Holiday rentals in Sea Pines

4.96 out of 5 average rating, 292 reviews

Ocean View! Steps to beach! Remodeled HHBT Condo

Newly remodeled just last year! Adorable beach front condo located in HH Beach & Tennis Resort. Watch & listen to the ocean waves right from your 2nd floor balcony! The condo is in a gated area within where guests will have access to a private beach, 2 pools, resort restaurants, tennis, pickleball, beach volleyball, playgrounds, cookout areas, bike rental, and a gym. We also provide beach chairs, coolers, boogie boards and coffee! It's all here! The getaway you've been waiting for and deserve!

4.93 out of 5 average rating, 14 reviews

Sea Pines 2 Bdrm/2Ba Condo W/Bikes, Pets Welcome!

Enjoy 4 bikes, tennis courts & community pool. A very easy walk or bike ride to the beach, Harbour Town, shops & restaurants. This stunning 2nd floor villa in the heart of Sea Pines boasts a single floor layout with a living room, dining area, kitchen w/ granite countertops and a spacious balcony w/pool and lagoon views. The primary bedroom has a king bed, bathroom, and a large flat-screen TV. The guest bedroom offers a queen bed & full bath, TV and walk-in closet. 1051 Sq. Ft. interior.

4.96 out of 5 average rating, 26 reviews

2319 Racquet Club @ Sea Pines | Steps to Beach

HOST & HOME presents… 2319 Racquet Club. Your slice of paradise awaits with tranquil lagoon views and the charm of Sea Pines Resort. Start your day with coffee on the deck, surrounded by nature. Stroll 10 minutes to Harbour Town’s shops, restaurants, and marina, or hop the free trolley to the Beach Club. Enjoy championship golf, tennis, a serene pool, and bike trails. Plus, your furry friend is welcome too! This isn’t just a stay—it’s an unforgettable experience. Learn more below…👇

5 out of 5 average rating, 38 reviews

Luxury Penthouse in the Heart of Harbour Town

15% off 7 night stays or longer - ask us about 2025 monthly winter stay discounts Plan your next vacation in this luxurious villa. It’s prime location is steps from Hilton Head’s iconic lighthouse, marina, shops and restaurants. There are only 9 villas in the this building. This unit is on the top floor on the end closest to the marina. If you are familiar with Harbour Town, Mariner’s Way is located between the live oak trees on the sandy playground and the Crazy Crab.

Flat in Hilton Head Island

4.96 out of 5 average rating, 80 reviews

KING BED!Ocean View, Free Bikes Poolside 3rd Floor

Nestled within the serene beauty of Hilton Head Island, South Carolina, this exquisite poolside villa offers the ultimate coastal retreat. Just steps away from the sandy shores and the soothing sounds of the Atlantic Ocean, this villa provides a perfect blend of luxury, fun, and relaxation. Enjoy the ocean view from our balcony or explore the island with so much to do within just a short walk or a quick bike ride away. Our bikes are free for you to enjoy during your stay!

5 out of 5 average rating, 86 reviews

5 Star Location! Pool, Walk to Shops/Dining

This luxury villa is in the heart of Hilton Head Island: Harbour Town in the world famous Sea Pines Resort- home of the PGA Heritage golf tournament! Walk to shopping, lighthouse, dining, water sports, golf, tennis, entertainment, and boat charters! The complimentary, seasonal beach shuttle picks up at the villa and drops off at the Sea Pines Beach Club. Impeccably appointed and sparkling clean with lagoon views. The complex has a private pool and clay tennis courts.

Flat in Hilton Head Island

4.95 out of 5 average rating, 38 reviews

SeaPines - Beautiful Renovation, Walk to beach

Take in the dynamic Golf and Lagoon views from one of the most centrally located villas in Sea Pines. Just a 5-7 minute walk to the beautiful white sand beaches of Hilton Head. The heated/cooled on-site pool is steps from the front door. New ownership, new everything! From the appliances to the flooring, furniture, paint, kitchen and baths-do not miss a chance to enjoy all of Sea Pines from a stunning property. Please note this property is no longer pet friendly.

4.97 out of 5 average rating, 294 reviews

Oceanfront Luxury! KING BED 65"TVs Pickleball BAR!

PANORAMIC OCEANFRONT VIEWS 🏝️1-2 min walk onto Beach🏝️ ✨Top 10% of Homes✨ Next to Beach Boardwalk! HGTV Decorator Beachfront Balcony 100% Renovation KING BED Expanded Bedroom (2) 65" SmartTVs Coastal Décor Full Kitchen Beach Chairs, Boogie Boards, Ice Chest & More RESORT: 4 Boardwalks Huge Oceanfront Pool Restaurants Beachfront Bar & Grille Sports Bar FREE Tennis, Gym, Pickleball, Basketball, Volleyball & More Bike Rentals Gated 24/7 Security Trolley Stop

4.99 out of 5 average rating, 154 reviews

Heart of Harbour Town - Beach | Pool | Golf | 2BR/2.5BA - Pool Access

In the Heart of Harbour Town Experience the best of Harbour Town living with exquisite harbour views in this recently updated 2 BR / 2.5 BA end unit just steps away from the waterfront. Villa is a short walk to pool, the pristine Harbour Town Golf Links, and the Sea Pines Trolley -- offering complimentary seasonal transport. Recently renovated with gourmet kitchen, elegant living area, and outdoor dining. Sleeps 8. Includes Harbour Town pool passes.

4.97 out of 5 average rating, 768 reviews

Guest house in Bluffton

Bluffton's Tropical Carriage House Getaway

Embrace the inviting atmosphere of this detached garage apartment. The guesthouse features an open-concept living/*kitchenette/sleeping area, a tropical design, a private entry, a luxury king mattress and blackout window treatments. This southern style hood offers ample sidewalks, ponds for fishing, a playground, and a park. Quaint Old Town Bluffton is a 3 minute drive or 20 minute walk to a number of shops and restaurants. Permit # STR21-00119

4.99 out of 5 average rating, 82 reviews

180º Ocean Views, Treehouse "Siren's Lookout"

Waterfront and sunset views abound in this unique "treehouse", with 360 degree views. On Deer Island, just steps from the Harbour Town Lighthouse, known for its' large-boat marina, restaurants, shops and Golf Club, host of the RBC Heritage Classic, PGA Tour Event. Enjoy all the amenities of Sea Pines, including the South Beach Marina, Sea Pines Beach and Salty Dog Cafe, only 3 miles away, serviced by trollies & bike paths.

Treehouse in Hilton Head Island

5 out of 5 average rating, 7 reviews

Luxury Waterfront Tree House | Harbour Town | Pool

One of our newest homes, see our over 1000 *5*-star reviews. Nestled on a tranquil cul-de-sac on Deer Island - an island on an island - our enchanting Treehouse offers the ultimate getaway, surrounded by lush gardens and bamboo forests, stunning reclaimed wood floors, historic Savannah brickwork, and marvelous mid-century design and furnishings.

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Other great holiday rentals in Sea Pines

4.98 out of 5 average rating, 86 reviews

Governor’s Quarters: Stately Sea Pines Stay on HHI

RyanRating, 5 stars1 month ago

Staying in the Sea Pines is pretty special, and this home was an amazing place to spend a week. The neighborhood is peaceful and surrounded by the beauty of the island. The house was pristine and very comfortable. There is plenty of space to accommodate a large family and they have included everything you could need with great attention to detail. The kitchen is fully stocked, beyond any other home we’ve stayed in and it felt above and beyond our expectations. We had access to a community pool about a mile away that is easy to bike to and also surrounded by live oaks in a peaceful neighborhood. The house has bikes, but we brought our own and took full advantage of exploring the area on the vast bike trails that connect to shopping, dining and the beach. If you’re considering a trip to Hilton Head, the Sea Pines is the place to stay, and this house has to be at the top of the list.

5 out of 5 average rating, 11 reviews

Hilton Head Island Beach House - Sea Pines Resort

GrahamRating, 5 stars1 week ago

We had a wonderful stay at this beach house! It was clean, spacious, and had a cheery, welcoming interior. The kitchen was well-equipped, and we appreciated thoughtful touches like the pack-n-play and beach gear. The private pool was a highlight—especially with how quickly Brian responded by sending someone to clean it after a storm. The location was ideal: a short walk to the beach, and not too deep into Sea Pines, so it was easy to get in and out. Highly recommend!

4.91 out of 5 average rating, 147 reviews

Water Views Treehouse walkable to Harbour Town

JohnRating, 5 stars1 month ago

Stayed at 2024 Deer Island Road and loved it. The place is beautiful, really well done inside, and had everything we needed. Check-in was easy, no hassle at all. Meredith was great. Would definitely come back.

4.94 out of 5 average rating, 62 reviews

Updated! Sea Pines Lagoon View Oasis

SarahRating, 5 stars1 week ago

This was our second summer staying at this house and it was even better the second time. It has a great floor plan for our two girls and I felt like I had plenty of space in the master suite. The rest is the house was perfect for mingling as a family. Highly recommend!!

4.79 out of 5 average rating, 33 reviews

Updated 1BR 2nd-Floor | Pool | W/D

MeggyRating, 5 stars2 weeks ago

This was perfect for my husband and I a little 4 day getaway. Sea Pines is our vibe- slow, beautiful views, beach access, and trolley to take you to beach and shops. We walked .5 mile to dinner one night at Quarterdeck. Live music and ice cream just right outside the restaurant for a night cap! Love the clubhouse at the beach access for lunch, drinks, and bathroom breaks while at the beach. Can’t wait to come back!

5 out of 5 average rating, 135 reviews

Walk to Harbour Town: Airy Treehouse w/ Bikes

JanetRating, 5 stars1 month ago

My friends and I had such a great time at this place for our girls weekend. We enjoyed bike rides to the beach, biking to Salty dog and also down to the lighthouse. Lighthouse and shops with some cute restaurants are also walkable. The host was very informative, helpful with recommendations and had quick response times. Home was clean, private with a marsh few primarily and we even had some deer visitors. Would definitely recommend this place again. We can’t wait to come back!

4.56 out of 5 average rating, 55 reviews

1BR Waterview 1st-Floor | Deck | Pool

GentryRating, 5 stars2 weeks ago

We loved of stay and this is a great location!