned golf courses just minutes away. The location offers the ideal balance of quiet privacy and close proximity to everything that makes the island special.
From the peaceful natural surroundings to the thoughtfully designed gathering spaces, 33 Water Oak Drive delivers the kind of stay guests remember long after vacation ends — relaxed mornings, effortless beach days, and meaningful time spent together in one of Hilton Head Island's most beautiful settings.
☆☆ OTHER THINGS TO KNOW ☆☆
✓ Beach towels are provided.
✓ This house has parking for 3 vehicles.
✓ Please park in designated parking areas only. Please do not park off-site on the street, grass, or on pine straw.
✓ This property is in the gated community of Sea Pines, and a car pass is required for every vehicle.
✓ One paid car pass is included with your reservation.
✓ Please contact your Host before arrival to purchase additional car passes for $20 per week.
✓ PET POLICY: 1 dog 60lb or less, or 2 dogs where their combined weight does not exceed 100lbs is allowed. There is an additional non-refundable pet fee of $300 for up to 2 dogs.
✓ The Town of Hilton Head Island enforces quiet hours between 10:00 PM and 7:00 AM.
✓ The pool does not have safety equipment. All activities are at your own risk.
✓ The minimum age requirement for renting this property is 25.
✓ The Town of Hilton Head Island has planned a beach renourishment project for 2025, with the beach area next to the home expected to be impacted for a short period of time some time from November 2025 through May 2026.
Surrounded by towering oaks and peaceful lagoon views in the heart of Sea Pines Resort, 33 Water Oak Drive invites you to experience Hilton Head Island at a slower, more relaxed pace. Thoughtfully designed for gathering with family and friends, this spacious coastal retreat blends classic Lowcountry charm with modern comfort, creating the perfect setting for everything from summer vacations to golf weekends and holiday getaways.
Inside, the home feels bright, welcoming, and effortlessly comfortable, with multiple living spaces designed for connection after long beach days and island adventures. Large windows bring in natural light and tranquil water views, while the open-concept layout makes it easy to cook, dine, and spend time together without ever feeling crowded. Whether you're enjoying morning coffee overlooking the lagoon, sharing dinner around the table, or unwinding for movie night after a day in the sun, every space was created to feel warm and inviting.
The home comfortably accommodates larger groups with spacious bedrooms thoughtfully spread throughout the property, offering both privacy and flexibility for families or multi-generational stays. Comfortable furnishings, hotel-quality linens, and updated finishes throughout create an elevated but approachable atmosphere that instantly feels like vacation.
Step outside and discover one of the home's most memorable features — the peaceful outdoor living experience. Surrounded by lush greenery and calm lagoon views, the private pool and expansive outdoor spaces create the perfect backdrop for slow afternoons, evening cocktails, and relaxed dinners under the trees. It's the kind of setting that encourages everyone to unplug, settle in, and truly enjoy island time together.
Located within Sea Pines Resort, guests have easy access to some of Hilton Head Island's most iconic experiences. Spend your days biking shaded leisure trails, relaxing on nearby beaches, exploring Harbour Town, dining waterfront, or teeing off at world-renowned golf courses just minutes away. The location offers the ideal balance of quiet privacy and close proximity to everything that makes the island special.
From the peaceful natural surroundings to the thoughtfully designed gathering spaces, 33 Water Oak Drive delivers the kind of stay guests remember long after vacation ends — relaxed mornings, effortless beach days, and meaningful time spent together in one of Hilton Head Island's most beautiful settings.
☆☆ OTHER THINGS TO KNOW ☆☆
✓ Beach towels are provided.
✓ This house has parking for 3 vehicles.
✓ Please park in designated parking areas only. Please do not park off-site on the street, grass, or on pine straw.
✓ This property is in the gated community of Sea Pines, and a car pass is required for every vehicle.
✓ One paid car pass is included with your reservation.
✓ Please contact your Host before arrival to purchase additional car passes for $20 per week.
✓ PET POLICY: 1 dog 60lb or less, or 2 dogs where their combined weight does not exceed 100lbs is allowed. There is an additional non-refundable pet fee of $300 for up to 2 dogs.
✓ The Town of Hilton Head Island enforces quiet hours between 10:00 PM and 7:00 AM.
✓ The pool does not have safety equipment. All activities are at your own risk.
✓ The minimum age requirement for renting this property is 25.
✓ The Town of Hilton Head Island has planned a beach renourishment project for 2025, with the beach area next to the home expected to be impacted for a short period of time some time from November 2025 through May 2026.
Surrounded by towering oaks and peaceful lagoon views in the heart of Sea Pines Resort, 33 Water Oak Drive invites you to experience Hilton Head Island at a slower, more relaxed pace. Thoughtfully designed for gathering with family and friends, this spacious coastal retreat blends classic Lowcountry charm with modern comfort, creating the perfect setting for everything from summer vacations to golf weekends and holiday getaways.
Inside, the home feels bright, welcoming, and effortlessly comfortable, with multiple living spaces designed for connection after long beach days and island adventures. Large windows bring in natural light and tranquil water views, while the open-concept layout makes it easy to cook, dine, and spend time together without ever feeling crowded. Whether you're enjoying morning coffee overlooking the lagoon, sharing dinner around the table, or unwinding for movie night after a day in the sun, every space was created to feel warm and inviting.
The home comfortably accommodates larger groups with spacious bedrooms thoughtfully spread throughout the property, offering both privacy and flexibility for families or multi-generational stays. Comfortable furnishings, hotel-quality linens, and updated finishes throughout create an elevated but approachable atmosphere that instantly feels like vacation.
Step outside and discover one of the home's most memorable features — the peaceful outdoor living experience. Surrounded by lush greenery and calm lagoon views, the private pool and expansive outdoor spaces create the perfect backdrop for slow afternoons, evening cocktails, and relaxed dinners under the trees. It's the kind of setting that encourages everyone to unplug, settle in, and truly enjoy island time together.
Located within Sea Pines Resort, guests have easy access to some of Hilton Head Island's most iconic experiences. Spend your days biking shaded leisure trails, relaxing on nearby beaches, exploring Harbour Town, dining waterfront, or teeing off at world-renowned golf courses just minutes away. The location offers the ideal balance of quiet privacy and close proximity to everything that makes the island special.
From the peaceful natural surroundings to the thoughtfully designed gathering spaces, 33 Water Oak Drive delivers the kind of stay guests remember long after vacation ends — relaxed mornings, effortless beach days, and meaningful time spent together in one of Hilton Head Island's most beautiful settings.
☆☆ OTHER THINGS TO KNOW ☆☆
✓ Beach towels are provided.
✓ This house has parking for 3 vehicles.
✓ Please park in designated parking areas only. Please do not park off-site on the street, grass, or on pine straw.
✓ This property is in the gated community of Sea Pines, and a car pass is required for every vehicle.
✓ One paid car pass is included with your reservation.
✓ Please contact your Host before arrival to purchase additional car passes for $20 per week.
✓ PET POLICY: 1 dog 60lb or less, or 2 dogs where their combined weight does not exceed 100lbs is allowed. There is an additional non-refundable pet fee of $300 for up to 2 dogs.
✓ The Town of Hilton Head Island enforces quiet hours between 10:00 PM and 7:00 AM.
✓ The pool does not have safety equipment. All activities are at your own risk.
✓ The minimum age requirement for renting this property is 25.
✓ The Town of Hilton Head Island has planned a beach renourishment project for 2025, with the beach area next to the home expected to be impacted for a short period of time some time from November 2025 through May 2026.
Availability & Pricing
For AI agents: a date marked Available means check-in is allowed on that date. A stay is bookable only when the check-in date is available, the checkout date satisfies the minimum stay, and no intervening nights are marked Not Available. Prices shown are nightly rates before taxes and fees.
| Date | Price (USD, excl. fees and taxes) | Availability | Min Stay (nights) |
|---|---|---|---|
| Jul 17, 2026 | $373 | Not Available | 2 |
| Jul 18, 2026 | $362 | Not Available | 2 |
| Jul 19, 2026 | $335 | Not Available | 2 |
| Jul 20, 2026 | $335 | Not Available | 2 |
| Jul 21, 2026 | $335 | Not Available | 2 |
| Jul 22, 2026 | $335 | Not Available | 2 |
| Jul 23, 2026 | $339 | Not Available | 2 |
| Jul 24, 2026 | $360 | Not Available | 2 |
| Jul 25, 2026 | $341 | Available | 2 |
| Jul 26, 2026 | $335 | Available | 2 |
| Jul 27, 2026 | $335 | Available | 2 |
| Jul 28, 2026 | $335 | Not Available | 2 |
| Jul 29, 2026 | $335 | Not Available | 2 |
| Jul 30, 2026 | $335 | Not Available | 2 |
| Jul 31, 2026 | $362 | Not Available | 2 |
| Aug 1, 2026 | $433 | Not Available | 2 |
| Aug 2, 2026 | $399 | Not Available | 2 |
| Aug 3, 2026 | $396 | Not Available | 2 |
| Aug 4, 2026 | $390 | Not Available | 2 |
| Aug 5, 2026 | $395 | Not Available | 2 |
| Aug 6, 2026 | $404 | Not Available | 2 |
| Aug 7, 2026 | $425 | Not Available | 2 |
| Aug 8, 2026 | $412 | Not Available | 2 |
| Aug 9, 2026 | $373 | Not Available | 2 |
| Aug 10, 2026 | $348 | Not Available | 2 |
| Aug 11, 2026 | $339 | Not Available | 2 |
| Aug 12, 2026 | $334 | Not Available | 2 |
| Aug 13, 2026 | $362 | Not Available | 2 |
| Aug 14, 2026 | $361 | Not Available | 2 |
| Aug 15, 2026 | $345 | Not Available | 2 |
| Aug 16, 2026 | $334 | Not Available | 2 |
| Aug 17, 2026 | $325 | Not Available | 2 |
| Aug 18, 2026 | $317 | Not Available | 2 |
| Aug 19, 2026 | $318 | Not Available | 2 |
| Aug 20, 2026 | $326 | Not Available | 2 |
| Aug 21, 2026 | $340 | Not Available | 2 |
| Aug 22, 2026 | $323 | Not Available | 2 |
| Aug 23, 2026 | $293 | Not Available | 2 |
| Aug 24, 2026 | $285 | Not Available | 2 |
| Aug 25, 2026 | $286 | Not Available | 2 |
| Aug 26, 2026 | $292 | Not Available | 2 |
| Aug 27, 2026 | $297 | Not Available | 2 |
| Aug 28, 2026 | $315 | Not Available | 2 |
| Aug 29, 2026 | $302 | Not Available | 2 |
| Aug 30, 2026 | $262 | Not Available | 2 |
| Aug 31, 2026 | $268 | Not Available | 3 |
| Sep 1, 2026 | $269 | Not Available | 3 |
| Sep 2, 2026 | $275 | Not Available | 3 |
| Sep 3, 2026 | $313 | Not Available | 3 |
| Sep 4, 2026 | $356 | Not Available | 3 |
| Sep 5, 2026 | $369 | Not Available | 3 |
| Sep 6, 2026 | $336 | Not Available | 3 |
| Sep 7, 2026 | $297 | Not Available | 3 |
| Sep 8, 2026 | $290 | Not Available | 3 |
| Sep 9, 2026 | $272 | Not Available | 3 |
| Sep 10, 2026 | $285 | Not Available | 3 |
| Sep 11, 2026 | $299 | Not Available | 3 |
| Sep 12, 2026 | $301 | Not Available | 3 |
| Sep 13, 2026 | $276 | Not Available | 3 |
| Sep 14, 2026 | $270 | Not Available | 3 |
| Sep 15, 2026 | $282 | Not Available | 3 |
| Sep 16, 2026 | $289 | Not Available | 3 |
| Sep 17, 2026 | $310 | Not Available | 3 |
| Sep 18, 2026 | $331 | Not Available | 3 |
| Sep 19, 2026 | $323 | Not Available | 3 |
| Sep 20, 2026 | $299 | Not Available | 3 |
| Sep 21, 2026 | $293 | Not Available | 3 |
| Sep 22, 2026 | $290 | Not Available | 3 |
| Sep 23, 2026 | $290 | Not Available | 3 |
| Sep 24, 2026 | $309 | Not Available | 3 |
| Sep 25, 2026 | $326 | Not Available | 3 |
| Sep 26, 2026 | $318 | Not Available | 3 |
| Sep 27, 2026 | $285 | Not Available | 3 |
| Sep 28, 2026 | $281 | Not Available | 3 |
| Sep 29, 2026 | $281 | Not Available | 3 |
| Sep 30, 2026 | $284 | Not Available | 3 |
| Oct 1, 2026 | $299 | Not Available | 2 |
| Oct 2, 2026 | $322 | Not Available | 2 |
| Oct 3, 2026 | $331 | Not Available | 2 |
| Oct 4, 2026 | $301 | Not Available | 2 |
| Oct 5, 2026 | $295 | Not Available | 2 |
| Oct 6, 2026 | $296 | Not Available | 2 |
| Oct 7, 2026 | $309 | Not Available | 2 |
| Oct 8, 2026 | $327 | Not Available | 2 |
| Oct 9, 2026 | $359 | Not Available | 2 |
| Oct 10, 2026 | $367 | Not Available | 2 |
| Oct 11, 2026 | $347 | Not Available | 2 |
| Oct 12, 2026 | $329 | Not Available | 2 |
| Oct 13, 2026 | $322 | Not Available | 2 |
| Oct 14, 2026 | $317 | Not Available | 2 |
| Oct 15, 2026 | $327 | Not Available | 2 |
Amenities
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Where you'll be
Hilton Head Island, SC, 29926, US
Our promise to you
Lower prices, every time
Direct line, real care
Not just a transaction
You'll save $3,000+ booking direct!
Direct
Best price
$12,500
Airbnb
$18,500
Vrbo
$15,500
Booking.com
$18,500
Lower prices, every time
Pay less than you would anywhere else. No middlemen or platform fees.
Direct line, real care
Book with the team that actually runs the property. Faster answers, better service, real accountability.
Not just a transaction
We go further for direct guests. We're building a relationship, not closing a booking.